#1150: “My unfashionable mom wants some style advice.”

Who would like to read a fluffy question about being nice?

Dear Captain,

I love my mom (1), I love feminism (2) and I am certain, that everyone has the right to dress as they want (3) (except for Nazi clothing, but luckily, that is not my topic). This three principles clash when I look in the drawer of my mom.

My mom is recently single again after 12 years of dating and living with her former partner. She is 65 now and a wonderful, humorous, intelligent woman. She likes dating and has an outgoing personality and wants to meet new people and eventually start a relationship again, but doesn’t mind dating for a while and having fun. She has always been the intelligent one, not the beautiful one in comparison to her sister and never cared that much about clothes, make up, and stuff (literally she puts on sunscreen and a green eyeliner. Since 40 years). Her mother, my grandmother, often asked me (or her sister) to go shopping with her, so that she can have something nice to wear. We do it sometimes, but just for fun and not because our beloved ancestor says, we have to look in a certain way to be social acceptable. She often asks me about a style choice and states, that she wants to look her best.

BUT. She sometimes dresses quite horribly. It’s hard to say and admit, but honestly – bucket hats?! Sometimes I want to say something, but when the urge comes up, I mostly stop myself because: see principle 3. It is even hard for me when she explicitly asks for my advice. Do you have any scripts how to tell her that this specific thing/the dress/the hat (!!!) is not suiting her (or anyone, in the case of bucket hats) in a nice, loving, supporting way without compromising my believe, that she should dress the way she feels most comfortable?

Your advice is highly appreciated, thank you

Daughter who is torn between her believes in feminism and the fight against socks in sandals.

Hi Daughter!

You’re right, a 65-year-old lady can & should dress however the heck she wants! (Including bucket hats, which sound adorable frankly).

Guess what, you can be a feminist and also have opinions about fashion. Does our culture focus on looks in a way that can be harmful and toxic, does it try to value women only for their looks, and does it lift up young/wealthy/able-bodied/cisgender/heterosexual/thin/white bodies at the cost of other kinds of bodies? Absolutely! And “Wear what you want, Mom, your worth isn’t in your clothes!” is an important message. But “The Intelligent One” isn’t something automatically distinct from “The Beautiful One” – these either/or categories diminish everyone. You don’t have to be pretty, you also don’t have to reject the whole idea of pretty in order to prove your seriousness or worth, either. There’s little room in our complicated capitalist world for the average person to make sure that every item we choose is ethically optimized and free of the male-gaze and liberated from any media influence. We communicate something about who we are with our clothing choices whether we intend to or not. Since we live in a non-clothing optional world, you’ve gotta pick out something to wear, it might as well be stuff that makes you feel good and suits you. Consumption (or lack of consumption) is not the same as activism.

Our bodies and our needs change with time, and moving from the working world to retirement and dating again after a long partnership seem like great reasons for your mom to want a bit of an update. Since she is ASKING you & her sister to go shopping and to help her cultivate how she wants to look, you have room to gently give her some opinions, some care, and some gifts. For example:

  • How does your mom want to look & be seen? Could you ask her to collect (digitally) some photos or blogs of women whose style she admires? (For example)(Such as)(Like so) Think of it as giving herself permission to care about this, to curate images, to train her eye, to imagine & re-imagine herself.
  • Since she enjoys dating, what if you helped her put a great first date outfit or two together?
  • Since she likes hats, what if you took her hat shopping for something that you think she’d look great in?
  • If she wears glasses, when was the last time she updated her eyewear?
  • If she wears bras, when was the last time she was fitted? If her lingerie drawer could legally vote this year, it’s probably time for an upgrade.
  • What if you & your aunt pooled funds and subscribed her to one of those style-subscription box-thingies for a few months? It would let her play around with things at her own pace.
  • Could you do a closet clean-out/donation drive with her and help her purge the stuff that no longer fits or suits?

As for scripts & talking to her about fashion stuff, here are some general guidelines:

  • “Is that what you’re wearing” is guaranteed to put shoulders up around ears. I’m sure there are times it’s technically okay to say those words to a fellow adult (like, the person is appearing in a court of law later that day and the neon “Crazy in the Head, Crazy in the Bed” t-shirt is not sending the optimal message) but the exceptions are few and far between.
  • Unless you’re specifically asked, probably the only opinion anyone needs to hear about what they’re wearing is “You look wonderful!” Remember,“Oh mom, I always think you look great! I’m not comfortable giving you that kind of advice” is always a valid option. Just ’cause she’s asking doesn’t mean you have to participate.
  • The correct time to offer suggestions/corrections about what someone is wearing is before they leave the house, so they can change if they want to. In my house this takes the form of “Babe, there’s a stain on that/a hole in that – do you have a different one you can put on?” 
  • When they ask and it’s a style that you think doesn’t suit them, what if you said “That’s not my favorite dress on you” or “That’s not the hat I would pick out for you” or “It might be time to retire that” + “How about this one instead?” Redirect them to something you like better.
  • If your mom joyfully throws on your least favorite bucket hat and the ol’ socks & Crocs for a fun day out with you and doesn’t ask or bring up the topic of style at all, leave it alone. When in doubt, be kind, which sometimes means “when in doubt, be quiet” and always means don’t treat the people in your life like projects.

Moderation Notes:

Readers, I cannot emphasize this enough: I 100% do not want to hear about specific clothing or clothing trends you think are ugly, unflattering, ridiculous, whatever. I guarantee that whatever you don’t like, someone else reading this loves it (and rocks it). Let’s just not.

Absolutely no talk about what is “unflattering” or not allowed for certain body types. No negative body talk and no diet or weight talk, period. As a reminder, here is this blog’s official position statement on all that:


What I do want to hear about & know about:

  • Do you have any people in your life who are great at giving style advice in a gentle way? What kinds of things did they say or do?
  • Have you ever transformed your clothing style into something you like much better? What kinds of things did you do? What helped the most?
  • Links to style blogs & outside resources are allowed, within reason. Like, link ONE thing if you think it might be specifically interesting or useful to the Letter Writer and her mom, and describe what you’re linking with some text to so we have context before we click.

Thank you!




407 thoughts on “#1150: “My unfashionable mom wants some style advice.”

  1. I love http://www.thesartorialist.com/ – a street style photography blog! It shows eccentric fashion, classic looks, and folks taking risks in looks with colours, patterns, etc. It helped me in learning how to style certain pieces of mine that were a bit wild while encouraging me to stand out fashion-wise. Hope it helps!

    1. Advanced Style,http://www.advanced.style, is another great fashion blog, focused on older men and women, with photos taken in the street. It celebrates individual, unique and artistic expressions of style ala Iris Apfel.

      1. And, of course, Tom and Lorenzo https://tomandlorenzo.com/ which is really fun to read and has also really helped me learn what looks good and why, and what doesn’t, in its coverage of the world of fashion and celebrity.

        1. I like their “Girl, that’s not your dress” feature, like, you are great and that dress is great, but you are not great together, and even professionally styled conventionally attractive people with all the money whose JOB it is to look pretty in clothes still have a hard time finding the right thing.

          1. I’m not a fashion person so don’t follow any of these blogs, but I really like the “Girl, that’s not your dress” way of phrasing it. When I was reading the original answer I was thinking of the director of my women’s a cappella chorus, who occasionally talks about “songs that don’t love us.” Nothing wrong with the song, not technically beyond the group, just doesn’t click for some reason. Outfits can be like that.

          2. T/L make a habit of focusing on “this outfit does/does not work and here’s why”, and they seem to keep their comments section focused the same way, which is a relief.

  2. Hey! So this is such a lovely question. My mum is charming and beautiful and entirely disinterested in dressing. But then! My sister and I got into fashion (a bit) and she was quite intrigued. What really helped was taking her to a department store which offered a free and pressure-free personal shopping service. Nice ladies brought her lots of outfits, to her budget, and talked her through why they looked good and what occasions they might be good for. She’s stuck to a lot of that (very good!) advice, and has taken great pleasure in clothes since, and is now the best dressed of all of us!

    1. I second this suggestion, lots of large stores offer this service, it’s a fun activity for a day out! Maybe you, your mother and her sister could all do a personal shopping session together so she doesn’t feel singled out or self-conscious? Also, detailed fashion advice from a professional who is trained to talk fashion all day long will definitely go down better than advice coming directly from a sibling or daughter imo.

    2. Yes to this. I won a free session with a personal shopper and as a very unfashionable person I was a bit dubious. But she was fantastic and basically helped me play dress ups with a lot of styles, cuts and sizes I would never have tried on my own, although getting a fair idea of what I was never going to like and not forcing that. There was nothing about flattering and a lot about what I wanted to look like – to summarise – professional at work, practical at home, wizard always.

      1. Oooh yes I like the idea of starting with how you want to look! I think the tips above about collecting some pictures may help with that but it would definitely be useful with a personal shopper or the LW if she wants to help her mom that way. I’m really short, and was often thought to be much younger than I was as a kid (/sometimes still am). My mom spent A LOT of time teaching me how to dress/style myself to look more grown up and what types of clothing worked for me. As an adult I’m really thankful she did this. Both because I like fashion and it’s nice to know how to “wield” it, and because unfortunately society cares a lot about image so knowing how to project a certain image can be helpful :/ Anyway I think this type of shopping day of just trying on a bunch of things and learning what looks/feels good to her would be great for the LW’s mom, whether that is a personal shopper or something the LW feels comfortable doing.

    3. Absolutely yes to using department store professionals to help. They know what they have and spend a lot of time helping people figure out what will work best for them. I love it when I get that kind of help Inc a store.

      Also, when I’ve gone shopping with my fashion-helpless best friend who invariably picks out clothes that do nothing for her, I found that framing my comments around how the clothing brings out – or not – her best features was a very good way to talk about her choices. So, instead of “that dress is awful,” go with “I don’t think that dress has enough structure to show off your hourglass figure. Let’s try something with more structure.” Or “the color of this blouse doesn’t do anything to show off your lovely skin color, how about this one instead?”

      In other words, the issue isn’t her taste or her body or her looks, it’s the particular piece of clothing that that’s at fault (because it is!).

      1. Also remember: It is ALWAYS the clothes’ fault, never your body’s.

        The pants aren’t the right shape for you. The collar isn’t the right proportion.

        1. As someone who’s struggled with shopping, clothes, and my own body issues over the years, this is always a helpful reminder to myself — there are plenty of clothes out there that look great on me! And if something doesn’t, it’s not that my body is wrong, it’s that the clothes are.

      2. “So, instead of “that dress is awful,” go with “I don’t think that dress has enough structure to show off your hourglass figure. Let’s try something with more structure.” Or “the color of this blouse doesn’t do anything to show off your lovely skin color, how about this one instead?”

        YES. As someone who struggles with fashion so much that I dug into my savings to hire a personal shopper, I cannot state enough how important it is to suggest something rather than just saying something doesn’t look good. The reason why I struggle with fashion is because, at present at least, I have trouble visualising what will look good on my body so I have trouble choosing things out of the massive, MASSIVE number of different clothes out there. So if I approached someone in my life and said “I want to look good, can you help me?” as it sounds like LW’s mum is doing, their advice would really need to focus on what WILL look good, rather than just what’s wrong with what I’ve picked out.

      3. Thirding “it’s the clothes, not you”! When I go shopping with anyone and am asked for my opinion I stick to things like “I (don’t) think this is really your colour” or “This particular cut (doesn’t) work(s) very well for you” or “I think this would really suit you and bring out [whatever], want to try it on?” and it tends to be well received. The CLOTHES aren’t right for you, personally (whatever right means in this context) not the other way round. It takes the focus off your age/size/body type or whatever – this particular piece and you simply weren’t a good fit, that’s all. Moving on.

        1. I did a clothing swap party with a group of women who were all different sizes. Different heights, different body types, with about a 10-year age range, I’d guess. And all of a sudden, you could see what happens when the right person has the right piece of clothing. Because I had pieces that I loved, but never wore, and all of a sudden I saw someone with a completely different body type putting it on and I had my a-ha moment. Because something that kind of ok on me looked amazing on someone else. And pieces from other people’s wardrobes that they never got much use out of are some of my favourite pieces now.

          It is always the clothes, and never the body, that’s the wrong fit. I always felt like I needed to wear tailored button-downs to look professional and I never liked them, and I was never comfortable in them, and when I finally started really embracing blouses and tops without buttons, it made a world of difference. Comfort is important to me, because if something looks good but feels uncomfortable, it’s ultimately going to end up shoved to the back of the closet, never to be seen again. But I can still look nicely put together with a soft top and a flattering cardigan.

          The other thing I’ve found is that certain stores will tend to have a lot of pieces that will work well for a particular person – I basically buy 90% of my wardrobe from the same store, because the way the clothes fit me is usually exactly what I want. That being said, I still try on everything, because something that seems like it should be perfect, sometimes is…not. My Mom shops at the same store and she realized that there were all kinds of options she hadn’t considered before, because she’d never shopped at that store. But she started seeing clothes on my that she really liked, and decided to try some out. The other benefit of this is that if you DO pick out a few pieces that have the same colour running through them, usually it’ll match with other things. Which is great for capsule wardrobes (something I’d highly recommend for someone who’s shifting their wardrobe).

          1. I love doing clothing swaps! it’s such a nice way to build community, save money, and conserve the production of new clothing.

          2. I love doing clothing swaps! it’s such a nice way to build community, save money, and conserve the production of new clothing.

    4. A guy a know who is very short and slight went to one of those because it was too frustrating to find pants. He was surprised to find out it was totally free! And very time-efficient.

  3. I know for my own mother, the biggest lesson she learned when updating her style was how important it is to try everything on.

    Especially for women who aren’t happy with their bodies (read: women, amirite), this is a tough tough tough thing. It’s much easier to just throw something in your cart based on how it looks on a mannequin or the rack rather than take the time to examine it on your own personal body, in a store, from multiple angles. But it’s the only way to ensure that what you’re buying is not only a piece that flatters you (whatever that means to you personally) and is stylish (whatever that means to you personally), but that fits properly everywhere you need it to. Even in brands where you “know” your size, it’s not remotely unusual to have a fair amount of variation in what that sizing actually means from piece to piece. (Shit, I’ve even had two “identical” pairs of jeans—same brand, same style, same cut, same color, purchased at the same time—fit me slightly differently.)

    So that’s my biggest piece of advice: LW, if your mom isn’t already comfortable with the idea of trying on clothes before she buys them, help and encourage her to get there!

    1. I second your recommendation to try everything on, even if you tried on an item, liked it, and decide you’re getting it in 2 other colors. Something a lot of people aren’t aware of is that in mass produced clothing, pattern pieces are made by piling up large amounts of fabric (say, like 20 layers) and then stamped out by machine. Because fabric is flexible, the results in pieces at the top of the stack being slightly differently sized than the pieces at the bottom of the stack, even though when they’re passed off to the people actually sewing them, they’ll all ultimately get a size (x) tag sewn on them. Also, I’ve seen it noted elsewhere that for production speed reasons, if the person sewing the garment runs out of size (x) tags, rather than go hunt more down, they’ll just throw on a size (x +/-1) tag that’s close by. TRY EVERYTHING ON.

      1. And sometimes the labels are wrong! I tried on a pair of shoes at Goodwill that were marked a 7; I’m an 8 1/2 – 9 and they were too big for me.

        1. I had that happen once, with a gorgeous pair of cream satin high heels, although in my case the *too small size* fit perfectly. I later discovered that they were a brand that catered to male cross dressers and so used men’s sizes. They were the most comfortable pair of heels I’ve ever owned – extra wide toe box, extra padding in the forefoot – a perfect example of “if men had to wear this I’m sure they’d make it more comfortable”.

          1. What brand is this? I have very wide feet and would like to wear something dressy but comfortable. Thanks!

      2. I absolutely agree with everyone saying to try on each and every garment as size and fit can vary quite a bit even if it is the exact same brand, cut, style, fabric and bought at the same time. There is a brand of sneakers that I like that I have in a size 7, 7 1/2, 8 and 8 1/2….I wear a 7 1/2 normally. Same style, same material….4 different sizes.

      3. so much this! I made this mistake with jeans one time in grad school. First pair fit like magic, so I grabbed another pair in a different color. They were easily 1 1/2 sizes smaller and didn’t fit until I’d lost about 20 lbs.

    2. Try stuff on and have *someone else* take photos! This made a huge difference for my mum. She’s in her 60s so she’s had decades of finding fault in mirrors. Seeing how good something looks from other angles and that [disliked physical feature] is actually not an issue has helped her really expand her wardrobe. No one else but you sees the specific angle you see in the mirror. This is especially true if your eye sight has changed over time (her glasses have super high prescription and varifocals so she genuinely can’t see herself undistorted).

      Also going shopping in nice undergarments, shoes suitable to what you’re looking for and whatever level of makeup you’re fancying can make a huge different to how to perceive new outfits.

      Best of luck to your mom OP!

      1. I am so glad to hear I am not the only person who mistrusts mirrors. I feel like I look completely different on different mirrors.

      2. Great advice, re: undergarments especially. I have a habit of shopping in errands-clothes, which generally involves a sports bra…which doesn’t tell me much about how a particular top will fit over a standard bra, or how much strap will be showing.

        1. Let’s talk about bras for a sec. Bras can be the f’n worst (US sizing at least, not super familiar with outside countries). Even if you know your size, the cut/brand/style of bra can change. There are no Victoria’s Secret T-Shirt bras that fit my boobs. IDK why, but they just don’t. Other VS bras do. Mystery??

          If you’re wearing a bra, take a look at https://www.reddit.com/r/ABraThatFits/wiki/beginners_guide because I’ve been wearing the wrong measurements for forever (tbh I hadn’t *really* measured myself since I was reading the body book for girls when I was 14, and my body definitely changed since then). And if you’ve had any weight fluctuations over the years, check your bra size again. Remember, bras shouldn’t hurt, they shouldn’t dig into your shoulders or make you suffocate, but they should also support you and feel *generally* comfortable.

          1. I don’t need a bra for support, which on one hand means that finding bras that fit isn’t too hard, but on the other hand means the only reason I wear one at all is to cover my armor-piercing nipples at work. I can tolerate the flex-size ones that don’t have underwire, but honestly I wish the idea that we have to hide the fact that nipples exist would just die in a fire. I don’t wear them on the weekend or even when exercising (I bounce like crazy, but it’s not uncomfortable to me).

          2. A Bra That Fits is like, the best thing that’s ever happened to lingerie fitting. I went from wearing stretched out “boob hats” that were three band sizes too big and two cup sizes too small and therefore served no purpose other than to cover my breasts with an extra layer of fabric, to wearing bras that actually looked nice and were decently comfortable. (And then I got pregnant and am back in overly large stretchy nursing bras for a while, but that’s only because my size is changing so rapidly right now that it’s not worth investing in decent bras until it stabilizes.)

            Turns out basically no US companies make my size (nor do they make a lot of other sizes that are much more common than most people think) – but British and non-American companies do! Also, it turns out that breast shape makes just as much of a difference as size, sometimes more so, and most of the bras you see in US stores are only gonna be the right shape for a certain subset of people.

          3. Can’t nest anymore, but Kacienna, I FEEL YOU. I’ve made a rule for myself–“No bra unless I’m getting paid to be here.” So I wear one to my day job for nipple coverage, and I wear one on stage when I dance, and other than that….no.

            (I do wear a sports bra for rehearsal and fitness classes, but that’s more so I can take my shirt off when I overheat and still be decent)

          4. Lirael, thank you so much for your comment! I’ve been fitted wrongly – by MULTIPLE SHOP CHAINS, no less! – for the entire few years I’ve been bigger, and your “stretched out boob hat” description perfectly described what I’d been dealing with. After reading comments like yours, I looked into it, found a shop that specialises in fixing this problem, and today an extremely helpful saleswoman confirmed that the reason why my previous bras had been either saggy boob hats or crushing my boobs (depending on how much I tightened them) was because I’d been fitted two sizes too big in the band and three sizes too small in the cups. I now have bras that actually fit me, and not only do they feel better, they make me look better too!

      3. Easy shoes! I always seem to be trying stuff on when I’m in jeans, laced boots, and layers of jumpers. I’m far more likely to try things on when it’s *easy*.

    3. “Shit, I’ve even had two ‘identical’ pairs of jeans—same brand, same style, same cut, same color, purchased at the same time—fit me slightly differently.”

      Same here! Because they’re assembled by actual buman beings (who are too often exploited, unfortunately – we need systemic solutions to this problem, since, as CA notes, ethical consumption under capitalism is impossible), garments will have some varience in fit. For this reason alone, I am utterly baffled by the concept of ordering clothes online. Unless one is having every garment tailored – which is not the worst idea, but is expensive – trying things on is key in my experience.

    4. In-home services like Stitch Fix, MM LaFleur, and Amazon Wardrobe are VERY HELPFUL for trying things on at home instead of dealing with the hassle of a changing room.

      1. My experiences with Stitch Fix have not been great. I tried it three times and bought one item total. This was after giving them Pinterest boards and everything. Like ‘I showed you guys colors, why are you sending me boring stuff?” and ‘I specifically said I wanted shirts I could wear without a bra, why are these see-through?’ Also seemed to me pretty expensive for the quality, even considering that you’re paying for service (since the service doesn’t do much of what I want). But I am also that weird mix of not interested in shopping but very picky about what I wear in specific ways, so I’m probably pretty hard to please.

        1. I had a similar experience with Stitch Fix. Like, I have trouble finding tops that fit both my waist and chest. I particularly requested this- I am also picky, but if someone else could just find and send me shirts that fit for the rest of my life, I would be completely content. They sent me… peasant tops. When I particularly requested fitted tops that were not huge in the waist. And they were all super-expensive despite seeming like Target quality.

          1. I had the exact same experience with the Dia box. Every month I commented, “Not X because this, I want Y instead” and the next month they’d send me X again. So I gave up.

    5. I’m going to second your advice, and add another turn to it: Try on EVERYTHING, as in, try on clothes even if you’re sure they are going to look awful.
      Especially if you have no idea what looks good on you.

      I used to dress awful mainly because I bought into the whole “dressing well always means you want to please men”, but at some point I grew up and realized that actually I felt extremely awkward and out of place in my bad clothes, and that I could dress well just to please myself, because being well-dressed makes me feel comfortable and confident. So I did! But it was extremely awkward at first, because I had to visit stores feeling very self-conscious about my clothes among lots of people who dressed better and seemed to know exactly what they wanted. And I had no idea what would look good on me and felt like everybody was judging me for the things I chose to carry to the the dressing rooms. But with time, I became more confident, and adventurous, and tried on clothes that might just work, or that I thought were ridiculous and tried on just to be able to make fun of it. And plenty of times I was surprised – what seemed like a silly idea for a piece of clothing looked absolutely gorgeous on me. Other times, I was SURE the color, style and cut was bound to work for me, and it absolutely didn’t.

      Another thing I learned was to work WITH my body, not against it. Originally I rather admired that strict, clean-cut professional look, but had to realize that that didn’t work for me. No matter how much I try, there seems to be something chaotic, scatter-brained, frizzy and girlish about me that I can’t shake, which makes strict governess-style clothes look like I’m a little girl that’s dressing up. So I ended up choosing a style that looks a bit sweeter and compliments my frizzy hair rather than juxtapose it, and that worked well for me. Obviously that doesn’t mean that you have to completely go against your preferred style, but you should definitely keep in mind that “clothing X is supposed to make people look Y” does NOT mean “therefore, clothing X is guaranteed to make me look Y”. E.g. revealing clothes are supposed to make people look sexy, but since I’m all thin and bony and flat-chested with bad skin, I remain convinced that I look more sexy if I keep the majority of my skin covered (but wear figure-hugging clothing that shows off my thin waist and long legs).
      Show off what you’ve got, downplay what you haven’t got, and judge clothes by the effect they have on YOUR looks, is my motto.

      As a side note, updating a wardrobe is cheapest if you don’t concentrate on purchasing outfits, but several pieces of clothing that work well together in many combinations.

      1. “I’m going to second your advice, and add another turn to it: Try on EVERYTHING, as in, try on clothes even if you’re sure they are going to look awful. Especially if you have no idea what looks good on you.”
        ^^^ QFT

        I generally have a good idea of what works/doesn’t work for me for my everyday wardrobe. However, I recently went wedding dress shopping, which was a completely different exercise altogether. For me, this meant 2 different rounds of “trying on everything to see what works” because in truth I had no idea what I wanted or what looked good on me when it came to a wedding dress!

        The first round was trying just about every silhouette they had, because while I *thought* I knew what I wanted, I really had no idea how they would actually look on me. From there, once I had narrowed down the basic shape of the gown I was looking for, it became a matter of trying on various necklines, sleeve/strap options, fabrics, etc. This was where the bridal consultant was able to flex her expertise muscles, and help guide me by asking questions about why I either liked or didn’t like something. She was able to pull options for me based on how I felt in different gowns, and the one I eventually ended up selecting was something I would never have picked up off the rack on sight alone, nor was it anything like what I thought I wanted at the beginning of the process!

        I totally second the personal shopper advice as well, they are used to helping guide people to what they like and what they feel best in.

        1. Gah, hit send too soon. My final tidbit also comes from wedding dress shopping – if you have something on in the dressing room and absolutely hate it, take it right off and move on to the next!

        2. Thirded on “try everything on.” My first job after my divorce (and subsequently transforming my body by caring and listening to it) was at a consignment shop, and I learned this from some of the fiercest dressers in my very-fashionable suburb.

          Be aware, though: this may be “I want to connect with you and make you feel loved and important and valued for your strengths,” as much as it is “I want to look good.” I made the same mistake with my daughter, who feels I am an embarrassing dresser (I tend toward flowing hippie styles that feel good to wear for me and she prefers the office-manager look that feels good to her, and she worries that people judge you for wearing maxis over a certain age, or hanging out with a relative who does). Now we bond by sending each other pictures of the WORST clothes and pledging not to wear them. (I’m currently winning on points because I found the pair of swim trunks with the unlicensed image of Thor and Loki from the Marvel movies on the left leg and right butt cheek and pointing out that “Thor shorts” are more correctly called “Thorts.” Thank you for coming to my TEDx Talk.)

          1. @laundryghost: Maybe you don’t, though? I’ll see if I can find the pictures and put them up on an imaging service, but can’t promise anything. I can tell you one thing, your imagination is not doing them justice. Hemsworth and Hiddles are absolutely bringing the smolder. From an ass cheek.

      2. There are some styles that just look horrible on me no matter what. Polo shirts. twin sets, khakis, etc. Basically, anything preppy. I think it’s a combination of my broad shoulders/long torso/rectangular body type and my lack of WASPy genetics.

  4. I love this website: http://www.thesartorialist.com/ It’s a street style photography blogs that showcases classic fashion, style risks, and amazing looks. It helped me in learning how to put looks together to have a more comprehensive style. It also inspires me to try new looks. Hope it helps!

  5. I have a suggestion (feel free to disregard it!). I am a member of Get Your Pretty On’s style challenges. For an annual fee, you get a list of clothing to buy each season (general things, like a striped t-shirt) and at least 21 outfits that can be made with those clothes. The *best* part of the whole thing is the private Facebook group. It’s a ton of women of all ages, sizes, shapes, and races (largely white, though) who post selfies of their outfits and, when shopping, ask for feedback. The site is heavily moderated and everyone is super helpful and nice. I was feeling really unhappy with my wardrobe after a job change a few years ago and signed up and have been an annual member ever since. It’s also nice because you can choose what to buy or what not to buy to stay within your own budget parameters. (Link: https://getyourprettyon.com/style-challenges/) Good luck to you and to your mom!!

  6. I am so glad you linked to Advanced Style! That was going to be my pick to link.

    First and foremost, I would definitely not give criticism like, “Mom, you’re too old for that!” first because 65 is not old! It’s not even the US Social Security retirement age now. And even if it was “old,” there is no expiration date on styles and fashions. SO, be super careful of being ageist, is my caution.

    I’d also check out @grombre on Instagram depending on your mom’s style hair-wise–it’s an account that posts pictures of women (of all ages!) with gray/white hair styled a million different ways.

    As for what I do since I am somewhat style-challenged: I love Stitch Fix, which is more size-inclusive and style-inclusive these days–it has a range of styles for many tastes, from the uber-trendy to the more conservative. It may not be for your mom, but it has been extremely helpful in a “look” transformation and for getting me to try things I wouldn’t otherwise think to even try on. I also like Gwynnie Bee a lot–and a model like this might be better for getting your mom to try newer looks with no commitment. Both of these are linked in the subscription box roundup CA posted.

