Confessions of a Walking Fashion “Don’t”

I have a somewhat humiliating confession to make. I’m 33 years old and still have no idea how to dress myself. It’s not that I wear anything truly hideous or embarrassing, but my wardrobe is just so boring. At this point, I’m starting to think I’ll never learn how to dress like a functioning adult. Most days I’m okay with this, but the thought that I might one day really have to figure it out is pretty unnerving. Help!

Part of my fashion cluelessness has to stem from having been born in central Texas in 1978. My mom sent me a couple boxes of my baby/toddler clothes when my daughter was born, and they are awful! Seriously, I considered using some of them for a Halloween costume but then I decided that that would just be too cruel. Lots of tiny cowboy shirts and strangely-colored corduroy jumpers with a few obnoxiously flouncy dresses that my grandparents must have gotten me. When I got a bit older, I was the comparatively poor nerdy redheaded kid who got glasses in 1st grade, whereas my classmates would go to Dallas to shop at the fancy department stores. My school’s dress code didn’t help matters much; skirts could fall no higher than two inches above the top of the kneecap, and I was tall enough that nothing that was in style was within the rules on me.

When I got into theater in high school and later as a theater major in college, wearing cute clothes would have been impractical even if I had been interested by then. I was always wearing torn, paint spattered clothes that I could paint sets in, or dressed in all black if I was working backstage, or wearing carpenter jeans because I actually used the extra pockets to carry a wrench and other tools around while crawling in the catwalks hanging lights and running cables. I had a few nicer outfits for waiting tables at my dad’s restaurant in college, but they never approached what anyone would call fashionable. Even entering the workforce didn’t help because I worked at a used bookstore for eight and a half years where pretty much anything was fair game. The only rules that were ever mentioned were “Don’t wear T-shirts with obscenities on them” and “Managers shouldn’t wear ripped clothing.” And even those rules could be broken as long as you did it on Sundays when none of the higher-ups were around. Some people still dressed nicely, but I just wanted to be comfortable. And since leaving that job, I’ve been a stay-at-home mom, which hasn’t exactly inspired me to start dressing up.

Polyvore image of jeans, t-shirt, flannel, hoodie, sneakers, tote bag, and nail polish
I had to add a lot of boring clothes to Polyvore. At least my nail polish is cute and trendy.

So what does my wardrobe actually consist of these days? Well, I decided to live large and buy some new jeans the other day, mostly because I ripped a huge hole in the ass of one of the two pairs I’d been alternating and I was tired of having to tug my shirt down to keep the whole world from knowing what color underwear I was wearing. Yes, they’re mom jeans. I’ve also started wearing yoga pants more often, though certainly not to actually do yoga. Now that it’s warming up, I need to dig out my jean shorts. I actually do own one or two skirts, but I only wear them under extreme duress. Shirt-wise, I mostly wear plain T-shirts, graphic tees, and tank tops; add a hoodie or flannel on top of those if the weather requires it. Some of these shirts, by the way, are probably five to ten years old if not older; when I moved last June I found a black T-shirt from a store that I think went out of business when I was in junior high and I bought the shirt I’m wearing as I write this while I was in college in the late ’90s. I bought new shoes the other day, but they’re the exact same sneakers I bought last year and wore until the arches collapsed and the leather tore. I can’t even remember how long I’ve been using the same Target brand purse because I’m too lazy to switch all my stuff between multiple bags, but based on a quick look through my facebook photos trying to find something to post here, I was carrying it at the Rally to Restore Sanity in October 2010, so it’s at least that old. Yikes. Also, despite owning a couple of big fancy diaper bags, I’ve been using the ugly turquoise one the hospital gave me for free because the others are too heavy now that I don’t use the stroller much and have to actually carry it.

Probably the most embarrassing part of my wardrobe is the number of shirts I still wear that are technically maternity shirts, even though my kid turns 3 next week. At least I thought ahead and made sure to buy items that don’t look like maternity clothes; I didn’t want to spend a lot of money on things that I could only use for a few months. (Don’t worry, I did put away the elastic-y pants and empire waisted stuff!) I doubt most people can tell the difference between my regular Gap ribbed tank tops and the slightly stretchier Motherhood Maternity ones, but I know and it’s starting to really bug me.