    1. I second the Stitchfix/fashion box rec! I have always hated shopping and been terrified of fashion, but over the last few years Stitchfix has helped me figure out what I like and helped me evolve from “idk, I probably shouldn’t wear a hoodie to the office??” to “business casual + bright colors is totally me!!” And they’ve sent me a lot of things to try that I would never have picked out for myself, but have ended up really liking. So that kind of a service could be great if style is something she’s interested in but not comfortable with.

      1. This may not be a desirable suggestion for everyone, but I joined a gym that offered a 3-D body scan for free. I was like, sure, why not? (Trying to start a new habit, etc…) Recently, the imaging company sent me an email saying they’d partnered with StitchFix to augment their clothing selection process. So, that could be an option? I feel like some people (maybe especially post-career women) get trained not to be ‘seen’ and so they don’t really know what they look like. FWIW, I have not tried this service myself, but I thought it sounded interesting. However, suggesting ‘Mom, maybe you should go to the gym’ is definitely not something I am endorsing or that should intrude on (hopefully) a fun fashion brush-up.

    2. Chiming in with another vote for Stitch Fix! My mom’s wardrobe improved considerably when she started using their service! I honestly want to borrow at least half her clothing these days. Their stylists had some really great suggestions for colors and cuts that pushed her out of her comfort zone slightly but still made her feel (and look!) really good. She’s used some of their suggestions as a jumping-off point to find new brands, colors, and styles that she can purchase on her own.

  7. Hi, I am a person who literally never wears makeup (okay, once in the last ten years – on my wedding day) and whose style when it comes to clothing is sometimes awful. I’ve been upgrading my wardrobe slowly over the past few years, as I slowly tackle some barriers that kept me wearing “not stylish” things. Those barriers included:

    –Body shame (thanks, mom + patriarchy!)
    –Many previous terrible experiences going shopping for clothes with people whose bodies look very different than mine
    –Lack of knowledge/understanding about what types of clothes would look and fit the way I wanted them to
    –Genuinely not caring about hair and makeup

    Some of these barriers I’ve worked through, some I haven’t and I’m okay with it. I refuse to give into the idea that I need to wear makeup to look professional, so that’s still a no-go. I’ve done a lot of working on body shame and understanding that I don’t have to wear certain types of clothes if I don’t like the way they look and feel. And thanks to one very long and frustrating shopping trip with a very patient friend, I learned about how to choose clothes that fit the body I have, not the body I think I should have.

    All of this to say – your mom may have a ton of reasons, histories, and hang-ups related to what she wears and how she styles herself. Proceed gently, with caution and love. I am so grateful to my friend for that shopping trip, but I needed to be ready to ask for her help myself. Maybe test the waters with some of the captain’s advice but be ready to back away if you get the message that your mom is happy the way things are or that she isn’t ready to do something different.

    1. I second the make-up thing. I’m 29 and can count on one hand the amount of times I’ve worn make-up in my life. It’s not personally important to me for a lot of reasons, but Society sure has a lot to say about women who don’t wear it.

      1. I am 67, and I still have the lipstick I bought in high school. The only lipstick I ever bought.

      2. I’ve found that society has a lot to say about women that always wear makeup coming in to work one day without it. I also super rarely wear makeup and I’ve never ever gotten a “you look tired” in my 35 years on the planet.

        However, I wore makeup one day and everyone noticed “hey, you’re wearing makeup! Do you have an interview somewhere?” (no, I found myself at a beauty counter with a friend I was meeting for lunch at the mall and figured why not when they offered a free demo)

    2. OMG another one!!! Yay!!! I also don’t wear makeup outside of weddings and christenings etc. I just can’t make myself care enough to spemd the money or the time 😂

    3. Add me to the no-makeup chorus. I mean, I’ll drag it out if I’m going somewhere with someone who cares whether or not I’m wearing any, hi mom, but otherwise I have a lot of other things that make me happier. (Also, I’m so unfamiliar with makeup these days that when I do put it on I feel super-performative and uncomfortable.)

      I recently started a pinterest board for myself exploring things that catch my eye when I’m browsing the web, and I’ve finally gotten enough in there to start figuring out what appeals to me. This may or may not work for LW’s mom.

    4. No makeup (not even for my wedding) and I failed at StitchFix (how hard is it for them to send something that fits my shoulders and is warm enough for the US Midwest?). Oh, and I have several bucket hats since they are the best for keeping the sun off my ears, neck, and face.

      My personal style may suck, but it’s mine and I’m keeping it.

        1. Bucket hats are wonderful. And cute! Seriously, if the mom wants to keep wearing them, then she’s the one who gets to decide when to wear them, whether her daughter likes them or not. 🙂

        2. Yeah, I don’t get the hate on bucket hats! Maybe they’re more common in Australia because they’re required for school kids, but who doesn’t have a bucket hat??? They’re great.

        3. Yeah, I don’t get the hate on bucket hats! Maybe they’re more common in Australia because they’re required for school kids, but who doesn’t have a bucket hat??? They’re great.

          1. Same here. I recently bought one in camo print from a surf shop and it’s totally cool plus mega cute. I haven’t worn it yet but it will be my forever hat for outdoor activities. these comments have me wondering if a bucket hat in America is different to what they are here in Australia as I just can’t see what the problem is with them.

    5. “… that I don’t have to wear certain types of clothes if I don’t like the way they look and feel.”

      FEEL. It’s so undervalued as a priority when buying clothes, but IME there’s no point getting something that other people say looks nice if it feels scratchy/sweaty/plasticky/etc. My mother and I look very strange when we go shopping because pretty much all we do is pat any and all garments that look like they might be soft or in a natural fibre.

      1. It took me until my mid-forties to realise that the main reason why I hate almost all women’s clothing isn’t just complicated feelings about gender and performing for the patriarchy, but feel. I don’t like the materials, I don’t like the seams, I don’t like the fit, and where other people may see a rack of fun colours/patterns/cuts, I feel a rack of getitoffmegetitoffme.

        And that won’t change. I’d actually quite like to get style advice – what are some other cool things that I could try that would build on the things I like the look and feel of? – but I don’t think I’ll find that in a mainstream department store.

        1. I’m not entirely sure when I turned into a fiber snob, but I second you 100% about the feel of fabric (polyester crepe is of the devil). Which is most of the reason why I’m going to try sewing my own stuff. Which will probably make me less-than-stylish in an entirely different way, seeing as I’ve only got pretty basic skills yet.

          1. OH MY GOD. I’m also sensitive to smells (seriously, depending on other health stuff I have werewolf nose) and polyester crepe SMELLS BAD after like 2 washes. Not on other people! But I can smell it on myself, it never smells clean again, and it makes me absolutely crazy to go around itching, staticky, and smelling unwashed-plastic smells all day.

            I have one thrift shop (1) that gets good-quality returned merchandise including a regular donation from someone my size who can’t make up her mind about Eileen Fisher. It requires getting there on a weekday, though, so I’m about to try just sewing it myself too.

          2. some commiseration –I, my mom, my brother, and a host of cousins/aunts/uncles on the maternal side have various sensory integration disorders that definitely influence buying stuff. I’m sensitive to certain textures and smells; my mom can’t stand being in a mall for any length of time because the noise, people and general set up will literally make her sick and she’ll have to spend the rest of the day recovering in bed. Any sort of tulle is right out for me. My mom learned that the hard way after I refused to wear more than once this (absolutely gorgeous) Christmas dress she made for me that, even though there was a layer of cotton between my legs and the tulle, scratched the heck out of me.

          3. @TootsNYC I picked up a sewing machine and have been teaching myself to sew, but the problem I run into is that things like Kwik Sew don’t tend to have things in my size (I’ve found quite a few online places that *do*, mind)

            Buttons are the devil. Coarse fabrics are the devil. There’s some kind of thread that’s the devil. And when I’m having a particularly bad day, pretty much anything other than velvet or jersey are the devil.

        2. Target has a (limited) range of “sensory sensitive” clothes that I love. They don’t have tags, the seems are sewn flat, and they’re cut loosely from soft material. I have a bunch of t-shirts that are the best, but I think they also have leggings. It’s a great example of how designing for disabilities helps us all, as I think they’re made for autistic people/people with sensory processing differences. They seem to be sold out frequently, so hopefully that means there’s lots of demand.

          1. Nice!

            Where I live there are a few stores that use bamboo fabric, and it is amazing. I also got bamboo sheets (both locally and off Amazon).
            That reminds me, my favourite bamboo shirt has worn out :/ I need to check whether they’re still being sold… Well crud, their site doesn’t have bamboo anything any more :/

          2. Oh the fabric wars… A couple of years ago Target had tshirts in 100% linen. Knit linen…nothing has ever been so comfortable against my skin, nothing wicks moisture like linen, and with knit there’s no issue of wrinkles. I bought 3 and wish I’d bought a dozen because I’ve never seen them again.
            And I have gotten frustrated with Amazon searches because they let vendors tag something linen when it’s not. Grrr.

          3. Thank you for mentioning this! I bet they would help me on the days when my fibromyalgia is flaring up.

          4. WOW. I am going to check this out, and I am going to post about it in the group I belong to for people on the autism spectrum. Thistledown, this is life changing! Thank you so much!

        3. @Friendly Hipposcriff, I have chronic muscle pain PLUS sensitive and fragile skin, and I relate to your comment SO HARD.

          One thing that has worked for me is stretchy bamboo knits: softer and smoother than cotton knits, and nothing tight to dig into my lower back or neck/shoulders.

          This link goes to one of my favourite examples, a stretchy bamboo dress.


      2. THIS.

        A good portion of the reason I’m generally pretty unfashionable is that I’m very particular about how things feel–certain textures and seam placements, tight waistbands and restrictive cuts are all no-goes for me, which limits my options especially wrt to ‘women’s’ clothes. But there’s nothing more annoying than spending money on an article of clothing that looks lovely but makes me want to rip my skin off if I wear it for more than a few minutes. How things FEEL is important.

      3. Yes this. My clothing choices are pretty narrow because I’m plus sized and HATE wearing synthetic fibers. Shit doesn’t breathe, give me cotton or wool every day of the week.

        1. 100%. Plus size clothing in natural fibre is like a magical unicorn that you can only find at the end of a rainbow on a blue moon. To the point where my best friend and I frequently think about starting our own plus size brand where everything is bamboo or linen or silk and the patterns are cut for real bodies. But then we remember we have no time. 😦

          1. If you start that company, I will 100% buy from you. It is so damn hard to find clothes made with nice fibres. And what _really_ winds me up is when they have a beautiful fabric (eg silk) lined with sweaty, gross, poly-fucking-ester! Why?! Why?! Why?!!!

            (I 100% support everyone’s right to enjoy polyester if they enjoy it, but as soon as I put it on I break into a sweat like I just ran the ironman)

          2. @tinylittlesoprano

            If you start a plus-sized clothing company that sells soft stretchy bamboo clothes, I will 100% buy from you!

        2. Me too! Me too! I learned to sew and knit just so I can wear natural fibers. Funny story: I was walking through a cafe and saw a woman (also plus sized) wearing an awesome linen top that was similar to the one I was wearing. I complimented her, she complimented me, we talked about the trouble of finding natural fibers, it was a nice moment. Then she pointed at my top and said “Flax?”

          And I was like “Uh, linen, which is made out of flax.”

          Her: “No, did you buy that at Flax?”

          Me: “No.”

          Her: “Are you sure? I swear I saw it there last week.”

          Me: “I’m sure. I made this.”

          Her eyes lit up, and she practically lunged at me, hungrily. “YOU MAKE CLOTHES? CAN I HIRE YOU?”

          Me: “I make this top and a wrap skirt so far, that’s about it.”

          Her: “Can you do sleeves?”

          Me: “Not yet, I’m sorry.”

          I’ve rarely seen anyone’s face that sad.

      4. God, yes, why are “professional” tops all thin uncomfortable stuff? I just want to live in cotton!

      5. Oh! Me too! A few years ago I had a virus that left me with severe reactions to many fabrics. For a long time after, I bought every shirt/blouse that I could stand to wear – that didn’t make me want to tear off my skin within 15 minutes and didn’t leave me with huge itchy welts. (And, yes, I went to every doctor I thought might be able to help.) Life is a bit better, but I’m not going to be fashionable because I have a very, very small selection of clothes I can stand to wear and fewer that I actually like. Petting fabrics is necessary to possibly find things I can wear.

      6. Do you know what the line is called? I’m getting a couple of Google results, but they contradict in some cases. Cat and Jack is for children, Universal Thread has mostly denim (ugh for my sensory issues), a New Day leggings are mentioned as sensory-friendly, but not the collection…

    6. Add me to the no make up train!

      My policy is “if it’s so important to you that I wear makeup to your event, you find a professional to put it on me.”
      This was taken up exactly once, when I was in someone’s wedding. (I paid for it, but they did the coordinating)

      If makeup is really *required* – which it is for stages and cameras – then it’s generally done by pros after all.

      The expense of acquiring a whole set of makeups and accessories therefor, and the time and effort of acquiring the skills involved in putting those on, is not something I am interested in doing in the first place, and social pressure to put all that work into it just makes me go RAWR NO :((

    7. I was inspired by a friend whose workplace has the kind of dress code that expects women to be “feminine”. She wears heels to work, and said, “It’s the price I pay for not wearing makeup.”

      So now I trade off, or mix and match–if I want to look more professional, I’ll upgrade my jewellery or do something different with my hair, instead of thinking I have to do ALL the femininity.

      1. Where I work is very much one of those “the dress code is unofficial but real and varies according to your spot on the corporate ladder” places. I do the opposite of “high heels so I don’t have to wear makeup” – I have foot/leg problems and a sometimes-noticeable limp, so high heels are not a thing I can do. Ever.

        On the other hand, with my particular body type (tall, plus-size, VERY pear-shaped), I find skirts and dresses easier to cope with than pants on an everyday basis, and “just throw on a dress” in the morning helps with the ADHD-related executive functioning issues. Most of my work wardrobe is dress + (optional cardigan and/or tights depending on weather) + cute quirky flat shoes. And I usually wear at least lipstick, since I’ve discovered a few long-wear lipsticks that actually stay on for me.

        It’s definitely true that you don’t have to do ALL the femininity or NONE of it, and keeping that in mind helps me a lot.

      2. ‘kind of dress code that expects women to be “feminine”’

        Hulk Smash! I have so many feelings about expectations of gender presentation! I’m a strongly cisgendered woman who wears skirts and dresses about half the time, but my gender presentation is nobody’s business! (Also on the no-makeup train, was on the no-heels train but discovered I can wear wedges comfortably, hair is long and straight and is either in a braid, in a ponytail, or down, the end.)

        1. Before my joints did a thing requiring me to wear flats forever, my one and only pair of heels (after trying a lot of different styles) was foam wedges from Zappo’s, with ankle straps and peeptoes. Astonishingly comfortable.

          1. I have a pair of heels from Ecco that I can *run* in! 🙂 Before that, I just did not wear heels. Finding shoes my feet will accept was quite enough of a nightmare already. (I was, like, over 20 before I managed to exit a shoe shop without crying)

    8. Another no-makeupper here. Dealing with that is very definitively A Skill – more power to those that have it, but it’s one which I don’t have the inclination to make space in my life to learn about.

      1. “Dealing with that is very definitively A Skill”

        I feel this so hard. One of my clients is a cosmetics company, and every time they describe a problem that their specific product is going to solve, I think “So all this time, people who wear makeup have had to deal with THAT TOO?!?!” Nothing against other people wearing it, but my frequent-flyer card on the Nope Rocket has reached platinum status.

        1. Hmmm, sometimes the “problem” to be solved is part of what the current makeup trend is, rather than a problem per se.
          e.g. brow products are different now that big brows are trending*, so you can get various products to fill in your eyebrows or make them look more bold. However, you can still wear makeup – even a lot of makeup or a very bold look – and still do nothing to your eyebrows at all, if you’re not going for that particular makeup look.

          There’s a saying in photography, Gear Acquisition Syndrome, where you buy a lot of stuff because it is fun to buy stuff, and makeup can sometimes head that way with really specific things that you would only get if you were very into makeup. From the outside it might look like you need to do a lot, but from the inside I can tell you that you don’t actually need a lot of the product categories, or one person might find it helpful but another person won’t because of different skin types or face shape or makeup style.
          Like. I have four face primers. My sister has zero. We both do nice makeup looks.

          The other thing is that of course your client is describing problems – they’re trying to sell something, and that’s one sales technique.

          * although there’s debate about thin brows having a comeback so basically you have a wide range of brow options to be in fashion with right now if that is a look you are going for. I am watching this with fascination.

          1. I don’t get this sort of thing and it always annoys me. How can eyebrows be in or out? You have the eyebrows you have. (I may have extra strong opinions from having plucking pushed on me when I was younger). And don’t even get me started on hips…

          2. @Kacienna some people enjoy knowing what the fashion is and showing skill in executing it (ala a peacock).

            Some people (like me) just enjoy grooming eyebrows to be a tidier version of themselves.

            And then to round it all off, the Frieda Kahlo option where you rock your eyebrows as they do their own thing.

            In an ideal world all these choices would be neutral, but we don’t so they aren’t. But I think there is more space now for more variation to exist. I do also think it’s a bit different to body shape as it’s so much easier/quicker to change them.

            You can use makeup to change your eyebrows. If you want, you can use coloured brow products to make your eyebrows be thicker, to be darker, to fill in any gaps, and/or to temporarily change the shape (longer or flatter, for example). And of course plucking/waxing/threading to thin them.

          3. Lol, I am definitely the Frieda Kahlo type! Of course I’m fine with people doing what they want to their own eyebrows, but I want that neutrality now now now! So I love seeing all the different ways people express themselves but I tend to push back hard on the idea of “in fashion” meaning anything other than “momentarily popular”. I will move this brick wall, dammit!

  8. The podcast “By the Book” had an episode last season about using a book called “The Curated Closet” to discover the one’s personal style. The process involves inspo pics and closet re-evaluation, and IIR is body-type agnostic. The episode and/or book could be helpful to your mom.

    On shopping trips with my own mom, I’ve had success with handing her a garment and encouraging “just try it on and if you don’t like it then throw it on the floor!” Finding awesome clothes involves a lot of trying things on.

    Something else to consider is strategic complementing. So, not only “that X looks great on you!” but “that X looks great on you because of how it shows off your legs / hits right at your waistline / the color complements your eyes,” etc. This is compatible with “the body you have is awesome” and also can give your mom ideas about what other garments/fits to look for.

    1. I have that book! I think it’s size-neutral too, but I’m not 100% positive. I don’t remember anything hugely “off,” anyway, and I thought it was super helpful. The only thing is that a lot of the “case studies” are younger women, so that could potentially be off-putting.

    2. Giving specific examples is a great idea, especially for someone who hasn’t ever given style much thought. It was eye-opening to me to be taught how to look at fashion, such as red is my color, be careful of blouses that cut me off at the hips, etc.
      As an older woman I do value comfort over style, and honestly it really is freeing not to care. I have totally embraced the whole pajamas in public thing, even though I know that really no over 6 yrs old should be doing that, but it feels great, I can, and so I do. But I understand you’re mom is asking advice and wanting to put her best foot forward for dating, so it’s great that she has a thoughtful and considerate daughter to help her!

      1. Hey, lots of famous people (who get photographed in public wearing stuff) wear pyjamas in public, and there are a lot of pyjama-style fashions out there night now (Shein.com and RomWe.com have several wrap/kimono sleeve tops + pyjama/palazzo pants sets for sale right now), so ONE, I vote that you wear what you want to wear, and TWO, if anyone looks at you cross-eyed, they are wrong, because you are in style, and even if you weren’t, THREE, it is your life and your body and you can wear what you want when you want.

        My rule of thumb for clothes that might look like other clothes (like slip dresses that look like slips or nightgowns) is to pay attention to my underwear sitch, so my privates stay that way, and wear something distinctly NOT bedtime-ish with the bedtime-ish thing, like NO to scuffs or mules or those shoes that were fashionable recently with the maribou poufs on top like bedroom slippers but YES to boots to heels or sneaks with a PJ-esque thing.

        But everyone should do what they feel most comfortable in, and I may be introverted, but I have no qualms about being on the edge of being a bit costume-y in my fashion choices, and I cannot resist an inexpensive (or at least affordable) thing that calls out to me to wear it. If I wouldn’t shame my ancestors if I were to die unexpectedly in public and everyone then found me wearing [thing], then I wear [thing]. Sort of the “wear clean underwear in case of car accident” rule (or the “be as naked as you like in your house, but know where your robes and shoes are at all times in case of fire” rule) taken to an absurd extreme, but it works for me, as does the “spin around in front of a full-length mirror and whatever catches your eye, take it off or tone it down” accessory rule, as I am a magpie and one thing can usually stay home so I’m not being EXTRA-extra.

    3. I came here to write that exact first paragraph! I haven’t read the Curated Closet yet, but what I loved about the epissue, and the responses to it in the podcast’s facebook group, was the focus on defining your identity, and how many people found that really exciting and liberating AND just as practical as any made-up rules on “how to dress for your shape/age/whatever” in actually finding new clothes or wearing ones you already have and loving them.

    4. Yes! Positive reinforcement! When you see your mom wearing something you think looks good on her, let her know! And why! Even if you don’t love everything about it compliment the thing you do like! “Wow mom, I love that color on you! We should try to find a dress for you in that color for cousin’s wedding this summer!” or “Mom, that top fits you so well! Where did you get it? You should get a couple in different colors, a blue one would really bring out your eyes!”

      When you go shopping with her focus on why things that look good on her look good. “The cut of that shirt is really flattering!” or “We should find you more things in that color!” . Give her ideas that will make her think about the overall effect.

    5. I want to second this recommendation. I read “The Curated Closet” on the recommendation of By the Book and it was actually super helpful to thinking about my personal style. It is a BOOK so it might be more info/structure than strictly needed, but I feel like the way the author things about clothes and accumulating a wardrobe is a really nice, actionable, conscious way of thinking positively about how we look and how we want to look and ensuring we have a framework for not bringing stuff into our life and closet that doesn’t suit us.

      Having just read the book I can confirm it is size neutral in its copy, and tells you to toss out conceptions of what is “right” or “flattering” for your body. It is not size neutral in its images, which are exclusively of young, thin conventionally attractive women. I was able to ignore that and benefit from it but do what works best for you!

  9. I have some experience with this because two different friends have asked me to go shopping with them for a more “stylish” wardrobe. The thing I always ask is what do *they* want to achieve, and then I ask them to start sending me pictures of stuff they like or women who inspire them, and I try to put it together into a kind of “look summary” – so my “look” is Grace Kelly meets Mad Dog Murdoch (from the A Team). Another friend is “1950s Sophia Loren starring in the movie Working Girl”.

    Unless you have lots of money, it’s really hard to start over with a wardrobe, so using this kind of summary can help find the things your mum likes/loves in her current wardrobe, then figure out what items would help her evolve that to the look or feel she’s going for.

    But the key is that it starts with how she wants to look and feel.

    1. I would devoutly like to see what “Grace Kelly + Murdoch from the A-team” looks like, either in inspiration sources, or outcomes. You seem to be great at doing -very- creative synthesis! Nice friending!

  10. My personal style can best be described as “whatever.” Someone once asked me in college if I had a hot date because I wore a shirt that was not a t-shirt. I am the opposite of someone with “style” but as my career has developed I’ve found it more important to learn how to present myself in an appealing way. Here are the types of comments and strategies that have helped me:

    1. Look at a lot of examples. Pinterest was BUILT for this. If tech isn’t your mom’s thing, you could go get the catalogs of a few businesses that are age and body type appropriate. I’ve had the most luck aligning my personal style with a business’ brand and then buying stuff from that business. That’s kind of the capitalist/consumerist way which isn’t gonna float everyone’s boat, so…

    2. Go to thrift stores! Stuff is cheap, so you can try a LOT out, and if you don’t like it you can donate it back. If your mom wants to be trendy, there are plenty of stores that specialize in updated upscale attire.

    3. Think the negative word you’re thinking in your head, and then think of a positive way to say that. For example, say classic instead of outdated. Bucket hats are a classic, but what’s trendy right now is X.

    Fashion is a great way for folks to reinvent themselves after a long relationship ends. Look at this as guiding your mom in inventing her NEW style, instead of critiquing her old style.

    1. I also love thrift stores because they tend to have more of range of colors and styles than whatever’s “in” right now.

  11. If she’s seriously asking around for advice, I suspect your mom is vaguely feeling like her current style isn’t working for her but isn’t sure what else to do. There are ways to give guidance in that kind of situation without saying “Wow your current style sucks”!

    For example, sit down with her and look at pictures of other people. Look at pictures of movie characters she might relate to, celebrities she admires, her friends, random stock photos of women around her age range, etc. Point out which ones you think look really put-together. Try to use words other than just ‘pretty’ or ‘stylish’–talk about how professional an outfit looks, or how fun it is, or elegant, or sexy, or cute, or practical. The idea is to show her how you think about clothes when you see them–by walking her through your thought process, you’re giving her a model for how to approach developing a sense of personal style. Hopefully at some point, she’ll start joining in, pointing out outfits she likes and saying what she likes about them.

    Once she does, you can turn that into a conversation. Maybe you notice that she’s pointing out a lot of knit sweaters–that can turn into “You like a more cozy style, don’t you?” Once you identify a couple traits that she likes in clothes, that puts her well on her way to finding her personal style…which may or may not be ‘fashionable’ per se, but will hopefully be comfortable and affirming for her, which is more important anyways.

    1. If she’s asking for your opinion on a specific piece, how you respond depends on the situation. If…

      …it doesn’t fit her right: Tell her it doesn’t fit. If it’s close, you can say “I think that needs some tailoring first.” If it’s a fair ways off, maybe it’s time to retire it from her closet.

      …it fits fine, but isn’t appropriate for the occasion: Point out that it’s (a little casual for the restaurant/too light a sweater for an autumn hike/whatever). If you know of something she has that would be better, maybe suggest it.

      …you think the pieces don’t suit each other: “I don’t know if I’d wear that shirt with them, but those pants fit you so well! You look amazing in them.”

      …you hate bucket hats: “Haha mom, you know I have this weird thing with bucket hats! All I can see is the hat–you should ask someone else.”

      1. Above all, do not do as I accidentally did because I was having a broken filter moment and tell her she “looks like a lemon in that dress.” (I immediately apologized and found the same dress in pink because it did flatter the woman in question cut-wise but the bright yellow color was a no.)

          1. I wish that either that was what I had been thinking or that I had been quick enough to cover with something like that. As it was, I’m pretty sure I’d blushed scarlet over saying it.

    2. Me and my sister and my mom have a code/saying for these kinds of things – “You could do better”. It’s the “It’s not you it’s me” of our clothes shopping. For us, it’s non judgemental about the body under the clothes but expresses our opinion that it’s not flattering in whatever way we’re looking for.

    3. Yes, this. If you really genuinely believe that she a) wants to change her clothes and b) wants you to be involved in the process, this is the way to do it. Basically ask questions and LISTEN.

  12. Based on shopping with my mom, I would also find out what is the most important to her – stylishness, texture, provenance (fair trade/made in US etc), comfort, price, low-upkeep etc. My mom is willing to pay more than I would, but she will never wear anything tight, and things must be easy to match to each other, which means that she goes for fun textures more than big patterns. Knowing that helps direct our shopping and makes sure I’m actually being helpful and not just imposing my own style on her. I see my role as broadening the range of things she tries on, not in choosing her clothes for her.

  13. She wears horrible things because she doesn’t know how to pick out flattering things, and it’s just easier to wear what she already has 🙂 It sounds like you two have a pretty good relationship, and enjoy spending time together, so: Tell her you want to take her out and try clothes on her, so she’ll have something cute AND comfortable to wear when she goes out. Pick out a couple of stores ahead of time, and go by yourself first, scout around for items you think she’ll look nice in, and get a few ideas before you take her. Don’t make her spend hours and hours on the first trip out – just maybe two stores, hour at each. If you’ve already done a scouting trip, it will make it easier. Have a goal of maybe 2 purchases on the first trip, and make sure those purchases are things she likes, and is comfortable in. You sound like a nice daughter. Reward yourselves with lunch afterwards. Make it fun!

    1. It’s also possible that she wears those “horrible” things because she truly likes them. I didn’t get the sense that the mother was absolutely unhappy with her entire wardrobe, only that she was curious and that the daughter didn’t like her clothing.

    2. Yeah, be careful about assuming that she agrees that ‘she wears horrible things’. Different people like _very_ different things.