I want to buy new clothes, but at this point I don’t even know where to start. I’m so used to buying plain, functional items that I don’t even know what styles look good on me. My most daring recent-ish purchase was last fall when I couldn’t find a plain old raincoat and found a waterproof London Fog trench at Sam’s Club; the daring part being that I bought it in red instead of black. Living in suburbia now doesn’t help my choices much; most of my shopping is done at Kohl’s with the occasional foray into the options at the mall. How do I go about finding out what looks good on me? Do I just go try on everything in sight and hope I find something I like before fatigue and despair set in? Do I submit myself to What Not to Wear? (Is that even still on?) What say you, Persephoneers? How do I dress like an adult?

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[E] Hillary

Hillary is a giant nerd and former Mathlete. She once read large swaths of "Why Evolution is True" and a geology book aloud to her infant daughter, in the hopes of a) instilling a love of science in her from a very young age and b) boring her to sleep. After escaping the wilds of Waco, Texas and spending the next decade in NYC, she currently lives in upstate New York, where she misses being able to get decent pizza and Chinese takeout delivered to her house. She lost on Jeopardy.

28 thoughts on “Confessions of a Walking Fashion “Don’t””

  1. I’m 65 and lost 57 lbs.  I have no idea of how I look anymore.  So I asked a friend and she said, go shopping.  Try anything and everything on.  See what you like and what draws your attention.  I’m bringing my camera and take a picture of the things I try on.  Then I’m going to put them up on the wall and see what I like.  Every day is an opportunity to either rediscover my self or recreate myself.  Both can be good.

  2. How do I go about finding out what looks good on me? Do I just go try on everything in sight and hope I find something I like before fatigue and despair set in? Do I submit myself to What Not to Wear? (Is that even still on?) What say you, Persephoneers? How do I dress like an adult?

    By dressing how you want to! I’ve had something of a “style” change since last autumn. I used to be in the jeans/vest/cardigan camp but have ended up almost exclusively in dresses (wrote about it in my “Hello Legs!” article, as it happens) over the past few months and damn, I feel better. I don’t know if I look like an adult but I feel more comfortable. Anyway! The biggest step for me was to just try things. I have always hated trying on clothes in shops but learning to was actually pretty great. Instead of getting into a tizzy over a piece of clothing, I try it on now and either it works or it doesn’t. With online shopping, I’ve also had to bite the bullet over buying two sizes or knowing I might return something. I have also found shops that I love. For me it’s primarily Dorothy Perkins and Monsoon. And instead of torturing myself in shops that I know I’m not particularly fond of, I stick to the ones I like. Buying from the same store has meant sizing is a little simpler and different items have a greater chance of going together.

  3. I describe my style as “Vintage Maritime.” Meaning that I buy all my clothes from Old Navy. Or Target. I have a uniform for each season: fall and spring are jeans, a solid colored V-neck T-shirt, and a cardigan. Summer is a tank top of some kind, and capris or a cargo skirt, with the occasional sundress thrown in there, and flip flops. Winter is jeans and sweaters.

    I am so boring. One of my problems is that I’m insanely tall, so some of my options are limited by sleeve and pant lengths. Summer is the easiest season for me, for this reason, but Old Navy has extra-long tall stuff on their website, so that’s where I end up 90% of the time. I’d love to buy classic, stylish pieces, but contrary to what everyone thinks, clothes are not made with the freakishly tall in mind. Designer runway looks that I can’t afford, maybe, but not anything else. Even most designer jeans are too short for me.

    1. I understand the freakishly tall thing – and also shop at Old Navy / Gap online almost exclusively.  Everyone points me to alternatives, but none of them work as well (or as cheaply) as my standbys at Old Navy.  I’ve started to branch over to Banana Republic (tall dresses!  In 60’s styles!), but am afraid to leave the Gap line entirely.

      At least, as you’ve found, Target occasionally has some stuff.  And there’s always shoes.


    2. I love you for “Vintage Maritime”! You made me laugh. Ninety-five percent of my wardrobe is from Old Navy; the other five percent is from Target. We are wardrobe sisters. Whoop!

      My former boss told me that she (and her sister) wanted to take me shopping so they could outfit me in “grown-up clothes” (meaning expensive designer labels from Neiman Marcus like she wore, like I could afford that). It took all of my will not to tell her to fuck off and die.

  4. This article is perfect because I was just thinking the other day that I need to find myself some sort of style. I live in Portland and while it is definitely more laid back, people definitely have way more style than I do. I can’t even pull off the “i don’t care” hipster style. I’m just BLAH! I’m way too overwhelmed by clothing stores and I am super cheap which makes it difficult. A lot of the comments below have really helped me though!

  5. I would say, start with some comfy, simple, ‘classic’ pieces, in neutral colours & get accessories (scarves! bracelets!) that really appeal to you for whatever reason. Forever 21, as flawed as that place may be, has some great cheerful, cheap accessories that are pretty much guaranteed to be current. ‘Neutral’ colours include black, grey, and brown. I’d suggest staying away from combining black or grey with brown for the most part. Not that it can’t work, but it takes a certain amount of confidence to pull it off. Places to go for ‘basics’ that are probably fairly stylish include (but are not limited to) the Gap and Banana Republic. Make sure not to settle for something that doesn’t quite fit right just because it’s on sale or whatever, because there’s nothing less ‘stylish’ than feeling uncomfortable in your clothes.


  6. Instead of shopping at a big department store with tons of different styles, find one store who’s aesthetic you like (Anthropologie, J Crew, Ann Taylor, Eileen Fisher, etc).  This will save you from being overwhelmed by a thousand different options.  Buy just a few pieces at first, to build 3 or 4 outfits, and see if you’ll actually wear them and if they fit your lifestyle.  Start slowly incorporating more stuff, until you have a clear idea of what you like and what works for you.  Once you’re at that point you can start branching out to other stores.

    I would also suggest talking to friends who have a style that you like.  You could borrow clothes, or take them shopping with you.

  7. I second (or third or fourth) accessories. A lot of really chic outfits are very simple, but a few great accessories make them look like a million bucks.

    I would suggest focusing on one item of clothing at a time to make it less overwhelming. Wear a pair of pants that you know are flattering and try on different shirts to see what stands out and vice versa. Also look at different necklines. A tank top or sweater with a cowl neck looks fancy and attractive, but still feels like you are wearing regular clothes (I hate being aware of my clothes, I want to feel like I am in jeans and comfy pants at all times, even if I don’t look like it).

  8. Know what’s sad? One of my “dress” shirts was definitely a maternity top that I bought at Ross. I’ve never been pregnant.

    I used to have a braver attitude towards dressing myself, but I list confidence along the way, and now I hide behind snarky t-shirts, jeans, and hoodies. One of these days, I’ll find my swag again, but that day might come when I start making my own clothes.

  9. Although it’s called Academic Chic and is no longer updated, is a great fashion basics blog. One of my favorite things about it is that the writers would give themselves challenges, like combining colors they normally don’t or wearing patterns they normally don’t. Plus, since it’s by grad students, all the clothing they wear is affordable, so it will give you a a lot of ideas of how to do creative things with mall clothes like Banana Republic and the Gap. (I swear I am not involved with the site at all, I just found it very helpful when I started shopping for teaching clothes a few years ago!)

  10. Accessories make a huge difference.  I wear a lot of basics, but make them more interesting and less boring by how I style them.  When I used to live in boring, college-kid, I’d wear, say, jeans, a t-shirt, sneakers, and a hoodie on a casual day when I wanted to be comfy and make minimal effort.  On a day like that now, I’d wear jeans (that are figure flattering and not too outdated… I suggest dark bootcut jeans as an option, though I normally wear skinny jeans), a simple tee in a solid color (but not a t-shirt), a cardigan or blazer instead of a hoodie, and flat shoes (sandals, ballet flats, or  boots depending on season) instead of sneakers.  And I’ll wear fun earrings.  I’m just as comfy, but I feel more like a grown-up.  Give it a try.  And you can still buy affordable simple basics with this approach.

    I also learned a lot about style by seeing how others dress themselves  (in person, in magazines, etc).

    I’ll also add that wrap dresses and  sundresses are easy 1-item outfits that are comfy and figure flattering but look “adult.”  In the winter, I’ll throw a cotton dress on over leggings and a long-sleeved tee, and I feel like I’m in pajamas all day, but I look like I made an effort.  Fooled ya!

  11. Accessories, baby! Find a fabulous necklace that you love and a plain t-shirt and jeans outfit goes fabulous. Or a big cuff, layered bracelets, brightly colored shoes. If jeans and tees work for you and make you feel good, stick with them, just spice them up a bit with little pieces. You can find all kinds of cool scarves, jewelry, and bags at Kohl’s or Ross or other places like that.