      1. I don’t think LW needs to worry so much about upsetting her mom. Mom is already asking LW’s advice.

  14. About 3-4 years ago, I decided to fully commit to my year round pumpkin-colour palate, and that’s been *so* useful for helping me to put together cute outfits that I feel great in. Because the majority of my clothes now are in oranges/greens/browns, it’s super easy to mix and match, and it also helps a lot with my impulse-buying at the thrift store (cuts down on the “it’s cute, but doesn’t go with the rest of my wardrobe and isn’t so cute as to make an exception).

    Seconding the comment to Try! Everything! On! There’s a great essay I read once talking about how all clothing you see in magazines and on TV or in movies has been tailored to the person wearing it –even jeans and a t-shirt! The stuff off the rack isn’t really designed to fit *anyone* so trying it on is the only way to tell what’s good-close and what’s eeeh-close.

    (I hear if you have the funds for a tailor or ability to do a bit of re-fitting yourself, that works wonders, but I am woefully inadequate with a needle and thread)

    Also, I am a huge proponent of SELFIES 4-EVER. Make #OotD* posts, or even just make a commitment to take a picture every time you feel cute. It’s not necessarily a style fix, but I find it helps with the self-love, and can even give you a better sense of how things look when actually worn.


    1. Yes! Finding and sticking with your favorite colorway is a great way to make shopping easier. I only wear black, white, red and gray. That’s it. Those colors look best on me and everything matches, and when I shop I only have to bother looking at clothes in those colors.

      1. When “know your season” was hot, I found that this framing really helped a lot of people in my mom’s cohort, and they still talk of being Autumns (e.g., sorcyress is likely an Autumn), Springs, Summers, and Winters (e.g., Commander Banana and I are likely both Winters). It really cuts down on the overwhelmingness of the options available if you know “your” colors in advance.

        FWIW, I should technically be a Spring, since few pasty white blondes who don’t have naturally platinum hair are Winters, and yet I generally look like poo in peaches and pale pinks and minty greens, which is partially because those colors tend to be popular in styles that look bad on my body type, and black, red, cobalt, fuschia, jewel tones and so on are definitely my colors, so don’t think you’re NOT a “season” until you try some of the colors on first. Also know the season that works least well for you. Autumn is the least flattering: khakis, olives, russets, pumpkins, true golds, creams–these look Not Good on me, but DYNAMITE on some of my friends (and probably sorcyress!)–because that, too, can eliminate some confusing options right off the bat.

        Dunno about you, but I find having five “probably-will-be-good” choices is a lot easier than having 5,000 “who-knows-if-good?” choices.

        1. _Color Your Style_ by David Zyla helped me a great deal for color. It advises you to take your colors from your body. Unfortunately, it’s obviously not written for POC’s, and it may have been a broken-clock moment, where the advice worked randomly in my particular case, but in my case, it was so helpful. (My skin is emphatically warm and cool on different places on my body— silver makes my feet and face look corpselike but the gold that suits them so beautifully make my hands look like I’ve been recovered from a bog, and dressing to “neutral” was NOT working….) The basics are here: http://www.davidzyla.com/the-color-of-style/

        2. Yup! Winter here (brown eyes, pale skin, black hair) and my mom is a Spring. She wears a lot of shell pink, mauve, soft grey, and cream, and I wear black, white, and red. I don’t own a single piece of clothing in green, yellow, or orange and no pastels.

      2. Learning a little bit about the seasonal color theory stuff and about undertones ‘n’ things is a bit advanced (especially if you’re me and you’ve been so Goth for so long that you can’t separate “silver looks better with my skin than gold because I have a cool undertone” and “gold near my skin looks weird because I haven’t seen that happen in 20 years”), but it’s really helped me branch out from “all black all the time” into finding a handful of colors that a) look good on me and b) still all match each other because they’re all in the same color family.

    2. I would like to second the suggestion to pick a colourway and stick to it! What I’ve done is, I’ve decided “my” neutral is black/grey – which combine in almost any combination of shades (as long as the blacks aren’t different degrees of faded), and I don’t buy pieces where the dominant colour is navy or brown/beige, because those generally won’t pair well with the black/grey I already have. With all that monochromaticism, beautiful and different textures are fun to combine in interesting ways, shiny with matte, smooth with fuzzy, and so on. And then to go with the blacks and greys, I have other pieces in all sorts of colours I love and find flattering, which for me means the entire cool half of the colour wheel, but especially purple, burgundy, and teal.

      One thing I watch out for with planning a wardrobe is prints – my eye loves wild multicolour prints on the rack/on the bolt, but to make an outfit, unless you’re a lot braver than I am, you do need some solids in your wardrobe too.

      Also: to get maximum bang for your buck, consider trying to create a capsule wardrobe – a limited number of items that can be combined in lots and lots of ways – out of favourite existing items plus a few new things to spiff it up. One way of organizing your thinking about it is called “wardrobe sudoku” – both “capsule wardrobe” and “wardrobe sudoku” are search terms that will yield you lots of food for thought.

      1. I also do a lot of pattern mixing in the same colors – like a polka-dot top and striped skirt but both in black and white.

        1. That’s a very Japanese haute couture thing, I think! Tonal dressing, where you mix patterns but stick in the same color family. Hard to pull off, but super cute when done right!

      2. I have a weird colorway that’s clear to me but hard to describe to anyone else. I love colors, and I can’t commit to just one or two. I’ve given up on yellow and orange because it’s hard to make them work, but otherwise I lean towards jewel tones and wildflower colors (include the greens of leaves and stems!) in everything, and neutrals in both grayscale and brown. Unfortunately it seems like the specific shades I like are the ones that are harder to find, so I’m always on the lookout for “clear sky or sapphire blue that’s not the popular beachy color” or “lilac or deep purple that leans towards blue, not red” or even “deep brown not taupe” and “true gray with no yellow in it.” I wish I could shop by RGB value!

        1. I swear, if an online store for clothing or makeup used accurate Pantone or RBG or even hexadecimal color references, they would be SO LOVED.

    3. Yes, color is so key! Mama sat me down with Color Me Beautiful when I was a teenager, and I figured out what colors suit me best. That lets me eliminate a lot of things from the start. I’ve heard the valid criticism that the version of the book that I read is … lacking … for skin tones other than white, white, and more differently white. I don’t know if they have updated their resources yet.

      For those not familiar, the CMB folks have grouped together 4+1 palettes which flatter different people (4 groups of people, plus “neutrals” which are equally un/flattering to most or so accepted that they’re a non-color). The evaluation process involves draping oneself in different colors and seeing how the pure color next to the face looks, absent the distracting factor of different fashions.

      Equipped with that knowledge, it’s then easier to evaluate whether that frock which looks hideous on you is really entirely unsuited, or whether you should try another color.

      1. In the video series “Color Theory for Makeup Artists,” she explains that all brown pigments come from mixing a primary and a secondary color. In human skin tones, this is usually 2/3 warm tone, 1/3 cool tone, on average (warm colors being red, orange, and yellow, and cool colors being green, blue, and violent). So brown skin could be 2/3 yellow, 1/3 violet, or 2/3 orange, 1/3 blue, or, more rarely, 2/3 red, 1/3 green. And then there’s definitely a range of hues in each primary and secondary color. However, people with very dark skin hues might have a reversal or pigment proportions.

        So, using Lupita Nyongo as an example, if you look at photos of her skin and then try to re-create the color in Adobe illustrator, her brown is 2/3 a specific blue, 1/3 a specific orange, and both the blue and the orange are direct opposite shades in the color wheel. Consciously or unconsciously, she seems to know this, as she rocks a lot of light blues– same “column” of the blue in her skin, just lighter– at the red carpet events, as well as a lot of blood orange dresses. When she wears prints, they often combine light blue and blood orange, or dark blue and a de-saturated orange.

        She rarely wears gold, yellow, violet, pink, or even pure red, as those are more apt to clash with her natural hues, especially in photographs. She does wear green a lot though! Obviously, color theory rules are decent guidelines, but they aren’t laws.

        A good resource on skin tones, color theory, and makeup for people of all skin tones and genders is TOMMY, a professional makeup artist based in Tai-Pei, who blogs in English and Chinese: https://tommybeautypro.wordpress.com/2013/01/05/makeup-101-colour-theory-make-up-artistry/

    4. Yes! Finding my dad’s (!) old ‘color for men’ book from the 80’s helped me so much when I was a teenager- at least I discovered I was an autumn even though I was still struggling with fashion. Now, like sorcyress, I pretty much wear oranges/greens/browns (with some yellows and navies and greys thrown in for good measure) Red and maroon have always brought out my acne, so I avoid them at all costs.

      I’ve had clothes tailored and it was surprisingly affordable. Like a lined shirtdress that needed taken up at the waist because I’m short-waisted. I was hesitant to go in, expecting the worst, and the tailor was like, oh, that’ll be $30. $30 for a dress that is now my favorite dress because it doesn’t sag at the chest. Well worth it!

  15. With my mum I tend to take a tack of positive suggestions, e.g. “Something else blue would tie in great with the rest of your outfit”! Or “I think this one would go really well”. It’s totally fine to say something like “It’s not what I would pick” as the captain suggested above, but I thought it might also be helpful for you to hear that advice-giving doesn’t have to be all about saying no 🙂

    1. Such great advice on being positive AND specific.

      My mom leads an exciting, adventurous, active, outdoorsy lifestyle. So she has the perfect camping/rowing/hiking wardrobe and puts a lot of effort and money into it. But clothes to wear to a relative’s wedding? Clothes for a dressy brunch? She is WAY less interested in maintaining go-to options for that stuff.

      When I was younger, I used to roll my eyes when she asked me to help her pick out outfits for Events and be like, “Omg Mom no. You can’t wear XYZ to a WEDDING!”

      Now, when she’s mulling over what to wear for so-and-so’s wedding, I’ll be like, “Hmmm that dress needs better shoes and a little evening bag. Let’s go see what Macy’s has.” Or, “I like the idea of pairing a jacket with that dress, but that jacket doesn’t quite go. Want to borrow my black leather jacket?”

      1. An outdoorsy friend recently tapped me to act as her “Fairy Gothmother” for a first-time club outing — we’re roughly similar in size, so I raided my own overflowing closet and brought some different styles/shapes for her to try on.

        Some of the pieces looked better than others (although none were bad!), and I think it helped for both of us that we agreed that one combination looked *fantastic* on her! After that, the last few outfits were less-spectacular, so she went for the standout one.

        We had a great time dancing! Now she wants me to shop with her for more going-out clothes sometime, which should be fun 😀

        (I am Notoriously Fancy, so I was a good person to play dress-up with.)

        The thing I kept in mind was that she usually dresses for comfort and function, so I didn’t bring anything super-restrictive or uncomfortable, and I tried to go with silhouettes that I thought would suit both her body type and her overall style.

        For the LW’s mom, I’d suggest finding the pieces in her wardrobe that DO look awesome and suit her well, and then build on that by looking for similar shapes, mixing up colors and fabrics, etc.

        1. I and another friend are the Fashion Ladies for our very outdoorsy friend. I’m a crazy eclectic lady and my other friend is a very Ann Taylor Loft type, so between the two of us we get at what our friend is looking for. Mostly we comment on cut and fit, and anything green is always a plus both because of skin tone and because of our outdoorsy friend’s love of green.

          1. Oh my goodness, I could be your friend. My style swings pretty much between those two poles, and I used to do field work, and green is the best! Does your friend want another friend? 😀

  16. I once gave my fashion-challenged mom a coupon for “going shopping with my daughter,” with a dollar amount attached, because she enjoys spending time with me more than shopping, and it was a fun activity for both of us (especially since I wasn’t shopping for myself). I also remember a separate time when we went to Chico’s with a very specific concept (Mom Is Single After 30 Years of Marriage, I think it was) and found theeeeee most helpful sales associates to help with the consultation and trying things on. (Chico’s especially is pretty good at this – I worked at White House Black Market, which is under the same parent company, and their training model emphasizes outfit planning with customers.) She found some really great separates and outfits and it was a happy experience for her.

    1. Chico’s is great – their particular style doesn’t work for me, but their sales associates are awesome.

      1. Chico’s AND WHBM are quality brands, too. Chico’s skews a bit mature and WHBM skews a bit trendy, but I’ve never gotten a badly-finished garment from either. It’s nice to know going in that this won’t be a problem with what you pick.

  17. Totally agree with the Captain that if your mom is asking for advice, there are ways to help her that are tactful, constructive and ultimately fun. I spent literal decades of my life saying, “I don’t care about clothes,” when what I really meant was, “I don’t know how to shop, so everything looks bad on me, so I’m going to retreat and act like I don’t care.” Obviously it’s foolish to put *too* much weight on appearances (yours and others’), but learning more about clothes and what actually looks good on me gave me a lot of confidence. I actually buy less stuff, bc I’m making fewer shopping mistakes. To me, at least, taking charge of something that once intimidated me was genuinely liberating. It may be like this for your mom, too.

    So encourage what’s good without raining on what’s bad too much. I second the suggestions about a subscription box that would let her gradually develop her style. And a BIG yes to Pinterest!

  18. My thought would be:

    On those occasions when she does ask you what you think about it, give an honest answer and don’t make a big deal out of it. “What do you think of this hat?” “I don’t like that style and I don’t think it suits you.” and/or “I think X would look better on you.” That’s fine.

    RESIST ALL IMPULSES TO either a) get at all apologetic about saying this (just makes it weird when it doesn’t need to be; matter-of-fact is much better) or b) generalise comments (if she asks you about that hat, she doesn’t need to know your opinion on her terrible taste in hats generally. Or whatever.)

    On those occasions when she doesn’t ask, don’t say anything unless it’s either a) complimentary or b) letting her know about something like a hole, a stain, spinach in her teeth, whatevs, that is solvable and that she genuinely might not have noticed.

    She can decide for herself whether she wants your opinion or not, which means respecting her wishes on the matter whether they’re ‘asked for opinion’ or ‘didn’t ask for opinion and can therefore be reasonably assumed not to want it’.

    (Also, I’m now thinking of the ‘wear purple with a red hat which doesn’t go and doesn’t suit me’ poem. Although probably about three people will have mentioned that in the time it took me to type this comment.)

    1. Reading these comments, I was just thinking of my favorite giving-Mom-fashion-advice memory — which should also be added to category b as a solvable & mentionable problem: if Mom leaves the house in her slip that is the same color as the skirt she meant to put on over it.

      Only kind of related, I give my mom a shirt every Christmas, more or less — something kind of dressy that made me think of her, or a casual shirt in stripes which I know she’ll wear until it falls apart. I’m not working to fix any of her clothing choices or style, but it’s been a really positive exchange for us.

  19. this is an issue i have struggled with for years with my mother. what i found to be helpful for her to kind of reset her style was a lot of separates, mostly black with pops of color in the form of a camisole or a cardigan. this allowed her to play with mixing different pieces that were easy to mix and match and work out what cut and fit she likes without being overwhelmed. and now, (wow, 15 years later….) she is much more confident in picking pieces and has expanded her style imagination to include all kind of prints and patterns and dresses. i almost never get a panicked email from her asking my opinion about something she is considering buying anymore. i think part of it was her letting go of her foundational myth that she is bad at style. it was a part of herself that she talked about in relation to her identity, stretching back in her stories to her days in catholic school and how uniforms were the best thing ever because you never needed to decide what to wear. which, as i am thinking about it, i basically gave her a “uniform” of black skirts + black open sweater + colored t-shirt or camisole, and over time she started adding in new things.

    the most important things, in my mind, are 1) to help her discover what will make her feel comfortable/what comfortable means for her. 2) this is not an overnight change.

  20. I don’t have any great fashion suggestions (my style is… well, I have five copies of my summer shirt, five copies of my winter top five pairs of jeans and three pairs of shorts, and they’re all the same shade of blue) but I hope it might reassure you to know that as a mother of a rather more fashion forward daughter, I would never be hurt by any advice she would give me because I know it would be coming from a good place. As with you. Your mum is very lucky.

  21. Hey, Dressaday! I loved that blog.

    In general, I think people like it better when you say what you do like rather than what you don’t. So not, ‘That’s an ugly hat you’re wearing,’ but, ‘Hey, try on this hat. I think it would look great on you.’

    Has your mom talked at all about how she wants to look/how she doesn’t want to look? Because basing your style advice on her specific goals will probably be helpful. As an example, I had a friend in her early forties who was really sensitive about people thinking she was older than she was. It really upset her when people would offer her the senior discount or assume she was her children’s grandma instead of their mom. The truth was that she had a very young looking face, but her hair had gone gray early, and people based their assumptions on that. I told her as much, she dyed her hair dark, and the comments stopped, and she was a lot happier. But that advice wouldn’t have been helpful to someone who didn’t care about looking older, or who loved their gray hair, or whatever.

    My best friend and boyfriend have both told me that it’s more fun shopping with me than shopping alone because of the way I talk about the clothes on the rack. I don’t know if your mom has this particular hangup, but they both tend to feel like if something doesn’t look good on them it’s because there’s something wrong with their body. Like the clothes are objectively right, and if they don’t look good in them, they’re wrong. But I talk about the clothes as objects, and about the decisions the manufacturer probably made that led them to be the way they are. Like, ‘Yeah, that fabric’s everywhere these days because it’s cheap to produce, but it’s super clingy and that’s why you don’t like the effect,’ or, ‘Yeah, about fifty percent of the sleeves in this store are too narrow for most people’s arms, and I think it’s either because they won’t spring for fit models or because their fit models are in Asia where the shirts are produced, and we’re in America, and the average person’s arm is thicker here.’ It makes them feel less self-conscious.

    1. yes! And if something doesn’t fit, it’s always the fault of the clothes.

      That top is too long in the waist; the pants are too tight in the thigh.

  22. I’ve been on my own 12+ year journey of learning my style (in my late 20s now) and I think the Captain’s advice is spot on. If she’s asking you for help, she probably does want it. It will probably be a slow process, so I like the Captain’s ideas of picking one type of outfit and starting there.

    I would also suggest not making any over the top/astonished compliments. When I started moving from jeans+sneakers to dresses+boots, several of my favorite people would go “oooh, why so fancy today!” and it actually made me feel ashamed. I love hearing “that dress is awesome!”/”I love that top!” in passing, without it being a big deal.

    Other things that have helped me a lot:
    – take a bunch of style quizzes – the options for each question can be a bit random, so see if any styles pop out repeatedly across quizzes
    – from there, google suggestions for dressing in that style
    – Pinterest is GREAT – try lots of different searches, pin anything you vaguely like, then filter through and see if any particular type of outfit pops out
    – Keep a board or folder for outfits that she loves, but doesn’t want to wear. E.g., I love fabulous evening dresses, and I just don’t get the chance to wear them. Also put things she doesn’t think she can pull off – I like going back to this board when I’m feeling more confident, and moving things over 🙂
    – try lots of things on, with a sense of adventure but without any obligation. One of the hardest things for me was learning to see myself with a different silhouette – it took some time to feel confident about what clothes I actually liked myself in.
    – save receipts and return things without shame if you change your mind later.
    – tailors are great, especially if your particular shape doesn’t correspond to ready-to-wear standards. Not everything can be tailored (blazers and coats are hard), but if you buy the size that fits your widest/longest part, a good tailor can usually fit the rest.

    1. (Does Pinterest count as my one suggestion? I’d also suggest Already Pretty: https://www.alreadypretty.com/, and there’s also a book. Her book has a process to walk through finding your style, and she focuses on defining/refining your own dressing priorities, rather than any one particular style or a set of predefined body shapes. Blog archives are also useful, but she doesn’t post anything new anymore.)

  23. Ask her what she likes specifically about her top favorite outfits. It may be the fit at the waist, or that washes so well, or color makes her happy. That’s a foundation to built on. Try on lots, and especially different sizes in the same item.

  24. I found sewing my own clothes was a big one for me. I’m not at that stage, and I know being younger makes it different, but I know a lot of women in their 60s who find the ability to sew their own thing in their own style that fits to be very liberating. Like those years when every clothing store is full of black and grey–and I never wear black and avoid grey wherever I can–being able to sew means I can make something up in bright yellow but a current cut.

    It also means a lot of time spent poring over *elements* of clothing instead of *finished pieces.* You look at the fabric type and the colour and the style/pattern all separately. Even if she ends up still buying her clothes, some time spent in pattern catalogs and fabric stores might give her and you a different way of approaching the “what I like” question.

    Ultimately clothing should be fun, I think. “It’s just clothes” is often used to denigrate fashion or style; like, it’s just clothes, so put on whatever and who cares. But “it’s just clothes” can also be used in a playful way: experiment, have fun, try on the chartreuse shirt with the magenta pants or the goldfish dress or the asymmetrical skirt with the weird pockets. What’s the worst that can happen? It’s just clothes.

    Clothing and fashion and finding your own style are so much easier and more fun when it’s all treated like a game, however that looks to you, whether it’s making your own or buying something nice or going to a secondhand store or embellishing or dyeing something you already own or mastering the art of putting together a fabulous outfit all from items that were 80% off.

    I guess what I’m trying to say is, maybe approach it less from the perspective of what she looks good in or what you think she looks in or what’s appropriate for her age/class/gender, and more like a kid fingerpainting: make a huge mess, try a bunch of different things, see what’s fun and what feels good.

    1. I have loved learning about sewing for exactly that reason! Curvy Sewing Collective has been useful to me, especially Shannon’s stuff. (Hilariously, my problem is “not enough grey in stores, too many prints”.)

  25. One word of caution, LW: your mother might wear bucket hats because she can’t fit into regular women’s hats (women’s hats that cost less than the moon and the stars are almost always “one size fits all”, meaning roughly size 6 3/4. How does that work if she needs a size 7 5/8?), and she might wear hats because she feels self-conscious about her hair or lack thereof. (There are other reasons, but this is a primary reason among the women I know.)

    If this is the case, pushing her not to wear bucket hats could come across as “show everyone your ugly hair,” “show everyone that you aren’t wealthy enough to get your roots touched up every 4 weeks,” or “show everyone your thinning hair and the bald spot you’re developing”. Older women – and I’m 54 so not quite there yet but still – go bald, go grey, or (if they had red hair like me) go ditchwater yellow, and these things aren’t always fixable – red hair doesn’t easily take dye even after it fades, for instance, and although there’s a drug that treats baldness in women it isn’t without side effects and isn’t cheap.

    If going without a hat makes her feel insecure and ugly and she can’t find a hat other than a bucket hat that fits her at a reasonable price, she isn’t going to listen to any talk about “style”. The pain of looking old and grey (or bald!) can cut far deeper than the pain of being thought unfashionable.

    This can also be an issue with respect to clothing. When you go through menopause – and nobody tells you this – your body changes shape and there is no amount of dieting or exercise that can stop it. Your hips narrow, your buttocks flatten, and your waist thickens. Suddenly you don’t fit into any of the clothing in your usual stores; the only items guaranteed to fit without expensive retailoring are either dowdy or unisex – things like sweatpants. If she’s never had to have clothing retailored she might not even know it’s possible or, again, she might not be able to afford it.

    1. + 1 It may simply be that the bucket hats were to hand and Mom likes working in the garden and needs a hat to protect her skin in the sun and ended up wearing them more and would like to discover other hat styles for other occasions, or she has some idea that older women need to wear hats because her mother and gran did. But she may also be wearing them for reasons that are fundamentally practical, and what she would like is to find the best bucket hat. They are after all comfortable, lightweight, easy, and crucially keep your thinning hair in place in the wind and that is why my mother has 4 of them.

      There are also different generational associations with clothes. E.g. I’ve seen people ask why Mary Berry (British TV baker) wears brightly coloured, tailored jackets when they think she’d look better in something drapier in stylish pale Scandinavian colours. Well, I can tell them, because my mother is Mary Berry’s age and likes jackets and wouldn’t be seen dead in drapey things, because to her drapey is not lovely layering in a gorgeous subtle blue-grey, it was what Old Ladies wore in her formative years and even if it were a fabulous garment that suited her brilliantly, she personally would feel old and dismal in it.

      An alternative to telling her what you like and think she ought to wear is to ask her what of YOUR clothes she thinks are nice. Then you could talk about if those are styles and colours she could try, especially if you have similarities in body shape or complexion/hair.

    2. Gray is notorious for being hard to dye, but there are color-correcting shampoos that leave a light tint to counteract yellow in graying hair. That’s why the image of the “blue-haired little old lady” exists, there used to be color washes that did the same thing in broad strokes, and blue/violet counteracts yellow, but the shampoos now are much better calibrated, from what I can tell.

      (And this proves that YMMV: I found gray hairs the last time I got my hair cut, and I was so excited! 🙂 ) Hair is so personal and so tied to self-image; I generally feel like “it’s just hair, if this cut doesn’t flatter me I’ll get it cut shorter”, and yet I’ve had this same style for a year and a half, but someone else could genuinely (and with good reason!) be in tears after a bad haircut. (Although maybe it’s just me; I’ve rarely gotten a bad haircut/style, at least not since the perm that made me look like a poodle in middle school…)

      LW, Charlene has a point about hair; is your mother willing to experiment a little with cut, with style or (possibly) with color? That could be a fun boost that helps her feel more stylish. It’s not strictly fashion, but to me it ties in.

      1. at least not since the perm that made me look like a poodle in middle school

        Serious question: has everybody had the poodle-perm in middle school/Jr. High?

        I love my grey hair; every one is a reminder that I have survived this long, and survived some shit in the process.

        1. I didn’t! My hair is super-straight and I like it that way because it’s easy to take care of. I’m strictly wash-and-go!

  26. When I’m shopping with my mom, her wonderfully gentle dressing-room code is “Hmmm, that (dress/hat/top/whatever) isn’t doing much for you.” I love that the message is that you’re perfect and the problem is that this particular item is falling down on the job and failing to grace your perfection to the fullest.

    1. My partner’s go to when shopping is “I don’t know how I feel about that shirt” (etc) and I love it for the same reason, because it puts the focus on the item of clothing and not my body and I also like that it acknowledges that this is my partner’s feelings (and my own might be different!)

    2. Oh — you reminded me of my wonderful mom! She ALWAYS blamed the clothes — “that’s not cut well”, “that’s a trying shade of green” sort of thing. I grew up thinking that clothing manufacturers were just careless, silly people who didn’t know what women were like. (Which, actually, isn’t always too far off.)

      1. I love the phrase “That’s a trying shade of green” (or whatever color). Thank you.

    3. Yup, I love that. I use it on myself too- a garment can be beautiful on its own, but if it doesn’t highlight YOU in some way when you are inside of it, then it’s just not as special. Caveat, not everyone cares about this and that’s fine, but for me, I want my clothes to feel almost like a part of me, and if the clothes ‘don’t do anything for me,’ it’s easier to make the choice to not keep them or purchase them in the first place.

    4. If you’re going to say something like this – any of these suggestions, really – pay as close attention as you can to what your mom thinks about the item she is asking about. I’ve had friends and family members say things like that about clothes I thought looked fantastic on me, and it really hurt.

      1. If shopping (because it’s MUCH easier to express negative opinions about clothes that haven’t already been paid for), paying attention to body language works. If someone looks uncertain then you can go with “you don’t look excited to be wearing it, which tells me it isn’t the clothing for you”, or “I’m getting the sense that you’re not in love with it”, or “you don’t look confident in that, let’s try something else” and easy things like that.

        If they look pleased, on the other hand, then you go with “[gently expressed opinion, if a negative one, but making it clearly about your own feelings] BUT you look really happy in it, which I think is way more important.”

        What people should never do is imply someone’s taste is bad. It’s the fault of the clothes, they’re not the right clothes [for you], the colour/cut/fabric is wrong, whatever. But it’s fine to LIKE the clothes, they’re nice clothes. Just maybe not the clothes that are destined for you and, like bad-fit boyfriends, it’s fine to free them up to find the owners they are a better match for.

        1. Or… it’s also fine to just buy them and enjoy them, and not bother with what some self-professed ‘better at clothes’ person thinks.

          I guess the key is 1) did they ask for your advice and 2) was it a real question or were they just looking for someone to say something nice.

        2. If you really think the person’s happiness is way more important, than how about keeping those negative opinions to yourself instead?

          1. While I get what your question is aiming at, I think perhaps a safer strategy is to only ask someone their opinion if you’re willing to hear it. If you love something and it would be hurtful to hear someone disagree with you about it, don’t ask them. Just buy it.
            If you’re asking just to hear someone agree with you, maybe rephrase it as “I love this and I want you to be excited with me” rather then a question.

  27. So, my only advice is contingent on something that may or may not be true, but is at least plausible.

    Lots of people, and especially women in your mother’s age group, were trained in basic sewing or knitting skills at some point in their life. If not, it’s pretty easy to learn, and the start-up costs aren’t outrageous if you live in a city with a sewing studio or some good second-hand stores. Sewing clothes is by far the most fun way to both explore what you want to wear and make things that fit you *exactly* the way you want them to fit you. If your mother knows how to sew, consider asking if she could teach you, or otherwise make it into a thing you can do together (lots of sewing studios have classes). If your mom has any interest in sewing, reminding her that she can turn what she wears into a fun hobby could be an inspiration. At minimum, a little bit of tailoring can make clothes that don’t fit her well feel like clothes that are truly hers.

    Moreover, sewing forces you to sit down and think about what you want to wear and how you want to wear it. It was instrumental in getting me out of the mindset of not being “””allowed””” to wear certain things. Once I could make anything fit me, I could make anything!

  28. Man, a fluffy question was JUST what I needed, so thank you LW! Also I love style questions because I love clothes in general.

    I think style blogs and Pinterest are great places to noodle around and see what you’re drawn to. I also love the idea of capsule dressing, where you have a number of pieces in the same color family that all go together.

    I think most people gravitate towards the colors that make them the happiest – I only wear three colors – and doing a closet weed-out is a great way to start, because you’ll realize what you’re wearing over and over and what you’re rarely wearing.

    I tend to gravitate to the same silhouettes over and over, because there’ll be a shape to clothing that just makes you feel good to wear. I think framing it that way – wearing what you feel happy and confident in – versus what you “look good” in – is a good way to think about it. And you’ll have missteps and sometimes buy something you end up not wearing. That’s ok! Donate it or return it, it’s no big deal. I used to hang onto clothes because I felt badly that I’d bought something but rarely worn it, or if something didn’t quite fit. Now I either get it tailored or donate it.

    ThredUP is great for cleaning out; they’ll send you a clean-out bag you can fill and ship for free back to them. And there’s always Goodwills or Dress for Successes or other places you can donate to.

    If your mom finds an outfit or piece of clothing she absolutely loves, buy multiples! I have several of the exact same pencil skirt because I happened to find one that fit really well and packed well and was machine washable.

    1. I can’t speak to the quality, but I have noticed that brands like LuLaRoe have skirts (e.g. “Cassie”) and dresses (e.g., “Julia”) that make this kind of planning easy, as all Cassie skirts in a size will fit within a centimeter of other Cassies on your body (allegedly), so if one Cassie looks great, another one SHOULD also look great. That makes life (when clothes shopping with limited time and patience) a lot easier!

      I definitely buy multiples of things that work. I have a mess of cowl-neck super-cheap solid-color machine-washable stretchy dresses that I can throw a blazer over and run out the door in five minutes and still look OK at a law firm. What more can anyone want from a $10 or $15 dress? Eventually they’ll wear out in some way, surely, but I have long since gotten my money’s worth. Buying duplicates isn’t boring, it is super helpful!

      1. A lot of my friends wear LuLaRoe stuff and love it, but I they’re also an MLM, in case that’s something that concerns people.

        1. I’ve only ever seen LuLaRoe stuff on eBay, as none of my social media friends are doing MLM stuff. Thanks for the info!

  29. My sister and I sometimes go shopping together. We have very different taste in clothes, but we value each other’s opinions. What helps us is, when we don’t like something, trying to be specific about why:

    — “I think that print overwhelms you.”
    — “I don’t think that shape does anything for you.”
    — “That color makes your skin dull, you’re more of a winter.”*
    — “That’s way too long, you look better in knee-length.”

    If we really, really hate something, we might shrug and say, “It just doesn’t speak to me at all.” Sometimes that’ll be enough; sometimes, the other one will say “Well, I like it” and buy it anyway.

    But this way we can be honest and yet not wind up killing each other.

    *Yes, we are still old enough to talk like this.

  30. ‘The fight against socks in sandals’… I guffawed. But seriously what a sweet predicament. I love everyone in this letter and the captain’s advice 💚

  31. These are lovely suggestions! I particularly want to co-sign the closet clean-out as a group activity. I have a very fond memory of helping a friend with this: she’d model items from her closet, and another friend and I would give our enthusiastic approval or equally enthusiastically reject clothes that didn’t fit well or suit her. (And by “suit her,” I don’t mean “make her conform to a particular performance of femininity that is appropriate for her age and class”; I’m thinking of Tom and Lorenzo’s “Girl, that’s not your dress” feature, where there’s nothing wrong with your body and sometimes there’s nothing wrong with the dress either, it just may not be the right dress for you.) She had a lot of clothes and specifically asked for this kind of feedback, which is why it worked.

    It was fun and good-natured (wine helped!), but my thinking is that this would be a good way to learn a little bit about what your mom likes and doesn’t like about her wardrobe. Who knows–maybe the bucket hat carries some kind of nostalgic weight, or maybe she grabbed it because it was cheap and functional. Maybe she actually thinks it’s cute but now wants to move away from “cute” as a style choice, or maybe she actually looked at some other hats but worried they were too young or too trendy and that she would feel judged or silly in them, so she went with something familiar. Maybe when she says she wants to look her best, she wants to wear clothes that express her intelligent and outgoing personality, and isn’t sure how to translate that into the language of fashion. It’s clear she’s not really sure how to ask for what specifically she wants–I can relate, I am absolutely the same way about haircuts–so the closet cleanout will be a good way to unpack that, as it were.

    1. I’ve done some closet swaps and they’re a lot of fun – anything left over gets donated.

  32. Also I try to frame clothing as something that makes me feel good versus something that makes me look good.

  33. I feel like I was in LW’s mom’s position about 10 years ago (early 20s): I had a set kind of clothing/look that I liked well enough and while I was curious about dressing differently, I didn’t know where to start. My friends would (lovingly) tease me, and I felt kind of stuck. I didn’t have a great self-image, which really hindered my ability to see myself as the kind of person who dresses in a thoughtful, stylish way (even though I desperately wanted to be).

    Part of my insecurity (and maybe a challenge your mom faces?) was that it felt like there were all of these style ‘rules’ and concepts that I just didn’t understand – clothing proportions, how to choose length of trousers, how to mix patterns, even just basic concepts of tailoring. Reading blog posts on those topics and seeing the principles applied on shows like What Not to Wear (I know, I know, I know, lots of problematic stuff there) helped me better understand why clothes might not fit as I expected, what would be realistic in terms of tailoring to fix fit issues, and just generally how to select clothes that fit my body well. I learned to look beyond size labels and pay attention to the actual measurements and proportions of clothing and how those worked with my body’s measurements and proportions. (Best thing I’ve ever done? Asked a friend to help me take basic body measurements and start reading every size chart to find my real size when I was shopping or browsing online.)

    One blog that really helped me learn how to think differently about clothing is Already Pretty (https://www.alreadypretty.com/). Sally, the blogger, would break down style concepts in visual ways and give examples from her own experience. Even though her body is very different from mine, her posts gave a lot of practical principles that I could apply to my own clothing decisions. She also started recruiting plus-size guest bloggers, which helped me get into the world of plus-size style.

    Good luck, LW, and have fun with your mom! I was scared when I first started learning how to dress myself, but supportive friends and learning more about the technical aspects of clothing really helped.

  34. My ex-girlfriend (now my BFF, don’t worry) did the best, amazingly subtle jon of helping me update my style preferences and thoughts post-transition, and mostly , what she did was ask a lot of *questions*

    – what sort of colours do you like wearing?
    – do you have a favourite colour?
    – what sort of clothes do you feel most comfortable in?
    – do you feel good wearing [jeans/shorts/black t shirts]?
    – how would you like to dress if you had a million pounds?
    – how would you dress if you knew no one would mind?
    – YMMV: I have some body image issues and this helped – “how would you dress if you had a makeover and lost 20 pounds?: *with the important followup*: “what if you tried dressing like that now?”

    She also did things like involved me in her thought process for deciding what to wear (she is VERY stylish and well dressed, but in an unusual sort of way), and reassured me that if I want to wear a lot of black I’m absolutely allowed and I do indeed look sharp and if other people think that’s depressing it’s not really their problem. Always she’d remind me that my choices and comfort were the most important thing, while sharing her own opinions on what looked good on me, and keeping to herself what she thought didn’t look good.

    If all this sounds too good to replicate perhaps it would help to hear that she made a few fairly serious slip ups RE body image/weight/etc, and I still think she did a great job, so LW, I’m sure if you go on encouraging your mum she will be happy even if you do stumble upon the wrong thing to say a few times.

  35. YES! the other thing from sewing that I spent all my life not knowing was: realizing how different bodies are and what are the key points to look for in the fit. Does the shoulder of the sleeve fall at YOUR shoulder? If it’s a dress, does the waist fall at YOUR waist?

    I don’t know if other people absorbed this or where they learned it from, but *I* didn’t know, and once you do, you see it all over. I don’t actually sew my own clothes much, but I think realizing it makes a huge difference in finding clothes that look good on you.

  36. I generally don’t care what I’m wearing, which is great and terrible all at the same time. I would LOVE it if someone gave me a style subscription box for a few months, it would be a real treat. I love that idea for your mom, especially with Christmas coming up.

  37. I’ve always loved the blog https://youlookfab.com/

    It’s written by a personal shopper and is a mix of her personal fashion journey (she even refers to it as such), generic outfit formulas (eg tomato red and orange, or graphic tees with jackets) with examples of how to pull it together, broad trends and various ways they can be incorporated, and occasionally highlights of other fashion bloggers.

    I’m not sure I would call it beginner friendly, but she does discuss fit and flattery in a way that is practical and easy for me to understand.

  38. I started watching Rupaul’s Drag Race like a year ago (I am slow, don’t judge) and one of the most visible effects it’s had on me is that I am not as afraid anymore of taking clothing, makeup and style seriously as a part of self-exploration. I think a part of me thought there is no power or fun to be had in experimenting with and having your own style. But seeing the power that makeup and clothes (and performance) gives to the drag queens on the show, I have completely changed my view of these things. It has helped me want to have a style, find the things that look good on me, be ok with the journey, be bold here and there, etc. Watching that show together can help you both see what certain style elements work for which personalities, how fun that search can be and how anyone can make anything look fabulous.

  39. It sounds like your mother doesn’t have a huge yen for fashion and maybe never will, so when she asks for advice off-the-cuff, it’s good to focus on specific actionable advice and key pieces she could add her wardrobe, along the lines of “You always looks great mom, but I’ve noticed you could use a smart jacket/some kickass winter boots/a nice casual dress?” Then you can make that the focus of a gift/shopping trip without overwhelming her, and without you taking on responsibility for overhauling her entire wardrobe?

    Also, make your compliments specific e.g. “You can really pull off bold colours, you should wear them more often!” or “I love those jeans on you, the cut really suits you!” That will help her learn more about what suits her and build her confidence around her choices.

  40. Stuff you like is maybe #2, because I suspect we’ve all had to wear a uniform or something we didn’t particularly like, but there were ways to make it work. Know your measurements, as that would be #1. Take a measuring tape when shopping, and you can eliminate stuff that won’t fit over your boobs or behind without the horror of having to get semi-nude in a store dressing room before realizing it won’t fit. Measure from armpit to armpit for tops and dresses. Add an inch or two for outerwear, as it is usually layered over other stuff. Measure hip seam to hip seam (if it has seams) or smooth it flat, look for the widest part, and measure there. While in the dressing room where no one can see you, and depending on your mobility ability, bend over and see if your undergarments show. Do a squat (again, if you can) or sit and lean forward to see if pants or skirts cut into you or gap in the back. Sit and see if you can feel your thighs touching the seat, and if you don’t want that to happen, choose something longer. Twist from one side to another to see if the garment acts funny or bunches. Try to raise your arms. (If you aren’t able to do a particular thing, that works in your favor, because you don’t NEED the garment to accommodate you doing that particular thing. So that’s a win for you right there.) When in doubt, exaggerated cuts are trickier than traditional cuts; i.e., knee-length skirts and dresses or dresses that skim right below the cap of your knee work well on most people (but not all). Mid-thigh and mid-calf are trickier to pull off and can be uncomfortable for sitting on vinyl seats or walking fast (to name two things). All bodies are perfect the shape they are in, but if you just don’t like a part as much as another part, choose to highlight the thing you like with a sparkly accessory, or textured fabric or bright color, and make the part you don’t like more boring by draping it or making that area less interesting. But really, your body is beautiful as it is. You do you. It will be good.

    FWIW, I HATE shopping in brick and mortar stores and my weight apparently goes up and down a couple of sizes seasonally, when I eat my feelings more often than usual, or when I get more super-busy than usual, and yet, no matter what size it is, I want to look nice, so my hint here is to be honest with yourself about your size and whether you fluctuate. Forgiving fabrics are going to be your buddies, so check the stretch and the seams and see if the garment will fluctuate a bit with you. You’ll get more use out of it.

    Also, be honest about whether you’re ever going to dry clean a thing. I will never dry clean a thing. It takes me, like, two years to take my stupid winter coat to a dry cleaner when I notice I need to take it to a dry cleaner. Therefore, I do not buy dry clean only stuff any more.

    #2: Definitely second “window-shopping” Pinterest or Instagram. Consignment stores tend to have better quality but more expensive “label” things, which LW’s mom may or may not care about. My mom and I are actually similar in that we don’t really care about designer brands per se, but they do tend to be well-made AND if you decide you hate it or it just doesn’t work for you, there’s resale value and you can still get rid of it on eBay, Facebook Marketplace, a local consignment store, or the RealReal or PoshMark. Another trick with regard to labels is being OK with second-hand stuff. Yes, at thrifts, but also from resellers as noted above. You can get new-with-tags or new-without-tags, but sometimes even a gently-worm item will work for you. Tumblr would also be a place to look to see what folks are doing, but I suspect it skews a bit young and might not be as helpful for LW’s mom.

    I’d be leery of using fashion magazines as inspiration, because they tend to make me (and a lot of other people) feel bad about themselves, and they promote ridiculously expensive items. They also don’t have a lot of folks LW’s mom’s age in them. BUT! If she likes a particular female actor’s style, and the person is still alive and kicking, then she can Google photos of that person and see what they are currently wearing.

    I’d also ask LW’s mom what 5 or 10 items in her closet make her feel the prettiest and are the most comfortable, and talk to her about what she likes about them. You’ll probably see some similarities. Maybe she likes double-breasted jackets more than single-breasted or vice versa. Maybe empire waists work better for her than fit-and-flare. Maybe she likes sleeveless tops because she does curls at the gym but hates capris because she is short and feels like they visually shorten her more and that’s not her preference, or maybe she’s tall and they don’t hit her at the right place on her leg.

    A homework assignment, if LW feels up to it, is to look back over vintage fashion layouts and notice what you’d still conceivably still wear, and what doesn’t scream “this is a vintage thing” at you. My mom likes Pendleton suits. She’s almost 80, has had the same suits since the late 50s or 60s, and they still look pretty nice. It’s very conservative, and plaid, and so it isn’t for everyone, but it is perfectly acceptable office wear for a lady her age or anyone who wants to wear a plaid skirt suit. My grandmother had a lot of A-line, sleeveless-with-wide-straps, knee-length sheath dresses that could be dressed up or down with a blazer or wrap and accessories. They, too, worked on her, and would work on almost anyone who liked that style, and she got many of hers in the 1930s or 1940s. Stuff that sticks around for decades may not be extremely exciting, but it tends to stick around because people look OK in that style and few people think it looks weird or bad on other folks.

    Lastly, if you want to be more trendy, costume jewelry is the absolute cheapest way to trend-up what you wear. Shoes are the second cheapest, depending on your taste and how well your feet cooperate with shoes (my feet are jerks, which makes most heels out of my grasp). You can find knock-off designer stuff everywhere, from Amazon to eBay to Etsy.

    Good luck!

  41. https://www.colormebeautiful.com/ helped because it gave me a system to LIMIT choices. Instead of walking into a store and being overwhelmed, I could eliminate more than half the clothes based on color alone. I don’t see it on the webpage now, but years ago they had a system for determining what neckline looked good on you once (based on the shape of your face) and giving advice to get that collar/neckline in all shirts and dresses forever after. Similar for where the hem on a dress should be (based on shape/length of legs, not on current fashion) and where the waist of jeans and dresses should hit (NOT based on overall size but based on proportions). I paid what seemed like a lot of money for a consultant, but I’ve used the advice forever after. It’s not based on fashion so much as basic advice tailored (pun intended) for the individual.

    I’m going to push back a little against the try everything on advice. That’s great if you enjoy looking at yourself, like trying on clothes, and wouldn’t be bored silly. If I tried to try everything on, I’d get fed up in about 10 minutes, and would stomp out of the store having bought more ill-fitting, don’t-look-good-on me clothes, or I’d get some hats which would be the least frustrating part of the process. Better to get some ideas about how something is supposed to fit: where the sleeve should fit at the shoulder, where the waist should be, how wide a belt looks good on you. Know your measurements in inches so you don’t have to bother with the dress that’s going to be too tight across the bust BEFORE you get to the dressing room.

    Could you get your mother an appointment with a fitting consultant as a gift? That’s partly because the professional is more likely to know her stuff and partly because it’s easier to take advice from a professional than from a daughter and partly because of the limiting choices thing I started with that makes it so much easier for people who get overwhelmed in this area easily.

    1. Yes! I’ve come up with quick guides to see if clothes on a hanger will fit me like:

      -If the shoulder seams are smaller than the width between my fingertip and elbow, it will be too tight and expose my stomach when I raise my arms
      -If the waist of the pants fit in a circle around my neck, the waist will fit me
      -If the shoe doesn’t fit exactly inside my forearm (with some allowances for socks/bare feet), it’s too big or too small for me.

      If something passes all criteria, it comes in the dressing room.

      My one exception for clothes that don’t fit are inseam length – if they’re too long, I’ll get them shortened since that’s an easy/cheap fix.

  42. With my step- mother I’ve found the trick is to never say I don’t like something she’s chosen (mostly because I don’t have the right in my view and partly because it’s counterproductive). ‘I like it – how about trying this one on as well? I think it’s even more you’, followed by, ‘Well, it’s your call, but I think X is the most flattering/more your colour’, seems to work well. If she goes with Y in the end, I just say ‘lovely.

  43. I used to be a huge fan of makeover shows as a teen, both fashion and interiors. (This was back in the golden era of Trading Spaces and WNTW when the episodes were mostly about helping people who wanted to project a certain image but weren’t quite doing it and needed a little shove in the right direction, and not what the genre became, essentially exploiting folks who are perfectly happy in with their albeit creative/alternative wardrobe for the shock factor of viewers at home with more mundane tastes. But I digress.) The best piece of advice I ever got from these shows, though, was the constant chorus of INVEST IN TAILORING.

    I used to scoff at the idea of having to do more work when I already done the work of going to the store and trying things on and getting frustrated looking in the mirror at myself, but tailoring my clothing has allowed me to have both comfort AND style because I’m not stuck with the choice between buying the smaller size that looks better on me but makes me feel like I’m choking or the larger size that hangs off me in the most awkward of places. I know it can get pricey (I was lucky enough to be able to save up and get a sewing machine so I do the tailoring myself) but if it’s in the budget, even taking a few old favorites that your mom loves but perhaps the cut or hemline no longer flatters her as well as it could, etc, in for alterations can make a huge difference. It can also open up doors that may have previously been closed, when you can look at clothing in stores as a base to work off of rather then the end product. (I don’t really like t-shirts but the franchises I like never make flattering tank tops in my size: me and my workhorse Singer have created quite the collection of customized fitted tanks out of baggy men’s tees)

  44. My daughter criticized me for dressing in “boring good taste.” Years ago. Still hurts.

  45. I think the hardes thing about being in the mom’s shoes is feeling so stuck….but not having any idea where to begin. And the hardest thing about being the daughter is seeing exactly where mom is going all wrong, but not wanting to hurt feelings by being totally candid. To that end, maybe LW could work through The Wardrobe Architect series on the Collete blog with mom. It was immensely helpful to me in culling my wardrobe and rebuilding it by really examining what I need, want, and like in terms of color, style lines, fabric, etc. This is a sewing blog, but the thought prompts would work for anyone that wants to rebuild their wardrobe.

    Is it hard for her to find great clothes because her shape is affected by a particular health issue or some other such thing? If so, she might benefit from joining group on Facebook that is a dedicated to her particular shape concern. These groups are usually private and very body-positive. I’m on a group dedicated to dressing to flatter my particular fit challenge and and it has been a godsend to have online support from people who have the same shape concerns as me.

  46. Lately, any time I compliment my sister in law’s outfit, she gleefully tells me she got it from her fashion subscription and recommends the subscription again. I don’t think it’s for me (logistical issues with a rural home and having to UPS my returns), but she really, really, really loves it. And she was a person whom I thought of as a “strictly wears sweatpants cuz she has bigger fish to fry than fashion” type. I think there’s something really “Christmassy” about getting that surprise box in the mail. Also, once you’ve got clothes “you’d never wear” in your house, you might as well try them on in private and maybe find “oh, I actually rock this.” I think, too, that it’s a lot easier to tell your subscription person, via email, that something doesn’t work for you, then it might be to tell your beloved daughter that the thing she thinks is delightful is (in your opinion) really, really unsuited to you.

    1. Do you know which one she uses? And what budget it ranges? I’m trying to build wardrobe after grad school for so long!

      1. I wish I knew — it’s one of the “style for all ranges of sizes” ones, and her stylist gets her cute scarves. Wish I knew more 🙂

        1. Stitch Fix ran a little pricey for me, but the items chosen were close to what I liked and fit. The problem was I had items in my closet already that were almost identical, and I like bargain-hunting and it turns out I am not that keen on surprises, so it wasn’t for me.

  47. I gained weight and so my current clothes didn’t fit me. I got discouraged shopping by myself, and so I signed up for Trunk Club (which was ultimately too pricey for me) and then (stitch fix). Stitch Fix ended up really working for me, and I found a style that worked with my new body. (I realize this sounds like I’m a salesperson but I’m not lol) I got the confidence back to start shopping again on my own once I figured out what clothing I liked for myself. I think a subscription service might be a great place to start, with a note to the stylist that she has trouble putting outfits together.

    1. I don’t like them on me, because I went to some Girl Guide camps where was forced to wear one 24/7, but they look cool on other people! Lots of other people think snapbacks are terrible, but you can pry my collection from my cold lifeless hands.

      1. They were super in when I was a kid and had no say about whether or not I was going to wear a hat so, of course I developed a hatred of them. There are a bunch of pictures of me looking ax emo as a 5 year old wearing a bucket hat I clearly hated. A friend my age, her friend real word was apparently “won’t” as inspired by one of these hats.

        1. I also dislike the way I look in them because I immediately see not now-me but 5-year-old me. Not that I dislike 5-year-old-me (she’s grinning hugely at having caught a very small fish), I’m just sensitive to being seen as younger than I am.

  48. My mom (lifetime achievement award teacher win all the cotton shift dresses that go with that accolade) has begun giving out advice that I used to give her, so I am going to take that as a ringing endorsement of my style advice skills.

    I used to tell her, “if you LOVE it, buy it,” and “if you don’t know what it goes with, then it goes with everything.” I found that by telling her those two things, her style—which has a clear point of view, looks great on her, and makes her feel good—came out once she started feeling confident enough to wear what she LOVED instead of just what she had. She also took different kinds of fashion risks, and I used to hear her whisper the two fashion mantras to herself even when she didn’t ask for my advice.

  49. I feel your pain LW! It’s not my mom though, it’s my 13 year old daughter. For the last two years she’s lived her life in oversized sweatshirts and jeans. What’s worked for me?
    – She’s allowed to try on anything she wants, but she also has to try on things I pick.
    – I don’t limit our shopping to stores geared toward her age group. Right now her favorite shirt is a pink, flowing bohemian style shirt that we got at a store that is usually frequented by middle aged women and older.
    – I remind her what she has at home that would work well with whatever she’s trying on. She loves boots – she has 5 pairs! – and I’m forever pointing out which pairs would work with whatever she’s trying. (In the case of the above mentioned blouse her skinny jeans, her black combat boots, and a black pleather jacket were the items I referenced in the fitting room).
    – I resign myself to the fact that she might buy things that will either only get worn in the house or under a giant sweatshirt. It doesn’t mean that she doesn’t like them. A lot of times she loves the item but hasn’t yet worked up the confidence to wear it where people can see it. There’s comfort in the familiar.

    It’s worked for me. This year she’s really opened up. The sweatshirt has come off and she’s actually got such a wide variety of stuff that’s hard to pin down her style. She likes it because a classmate told her that she looks very “European” and to her that is the highest praise. LOL!

    1. Finery recently changed formats, so I don’t know if it is still as helpful as it once was, but you can take pictures of stuff in your closet and have Finery on your phone when you shop, so you can see what might match or look good. You can also set it to scour around and automatically upload stats and photos of stuff you buy from your favorite stores online, like Amazon. To be honest, I didn’t want to put the time into taking a photo of everything I already own, but, next time I move households, I might consider it.

    2. I was similar when I was in middle school, re: using very large sweatshirts to cover my body. I remember my mom once remarked that she knew a certain green shirt was my favorite because it showed up in the laundry the most!

    3. I certainly did a fair amount of the camouflage clothing as a teenager. If being noticed gets you picked on or hassled then a lot of us adopt clothing to hide in. If the only place she’s comfortable wearing the nicer clothes is where none of her peers will see, then that’s cool. Whatever she needs to feel safe and comfortable. Sounds like she’s finding a bit of courage.

      1. I did too. I remember my mother getting angry with me when I reached for the same hoodie every day. I promised myself that I would not do that. Sometimes I literally bite my tongue to keep from saying anything. I think it’s working…last night she told me, in the most nonchalant teenager way, that she’s the happiest she’s ever been with her body. I gave her the fist bump of pride, got up and went into my bedroom where I did the mom dance of joy! .

  50. I got a Tim Gunn book from the library one day, (‘A Guide To Quality, Taste, and Style’) read it all in one sitting and then immediately ran to my closet to clean it out. I highly recommend it to everyone, and it’s very novice-friendly. Tim’s a very engaging writer and just seems like a lovely person.

    The basic steps of the book are:
    1) Try on EVERYTHING in your closet. If it doesn’t make you feel good to wear, it DOES NOT go back into your closet. Instead, you put it into one of two piles: Donate (for things that are irredeemable for you) or Tailor (things you would love if they just fit right). Get rid of the donate pile, and take the Tailor pile to your local tailor and see what can be done!
    2) See what is left in your closet. What specific items are you missing to make complete outfits you would wear? Tim has a short list of categories to help you think of what you’re missing.
    3) Go shopping (or have made) for those specific items. Only buy them if they make you feel good.

    I ended up getting rid of 5 bags of clothing! I love the book because it doesn’t make any judgements on your personal style (Tim does have one or two fashion vendettas, but found them humorous rather than oppressive.), but rather just tells you to only wear things that make you happy and helps you target your shopping (if you hate shopping, or you over-shop). And it really helps me in the morning when I’m getting ready because I know everything in my closet fits and looks good, so I can dress on auto-pilot while I wait for the caffeine to kick in. (Also, my friends had a field day going through my ‘donate’ pile. Things I hated on myself looked AMAZING on them!)

  51. Off topic, but Cap, you posted a link to that article about not having to be pretty a few years ago and it legit changed my life. So nice to read it again now and find that I know all the things it said in my bones, where before they were revelations. ❤

  52. marie kondo honestly got me on the path of fashion truth, by making me realize that everything in my closet should be delightful to me, not a boring thing i have out of obligation to be “normal.” (this approach might mean a rainbow of bucket hats if it turns out that’s where her joy lies!) secondly, I’m in my 30s but the advanced style Instagram account and books, which feature older peeps, have been HUGE inspirations. honestly i would just scroll through that insta with your mom and see what makes her go “ooh i love that!!!”

    1. Me too! Combined with winnowing my wardrobe down to a capsule of colors I LOVE in styles that feel good, from my previously bulging closet of things that “almost worked” made me so happy! It’s a bit harder that I got into sustainable/non sweatshop clothes simultaneously so adding new things is harder, but feeling good about the look and the societal/environmental impact of my clothes has made me feel so much more at home in my skin.

  53. P.S. to C.A. — THANK YOU SO MUCH FOR A FLUFFY / NICE / HAPPY QUESTION. Did not know how much I needed one until you bestowed one. You are the best.

  54. Part of what’s helped me be more body-positive about my own clothing choices is developing a tiny bit of a fashion vocabulary—e.g., learning that dresses where the waist is high up and closer to the boobs are called “empire waist.” That way, instead of saying, “I don’t like the way a lot of regular-waist dresses look on me,” I can say, “Empire-waist dresses make me feel really confident!” And then I can more easily seek out those styles because I know what they’re called. It’s also helped me to have a few go-to brands where I know my sizing and know the quality’s good. That way, instead of getting discouraged by sifting through all the pants ever, I can browse a few specific sites/stores and watch out for coupons and sales.

  55. Well, I’m going to be stalking the comments here since my lovely, unfashionable mom (61) asks me about this every few months, bemoans not having anything to wear, and wants help (kind of) but also feels bad about shopping (because of horrors of consumerism – totally fair – and wanting to lose weight first, which is an attitude I am wondering how to counter supportively/constructively… she’s healthy, active and lovely, and I want her to feel that way, bu she doesn’t and I am not sure what to say).

    1. Stacey and Clinton from “What Not to Wear” had a great line: “Dress the body you have now.” Some of their advice was definitely problematic from a body-positive POV, but that line has always stuck with me. Tell your mom she deserves to feel good about what she’s wearing RIGHT NOW, not once she loses weight.

      1. I agree. And Stacey really liked to push pointy-toe shoes which, I am sorry, do not work for all feet. This is a case of doing what works best for you and your body, and not doing something just because a style guru tells you to. I don’t want bunions, so I own very few pointy shoes!

  56. I’m in college. I’m also 40 and started exploring my style a couple years ago. I found that thrift stores are a good place to find the most amazing assortment of things to try out for cheap. Admittedly, I also have my selection pared down a little by apparently not being a very common size, but it’s still more varied than what I used to wear. I do my best to try things on when I can, but with things like elastic-waist skirts, it’s less of an issue. 🙂 I’ve made some missteps, but that’s ok… it was like $4, I tried, the world didn’t end, and I can give it away or re-donate it, and I’ve learned something about what works and what doesn’t, so I continue on with more knowledge.

    1. I agree with this. In grad school — trying to figure out what my professional style would be — I bought a bunch of things at thrift stores. Sometimes they worked, sometimes they were an experiment that didn’t (I didn’t want a suede blazer, it turned out, even if it had been altered by chance so the sleeves were exactly the right length, and I was never going to wear that neutral animal print cardigan). But the process of looking through what was often full of so much variety helped me train my eye differently.

    2. Seconding thrift stores for experimentation: I recently cut my hair quite short, and a lot of necklines I formerly liked are not making me as happy, so I’ve been experimenting with mens collared shirts (button-fronts & polos). My hips are pretty wide compared to my shoulders, -and- a lot of collared shirts literally give me headaches (have not yet been fully able to pin down the parameters of this; some don’t), so I have been digging through the racks and trying a variety of things on, and experimenting with home alterations.
      Discoveries: polos are weirdly hit-or-miss; I like wide-ish white-and-one-other-color pinstripes; I like more dad-plaids than I thought I would; I think certain collar sizes work better for me than others, and tailoring tailored shirts is hard. But I now have about four collared shirts I like wearing for work (and god, they’re easier than a lot of traditionally-women’s styles), some partially-successful alterations, and some ideas for purchasing more intentionally – and I’ve only spent about $30.

      1. I find that if a collar is tall enough at the back, it pokes my hair all day. Finding shirts that don’t impinge upon my hairline is amazing!

  57. The color seasons idea has been around for a long time and is a simple way to find flattering colors and simplify shopping. Plus, I no longer feel bad about almost every single thing in my closet being navy or white, lol.

    A fashionable friend was happy to help me at a time when I’d been really out of it clothes-wise but wanted to spruce up and didn’t know where to start. She encouraged a little flurry of scarf buying. Buying 2 or 3 scarves was inexpensive and low stakes but let me experiment with color and style while feeling instantly dressed up and pretty.

    Collecting pictures on Pinterest was a great help for me to experiment without risk and find a new, cohesive style that I felt happy with.

    1. When I was in high school I took a sewing class. The sewing teacher and art teacher invited a fashion designer to speak to us about the seasons of color. I remember going into it thinking “this is stupid” but walking out thinking “that was interesting”. I learned that colors are important. I was wearing a pink sweater the day of the class and the woman asked me if when I wore it if people asked me if I was sick. They always did! She said that while I could wear pink I would need to lean towards certain shades and avoid others because they weren’t flattering to my undertones. I don’t remember what season I am but I do remember that I am a “cool” and not a “warm”.

  58. Honestly, one of the biggest turning points re style was when I realized that I wasn’t obliged to wear every damn thing in my closet that I got from Cousin’s Friend’s Daughter’s Pet who didn’t like it anymore. I could just throw it out (well, I don’t throw it out but rehome it somewhere so the cycle is unbroken) and wear only stuff that I like and that suits me and and doesn’t feel unconfortable on me!
    Coming from a “Let’s be resourceful” Home that was really, really hard to learn, and I’m still struggling with it. Even worse was it when it wasn’t something I “inheritated” but someone/me myself had bought for me. I could imagine that your mom has some similar hang-ups re “But it’s still wearable” and “but it was expensive!”, many women have them because they have been taught to be “modest” and to not be “vain” etc and basically to never have wishes or inconvenient opinions.

  59. The internet just ate my reply, so here it is again – feel free to delete if the original one shows up. I love Stasia Savasuk, who recently did a TED talk on being allowed to take an interest in your appearance – it changes how you feel and act, and these are important things. She had a website and blog, with more details of her story (her daughter has visible and invisible disabilities, and through watching her daughter find ways to express her identity through her appearance, Stasia got interested in her own style – it’s much more interesting than that sounds).

    1. Ah, I searched the page for Style School (the name of Stasia’s class) and didn’t see it so also just posted a reply mentioning her class and her recent TEDx talk. She is also super active on Instagram. I knew I could not be the first person to recommend Stasia and her work!

  60. Just wishing that you could make moderation rules for all social media and all Thanksgiving dinners. Thanks CA for being your wonderful self!

  61. Maybe it would be easier to give comments to your mom if you focussed on the positive/new directions? Like re: the bucket hat, “It looks fine, but I’d love to see you try a cloche instead”, “It’s ok, but I feel like you’d really shine in in a straw sunhat”, or whatever it is.

    I am on a big wardrobe and style journey atm, and I am loving it. However, it’s very involved, means lots of introspection, reading blogs, pinteresting, etc etc. Does your mom actually want to do that? It sounds like she asks you about specific style choices, but she’s not necessarily looking for you to be her personal image consultant and/or wardrobe overhauler.

  62. I have issues spending actual real money on clothes when there are so many other valuable ways to spend it. I’ve learned to watch Facebook sale sites and visit thrift stores to find options that I might enjoy so I can try them out. This has been especially helpful as I transitioned from nursing to a professional role and needed to change my wardrobe from jeans/t-shirts/scrubs to business casual (I had ONE suit for job interviews so I was building from scratch). It meant that if I tried something because it seemed okay, until I had to wear it in front of people, I didn’t feel very attached because it cost a lot of money. In a few cases, it led to me going out and buying new ones from the actual retail store because now I knew I loved it (such as my favorite dress pants ever).

  63. LW’s love and affection for her mum shines through in the way that this letter is written!

    I adore clothes (and am a rampaging feminist and do not feel that my clothes enthusiasm is an affront to the sisterhood), but finding what was right for me took time. Things that helped:

    Understanding what colours make me happy and light up my face – perhaps you could ask your mum which colours in her wardrobe she is drawn to when she is feeling her best?

    If you have the means to do so, treating your mum to one or two quality, well made items (that still feel wearable vs “save for best”) might make her feel good – she deserves nice things! I liked the suggestion of putting together a first date outfit that she feels confident in, that could be shopping in her own wardrobe together or getting something new.

    Your mileage and budget may vary, but a friend who lives in yoga pants needed to get a new work wardrobe and so, after some online research, found a personal shopper in her budget with good reviews. She set boundaries up front about what she was and wasn’t ok with and did and didn’t like. She found it really helpful to be able to sit in a quiet fitting room while someone else braved the busy shop to find her clothes to try on, and had good steer from a neutral third party about what cuts and colours to look for when shopping solo.

    As others have said, I love https://www.advanced.style for showing photographic evidence that age does not mean fading into the background! Your mum’s green eyeliner sounds cool.

    Wishing her the best for dating!

  64. Along with the digital image curation: if she has photos of herself and is comfortable with the idea, pull out photos from her collection that she especially likes, and quiz her about what specifically she likes about those? Color? Line? &c? That might make a useful frame around future searches.

  65. One small additional suggestion: somebody having a style goal of “meet mainstream standards of stylish/attractiveness/beauty” is okay. Please don’t shame somebody who wants that. A lecture of “but you don’t neeeeeeeeeed to worry about that” or “it’s not heeeeeeeeeealthy to care about that” isn’t going to make them want something different, just feel bad about themselves for not being “evolved” enough. Whether they want it because they have been infiltrated by the messages of society around us that that’s something they need, or whether it’s just what brings them the most joy, nothing good comes from trying to browbeat someone out of feeling that way.

  66. Does she want to find a personal style or just fit in to current social norms? If the latter, scripts like “I know you love bucket hats, but they’re not in right now [substitute “are only in style for teenagers right now” as appropriate], so wearing one would be A Statement; only you can decide if that’s a statement you want to make”. Like, I am team at-waist boot-cut jeans forever; I do not care if they’re in or not. Whereas I’m happy to go with whatever the current zeitgeist is on length of skirts as long as it’s long enough that I don’t have to worry about showing my underwear if I bend over without thinking.

    1. That’s a good point. I’m thinking of this as three axes: expressing personal style, fitting in/looking good by conventional standards, and comfort/practicality. Maybe a fourth axis for price. It’s hard to offer good fashion advice without knowing where a given person’s priorities are.

      I’m not sure whether subculture fashion rules/signifiers fall under person style or fitting in.

  67. Happy/successful shopping story: Several years ago, a bunch of similarly curvy friends and I decided that we wanted to take on swimsuit shopping. We had all had traumatic experiences doing this over the years and we decided to band together and be the Swimsuit Personal Shoppers we’d always dreamed of.

    We had two rules:
    1. Be adventurous and try on every possible style.
    2. If the rest of us didn’t think something looked great, we were to say, “I bet we can find a more flattering style for you.”

    We went to a whole bunch of stores and not only did each of us find a swimsuit that we loved, it was the best experience ever, and forever changed the way I feel about swimsuits.

  68. My beautiful mother, who died in November 2017, dressed very nicely, and rocked bright colors and animal prints. A few times, I’ve told young coworkers wearing, say, cheetah print, “If you sense a petite, redhead, presence around you, it’s my Mom admiring your shoes/leggings/top.”

    So, I don’t have anything to offer the LW, and I miss my Mom.

    1. I think you have offered something. Thank you for telling that story, and I’m sorry for your loss.

  69. Chiming in with “you MUST try it on,” because even the same general style of shirt from two different makers will fit differently. Bodies just aren’t the same, so when you find the brand that makes what fits you, make a note of it. Once I put some actual time into trying different brands of the same thing and finding my fit, things got so much easier. I could walk into a store and think, “I’m not going to the “Brand A” section, because those things don’t work for me; I’m going to the “Brand B” section where a lot of stuff fits.”

    Also, for the sake of sartorial fun, I’m just going to leave this here.

  70. I am working on improving my personal style and it’s a long, tough, expensive project. But the things that have worked for me:

    – Finding people with a similar body type to my own who I can follow – both to see what I like and what I don’t like, style-wise. I can admire the fashion choices my friends make and still understand there is no way the things they own would look good on me (literally, I have a specific friend I love shopping with because anything that she doesn’t like on her body will look great on mine and vice versa – it’s very common to hear one of us say, “I hated this on me, I grabbed it in your size for you to try because I think it’ll look awesome on you”).
    – Pinning the heck out of things *from stores I know make clothes in my size and that regularly make me feel good when I wear them*. I do have a general style inspiration board, but a more specific “I want to actually try/buy these things” board helps me see my whole closet come together.
    – Understanding that my style is my voice to people who don’t know me. Maybe your mom’s style is “Friendly, funny woman who doesn’t like squinting” – that’s cool! Once I decided on the voice I want (kinda retro, kinda punk, not too fussy or layered), it was easier to narrow my shopping trips down.
    – Giving myself permission to stop when I start to feel shitty. I don’t HAVE to do any of this, it’s not a requirement for anything, so when it starts feeling bad, I can leave. Full stop.

    When I have friends who have helped me with this, the only thing they can really do is ask questions. “How do you feel in that?” is great. “What would you wear with that?” is solid when it’s not critical but actually helping me design an *outfit* instead of just buying mismatched pieces. “Do you love it?” is also great.

  71. Oh, this is such a lovely question!

    I think the Captain has some great suggestions here. Maybe something to think about when you mom asks for advice is, what advice is _she_ looking for?

    Family and fashion advice and personal taste is such a sticky wicket. It’s often easier to get direction and advice from impersonal sources (blogs, books, personal shoppers), because self-image and family dynamics and approval are precariously entwined.

    So, if your mom.is just looking for easy-to-answer feedback like “are the sleeves on this jacket too long?” And you can give a neutral, non-judgmental answer, you should feel free. But if you get the sense that she is seeking your approval of her bucket hat (and by extension, her life choices in general), or if she’s feeling lost and wants to be told what to do, you might serve her needs better by asking how she feels about what she’s trying on, what she likes or dislikes about it. If you can position yourself as a “fashion therapist” and let her process her feelings out loud, that may be the most helpful for her in developing a personal sense of style.

    And it’s okay if you can’t! Its perfectly fine to seek out a sympathetic-seeming salesperson to play that role for your mom, and you can allow yourself to step back and just offer supportive compliments or intervene if the salesperson is too pushy. A good salesperson not only has experience helping people pick out clothes, but has the advantage of not being your mom’s daughter. Sometimes it’s easier to be vulnerable to a pleasant, professional stranger than it is with family, because humans are messy creatures.

    Worst case scenario, your mom decides to stick to socks and sandals and bucket hats, and be one or two people’s shot of whiskey, rather than most people’s cup of tea. Which is, really, a pretty good worst case scenario.

    Best of luck to you and you mom! (And now I want to go shopping.)

  72. Yesss I have a degree in this stuff! Growing up, my mom would sometimes lament her lack of style, and I had a hard time with that because I wanted to help her, but I didn’t quite understand her yet. My mom is not trendy. She doesn’t like cap sleeves. She doesn’t really wear dresses. But what she does want to be able to do is put on a pair of jeans and a blouse that fit her well, and feel like she can exist in the world without worrying that she looks out of date or poorly dressed. Over time i got a better sense of styles and colors and garments that my mom was comfortable with, and learned to help her find things in those parameters that were also incredibly classic and well tailored, things she could throw on without thinking and still look great. I also learned to work within her limits on patience- when we go to a store, we are not spending all day. She can’t do that, she wants to be outside. So we will go in looking for a knit top or a pair of loafers, not to try on the whole store. And always always thrift stores, but with the reminder over and over again to her and you that if you don’t find anything, it’s ok! Thrift stores give you a range of unique clothes at a small price so if something doesn’t work it’s not big deal. My biggest advice- help your mom learn to dress for HER. Be patient, be supportive, and don’t try to make her stylish in a way she isn’t. Make her stylish in the way that works for her life and her comfort!!!

  73. LW, this is such a great question!

    I go through fashion revolutions every few years, mostly for gender-related reasons (my gender oscillates from super dapper to super femme and back), and just had a BIG one when I turned 40. While on a femme kick, I decided I was absolutely done with dressing in ways that made my body the center of attention, and from now on I was going to dress in ways that made what I was wearing the center of attention. I’ve spent a quarter-century wearing dresses with the same hourglass silhouette and muted winter palette, all in solid colors, because that was what I’d learned was most flattering to my shape and coloring and got me lots of compliments on how great I looked. Now I’m diving into patterns of all kinds, new colors (I bought a tunic with flame patterns in bright orange! I’ve never worn orange in my life! I love it!), and relaxed styles that are extremely comfortable around my middle. THIS HAS BEEN SO LIBERATING. I still get compliments, but people compliment my clothes and attitude instead of my body. To be clear, I really liked being complimented for my body when I was in my 20s and 30s, and that’s an absolutely valid way to dress! It’s just not what I want for my 40s. If your mother is looking for new ways to dress for her 60s, she might want to try an attitude shift like that.

    What really changed my perspective was dressing my toddler in any and every color and style, and realizing that any and every color and style looked good on them. They wear bright orange and pink one day, and bright green the next, sometimes dresses and sometimes polo shirts, and no one cares, because the toddler is unaware of any factor other than “these clothes keep me adequately protected from the elements” and so always has an awesome attitude no matter what they’re wearing. When I realized the same could be true for me, my whole world shifted.

    I started by shopping on eBay and in thrift stores so I could experiment without breaking the bank. Thrift store trips can be a blast to do in good company, so maybe you and your mom could try that. I shared photos with people I could trust to be honest about what looked good on me and what didn’t. I didn’t hesitate to put back or return the clothes that didn’t flatter or felt uncomfortable. I understood that this was an experimental stage and that meant there were going to be some successes and some failures, and none of that was my failure—as others have said, it’s about the dress not fitting you, not about you not fitting the dress.

    I’m diving into the current fashion for tunics, because they have plenty of room for just about any body shape; my bottom half is four sizes larger than my top half, so it’s really nice to have a style that both fits my shoulders and accommodates my hips. Zulily has some gorgeous, inexpensive tunics and A-line dresses up to size 3X. I have black leggings, boots, flats, and sandals, so I only ever have to pick out what tunic or dress I’m going with and wear the right shoes for the weather, and I automatically look stylish and coordinated. I also wear men’s jeans for their deep pockets and throw a flowy tunic or short dress on top to femme it up. In the summer I did the same thing with plain cotton beach cover-ups, which are long enough to look like actual clothes and comfortable enough to wear to bed. (In fact, most of my dresses can and do double as nightclothes, which is great for those days when I roll out of bed late, work from home for a few hours, and realize I don’t have time to shower and change before I run out to daycare to get the toddler who’s just going to get snot on my clothes anyway—so I leave my nightshirt on, pull on leggings or jeans or shorts, and go.) I got some thigh savers from Thigh Society, which I think I saw recommended here?, and they did indeed save me in the hottest parts of the summer when jeans and leggings were unbearable.

    I also bought some dresses on eShakti, which makes clothes to measure. My first dress from them had to be remade three times (at their expense) while they figured out how to size it properly to my chest and shoulders, but once it was done, it was magnificent. Now they have my correct measurements on file and I’ve gotten several incredible dresses from them. They have a huge range of styles and put new ones up all the time, and you can modify necklines and hem lengths and sleeve lengths as well. Scrolling through their website can be pretty trippy because it ranges from “simple and elegant” to “plaid with tassels”, and is another fun activity to do with someone else so you can exclaim over both the glorious and the dire. My mother’s birthday present to me was a “shopping trip” of looking through my eShakti favorites and picking out the three we both liked best, and it was a great way to spend an hour. Their return policy is very good and their customer service is excellent, they (at least claim to) pay their labor fairly, and they have constant sales on top of their already very reasonable prices.

    Do make room for your mother to find her own balance of flattering and comfortable, and to experiment and explore. If she loves that bucket hat, let her wear a bucket hat! Life’s short. Have fun.

    1. Great comment, and I’d like to second eShakti. They have lots of natural fibers (I think you can filter for this). In addition to the option of making clothes to your measurements, they give options for sleeve type/length, neckline, hem length, and presence of pockets in most dresses (!!! at no charge!!!). If your mom has some idea of what styles she likes but doesn’t see them in stores or it’s hard to find them in her size, this could be a great option.

      (Side note: eShakti manufactures in India and seems to offer fair wages and good working conditions. I was worried at first that affordable custom-made clothing was only possible if someone was being taken advantage of—but it seems like they can customize easily because they have good technology (e.g. embroidery machines, good procedures for handling customization) and skilled workers (who have a lower cost of living than in the U.S.).) (Typing this paragraph reminded me just how overwhelming it can feel to simultaneously feel like I’m supposed to be frugal and globally- and eco-conscious, while also finding clothes that are appropriate AND express my individuality AND conform to fashion rules AND…. This kind of overwhelm or ambivalence would probably be helped a lot by the LW’s affirmation and encouragement.)

      1. The one thing about eShakti that’s hard is some of the clothes don’t drape/fit well on different frames. I’m super curvy, and found these *amazing* dresses (chelsea knit I think) so I bought three durinf a mega sale…but less stretchy fabric dresses have not worked for me. Some of their stuff doesn’t even look right on their models, so it’s like any other clothes maker—gotta see how it looks on people! But they’re great on returns and customization (and have regular free customization sales!) so I love them anyway 😉

  74. This is my style advice. It’s not a “top 10 hot looks of the season” it’s a life long mantra. When you go out to the world people view you based on your looks. So how do YOU want the world to view you. Who are you and how do you want to visually convey it.

    We also live in a visual culture, so use it to help you. Think about who you really are and how would you like to be viewed and then think about other people/movie characters who are similar archtype. And then look up their inspiration and inflinces and their inspiration. Expand your visual vocabulary.

    (Im on mobile so sorry for any typos)

  75. I have a background in design, and have helped multiple people pick clothes, and one good friend redesign her wardrobe. When I do this kind of thing, there are two techniques I use primarily:

    The first is I focus strongly on the purely technical, which is to say color and fit. Is the color (and by this I mean that very specific shade, hue, and intensity – it’s not as simple as “having your colors done”) flattering (check under multiple light sources!) and does the item fit the individual body in question. Actual style I encourage the person to develop for themself.

    The second is even more important – I explain *why* a given color is off for them and *where* the fit problem is, and then I use concrete examples (see: try everything) to demonstrate how differences that may seem invisible to the untrained eye make a significant difference in how they look and feel.

    The final point should be basic, but is also vital. They are the boss of them. If a garment doesn’t fit properly (and tailoring isn’t possible), or the color is not fully flattering, but they like it anyway, great. Loving one’s clothes is more important than any other detail. And I respond to guidance rather than guiding. Someone wants to downplay a trait? I can help with that. Saying “flaunt it” when they are uncomfortable is not helpful. And saying “cover it” when they feel awesome is cruel.

    My job is to help someone else look their best by *their* definition, not to treat them as living dolls. Only actors and models at work are put in clothes without regard for their tastes, and they are paid for it (uniforms obviously excepted, but there payment still applies).

  76. Oh also, when offering advice (when asked!!!) on what someone is wearing, I try to stick to descriptions of fit and proportion, not descriptions of the body in the clothes. “I know you love that bucket hat mom, but if you want to feel fancier, I think something with a wide brim would frame your face in such a lovely way!” Or “See where the waist is cut on this dress? I think if we found a dress with a drop waist instead of an empire, the lines of your outfit would flow better” or even “I know you love pink! I bet if we tried that shirt in a dusty rose it would go with even more stuff than the neon pink one you are wearing now and would be so much more versatile.” Those sound so much better than “Your bucket hat is kind of ugly Mom” and “That dress isn’t flattering.” They are actionable suggestions that criticize neither the garment nor the wearer and no one gets their feelings hurt.

  77. I don’t have any advice, but the beginning of your letter really struck a chord with me – my oldest child (who just turned 4) recently informed us that she was assigned male incorrectly at birth. She also started pre-school this fall. She was really upset by the idea that people at school might think she was a boy and so I told her that if we told everyone she was a girl, and she dressed in girly clothes then everyone would know she was a girl and so far that has been true. But I hate for any child of mine to feel like she has to perform femininity to be properly seen as a girl. The feminist in me, who believes that everyone should wear what makes them feel happy and comfortable, is buying pink and ruffles to make sure that her daughter is girly enough to pass, is so outraged at the idea. But then again, pink ruffle skirts do seem to make my daughter happy, so I guess that’s all right then? I can’t wait until she’s old enough to pick out her own clothes at the store (Don’t tell me that she is currently! She does not handle stores well, just trust me on that one).

    1. Whoops – hit submit too soon.

      The bucket hat comment reminded of this article about the fashion trend / concept menocore. It’s a little off topic, but I love the idea of younger women looking to older women for fashion inspiration. And it gives a nice overview of how someone put together looks based on several different inspirations.

  78. I don’t have a lot to say, just YES x 10000 to offer your mom to go through her closet *together* so she can have your support and opinion (which can 100% be “I think they all look great on you, how do YOU feel?”) as she finds out that she doesn’t like that sweater’s colour anymore, those boots are actually great and she had forgotten she had them, what she really would like on that skirt is a purple blouse so-and-so, etc. IME, going through my wardrobe gives me a very nice feeling AND a rough idea of the style I’m looking for (plus it makes room for new clothes and I can pass on the ones I no longer want)

  79. Ps love this question and the video, and although my mom falls a lot into the “good/bad for your body type” bullshit, now I miss her and want to take her shopping.

  80. I was never fashion confident but I needed to update my closet pretty completely shortly after menopause. I found that things that used to fit just didn’t look right after all the shifting around. First, I’d pretty much quit wearing heels and switched over to cowboy boots (so comfortable for me! even at work! who knew?) Clothes were harder. Things that helped: I found a local branch of a used-clothing chain which accepted fairly recent clothing, and resold it in the $10-$25 range. Then I tried on a bunch of different things. At those prices, if I got something home and it didn’t work, I could pass it on without guilt. I could experiment and discard. After I began to get a sense of what I liked and felt good in – and thus what probably looked good on me – I branched out to department store designer sales. Also, places like uniqlo and h&m were great for inexpensive update pieces. Ironically, now I’m wearing clothes I would have loved to wear 30 years ago, but then didn’t have the confidence that I could carry them off. Now I don’t care, which is probably what gives me that confidence now. If you can help give your mom that gift – so she feels like she looks good, whatever it is she’s wearing – it’s a precious thing.

  81. I have nothing to add (but a love of bucket hats/cute femmes in cute bucket hats) but I love this question and the breather it is. Nice questions about nice problems at A+++ sometimes.

  82. The best two pieces of style advice I’ve ever heard both come from Tim Gunn– one when he did an AMA on Reddit and the other in an interview on NPR. The AMA, he emphasize “quality over quantity,” and saying you only need to have twelve (or maybe ten?) outfits. I forget the exact designations, but they were like, five suitable for work, one for an outdoor cocktail party, one for a fancy party, one for not-fun formal events (funerals, board meetings, etc) four for after-work casual times. YMMV, but the gist was, consider the settings you wear clothes in, and then choose the ratio of outfits based on how often you’re in those settings.

    The key is, make sure each outfit fits your body; spend the money you would have spent just buying tons more clothes and use it to pay to get your clothes tailored. Also, pay for higher-quality, longer-lasting fabrics. According to Gunn, nobody will notice if you wear the same five outfits to work every week; they *will* notice if you keep an outfit in rotation after it starts getting holes or stains, which people are tempted to do when their clothes take on damage quickly after buying them.

    The other advice was, “You don’t have a fashion statement. You have a fashion story.” So, if you’re a character, and you’re in a setting, what are your clothes communicating about your character in that setting? There’s no “wrong” story–but, there *is* accidental miscommunication. This is especially true with clothing because the social cues of clothes can be as hard as any other social cues to pick up on, but the particulars of the message will change depending on your setting.

    So, take the bucket hat. Bucket hat says, “I like hiking, fishing, or sailing, but I’m only middle class or working class.” Or it might say, “I’m oblivious to trends (because I spend so much time outdoors, or because I’m at an age where nobody expects me to keep up with trends, which I find a relief, rather than an insult.)” On a woman, it might say, “I like expressing some of my androgynous / masculine energy, but in a pragmatic way rather than a ~provocative~ way.” This goes double if she also wears cargo shorts.

    Because it’s so unfashionable, a bucket hat can come out the other side seeming playfully confident, or someone has a sense of humor about themselves and doesn’t take themselves too seriously.

    On the other hand, bucket hat does *not* say: sexy, professional, urban, sophisticated, upper class, powerful, feminine.

    Maybe the bucket hat becomes a bit of a shield (now I’m riffing, I’m not talking about your mom specifically). If someone says they want to be seen as sexual and powerful, but they wear a bucket hat, it’s almost like the thing where someone avoids trying 100% because they’re afraid that failing when they *really* try means they *really* fail.

    Many episodes of ‘Tim Gunn’s Guide to Style’ are on this theme: people both want to look more sexual, powerful, or sophisticated, but they’re also afraid of some element of those styles, some insults hurled at powerful or sexy women. Or they’re afraid they are fundamentally un-sexy or unsophisticated, so trying to look that way will out them as a poser or a wannabe. These episodes are about getting someone to face their fear.

    On the other-other hand, there have been episodes where people say they want to be sexy and feminine but, in truth, they don’t genuinely want that. They just think that’s what they’re supposed to want. In fact, their deepest story is more about androgyny, a-sexuality, a transfiguration into a completely new being disconnected from their current culture. Acknowledging that, and embracing the vulnerability that kind of minority-ness can bring, allows them to bravely choose a style that reflects their truest self.

    And some episodes are about people caught between cultures, and the values and aesthetics of their multiple cultures. Understanding who they truly, distinct from their family, friends, and coworkers, can help them write a fashion story where they can demonstrate where they come from and belong, while also emphasizing their unique thoughts and desires.

    ❤ Whatever you choose to wear, make it work

    1. I watched What Not To Wear religiously in the early ‘aughts and despite it’s many faults, sometimes I miss it – this sounds even better.

    2. I’m going to look up those interviews, sounds like a ton of excellent info and advice. Thanks for posting this!

  83. When shopping with friends, if they ask my opinion (and only if they ask), and I don’t like the item in question, I’ve found “I think you can do better,” to be a gift. It emphasizes that it’s the clothing, not the person that isn’t working out, and isn’t too negative (I hope).

  84. An honest and kind reply to a request for an opinion can be “the (article of clothing) doesn’t do you justice.” Nothing is wrong with you, all bodies are great! Just this particular item is not worthy of your awesomeness.

  85. At least in the US, it is super easy to return clothes to the store (granted, tags on, with receipt, within 30ish days). Sometimes, if there’s something that I am on the fence about, I just remind myself that I can take it home for a few days and try it on in my own bedroom before I commit to keeping it. You’re doing great!

  86. I have two thoughts to contribute. First, “What will I wear on my body” was a thing that got significantly easier after reading The Art of Manliness’ styleguides on building a wardrobe. This helped a lot, personally, because I’m gender fluid but mostly play femme or androgenous, yet really, really love men’s fashion. An unexpected result of reading those guides, though, made me think that getting dressed can and should be easy without sacrificing my sense of style and the chance of leaving professional, positive impressions. Plus, reading that made me understand some parallels I could create for myself that were feminine yet equally simple and reliable.

    Second, regarding things people have said that were helpful: “That’s not my favorite dress on you” style of response (that whole paragraph of advice = <3) is my FAVORITE to hear and to give. I was recently fitted at MM LaFleur, where this was the stylist's responses, and together we navigated my sense + what fit from / items the brand had. Her attitude made me feel like I had a fashion-savvy friend in my corner. Like, she recognized that the brand ran small and, as I apologized for having to incrementally work multiple sizes up (5 or 6), she said, "Oh no, there's nothing to apologize for. This is all part of the process. We're just going to figure out what fits and that's when the real fun starts!" And as we moved into dresses, they were all generally sheathe-style, which I don't find flattering on myself, but she didn't go, "Yup, that's terrible," she just observed me in the clothing and said, "Hmm, maybe not that. Let's see if I can find something else," and eventually, when I'd eliminated all the dresses but loved a lot of pants, skirts, and tops, said, "We definitely found a lot of great separates. And that firecracker red is your color!" Which I agreed with ^.^

    1. I’ve found that AOM is really good for breaking down different types of clothing- sweaters, pants, etc., and for helping pull together a wardrobe that covers your needs and wants without suggesting you should have a zillion looks if that’s not your thing. They’re also good at “this is a basic look for this sort of occasion,” so it gives you somewhere to start if, say, you’re going on a first date in October.

  87. LW, It’s a shame you don’t live in Australia as if I was in your position, there are only 2 shops I would need to take my mum to in order for her to get everything she wants, and at one of my local shopping centres, they are right near each other. Both have absolutely perfect clothes for a woman of that age for all sorts of situations ranging from quite formal to causal, and the clothes are so nice, I buy quite a bit from these shops as well and I am only 42. Anyway, have a bit of a think if there are certain chain stores where you live that really do cater beautifully to women of that age, and then just take her there and see what she likes. Maybe also get her to try on a few things that you like that might be outside her comfort range, just to give her a little push. She may end up loving them and thereby broadening her fashion range.

  88. Does she love the stuff she’s currently wearing? If she does, then great. Everyone deserves to have a wardrobe they love (in their size! @ the entire fashion industry) and be able to enjoy getting dressed. But if she’s defaulting to what she’s always worn because she doesn’t know what else to choose, it doesn’t have to be that way, and if she wants to change that there are tons of resources available on how to use colors and patterns and outfit proportions. Some of those resources are full of body shaming and not a few of them also shame any non-mainstream fashion styles. I wish I could remember which of the many (many) fashion books I checked out of the library were the worst.

  89. Things that have been most helpful for me:

    1. Developing really clear criteria for what I want to wear. The shapes and colours that I think look good on me (based on my own eyes, not “rules”), the sort of clothes that make sense for my personality and lifestyle, what I find physically comfortable. I’m particular about fabric and fit too – not everybody is and that’s fine, but for me it makes a big difference.
    2. Applying those criteria strictly. (Including taking the popular but rarely followed advice of throwing out every single thing that I didn’t love and feel great in.)
    3. Tailoring! In the past I passed up a lot of items I really loved because they were too loose in the waist or I didn’t like the sheer panel or whatever. Sadly I also bought a lot of them but never wore them because they weren’t quite right. No longer! It’s not too expensive either, I usually just take things to my local drycleaner or a place in Chinatown.

    1. These three things make a huge difference. Especially that second one – and I now don’t buy anything if I don’t love it right now AND know I’m going to actually do the alterations it needs. There’s a really cute dress on clearance at work that I would love if I took it up in the shoulders, deepened the bust dart, and made a sway-back alteration, but it’s fully lined lace, and I’m not messing with taking that apart, so I’m not gonna buy it even if it goes down to $5.

      I’ve got some complicated fit needs such that nearly everything I buy that’s not a 3/4 or shorter sleeved* petite knit top or a full skirt needs to be altered, so I’ve learned to do my own alterations, but I have also come to accept that the time and energy I want to spend on that is limited. Anything that needs more than three things done to it or that I think would be complicated and/or frustrating enough that I’d keep putting it off and it would just hang in my closet, I don’t buy.

      Right now I’m also not buying anything that I can’t wear to work, because I’ve got more casual clothes than I can keep in rotation, and this weekend I’ll be doing a closet purge and wardrobe audit because the new dosage of my medication earlier this year has caused my body size to change.

      All of this stuff is work and takes effort, and I fully respect the people who choose not to bother with it. I happen to enjoy it and consider it one of my hobbies since I principally dress in vintage and vintage-style clothes. Lots of people find it suits them more to figure out a “uniform” that works for their style preferences and daily life, and then just stick to that.

      * I’m short-waisted and long-armed. If I want to wear long sleeves, I need a tall size, but then the entire torso of the garment doesn’t fit, so now even my winter coats have bracelet length sleeves because life is too short to be messing with that. I can however buy sweaters in the men’s department.

  90. I used stitch fix for a while and really liked it – I like fashion, but I’m also a) very lazy about actually shopping 2) often paralyzed by choice and, when in doubt or pressed for time, usually end up picking up stuff that’s almost exactly like what I own.

    The beauty of a box subscription of course being that they send it to my home, and somebody else picks it out. I did eventually stop, because the cost CAN be pretty steep, and I was having a bit of a hard time getting them to match my style (mid 30s and living in seattle, I tend to dress a lot more…young? Than they seemed to expect. I got a lot things that were nice, but ultimately made me feel like someone’s cool mom rather than an unattached nonbinary person) But! In fall and winter their warm but stylish sweater game is on-point! They also encourage you to make a pinterest/intsta/etc board just for them and link it, with examples of things you think look great – much like the captain suggests for LW’s mom. Especially nice since I can pin stuff while idly using the computer and don’t need to remember later that I liked it.

  91. I don’t wear makeup much and I’ve never worn makeup much, but I’m quite good at makeup when I do wear it, which I attribute in very large part to the Napoleon Perdis makeup/stylebook a friend loaned me a couple of years ago. (I’m sure you could find something similar at a library.) What I liked most was that it focused less on specific looks and more on the way skin care and skin requirements vary with age. Obviously, it depends on if she’s ever shown any interest in varying her makeup, but if she’s interested and just doesn’t know where to start, that was what gave me an indication of the handful of products I might want on hand for special events to feel nice but not self conscious or like I wasn’t being myself.

    As for general fashion, my only real advice is to emphasise the good Captain’s advice to find out how she wants to be seen, and learn to love that style rather than imposing your own. To that end, try to keep your advice to things she’s not sure about, rather than things she loves. If she thinks her bucket hats look great on her, let her wear those bucket hats, but if she’s tossing up whether or not to wear one, that’s where some gentle advice could work.

  92. My mother is a hair stylist/beautician by trade, and I am the daughter who always got the shortest hairstyle possible, never put product in it, and wore no makeup. It took us a long time to realize two things:

    1) She has a lot of expertise and ideas about things she thinks would look good on me, and it’s an act of love for her to share/offer.
    2) Pushing me on what I *should* do with my hair (e.g. “Don’t you want to look like a girl?” “You’re going to need to wear earrings if your hair is that short,” “You’re SURE you don’t want highlights?”) is hurtful and makes me feel like the way I prefer to look is ugly.

    With that in mind, I would say the best thing to do as the advice-giver is to ask and listen to what your mom likes best about her own looks and fashion. Like, “Mom, what in your closet do you feel most fabulous in?” “Which of these outfits makes you feel confident/comfortable/sexy?” Pay attention to what she says. If she has strongly favorable opinions about a particular style or outfit or look, I’d say don’t try to take that away from her. It’s giving her something important and intangible in her sense of self and her own image.

    On the other hand, it sounds like she’s coming to you for advice on elements of fashion where she has NO opinion or else a lot of confusion. That’s your place to shine! Get excited about styles you’d love on her and just approach her with that. Instead of “Wear this instead of that,” it can become “I saw this and I thought it would look great on you!” And then she can decide.

    My mom is doing my hair for my wedding next spring, and she just came to me and said, “I found this intricate headband I thought would look gorgeous on you if you want your hair up. Do you think you’ll want your hair up?” So this system has worked for us.

  93. 100% yes to helping her pin down her own fashion style/icons/goals. But also – make sure you know yours too. it’s easier to accept ‘androgynous woodsperson’ as a style when you realize you personally don’t like it because you prefer ‘refined executive’. My mom, sister, and I all have wildly different fashions, and I would never wear at least 80% of their stuff. But we’re pretty good at figuring out what each other are going for, and supporting each other in that goal.

    Also my association with bucket hats is Ariana Grande, which I think by definition makes them stylish 😛

  94. Dear LW,

    I’m almost 60. I haven’t worn makeup for roughly 20 years. I would bet actual money that more thought went into your mother’s presentation than you believe.

    I think your best bet is to keep schtum.

    The exceptions occur if she makes specific requests.

    Example :

    What about this [item] ?
    Good answers:
    Lovely !
    I like the green better.
    I think it’s too heavy for this heat.

    Not so good answers:
    Mom, no!
    Really mom?
    That blue looks bad.
    I think you should wear something that fits better.

    Makeovers aren’t easy, and a daughter may not be the right person to do it.

  95. I think one of the most important questions Is what image are you trying to project, My personal taste tends towards what most people would call loud, but some times That isn’t the image i need or want. I also only got into clothes in my mid to late 20’s because really thats when plus size started offering more options at a price I could afford and I gave up waiting until I looked a certain way to dress how I wanted to dress.
    Also and For me trying it on makes a big difference there have been things i loved on the hanger I hated on and the reverse.
    I have also tried to give up what I call aspirational clothing pieces those items which i think look cool on other people but I know will languish in my closet ignored and unworn. Sometimes you can like a style but it isn’t something that suits your life style. I love all the layered looks but i live in the hot hot south and layers are not my thing. There are somethings I think I look good in but I dont feel comfortable wearing for whatever reason
    Tailoring is nice as well I have really broad shoulders and generally when I get something that fits my shoulders it is a bit baggy everywhere else so tailoring is helpful
    Also looking into custom clothing particularly for formal wear can be less expensive than buying off the rack and having it tailored at least in the plus size world I have a perfectly tailored black it can be dressed up or down that cost me 100 yes it little pricey but I chose the color the skirt length the fullness sleeve length and with different accessories it is very versatile and I get a lot of compliments on it
    Some times just having some really nice basics you cant go wrong with whether plain or then adding whatever accessories makes things less difficult when it comes time to dress

  96. Lovely post

    My mother got her colours done as an experiment and ended up loving the result. She felt more confident picking out new clothes, did an audit and ditched a third of her wardrobe, and carried around this little swatch of colours for years after to lovingly pick new clothes.

  97. If there’s a particular garment your mom likes that you think is unattractive on her, ask what it is about the item that she likes.
    E.g. hat might be because she just needs extra sun coverage per her dermatologist. So then you suggest other shapes of broad-brimmed hats.
    Or crocs because of easy on/off with a wide foot…you introduce her to leather clogs & slides, and urban mocs.

    Let us know how it goes!

  98. For a long time, I didn’t feel great in my clothes and I didn’t feel fashionable. Two things happened: First, I started wearing clothes that fit me, nothing too tight and nothing too big. Second, I figured out what styles of clothes (dresses that emphasize the waist and flare versus a shift dress) are best for my body and what colors look good on me. I love gray but it looks terrible on me. My sister can rock muted and rusty tones but I always look best in jewel tones, navy, and black. I don’t buy anything if it doesn’t fit or isn’t one of my acceptable styles or colors. Shopping becomes so much easier because many options are eliminated immediately.

    One way your mother could figure out the styles and colors of clothing that work best for her and she feels best in, is subscribing to a clothing service. I did Gwynnie Bee, which I think of as Netlfix for clothes. I paid one monthly rate and had three items out at a time. When things came, if they didn’t fit, I could send them right back. If they did fit, I could wear them. Some things I only wore once and others I wore a few times. Because I wasn’t buying things, I was more adventurous in picking things out. It helped me refine my style and my color palette. I also learned what size I am in a wide variety of brands so I wanted to purchase something from a specific brand, I knew what size to select.

  99. My mom gives great clothing advice:
    1) Rarely – once every decade or so
    2) With examples / questions, like, ‘this is cute and I think it would look good on you, what do you think?’

    The woman actually persuaded me to wear coral pink during my turquoise & black phase – I had 2 pieces of clothing that weren’t black or turquoise – one pair of blue jeans and that coral pink, princess seam sundress. It rocked. I have never owned anything pink since, but I still have that dress tucked into my closet 30 years later.

  100. When I started my journey from call center work to a corporate office job I really had to overhaul my whole wardrobe. I went from jeans and gamer/pop culture t-shirts to slacks and tops/blouses. Nothing I felt remotely comfortable in without feeling “dressed up”.

    I had a couple awesome personal shopper friends, and the advice/feedback that helped most was when they got really specific about the details.
    “This pattern/colour looks great because…”
    “The cut/gather/shape compliments… really nicely”

    It helped put context around what features worked and a why. So I can take a particular colour or shape and look for that in a dressy blouse, or a casual shirt and dress how I want rather than going for specific pieces.

    Now that I write this out, oh boy does that ever sound like the old TLC show What Not To Wear! Haha

  101. Once I tried on a top at a store because I loved the print. I wasn’t sure about it, so I consulted a friendly (but not overbearing) saleswoman. She said, “You know, I think a brighter blue would really highlight your pretty eyes.” It was such a kind way of giving me her opinion that something else might flatter me more (and I wasn’t hurt because I wanted her honest opinion).

  102. I actually kind of had a similar situation once. My mother was 62 and we were all going on a cruise soon. She asked me (28) for some style advice, as I was working in fashion and she wanted to look a little more put together for this cruise. She tends to dress casually and somewhat … older? Lots of tshirts and sweaters with things on them, dressing up is like coldwater creek from the 90’s. She also will not spend more than $10 on an item of clothing and prefers to be under that, which means lots of thrift shopping, in a very small rural community (so not great selection). Knowing that she wouldn’t be willing to look at new clothes and dreading the thought of endless thrifting (I was also pretty severely depressed at this time), I kind of shrugged it off, acting like I didn’t really know what would work, and that it would difficult to find current fashions that she would like.

    She had never asked me for fashion advice before. She has never asked me since. I regret horribly that I didn’t take the time and try harder and accept what she wanted to feel comfortable and pretty in, vs what I thought she should. I still feel awful that I rejected her and probably made her feel hurt or sad, and I have no idea how to readdress it.

  103. Hello! I changed my style recently! Twice, and once was a good/comfortable change and once was a pressured/uncomfortable change.

    About ten years ago my style was extremely casual. My partner at the time (no longer, thankfully) was the master of the sidelong disparaging comment on my outfits. A desire to avoid those comments + a need to dress more “professional” at a new job led to me forcing myself into a style that really didn’t suit me. Even though the clothes fit well and would be a fine style for someone else, I felt self-conscious in them and disliked looking at myself in the mirror.

    Takeaway: pay attention to how your clothes make you feel, in your emotions!

    The second style transformation was spurred by me. I made a new friend who loves to chat about fashion. She really reshaped my view of personal style and self-expression. (Pretty basic stuff, like “you should feel good in your clothes and like how you look,” but I didn’t know that before.) I would ask her input on my outfit or about an item I was considering buying. When I was enthusiastic about an item but trying to talk myself out of it (like, “I don’t know what I’d wear it with, it’s nothing like what I wear, but I love it”)…she sent me links to whole outfits based around the new pieces I was liking. I loved them. When I started wearing new items that I wasn’t sure how to style or combine, she would offer constructive suggestions or assure me I was doing just fine. She would also remind me that even when items didn’t match the Style Goal, the real goal was to feel good and enjoy my clothes.

    Takeaway: it was very helpful to have a friend whose opinion I trusted, who offered good specific advice *when I asked for it* and wasn’t judgy.

    Other things that helped: browsing online clothing websites just to see all the options; trying on A Lot of things; taking little videos of myself in the clothes to see how they looked when I moved.

    Good luck!

  104. My daughter has a very distinct style, and she doesn’t like to have people pressure her to “be someone else.”

    I had the hardest time getting her to tell me what she liked when she was younger (it’s still a little hard sometimes, because she’s regressed)

    I finally sat her down and said, “I want to help you look for clothes–it goes faster when I can be part of the screening process in the store. So please tell me what you like. When I hold up a shirt and say, ‘Do you like this?’ I want an honest answer. And when I say ‘What don’t you like about it?’ I want an honest answer.
    “Because if you say you don’t like those gathers right at the bra line, I’ll stop suggesting those shirts. If you like the color, but hate the sleeves, say that. This is all data I am putting in the filters so I can help you. I really don’t care if you don’t like stuff I think is cute.
    “Oh, and sometimes when I say something is cute, I’m thinking about ME, not you. Or fashion in general.”

    But then I had to aggressively model this: “Ooh, look, this is your color–but it’s got those gathers at the bra line, so never mind.” Or even “I like this–it’s not your style, but it’s really cool!”

    So you might do something similar–tell your mom you want her to educate you about what she likes, for present-buying purposes, or so you can help her if she asks. And then sit down and look at pictures; or go to a store and play “who likes what about this?”

  105. I love the podcast “By the Book” and they just read “The Cultivated Closet”… which is a book about how to cultivate your own style. No pressure. No “don’t wear stripes”… just about finding your look. The clothes and styles that you love and that make you feel good.

  106. I am just starting to achieve The Way I Want To Look. I took basically two steps:
    1) A mega closet clean out. Think one step below KonMari– not *everything* in the closet brings me joy, but because of my job, it’s best to have a few t-shirts and jeans that I don’t mind getting destroyed by paint and adhesives. Everything else, I love. It means I have to do laundry more often, but that also means I’m wearing ill-fitting t-shirts I hate less and less.
    2) I started a Pinterest board called “Style Guide.” Every time I see a photo of someone and think “that outfit rocks!” or “they look so hot!” I add it in. Then I think about why– common themes have become: “all black with a small pop of color,” mixed metals, simple jewelry, bold lips, fitted leather jacket, high waist pants…things like that. Then when I’m shopping, it helps me narrow down what I’m looking for in the chaos that is the mall, because I’ve seen the general color schemes, patterns and fits I like.

    I don’t know how tech savvy your mom is, but when she asks for help, would it be possible to flip through some catalog and magazines and ask her which outfits she likes, and try to figure out why? I also think a gentle, “Mom, you look great in red!” is super helpful. I look awesome in jewel tones, but it was only when a friend pointed that out to me, that I realized that’s what those colors were called.

    Best of luck!

  107. I have always been unfashionable, anti-fashion, bored by clothes, put off by a lot of what was popular, and unwilling to be physically uncomfortable (including things like scratchy clothing or stiff shoes, never mind even thinking about stuff like heels).

    I am never going to be very interested in clothes, and never going to be willing to wear things I dislike to be ‘stylish’, but I do like wearing clothes I like the look of.

    A couple of things that helped me find more such clothes

    1) just looking at other people, especially women, physically sometimes. I tended to look at what they were doing and not really notice their clothes or hair or eyebrows or whatever. So now sometimes I try to just watch a bit. Just taking note of people or styles I like the look of. Like I might admire different architecture, or home decor.

    2) Second hand stores, other people’s clothes they’re getting rid of before it goes into the donation bin, etc. For me the idea of spending a bunch of money on an item of clothing has always been a big barrier, even during times when I could afford it. Partly for philosophical reasons but also because it makes choosing something feel like a massive commitment. The cheaper something is, the more comfortable I feel actually experimenting and trying new things where there’s a finite chance I might not end up wearing them a hundred times.

  108. I’m pretty terrible at shopping for clothes that aren’t t-shirts. Those clothing subscription boxes are super helpful for me because they send me stuff I wouldn’t even try on in a store, it’s less overwhelming than facing a rack full of clothes, and I can try them on with things I already own. I usually end up keeping at least one thing from each box. I dont know if we can buzz market but I use the one advertised on all the podcasts.

  109. Something that was really helpful to me when I had a similar issue with my aunt, who suddenly had to navigate casual Friday after being Suits Only forever and came to me for advice:

    My aunt’s style preferences were VERY different from mine. So I figured out her general style preference then I tried to keep myself focused on finding the best version of that – the one that looked the best on her and made her feel relaxed and confident. I didn’t try to change her mind about, say, socks and sandals – I focused on finding the most comfortably flattering sandals and cutest socks. Is there a color of bucket hat that looks better on your mom than another? Or maybe something else she can pair with it that gives the hat a different feel? Focus on that.

  110. That video, though! I cannot wait to share it with a few good friends. I’m roughly the shape of the person in the pink bikini, and now I want a pink bikini.
    “Mom jeans all day, why you mad, tho” will be stuck in my head…
    I’ve changed up my clothes to be more FUN I teach teenagers, and things like silly leggings, t-shirts with glitter, or subtle nerd references are things we all enjoy. Big swoopy cardigans with thumb holes are cozy. Those are all more important to me than being stylish. And bucket hats keep the Cancer Star from further damaging my cells.

  111. I’ve gone shopping with quite a lot of people in my day, including ones who Do Not Like Shopping but do need clothes, so I have suggestions in that vein! Which are basically: know what kind of shopper she is and make it the most fun possible for her. I know my boyfriend hates making multiple stops, so I’ll take him to a huge store where we can just shop there and then do a fun food thing after. My dad doesn’t mind multiple stops, but wants The Perfect Version of the thing he wants (sadly, they’re usually cargo shorts… but in the hunt he’ll take some side suggestions like a sweater or shirt). It helps a lot if we do research before hand so he’s not wasting time then. If she’s open to making it a longer outing, then try stuff on too so it’s more of a mutual thing and not just targeted at “fixing” her clothing. Stuff like that! Basically, if you make it a pleasant experience overall and tailored to how she likes things, the actual clothing part goes much easier, and makes it more likely to make her more open to trying a new thing if she is picking her current stuff because it’s “default” or “safe” instead of actually her preference.

  112. I do a lot of partner dance (swing dance, etc), and for a while I was an official “dance tutor” in my scene- folks could dance with me and ask for advice/feedback. I’m realizing my opinions about dance are similar to those about clothes- the most important part of dancing is that you are comfortable! having fun! expressing yourself! It’s difficult to give people tips or new ideas about dance without suggesting that what they’re doing is “wrong” and thereby quashing their hard-won comfort and self-expression. I found two methods that worked pretty well:

    1) explaining that I’m not telling them the right or wrong way to do something, just the way to do it that is accurate to this particular dance style. e.g. “I love the way you move your shoulders to the music, it’s so compelling! Now, if you want to focus on traditional Argentine tango styling, you’ll want to keep your shoulders quite still and calm, and put all of that movement into your feet.” For clothes that might mean something like “If you want to go for classic Audrey Hepburn elegance, maybe this gorgeous sunhat is a better choice than your bucket hat.” or “If you want to look like a professional, put-together businesswoman, try…” “If you’re going for paparazzi photo casual chic, try…” etc etc.

    2) Instead of telling them to “fix” something about their dance, I tell them to think about adding something new to their dance. “Wow, you have so many big cool shoulder movements in your dance. What if, sometimes, you danced with your shoulders calm, and tried putting that movement in your feet or hips instead?” For Mom’s style that might look like “well, you always love hats, what if you bought a few new hats of different styles? Maybe we can find some that match your favorite shoes and bags?”

  113. LW: I think you have some stuff it might be worth unpacking. Even if this dynamic has probably existed between them since before you were born, ‘the intelligent one’ and ‘the beautiful one’ are shitty boxes for human beings to live in, let alone for a sisterly relationship to thrive in.

    You might not feel comfortable calling it out when your mother, aunt, and grandmother talk that way, but it’s a habit that might not deserve rooming space in your own head. And it’s worth remembering that that dynamic has probably contributed to your mom’s baggage re: not trusting her own taste.

    Okay, fun part now!

    Positive advice is much easier to give and receive than negative advice. You say ‘sometimes’ she dresses horribly – which means other times you like what she wears. Tell her! Offer to help find more things like that! Or, on shopping trips, suggest she model a few outfits and you’ll vote for which one you like best (even if none of them are things you’d wear personally).

    Maybe even make it a two-way street. If you’re torn between outfits for yourself, try letting *her* pick. That can be a nice confidence boost.

    It’s about supporting her in finding her own style, rather than you projecting your own style at her. Yeses should be enthusiastic; nos should be silent unless specifically requested, and then diplomatic.

    *looks down at boxy tee and elastic-waisted jeans covered in barn dust* All advice offered with a shaker of salt from the fashion-clueless corner, of course.

  114. I’m plus sized, and a lot of my style evolution in the last 10 years (as I’ve gotten bigger) has been to simultaneously get louder. In college, I dressed in a lot of demure blues, berry tones, and dark colors in pretty standard silhouettes. In contrast, in the last 5 years or so, I’ve taken to wearing vintage inspired skirts and dresses, and deliberately collecting elephant print clothes (it’s funny because I’m plus sized, and because elephants are awesome). And what I’ve discovered is that a deliberate choice confidently made will earn you LOADS of compliments. Every time I wear my pouffy elephant print skirt to work, someone has good things to say about it. So I’d ask your mom what her dreams are en re: her wildest and boldest self. Then go out and create it for her.

  115. One magical day, I found a dress with pockets, and my life was changed. I owned dresses to wear at special occasions, but otherwise I only wore jeans and t-shirts. That wasn’t something I’d arrived at by careful reasoning, it just seemed to fit with my self image of “I don’t care about clothes”. Then this dress came along, and I realised some important things:
    1. If you wear a dress, it takes very little effort to look like you’ve made an effort
    2. It’s kind of freeing not having to worry about showing your butt crack when sitting down (I never managed to buy jeans that actually fit me. I’m not convinced they exist)
    3. Compared to just about every dress I own, my jeans are more uncomfortable

    I now exclusively wear dresses. That transformation took place within a few months. The thing is, I don’t think it would have happened if not for my husband pointing to that dress in a store and saying “I think you would look good in that. Why don’t you try it on?”. I’m certain he didn’t pick it at random, he knew me well enough to see that it would have som appeal to me (pockets!) while still being too far out of my comfort zone for me to pick it out myself. If could have fallen flat. Other times it has. Hearing other people tell you you look good is obviously nice, and they are probably right, but the difference this time was that I actually felt it myself, and that’s what made the difference.

    It’s about giving people more choices. They will decide for themselves if they like those choices or not, and you have to let them. But in the end, if they just find something they like outside of what they normally wear, it can be a true epiphany.

  116. I had a similar dynamic with my mom. She was not exceptionally good at picking styles that suited her, she knew about the problem, and she asked for my opinion/comments which made me uncomfortable (commenting on mom’s looks: weird!). What ended up working was for me to help her find nice combinations of items that she already had in her wardrobe. We would go through her wardrobe together and I would pick combinations and styles for her. (We even took photos that she then printed out to remember which trouser to go with which blouse/jumper/scarf). That way I could be sure that I was not being paternalistic: the clothes were already hers, she had chosen them at some point and liked them. All I was doing was helping her develop her already existing style based on her own preferences, instead of opposing something that had nothing to do with her.

  117. Wanted to comment on this because my friend got into drag/burlesque and created her character for the purpose of trying to reclaim her body/feminity from the rampant femmephobia in academia that she has also internalised. And I can’t get enough of how cool she is.

    I don’t really have any advice here as I’m trying to figure out my own dressing style now that I’m actually interested in the subject in my 30’s.

  118. If this is feasible and something your mom wants to do I recommend the following (actually I’m recommending this for everyone): Go through her wardrobe together and Throw Stuff Out. Don’t focus on what to remove, focus on what she wants to *keep* and toss/donate/sell the rest. Yes, even if she bought it fairly recently. Finding the right clothes is a lot of trial and error and one of the most liberating realizations of adulthood was that it was pointless to keep clothes I avoided wearing because I just didn’t feel quite comfortable (it was very expensive!)/didn’t like the colour on me after all (but it’s a colour that suits me!)/my taste changed (but I only bought this last year!)/they stopped fitting (but I might fit in again at some point!) so I gave myself permission to give them away. It’s a lot easier to change your style/reinvent yourself when you’re not thinking “I already have three sweaters [that I never wear], I shouldn’t buy another one” or “This has never been my style and I have nothing that goes with it” Now you have space, get something that goes with it. Have 5 pieces you really like and actually wear rather than a whole closet full of Meh Not Today.

  119. Dear LW! Are you German? Your commas and adverb endings make me think so 🙂 I’m a half-German living in Germany with a German mama and I recognise your mama in my mama. However even if you are not German I hope this applies to your story…

    I’ve always admired my mama for throwing a big middle finger up to the fashion-beauty complex. She dressed in my dad’s XXL t-shirts and old ragged fleeces and charity shop jeans for most of her and my life. As a cis young lady trying to figure out how I wanted to perform my gender, I went through a (completely silly) phase as a teenager of resenting her for not ‘teaching me how to wear makeup/shop for my shape/be a woman’ and that similar gender-normative garbage. I ended up going through a long phase of trial and error between 15 and 25 before figuring out that I like filled-in brows, cat eyeliner, matte skin, dark lips, minimal lines, cool colours, botanical patterns, tailoring at the waist and black trousers. That was my journey and I definitely stopped off at sexy goth, resolute tomboy, organic hippy, corporate prep and british aristocracy amongst many others along the way. What I wear now, I like to call “farmer chic”.

    What was interesting and why I bring this up is that my mama started experimenting with makeup and fashion around the same time I did. While I was busy being annoyed at her for not knowing the difference between eyeliner and eyeshadow, she was busy watching me perfect the cat-eye flick and copying it. When I was 18 and spent weeks picking out “my scent”, she ended up deciding it was “her scent” too, 6 months down the line. What started as shopping trips where she’d treat me to a new pair of high-heeled leather boots which I’d wear three times then donate because OUCH became shopping trips where I’d encourage her to treat herself to that dress which made her feel beautiful and strong. Basically, I taught her all the stuff I’d wanted her to teach me and it was so much fun. Seeing me explore my femininity made her feel she was allowed to explore hers and I think it was really exciting for both of us.

    It would be neat if I could transform this into advice for you but I’m not sure it’s that straightforward. All I can say is that I think certain women in their 50s-70s were around in the wave of feminism that preached that tending to traditional feminine interests like your appearance made you weak and subservient and not a feminist. Anecdotally, and as someone with a mother and four aunts, I think this is particularly strong in Germany. Those stereotypes about us not shaving our armpits and wearing socks in sandals are kind of true, aren’t they? I think maybe you can model for your mum what it looks like to be a feminist who enjoys playing with makeup, who looks in the mirror and makes decisions, who likes what they see and is allowed to own that.

    Good luck and viel Spaß!

  120. Former (?) QVC designer Bradley Bayou has a now out-of-print book titled “The Science of Sexy: Dress To Fit Your Unique Figure.” You should be able to find it for under five bucks. It’s a great starting off point. Also, if you can find a really good — because done if them are gawdawful — boudoir photography studio, that might be a fun thing for her to do. I’m sorta like your Mom… I work, take care of my elderly mother, and I live in jeans, clogs, and t-shirts. It’s odd, but I can “dress” other people but not myself.

  121. My mother has always been my champion when it comes to style. I’ve heard stories from friends where their mothers, to this day, make comments about their bodies (‘if you just changed x about your body, that would look good on you’) when shopping and I’m horrified. One even did it when they were WEDDING DRESS SHOPPING. My mother never mentioned my weight, body shape, or told me I should look different than I did (or dress a certain way because my body looked the way it did). She still doesn’t.

    I recently found some old school photographs of myself, and I laughed at the Terrible Haircut I had. “This makes me look ridiculous.” I said. “Why would you let me walk around like that?”
    And she answered, which I thought was really profound: “I loved that haircut on you, you felt like such a badass.” No mention of how it looked, just that it made me feel cool.

    Pol’s magical rules for shopping are:
    -How do you feel in it?
    -Do you like the way it looks on you?
    -Does it fit/ is it comfortable? If it’s not, I’ll go get you a different size. If different sizes still fit weird, that piece of clothing is just the wrong shape/made for someone else’s shape.
    -This (blend of) fabric means it’s warm/wrinkles easily/kind of sweaty. Do you still want it?
    -If you buy this, remember you have to wash it like x. Inny, DON’T SHOVE THIS IN THE DRYER. I MEAN IT.
    Specific to me: Are you getting that because it reminds you of a fictional character?

    No ‘you should wear x because it will make your bodyshape look more appealing’. No ‘you can’t wear that, it’s unfashionable’.

    I walked around 6 months in turtlenecks and the specific kind of jeans that were 100% Uncool at the time because it made me feel like a cool fictional character? You go, girl, I think your aunt has some of those jeans she doesn’t wear anymore, because you can’t buy them in stores right now. A coworker at the clothing store she worked at told my mother I shouldn’t be wearing a certain turtleneck because it had a print that ran across my breasts, she basically told her to shut the hell up and never talk to me about it if I stopped by, because I felt like a Hogwarts student in that turtleneck.

    So basically, focus on how certain clothes make your mother feel. She wants a super fun date outfit? “Hey, mom, why don’t you try this swanky dress, I think it will make you look fab and feel confident.” She feels cool in hats? Take her to a hat store and try on hats that make her feel cool! (And, I think it’s okay to say: As A Fashionable Youth, I want you to know that x hats are considered really cool/I think you look much cooler in this hat/have you considered this stylish way of wearing a hat?) She wants to wear socks in sandals? “Hey mom, if your feet are cold, these comfy lightweight sneakers are a great alternative.” If she still wants to wear socks in sandals, give her some rad socks with her favourite animal on them, at least. ;D

    1. Inny, these are really good, kind thoughts! Your mother sounds awesome.

      I especially like the focuses on:

      1, practicality (if this clothing item requires ironing to look good, Mimi cannot have it, because she is going to die without ever having ironed anything, so it’s important to have open eyes about that)


      2, spirit– I think it’s good to compliment the way a style matches or complements or augments the personality of the person wearing it. I think we have all had Opinions about clothing trends and then seen someone out in the wild wearing it and looking awesome and thought… huh, I guess that’s not a universal rule and different stuff suits different people. or at least, it’s happened to me, often. And I wouldn’t *ever* say to someone “oh man I thought crop top turtlenecks were hideous and silly until I saw YOURS” because it’s a really backhanded way to get at what is essentially a positive feeling you had about the way someone else has chosen to style themselves, but it’s helped me to reframe in my own mind and to help change the way I talk about other people’s sartorial choices.

      The clothes are supposed to work for you, you don’t work for them. they’re inanimate, so definitely reject them if you’ve got to. Way better than rejecting yourself.

  122. As someone who’s never really been good at fashion but was once much worse, here’s a few tricks that helped me get better.

    First, looking at inspiration pictures of people who look more like me. I’m fat, so clothes never look on me like they look on a slender model and that’s jarring and dissapointing. However if I look at a lot of pictures of other ladies with my kind of body shape I start to get ideas for what might suit *me* and as a bonus I get better self esteem from not soaking always in images of women who look nothing like me. For your mum that might mean finding inspiration pics of women her age.

    Uniform dressing. As in, getting a wardrobe of simple things that all go together. I do deviate from this sometimes but it’s a god send if you don’t care very much about clothes and tend to do it wrong when you try. If everything you have goes with everything else it’s harder to mess up. If everything is simple and “classic” it doesn’t date as fast, so you can keep wearing it much longer. And it doesn’t stand out, so people don’t notice what you’re wearing so much. It blends in. But mainly you do a bunch of effort at the start and then you can forget about it. The downside is that it can be boring, so for me it will never be a strict thing, more of a set of guidelines.

    For makeup – I’ve found I’m much more likely to wear it now that I’ve built the skill to do it well. I used to put it on and then hate it because it didn’t look good or wasn’t what I was going for. A bunch of time watching YouTube makeup channels later, especially basic/natural looks, and I’m now much more likely to wear it. Also practice means I can apply it faster. I should say, I still don’t wear it to work or in my daily life – just for going out and only if I feel like it. But also it’s fun now that I’m better at it. *However*. It’s a big investment of time to practice and get better at it and it can be a financial investment buying a bunch of products that don’t work out while you figure out what works for you. Beginner pro tip though: you can get massive payoff for your effort with some mascara, a little concealer (only on the dark bits) under your eyes, and bold lipstick.

    Finally, as I’ve gotten older I’ve also started to care a lot less what people think and just wear what’s practical. I wear Lycra while cycling long distance. I wear quick-drying tan clothes covered in pockets when hiking (and a bucket hat!). I never *ever* wear high heels because I like not being in pain. I love my stompy boots and don’t care that I’m doing it for the second time round (I was all in on stompy boots in the 90s too). LW, if your mum is happy let her be.

    As someone who’s also just tentatively getting back into dating it makes you wonder if you should look different or try to fit in more. But like…there’s probably humans out there who’ll love a 65 year old lady with green eyeliner and a bucket hat and LW your mum should be trying to find those humans. Not the ones who want a glamazon. I too have felt the pull of “what if I’m not good/pretty/stylish/interesting enough?” Sometimes the nicest thing you can do is remind someone that being themselves is actually best for dating.

  123. I’m about the LW’s Mom’s age and one thing I found super-helpful was to select a persona for what I wanted to project and then to choose things only in that area.

    Some personas:

    French Librarian
    Greenwich Village Bohemian
    Upper East Side Doyenne
    Malibu Grandma
    Country Club Preppie

    You get the idea. The reason our wardrobes don’t work well is that we often select things for the lives we live in our head. So we get these weird items that don’t suit us, have no occasion for our real lives that will work and that we may love but will NEVER work.

    I also think the idea of a capsule wardrobe is genius. It’s cost effective and easy to make selections that will work!

    If you have an upscale beauty school near you, getting an update on hair and makeup will be cheap and cheerful. Paul Mitchell and Aveda Institute are both places that will give a consultation and are very affordable. Nothing worse than wearing dated hair.

    Seconding a bra fitting, it makes a HUGE difference!

    As far as makeup, at nearly 56 I am now scaling back to just a mineral powder foundation, blush and lipstick. It’s a drag because I love makeup, but any more than just that and I start getting into Bozo territory, or my 80 year-old Mom who puts on a full face to run to the grocery store. If nothing else, perhaps go through your Mom’s make up and toss anything that’s over a year old.

    She may really lean into this! It’s a bonding experience.

  124. At the mall in my town, there is a store called Christopher & Banks. They do fashion shows. Anyone can go in and sign up for a fitting (sizes go to 24W) and you get to pick out two outfits to wear. Then you walk the runway and you get 40% off in the store that day. I signed up but chickened out but when I was there, a woman of a certain age was having a great time picking out her outfit and getting advice from the clerks and friends. The person running the store told me they have a lot of fun. Some people travel down the catwalk in wheelchairs and some just strut. So maybe your mom and you can go be in a fun fashion show together.

  125. One thing that made a huge difference in my life was hiring a stylist when I needed to update my look so that I would be taken seriously when I spoke. I’m 4’11”, so it’s hard to get taken seriously in the first place, but my clothes contributed to that.

    The number one thing that she did was get me to get clothes tailored, not just hemmed. Huge difference.

    She did my colors and we replaced all the pastels in my closet with vibrant jewel tones.

    And she picked items out for me that I would never have chosen on my own in a million years, but that made me look like a million bucks.

    That said, I ditto what the good captain said about lingerie, a good bra can make a $5 t-shirt look like couture.

    Ask your mom if she would be willing to shop with you, where she goes into the dressing room and you pick things for her to try on? But start at a specialty bra shop for a proper fitting (choose a place that has cup sizes going beyond DD, they’re the only places that fit folks correctly)

  126. My grandmother went shopping with me once after I had my firstborn. I was excited to buy something that non-pregnant me could wear, and I tried on a handkerchief halter top that I would have rocked pre-pregnancy. I, um, no longer was capable of rocking that look. My grandmother said gently, “That doesn’t quite bring out your best features.” I was so grateful to her for giving the impression that it was the top that was defective, not me. Hope that helps!

  127. A lot of the comments here seem to be assuming that the mother is unhappy with how she dresses and wants to spend a bunch of time and energy changing it. I reread the letter and I don’t really see where that’s coming from. It seems that she does occasionally ask for advice or an opinion, but that’s different from wanting a makeover…

    I would tend to assume that most adults dress how they do because they want to, and my general rule is that it’s very rude to comment on someone’s appearance or clothing unless very directly asked, and even then, it only applies to that moment and isn’t a free pass to comment in the future.

    When she asks a direct question, I’d answer it, briefly and honestly, but other than that I would just leave her alone, and focus your energy elsewhere.

    1. Yeah I re-read it after commenting and now kind of wish I hadn’t. As far as I can tell this lady isn’t asking for help much so much as surrounded by a mother, sister and daughter who think she’s doing it wrong.

      I’ve had people offer to “fix” me where “fix” meant make my clothes more “femme” and it’s actually annoying and insulting and I had to tell them over and over to stop. I didn’t look like they wanted me to look because *I didn’t want to look that way*. The occasional moment of uncertainty about some things didn’t mean I was going to start wearing high heels for example. One of these people described my flat sandals as “giving up”. Actually, I love those sandals and went to some effort to find a style I like – it was just rude and irritating.

  128. A huge step for my wardrobe was going to a tailor for blouses. Most of the ones I could get off the rack didn’t fit properly, with one sales assistant going so far as to tell me I should just put on a push-up to make myself fit their offerings. It turns out that in the mid-price range there’s little difference between going to a blouse store and a tailor money-wise. But there’s a world of difference in the resulting look.

    Also seconding the point about making sure the bra fits properly first to make sure everything else fits well.

  129. My gut feeling when reading this (and _especially_ when reading the comment threads) is just leaveheraloneleaveheraloneleaveheralone

    She very occasionally asks for a comment here and there. That doesn’t translate to ‘permission to treat me as a project or a problem to be solved’. Let her like what she likes and enjoy what she enjoys and be bored and indifferent to what she’s bored and indifferent by.

    If she asks a question answer it! But in all the other moments when she isn’t asking a very direct question or a very specific favour, go do something else. See what you can learn from her.

    Let her be and let her be and let he be and also, let her be.

  130. I grew up having absolutely NO idea about what looked nice or how to put clothes together, etc. and found it horribly intimidating to consider clothes or what I looked like at all (because looking nice was “vain”). What helped me was a good friend who drew me some pictures of clothing that would look good on me (i.e. specific cuts for my figure, not a specific item per se) so I could get an idea for what would work for my frame. She also gave suggestions on specific colors I could wear that would look good with my skin tones. If this isn’t an option, there are also websites I found (through Google) that help you figure out your shape and then tell you specific cuts to look for. I haven’t found something similar for colors, alas (the closest thing I found was along the lines of here are things in whichever colors you look best in so you can wear them, when I wanted something more along the lines of of you know that colors X, Y, and Z look good, A and B should also work but stay away from C and D), but the internet grows daily and it might exist somewhere by now. I also found that putting something on Facebook about “Hey, I’m having a hard time finding clothing with feature X, does anyone know where I can find it?”

    (I will take a moment to complain about the rampant belief that there’s something that looks good on *everyone*; my personal least favorite is the trope that “everyone looks great in black”. This is NOT true of me; I’ve had enough conversations with people who said this to me confidently and when I told them no it doesn’t they thought I was wrong, so…. I showed them. And they believed me once they saw me. But this sort of trope tends to make you feel like your body is broken somehow.)

    1. oh my god seriously what is with that. I don’t look good in black, I don’t look good in white, and navy is really pushing it. I also want an all-neutral wardrobe so I have to jump on things like “camel is neutral now”

  131. When I ask someone if an outfit looks alright, I do want an honest answer. I don’t always know if something matches as well as I think it does, and I’m normally looking for a simple “yeah, you’re good!” or a “hmm… maybe try a different shirt?”

    My roommate is good at giving this kind of advice. Her tone is always thoughtful and positive, and she typically makes a sound to let you know “I’m considering this now that you’ve asked – I wasn’t really thinking about it until you said something.” She ALWAYS points out a positive and gives you something solid to change. Your shoes clash with your ensemble? “Mmm… well, I really like your skirt, but I think you might want to find a pair of shoes that have a similar color scheme.” Your hat doesn’t go well with your outfit? “Hmmm, that’s a really cute outfit. I think your hat might be a bit too much, though. It’s taking away from how cool that shirt is.”

    I always find this approach to be nice. I don’t feel attacked, and I don’t feel like she’s making fun of my clothing. Again, when I ask someone to tell me if an outfit looks good, I DO want to know. I’m not sure, and I want a second opinion. But that’s just me!

    LW, check with your mom to see if she’s asking because she doesn’t feel good about the outfit or if she’s just using a route phrase to signal “I’m dressed! Are we ready?”

  132. My girlfriend has been helping me update my style for the past few years. Here’s what helped me the most.

    -going shopping together at thrift stores (where I could practice finding clothes that flattered my body and check in with my girlfriend for a sanity test)

    -getting rid of old clothes from my closet.

    -finding better looking alternatives to my clothing staples. I love hoodies so much, but when I go out I wear a blazer or a leather jacket and I look 4663 times better. Nothing else has to change.

  133. My mom and I actually have gone/are going through the same thing.
    I let her when she’s not worried about it, but when she has a date or a networking event she gets nervous about what to wear.
    The best solution is more prevention than anything. When she wants help we plan an outfit together, and if she doesn’t like any of them, we go to a thrift store and find that missing piece.
    I also just try to remins her that she’s beautiful so that she knows it’s okay to see herself that way.
    Long story short, the more we find items that are flattering and she loves ahead of time, the easier it is to help her. So just keep doing what you’re doing and remind her that she’s pretty and allowed to feel that way.

  134. I started laughing immediately when I read your opening lines. Bringing principles to the level of one’s interpersonal relationships is hard, fraught stuff and it’s good that you recognize that! I think your instincts are good and you are probably doing juuuust fine.

    Something that I find useful for channeling the urge to SPEAK ON THIS TOPIC (I have a lot of trouble not speaking on topics, it is something I am working on) is to try and focus on the positive aspects of her style. Like, the times you are running up against this is when she is wearing something totally OH GOD MOM WHY* but what if you continued your practice of white-knuckling through those times and let off a release when there’s something nice you can say instead?

    “I really like that color on you” or “that’s a cool dress” or whatever can go a long way toward empowering her to make good choices she feels good about, and never runs the risk of ruining her joy in something you just don’t personally like. It sounds like you won’t want to do this every time– it doesn’t seem like it’s a regular feature of your relationship, it doesn’t sound like you want it to be, you don’t want it to become obvious when you don’t have anything nice to say, you don’t want her to feel over-observed and scrutinized, which are all very good reasons to limit your interaction on this subject. But if you feel like you really have to/want to engage a little, this could be one way to approach that kindly.

    *this is a subjective measurement, having at least as much to do with the child as the mom in question

    1. There’s a lot of great advice both on fashion and how to deliver fashion advice in these comments. I want to kind of push back on the “empowering her to make good choices she feels good about” framing though. Trying to get another human being, especially an adult, to dress the way you want them to dress is not “empowering” them, and doing it through positive reinforcement of the things you like rather than criticism of the things you don’t like doesn’t actually change the fact that you’re trying to get someone else to change their behavior to conform to your standards.

      Maybe LW could find out how much sartorial feedback her mother actually wants? And accept that if she actively likes bucket hats and socks with sandals and doesn’t want to change, that that’s OK? Or if it’s really bugging LW, possibly owning that and framing it as “hey Mom, you know I’m more appearance conscious than you are, would you mind not wearing socks with sandals while you’re with me as a favor to me?” Let’s respect Mom’s agency here. She’s not a two year old who has to be cajoled into brushing her teeth.

      I’m pretty fashion-oblivious most of the time. If someone talked about encouraging me to wear clothes that they think look good on me in terms of “making good choices” or “feeling good about” myself, I’d be deeply offended. I feel good about my gray sweats, thanks. They’re *comfortable*. How about I don’t judge the fashion-conscious as superficial, and you don’t judge me as making “bad choices”?

  135. I’m the friend/family member who everyone goes to for style advice. My biggest tip is always to start by looking at the clothes you already have and try to identify patterns in what you’re buying. This can help you figure what you like and why you like it.

    For example: maybe you tend buy a lot of earth tones but almost never wear pastels. That’s useful information–you probably prefer earthy colors so that means you should focus on shopping for and building outfits around those colors. Or: maybe you tend to buy clothing basic styles and neutral colors. This might mean you prefer simple minimalist or classic styles over brighter, more flamboyant looks.

    The other tip I have is that there’s no right or wrong in personal style. A lot female friends tell me they’re afraid of trying new/different styles because they’re worried they’ll “do it wrong.” So I tell them: the goal is isn’t right or wrong, it’s to wear styles and looks that make you feel good.

    Maybe that’s what you should tell your mom: “Does this outfit make you feel good? If it does, then you should wear it, and if not, let’s shop for other options together.”

    1. Also look at what you do and don’t wear. I eventually figured out that I like the look of red in theory (especially for shirts) and in practice never take them out of the closet or dresser and wear them. I don’t know why, but it’s clearly true, so I gave away some things and stopped buying red shirts, no matter how good a red.

  136. One thing I’ve found handy is to do some googling for brands that fit your body shape. There are some sites where you can enter your measurements and they’ll make suggestions, but I’ve had better luck just googling general descriptions. You have to be careful because there’s a lot of stuff out there trying to tell you how to “fix your body” because general sexist nonsense, but it really helped me to get an idea for brands that were me-shaped. It makes shopping and finding clothes I feel good in much easier when I can focus in on what sort of styles and brands are likely to fit on my body.

  137. I was very much a tomboy as a kid, I wore dresses only for weddings/dances/recitals, otherwise it was comfy pants and a baggy t-shirt 24/7 (with slight modification for weather). I also hated male gaze (ie dudes starting at my boobs/butt/etc.), so wore clothes that hid/masked my body to minimize it as much as possible. I also had some very anti-feminine attitudes for a lot of reasons (thanks patriarchy!) and clothing was a big one that I held onto a long time even with all my growth as a feminist. Finally, I am in a field (mechanical engineer doing design for building construction) where I am often the only woman in the room. I’m also in sizes that are sometimes in stores, but in limited quantities. But I have been slowly figuring out that I really like and have been reclaiming feminine clothing, ramping it up even more the past 5 or so years, playing with what I wear to work/meetings/etc.

    Some things that helped me: https://www.alreadypretty.com/ – I find this site a wealth of information delivered in a gentle way for people who want to learn about fashion, but have no clue where to start (ie me!)

    Looking at the (few) professional women around me and figuring out ways I can incorporate some of their style (do NOT copy someone’s look to a T, that is creepy!) – sometimes I have to look engineer adjacent for ideas (I work with a lot of women architects, landscape architects, owners/etc. from various buildings/companies, etc.)

    Finding Lane Bryant & Torrid – both have their problems, but being able to try on clothes that are really designed for larger bodies and that make me feel fashionable is huge!

    Making peace with sometimes wanting to dress feminine and sometimes wanting to put on my “blend in with the guys” engineer outfit of button down/golf shirt and slacks. Being ok with experimenting and sometimes it just doesn’t work personally or professionally. Having fun finding/creating my own personal style, I find accessories and wraps/cardigans/etc. are things I really like and can give just enough fun to make me happy sometimes and feel more stylish!

    Also, my sister and I would go shopping together and be honest, but kind about it. We could trust each other to call it like it is, but never in a mean way. We haven’t been in awhile, but it can be really nice to have a shopping partner you trust which may be what your Mom is looking for in you.

    1. Huh, I looked at the website and the top post right now is this body-positivity thing that seems to assume that the audience is 1. not disabled and 2. not the sort of fat where, you know, you actually have to buy plus-sized clothing and don’t fit into some chairs and that sort of thing. And 3. have an unrealistically negative body image, which, I don’t think I do that much? Like I’d rather be thinner but I don’t get worked up over wrinkles, acne, or cellulite and I feel weird when it’s assumed that I do just because I’m female. I’m kinda disappointed. Maybe there’s better posts further back?

  138. learning to sew / learning clothing terms is the biggest game-changer here. add in some knowledge of fabric and sewing and color, and you’re golden.

    what necklines work with your body? how about types of waistline? do you like a defined “crisp” style or a flowing one? it helps so, so much to eliminate the obvious duds, so you don’t waste time & get discouraged.

    this is what thrift stores are good for: trying on a bunch of outfits and paying attention to the elements of what makes one look good (or bad).

    it took a while but nowadays i can look at a dress and tell my wife with 95% sureity if it will compliment her “complicated” figure — she is plus-size, with very different top/bottom measurements, and an hourglass waist. “Hmm … raglan sleeves work on you, wrap dresses are great, it’s got bust darts and rayon and muted jewel tones? YES TRY THIS ONE ON.”

    … whereas i avoid raglan sleeves, they make me look awful. so.

  139. A lot of people think it sounds weird, but I’ve sounds seasonal color palettes so helpful in building my wardrobe. Cardigan Empire and Truth is Beauty are two of my favorite sites, but there’s stuff everywhere. The basic idea is everyone looks best in colors that are either light or dark, soft or bright, and cool or warm. (You determine your season by “draping,” or looking at your face surrounded by difference shades. The ones that seen to harmonize best are in your palette).

    Each combination fits into one season and there are subseaons based on which trait is dominant. I look best in soft, cool, light to medium toned colors, so I’m a summer (a soft summer because soft is my most dominant trait). I don’t look as flattered in bright or very dark or very warm colors.

    It’s a special style that goes for harmony and clothes that accentuate rather than steal focus.

    I still wear whatever colors I like (and dye my hair a non natural shade), but knowing my most flattering colors off hand makes shopping easier. All the colors in a palette flatter each other, so if I focus on buying on my palette I build a more versatile wardrobe.

  140. I have a wildly different style than my friends and I think the answers my friends are looking for either fall into the “I Just Need Reassurance” or “honestly, how is this looking on me, fit-wise not should-I-even-consider-this-because-i’m-obviously-already-interested-wise”

    If I can’t have a response of ‘OMG YASSSS” I try to frame my responses into either questions or “I think” statements and to focus on the fault of the clothing. So my answers are usually along the lines of:

    “That’s not my style at all but it looks good on you!”
    “I think X color may make you pop more! but if you are diggin’ that one, go with it”
    “I think the fit is odd in x, y, z places. Perhaps a different size or a [solution base on accessories that she already has like a belt or scarf]”
    “Is there something about that that you’re concerned about (ie. if its too sheer, or the hem, would it pair well, etc…?”
    “Does it make you happy/are you happy wearing that?” (Not in the judgmental way, but rather does wearing that bring you pleasure? if so, sail ahead and let haters hate!)

  141. I would like to throw a question to the readers. Does anyone know how to DO a closet clean out in a good way?

    Like, in an ideal world, I would get some money for new clothes I have that don’t fit etc?

    Or if not possible without requiring too much effort, does anyone know of a good charity drop off that doesn’t send old tee shirts to blanket Africa or other questionable practices?

    1. Old tee shirts etc = cleaning rags in my house. I don’t do paper towels, so I use rags A Lot. Between simply wearing out from use/multiple washings and “ew I am not putting this in my washing machine!” it’s handy to have a ready supply on hand.

  142. “Have you ever transformed your clothing style into something you like much better? What kinds of things did you do? What helped the most?”

    It all changed for me when I stopped shopping in physical stores and started shopping online. None of the physical stores I have in my very fashionable country have cuts and sizes which I think fit my silhouette (short and fat). I pick from online brands/shops with explicit, precise and consistent size measurements not only for breasts and waist, but also for sleeve length, back length, leg length,… so the item has a good chance of being like I expect it to be. Fabric is also very important as I don’t want to iron anything and there is some stuff my body dislikes. I’ve found brands out there which consistently make clothes I like and I know will look comfortable and good in. This makes for a very hassle-free and pleasant experience.

    Buying stuff online also lets me try things out in my own home several times, see if it compliments clothes and shoes I already have, ask for second opinions I want to and don’t get anyone’s opinion if I don’t. 🙂 I have plenty of time to send the items back, for free. This has allowed me to stop wasting money on stuff I’ll barely wear in the end and to try out new things, experiment and change styles easily. Now I only buy clothes *I* absolutely feel comfortable, beautiful and confident in. I don’t have to buy expensive stuff either because there are ordinarily-priced clothes out there for me! I just had to find them! On the rare occasion I don’t end up wearing something often I donate it or resell it. No harm done and that’s room for new stuff 🙂

    I stopped assuming something wasn’t going to look nice on me. I started thinking about different ways to wear things (with a belt? bottoms rolled up? in a different color?), w/ or w/o jewelry, etc. Surprisingly it didn’t take long to find my look.

    1. You know who wore socks and sandals? The Romans. The best fact I ever learned from a knitting magazine.

  143. This is great advice.

    I did get my shoulders around my ears at the “help her clean out her closet” advice, but only because of a very unhappy memory where someone did this for me…while mocking clothes I had and liked to get me to agree to throw them out. I still miss some of those clothes, which I felt fit my personality and made me feel good. Worse, I felt like my personality itself was being judged, because I identified so much with my clothes.

    So if you do this, you should ask your mom what sparks joy FOR HER in her own closet. Ask her how often she wears things, with what, and how they make her feel. If she loves them but you don’t think they look good, give her advice on what to pair them with so they’ll look better, or what sort of occasions they’ll be appropriate for. Don’t try to pressure her into getting rid of things she likes. They’re a part of her in some way, and teasing them will tear her down.

  144. I experienced a trauma in my life that sent me on a path of revamping my ENTIRE look… Hair, clothes, style, jewelry, etc. I also changed my style quite a bit as I went through a process of gender dysphoria.

    My experience around it:
    -advice from folks about where I could find certain clothing that I already started I was interested in.
    -doing a full (over the top) makeover with people and having a good laugh, but also getting some ideas about things I liked when taken to an extreme.
    -all the compliments. Anytime someone told me something was unflattering, it made me self conscious and uncomfortable, but not willing to change it…. So don’t bother.
    -when I asked “how do I look?” And a friend didn’t like it… They would say “Overall, wonderful as always, but I do have some advice on something that I personally don’t like if you want to hear it” then I’d say yes or no depending on what mood I was in.
    -selfies. Seriously, rocking a picture instead of a mirror can sometimes help me envision my outfit and presentation better.
    -Shopping fun and support, but no unsolicited advice.
    -having friends who supported me in wearing things that challenged norms about what societal beauty is. I love showing off some chub, some neon colours, some ‘improperly fitted clothes,’ and some clashing patterns. They gave me the confidence to own it.
    -Not having my fashion, style, clothes being the centre of attention, but rather a visual representation of comfort, a statement, or just ‘whatever I damn well want’ kinda thing.
    -style change takes time to curate and development. Mine is always changing now.

    Ps- I absolutely LOVE bucket hats and wear socks with sandals ALL THE TIME ; )

  145. I found the free quizzes and emails at Dressing Your Truth to be very helpful. It’s not about conforming to any particular trends or making your body appear a certain way – it’s about making your clothes reflect your personality and energy. I found it very affirming, and the before/after photos show folks of different races, sizes, and ages.

    (Caveat: the author pushes “…Your Truth” very hard as a brand, and has a lot of “find yourself” type woo in different areas of the site. But the fashion section is pretty well focused on the topic.)


  146. I have done this with my mom! It took time, patience, gentleness, and tact. I found “I think that that is not the most flattering silhouette (or color or length or print) for you” to be a very useful phrase. If you can follow it up with something like “I think you look better in greens that don’t have a yellow tone” or “I really liked that A-line shape on you”, all the better.

    New, properly-fitted bras are important! I was just direct with this one. I asked her what she would do if she had an employee who was simply incapable of performing their duties, and she said she would probably have to let them go. I told her her bras were not doing their job and that she needed to fire them. Fortunately, she laughed and got the message. I told her everyone needs a fitting every few years, then handed her a list of stores where she could get a fitting, and told her she needed at least four, including at least one “t-shirt bra,” and that she should try on some molded-cup bras. This all took a little convincing, but was worth it.

    We did a bit at a time – we went through her current wardrobe, got rid of outdated stuff or things she hadn’t worn in at least teo years, then came up with a list of what she needed (jeans, black pants, mix and match work basics, fun casual outfits, a few dressier date outfits, outerwear, underwear, and a couple of dresses for weddings or other events). We tried to tackle one category at a time, then add shoes/accessories. This made it feel less overwhelming, and if we happened upon things she liked that weren’t in that outing’s category, so much the better. I had a friend who is great with accessories come help with jewelry and scarves and stuff.

    My mom is short and has always needed pants hemmed, which made it a little easier to convince her that tailoring is a good and useful thing – most clothing doesn’t fit most people off the rack, and a bit of extra investment this way is worth it. Also, we made sure that pants/jeans were tailored for either heels or flats. We found a great pair of jeans and bought two pairs so she could have them hemmed for both lengths.

    The most important thing was making sure she knew I was trying to dress her like her and not like me. Her style is… not my style. We bought her lots of stuff that I would never wear – but that’s fine, because it was her style and it made her happy and it fit her well and it looked good on her. (So much teal and dusty rose. So. Much.) I had to remember to put my style choices aside and make sure she knew I was doing that, and then she would trust me and trust the process more, and even let me push her style boundaries a bit more. If she didn’t like something, I didn’t try to push her to buy it, because I knew she wouldn’t wear it. I might tell her why I thought it looked good, or to get her to understand why I thought the shape or color was flattering even if she didn’t like the garment, but that was it.

    It was a process, and at times more emotional than either of us imagined it would be, but it was so worth it. Good luck!

  147. What helped me (plus-size hourglass) was a trip to Macy’s in NYC. Lo, there was an entire floor dedicated to clothes that fit and flattered me! Also, my wife threw out five trash bags full of clothes that had holes in them/did not fit. She also taught me how to put on makeup. I didn’t know the fun parts of being a woman until I met her.

  148. I was in a similar position in college. My mom, who also was raised during the era of binary (you were either smart or pretty, and apparently both was not an option in her high school era) and choose to be The Smart One, still struggles with feeling clueless about what to wear or how to wear things. We watched a lot of Clinton and Stacy together.

    I pointed out once that the perfect makeup to go with such and such outfit would be rose gold eyeliner, which was just starting to be popular and she became that Julia Roberts meme so, for the next Mother’s Day, I went to Sephora and got here eyeliner, eye shadow that goes with it, primer, and mascara (which is hard to find the right color for a redhead), and then went home and taught her how to put it all on. She still wears all those things whenever there is a posh occasion.

    I think the key aspect that made it “A fun thing we’re doing!” and not “A lecture or reflection of your deficits as a person!” was that there wasn’t A Problem To Solve. It wasn’t “you look bad, let’s fix it” it was “hey, you wanna look extra special for this occasion? DOABLE LETS DO IT”

    So, yeah, if your mom asks for help, that’s a good indication that she would welcome some information and none of your feedback has to be “Oh, thank god, we can finally throw out the damn hat” and can be more “Ya know, you would look so good in this other hat that really brings out your ____”

  149. My mom also dresses in a way one might describe as frumpy casual, and also asks me for advice for weddings, etc. when she wants a fancier outfit. She usually wants to look a little more fashionable and grown up but is afraid she’d be putting on airs or seeming out of place.

    What has worked the best for me is suggesting she find out what her friends/family members of a similar age are wearing. Once she hears from them that they’re wearing a nice dress she will (sometimes) decide she can too. I’ve also learned to talk about it more specifically (“a dress that isn’t made of cotton”) rather than with anxiety producing fanciness indicators (“a cocktail dress”).

  150. 3 Ideas as someone who’s reinvented her style a lot for the corporate world:

    1. Studying people who dress well is huge. That’s something I do.

    2. When out shopping, encourage your mom to buy something ONLY if she loves it and feels great in it. If she looks in the mirror and says, “This’ll do.” THAT’S NOT GOOD ENOUGH.

    3. I don’t know if this was suggested yet, but you guys can watch What Not To Wear! It’s entertaining and extremely informative. Sometimes if I’m updating my style I’ll look it up on YouTube and watch a few transformations.
    Because of that show, every time I look at my outfit I check that it has Color, Pattern, Texture and Shine. 😉

  151. My extra bit of a suggestion is that when you and she are in good head-spaces and shopping, try on things that you *expect* to be terrible. The weird shapeless thing, the thing that is incredibly not her, the thing you’re sure you need to be 10x taller to pull off. And take the intriguing, and likely things in, too… but trying on ridiculous things helps to cement the “it’s not my body it’s the clothes” thing, and it also sometimes leads to stuff *you thought* was ridiculous, but actually looks and feels good to wear. (Just like some things look good on hangers but not on people, some things look weird and terrible on hangers but good on people.) And sometimes you still don’t have anywhere to wear a black cat-suit, but sometimes you come home with things that open up your wardrobe options.

    1. This is a brilliant suggestion! It does require the right headspace, but can ultimately do wonders for letting go of feeling like our bodies should fit the clothes instead of the other way around.

  152. Hi LW, I guess my question is, when your mother explicitly asks for fashion and style advice, how involved do you want to get? Put another way, how much emotional labor do you want to do?

    If you feel up to it, I suggest what a lot of other have recommended: ask her questions to narrow down what she really wants advice on. What setting or occasion is she dressing for? What about her or her personality is she trying to convey with a specific outfit? Does she feel comfortable (physically, mentally, emotionally) in what she’s wearing? Is she dressing for herself, someone else, or to conform to or in protest of social conventions of appearance? Or as someone else commented, is she looking for approval? (Tread carefully, if it’s the last one.)

    Then, tailor (pun not intended, but left for fun) your gentle advice accordingly using the many given examples. That way, your mother can get the most useful advice, and you can maintain your boundaries and hopefully lower your own stress.

    If you don’t feel up to engaging that day/time/ever, then direct her toward other resources — there are lots of great ones mentioned here.

    Oh, and there is definitely a story behind the love of bucket hats. Find out what it is! Right now, I can think of several fun ways to make an ordinary bucket hat really snazzy and a nice accessory to several outfits.

    1. All of this says most of what I was going to say but better. I also feel like the answer to “how do you want to look” needs to be as varied and specific as Captain Awkward’s advice on dating profiles.

      “I’m going for a studied indifference that doesn’t push people away but also doesn’t let on that I put any effort in whatsoever.”

      “Like if Cher were a Muppet.”

      “Just so many lobsters on everything…but make it fashion.” ( https://en.wikipedia.org/wiki/Elsa_Schiaparelli )

      “I want questions from interesting strangers.”

      “Honestly, I’d just like to be objectified a little for a change.”

      The best thing anyone ever said to me about my look was, “Your hair is doing what you want it to do.” This in my executive butch look for business school presentations, when the person I was asking definitely would not have slicked her own hair back like a millionaire playboy, but knew I was going for that.

  153. I don’t have anything really to add except wow, I hear you. My mom who wears crocs and hats used to send me a picture of herself, and caption it, “isn’t this the worst outfit” and I would respond yes, and she would call me crying and saying “why do you hate my clothes so much.”

    I think the Captain’s advice is right that maybe it’s askjng, and not telling. But what makes you feel good? What parts do you want to show off? I was surprised to hear that my mom loves her ankles – sure we can work with that!

  154. First of all I would like to applaud the letter writer for this positive, supportive letter. It is a delight to read something so filled with love.

    Secondly I suspect the letter writer is based in the US as in Europe, the socks in sandals look is much more common. If you cannot ween your mum away from it, then a move away from plain white or beige knee socks with 10 year old birkenstocks can be a style victory. My mum for example has beautiful ones with flowers on, and she colour coordinates coloured socks that match some of the flower petals on her sandals. She also has similar wellyboots. They are considerably more stylish than my swamp green ones. Socks without holes, again = good.

    Following The Captain’s advice, I very much improved my personal style thanks to my siblings input. It is very easy, for me, to get caught up in what colours I like and ignore that certain shades make me look washed out. E.g. I love green and blue. Bold blues and greens work well, but pastel shades make me look sickly due to my skin tone. My siblings are the ones who educated me in this.

    I also very much want to know what a bucket hat is!

    1. As someone who loves socks with sandals for the comfort, and who could use help on how to project what I want to project with my clothing, THANK YOU for this advice! Pretty socks with sandals sounds delightful.

  155. Everyone looks good in the clothes that make them feel confident. We feel confident in clothes that reflect how we want to be seen. Who are some of your moms favorite characters/public figures? Who does she relate to the most? How do those people dress? Use those people as your inspiration.

    You’re going to also need to figure out the appeal of the crocs and the bucket hat so you can find suitable replacements. Crocs are cheap and great for people with foot issues. Bucket hats keep sun out of your face but can also be stuffed in your purse. Those are probably important factors your mom is going to value more than style.

    It seems like your mom is a “daily uniform” person, which is great. You can build her a capsule wardrobe pretty quickly by getting matching separates that all match with one neutral color. It’s a lot easier for the stylishly-challenged to get dressed when everything in their closet is in the same color palette.

    You mom sounds lovely, best of luck to her in her dating life!

  156. In my house, it tends to be ‘dad, you do realise what colour that shirt is?’, because he doesn’t want to wear clashing clothes, per se, but he’s colourblind. Sometimes the answer is ‘yeah, I don’t care’, and sometimes the answer is ‘was this not the blue one?’. (Answer: no. It’s pink. Lovely, but not with those trousers…)
    It’s not pushy or unkind to simply make a comment or share an opinion, especially if asked. Unless the comment itself is pushy or unkind, but you seem like you’re on top of that, LW.

    1. “It’s not pushy or unkind to simply make a comment or share an opinion.”

      Could you say a little more about what you mean? I’ve certainly been hurt by people who were only sharing their opinions.

      1. Could you say a little more about what you mean? I’ve certainly been hurt by people who were only sharing their opinions.

        Me too!

        When I was 11, I had a bright orange tshirt that I LOVED – it was the colour of the sun setting into the ocean. It made me so, so happy. I felt like a rock star in that tshirt.

        And then a Mean Girl told me in a “I’m-only-saying-this-to-help-you” voice that orange REALLY wasn’t my colour and REALLY didn’t suit me… 😦

        I was very upset.

    2. “It’s not pushy or unkind to simply make a comment or share an opinion, especially if asked.”

      If asked, true, then it isn’t pushy or (usually) unkind. But if not asked? Then it may or may not be unkind… but it is almost definitely pushy.

  157. I always like pointing out the things that look good and why (e.x. “Wow mom, that blouse is a wonderful color on you! You rock jewel tones”)

    I also like gifting clothing. I will see something on sale months before Christmas/Birthday and store it away or find an excuse to gift it early (even “I saw this on sale and I couldn’t resist” is an excuse)

    Gifting makeup is great too. I have a few products that I love that wind up as stocking stuffers. Alternatively, sometimes I buy online and get a color that doesn’t quite work on me that would suit a friend/family member.

    1. I second pointing out what looks good and why! People complimenting my awkward teenage self on colours that worked on me is what led me to discover that some clothes actually can work on me, and, with some trial and error, I can be made to look beautiful!

  158. I don’t have anything helpful to add because I am bad at fashion, but I also have a very fun, newly single mom in her 60s who I love very much and I feel this. I want her to be happy but also not to unwittingly wear an obscene Halloween costume but also, I guess, it would be fine if she did that?! The struggle is real.

  159. I think the bras should be encouraged to register to vote and driven to their polling place on Election Day

  160. I was introduced to Cabi clothing a couple of years ago and I love it! A Cabi stylist comes to your home with the full collection and you can try it all on at home. I’ve had a few gatherings were several of my friends and I enjoyed snacks and wine while the stylist showed us the latest pieces and then we all tried on clothes and ordered what we liked.
    Their selections change twice yearly and I always get compliments whenever I wear a Cabi piece.Visit the site to find a nearby stylist: https://mailemckown.cabionline.com

  161. My clothes as a kid/teenager were exclusively hand-me-downs from a family friend, so when I could buy my own clothes I had absolutely no idea what looked good or what suited me.

    One thing I found really helpful was making a pinterest board of the styles I liked. I looked at all of the things these outfits had in common, and tried to buy those things when I needed something new. Now my wardrobe is super comfy and all things that I like. Doing this gives you more of a cohesive ‘look’.

    Maybe it would be a fun thing for LW and her mum to look at some different styles, and find the types of clothes her mum loves. Then LW could gently guide her to finding versions of those clothes that are fashionable/flattering.

  162. Captain, this question is a breath of fresh air and the comments are full of amazing suggestions! Thank you so much.

  163. I would say, try not to make assumptions about why your mum is choosing certain items. I am a member of the Curvy Sewing Collective (dressmaking is my hobby) and I have been able to learn so much about how individual style is; especially for women who have aged out of the phase of life that conventional ‘fashion’ is aimed at, who are now expressing themselves as they wish. Some of that comes along with body considerations, we regularly talk about how shorts ride up on curvy inner thighs or how ready to wear fast fashion has bust darts three inches higher than our bust, that a good fit around the waist often means baggy gaps at the hips/shoulders because the fashion industry thinks plus size equals long arms, legs and huge shoulders. Health issues often make certain items unbearable to wear (tight jeans and button fastenings are a no no for chronic pain or IBS ladies in my group.)

    Some of it is aesthetics. My Mum grew up in a home where she was forced to attend Sunday school in hideous polyester dresses. We found one in a thrift store, I tried it on and it was AWFUL to wear next to my skin. As a menopausal woman, my mum is all about breathable layers. That makes sense. When she got remarried, she was EXTREMELY self conscious at being a 50 year old bride and I had to be very gentle and respectful when we went dress shopping, there was a very real vulnerability about how others would see her if she got a dress vs a suit. She did get a dress made and looked beautiful as she walked down the aisle to marry my step dad. Not only was she beautiful, I could tell she felt that. And that was what mattered most.

    It’s a great sign that your Mum can express her individuality and love of hats. It means she has passion for her life. My advice is to build on that by encouraging her to talk about what she likes, on her and on others. Make any fashion experimentation relaxed and low stakes. My Mum and I had a joint personal shopper appointment which was great because she got to ask the personal shopper to grab me a bunch of items my Mum would like to see me in, and I was able to show some reciprocity by trying on mustard coloured leggings. It also gave Mum and excuse to try new clothes without the stress of trying all the sizes on, picking things out and getting discouraged. Maybe it could work for you both if and when your Mum ever wants some new ideas?

  164. Hello! I can so feel the love in your question.
    I have been in bit of a clothing rut myself and am slowly getting out of it. ( read owning 5 of the same blue and black t shirts, albeit if good quality, but my, my, not exactly something that brings joy)

    In a whim I bought “magical Fashionista” by Tess Whitehurst and I really loved how she asked a whole bunch of questions and referred to, if you where a landscape, what kind would you be? Atmosphere, colours etc,

    Now a bit of warning, there is Feng Shui and a little bit of elemental/ energy stuff in there too, so if that is not your cup of tea, either you can just enjoy the book and only take what reasonates with you. Or ignore the book 😉

    I havent done all the work yet in the book yet. However this gave me the permission to just wear the fancy silk blouse, that I normally only wear for fancy occasions, on a jeans, because I like the feeling of the silk and because I love the colours and well what’s the point of owning a thing and almost never wearing it….

    So maybe you could read it and use some of the questions inspiration, to gently guide your mother?

    And I second the “ buy really nice luxurious almost silky/cotton socks , and wear those with some shiny glamorous birckenstocks” basically, find the joy in dressing again? In what ever way that means to you.

  165. Queer Eye doesn’t have much women’s style, but I think it’s a great example of how to make suggestions for people while keeping their own personalities and comfort zones in mind. If your mom is asking for suggestions you can phrase stuff like, “I see you like this type of hat, I wonder how this similar function type might work on you.” And then she can let you know whether she would be open to giving that a try or not.

    I love shopping with my sister because we are very differently gendered but have similar enough body types that we deal with the same fit stuff with pants, for example. We tend to go through stores and talk about what we like about what’s being sold now and what we think will and won’t work for us.
    “I like this sweater but I’m not sure if it will work for me.”
    “I think you’d look great in that.”
    “Isn’t it better for high-waisted pants though, and those are too feminine for me.”
    “Nah, what if you tucked it in in this way, I think if you like the piece you could try it!”

    We try to focus on positives and always wait for the other person to raise a concern themselves before commenting on it or trying to help. We also don’t pick out pieces for each other, we let the other person direct it first, like identifying that they are looking for a new sweater or they want to try wide leg pants. I think if you try to focus on positives and let her steer the conversation, you might be able to help direct your mom to some new pieces without making her feel bad.

  166. My body changed a lot when I was sedentary due to illness/injury for a long time (on crutches for about a year), so none of my professional-type clothes fit anymore. I looked at some of the fashion bloggers people have linked, but most of them aren’t shaped similarly to me, so it’s hard to figure out what will work. Any suggestions for fashion blogger sites focusing on curvy (larger “straight” sizes) petite “pear” figures?

  167. My mom, now approaching 80, went back to college in the 1990s and really embraced (a clean, non-shredded) version of the grunge look — jeans, t-shirts, flannels. After she retired, she went back to that, but liked that people complimented her whenever she showed up to church wearing anything else at all. That motivated her a bit, but we also figured that if she bought jeans every five years or so, the whole style didn’t look too dated and she could just roll with it. I’ve kind of gone the same way (but it took longer, as I’m not retired). I recently listened to the By the Book podcast episode where they covered The Curated Closet, that has a system for defining your own style. I found it helpful, maybe the LW & mom would, too.

  168. So, a few years ago I changed my style. From natural long auburn hair, and pretty lace shirts over camisoles, to short purple hair, neutral androgynous styles in navy, grey and black, and when it came time to sing with my choir, instead of a pretty long black dress I sought permission to wear a tux like the men.

    How I went about it was that I had the epiphany of “these clothes are lovely, but they aren’t me anymore”.

    I really am not into fashion. Never wear makeup. Cringe at clothes shopping. But I first started just throwing on neutral jeans and plain t-shirts, then went to the hairdresser with a selection of pics I’d found online. We discussed what I wanted, and she did it (rather than what she thought I ought to want). I was offered cut n colour on different days but no, I’m gonna make the change damnit, let’s do it together. (nowadays I dye my hair myself, but I’d never done it before then).

    With the clothes, it was harder. I already knew that what looked good online might not fall right on me. So I went to a big store (marks & Spencer) which has a range of sections – for young trendies, for old grannies, tailored, casual, you name it.

    And then I forced myself to look at all the racks. It was horrid. But I took one of each shape of jeans, a selection of tees, jumpers and shirts, and tried them all on. I discarded shapes that didn’t fit my body. Then I asked the staff what suited best from the remainder (“is this too tight or meant to be like that? Should I get a shorter leg, or is this length OK?”) and friendly customers also chipped in. Which again I hated but I forced myself to do.

    I’ve come away with some jeans I really like in my new neutral colours. Although I’m aiming for gender neutral, I’ve found women’s fitted tops suit me best. And I’ve got some comfy but smart-enough jumpers that I can just grab and go.

    Since then, I’ve added things here and there when I’ve seen someone online or tv and really like the style. Black Button down dungarees? Check. Clingy faux leather trousers? Check. Super comfy chino style shorts? Check. So my basic wardrobe now has these extra items for when I’m in that mood, or the weather dictates, or whatever.

    I hope that experience is useful.

    Btw Cap’n, I love that advanced style website! Right now it’s a bit old for me, but I’ll remember it and I bet it helps OP discuss fashion with their mother.

  169. Also, in terms of the hairstyle, I really felt like *me* afterwards. Every time I re-dye to stop the orange coming thru, and then go to get it clippered short again, I feel I’m getting ME back again. That’s how I know what’s right. If you make a leap and it doesn’t feel quite right (one time the shop was out of my regular purple dye so I tried a blue – big mistake!) just remember nothing is forever, so just roll back to what’s familiar – or keep trying til something sticks!

    The clothing change for me was preempted by a weight loss and needing to buy clothes that fitted, at which point I had the realisation that I didn’t need to buy pretty stuff just because I always did – and when I thought about how I felt I was, how I wanted to dress and identify / be perceived, that was the starting point. Not everything felt truly ME at first, but neutral classic stuff is safe and comfortable, and then as I said, I grew confident to add items I saw and liked. Sometimes I’d have to ask friends if they truly thought I fitted / suited / could get away with what I wanted to try – luckily my two best friends are a man ten years older than me, and his daughter half my age, so two very different but honest perspectives to reassure me I’m NOT looking like mutton dressed as lamb, or that maybe the blue looks better than another black thing.

    I guess I’ve kinda grown into the clothing style rather than completing me, but it’s me now and as I get more familiar with what feels right and comfortable, I get more confidence – even just to try something on and not be afraid to laugh, shake my head and give it back! The old me could never have tried that!

    I think it’s one of those things you kinda have to bite the bullet and just DO. For me, I preferred to do it alone so nobody saw me if I looked silly. Particularly as I used to be strictly plus size but now I can go into high street stores and the staff treat me as if I have every right to be there, which took a while to get my head round!

    But also, when I was less confident, in the past (when I’ve had specific clothing guidelines for TV etc) I’ve needed someone with me to help pick out a few things and encourage me to try them (“just try them. I think it could look nice! The worst that happens is you hate it and we try something else!”). In fact that’s how the old style of pretty tops began – but that’s a different story! But again it followed the pattern of having some guidelines (or deciding some for myself), pulling things that ticked those boxes, trying them on, and going from there. Go OP’s mum – you can do it!

    Thank you OP for being kind and supportive to her, too.

  170. Maybe your mom would dig this thing about style being about inside-out congruency, OP. https://www.stasiasavasuk.com/stasias-style-school/ I did it and got a lot out of it, and I know other people have been signed up or gifted the class by their daughters or sisters or whomever, so maybe it would be something you could gift to your mom as a way to give her the help she’s seeking without having to be the one to give it yourself? The woman who runs the class, Stasia Savasuk, also just recently did a TEDx talk, “Dressing for confidence and joy,” that is up on YouTube, and I know that many of my fellow classmates were taking the class at a time of transition for them as it sounds like your mom is also currently experiencing.

  171. I’m obviously late to this post, but might I also recommend Justine Leconte’s Youtube channel? She’s a lovely French designer and fashion nerd who celebrates personal styles and covers topics like ethical vs fast fashion. ALSO, she has one of the most relaxing voices I’ve ever heard–sometimes I just put on her videos for ambiance while I’m working.

  172. I’m transgender, and have had a lot of conflicts with my mom about what I wear and how I present myself (mostly along the lines of “not ladylike” and, well, actually I’m not a lady). Also, clothing issues are fraught for many trans people, since often what fits our bodies and society’s idea of what we should be wearing does not fit who we are inside. So, this may seem like a fluffy topic, but it’s definitely not to me.
    There are so many good ideas here. I am going to be trying a lot of the suggestions in this thread, up to and including having booked an appointment with someone from a style agency in my area who has experience with transgender folks.
    One thing this thread inspired me to do was to ask a few close and trusted friends how they would describe my style – not its shortcomings, but what they think I am aiming for. That helped me get a sense of how I am being perceived, and what parts of that I like and want to expand on. (My best friend described my style as Neutral Nouveau Bohemian, which I love!) I wonder if that might be a help to your mom? Part of what worked about it for me was asking people who dress kind of the way that I would like to dress and have similar lifestyles to mine. I wonder if your mom has some friends of similar age and lifestyle that she might be able to have some conversations with about style generally?

    1. Hi there, thanks for this reminder and perspective. When I identified it as “fluffy” I didn’t mean “unimportant,” just, a welcome break from #thisfuckingguy and abusive situations. But clothing/style/perception are important!

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