    I love to shop and I love clothes, shoes, accessories, all of it, but I realize it can be totally overwhelming. I wear a lot of black, white, grey, and neutral colors and then throw on the “pop of color” nonsense with little things here and there. It is easy to find fun and affordable jewelry, check etsy for huge selections of really cool stuff.

    And if you’re ever in the Bay Area, I would LOVE to take you shopping. My dream job would be as a personal shopper for people on budgets so I can see how much awesome I can create on very little money.

  12. I think a big issue with a lot of people is that they overthink it – or at least worry when the worrying is not that necessary. And there is nothing wrong with Kohl’s. It is actually a very decent store. But yes, you do need to try things on. You don’t have to do it all in one day and just because a store sells it DOES NOT MAKE IT GOOD. I’ve side-eyed many things at the mall. Maybe once a month see what a new store has to offer. Try out Kohl’s one month, Macy’s the next, JCP whenever. Take a friend if you like. Go alone if that works better. I shop with friends but when I’m buying clothes for myself, I go alone.

    If you’re comfortable in teeshirts and jeans, there is nothing wrong with that. At All. The idea that beauty is pain is rather false. There are no real fashion police that will hunt you down and tell you that you’re wearing last season’s boot. Don’t wear the shoes if they hurt, don’t buy the jeans if they pinch or sag funny. Comfort is the best goal you can have.

    I’ve built my closet around basic pieces like solid and striped shirts, blue pants, gray pants, khakis, jeans. Seasonal stuff and things with ‘character’ jazz up those basic pieces. Basics just need to fit. Character pieces need to compel one to dance in the dressing room to whatever music is playing. This is a test I apply all the time. What Not To Wear never seems to mention it. But I recommend it. If you’re dancing that means you feel good.

    And Do Not Read The Magazines for advice on specific items. They are never helpful, tend to focus on what a skinny white woman with a shit ton of money would wear and styles vary by season, region and workplace. The mags are best for inspiration. Nothing more. They just don’t know you – that’s the main thing.

    Find things that make YOU happy. Wear that shit out. You don’t have to buy clothes every season. The fact that your jeans tore just means that you got everything you could out of them. :) Your purse is over a year old? That’s okay. Built to last.

    Just flip the instinct switch. You’ll feel great. Promise. :)

  13. Being a grad student starting the dissertation writing portion of the degree and having no teaching (only grading) this term is eroding my fashion sense. Most days I wear the following: a long t-shirt (from like a run or something or today I am wearing a “George Orwell 1984” shirt), leggings from when I was in highschool that I kept to wear under pants in the winter but that I now wear as pants, a hoodie or a giant wool sweater that was my grandma’s, thick wool socks. If I cared slightly more I think my outfit could pass as being hipster, but no, it just cannot in its present state.

  14. I don’t know if dressing like an adult is even possible for most people (and not as a ‘people are fools’ thing but ‘dressing adulty equals boredom most of the time’). Dressing your age would be a nice start, so no wise crack texts on your shirt or JUICY on your bottom, but you don’t sound like such a woman anyway. Besides that I think that the wholeness and fittingness of a clothing item are two of the important things (no ripped jeans, no scuffed shirts, not too tight but certainly not too wide either).

    I’m a big fan of the golden oldies and signature piece theories. Have a majority (this doesn’t mean a stuffed walk-in-closet) of plain but good clothes (jeans, pantalons, blouses, shirts, vests etcetera) in neutral colors. Freshen those up with the colors that suit you but keep you feeling comfortable. For the bag: use a toiletry bag in which you have all your keys, wallet and stuff and move it from bag to bag (if you want to), because bags are a great acessory. Same for scarves.

    Still uninspired? Ask friends/family/colleagues in what they would love to see you. Step out of the comfort zone, but don’t let yourself be pushed, take your time. After all, how much is wrong about plain clothes? Comfort (both physical and mental) should always be first.

    And how did I suddenly write an epistel about clothes.

    1. Oh, no, no JUICY butt pants! I do have a few snarky tees, but you’ll pry my “Mt. St. Helens Blows” shirt from my cold, dead, nerdy hands. I actually did manage to buy some black pants over the weekend; they’re almost but not quite denim because the fancier pants I tried on were itchy and unflattering. I tried on a few shirts with patterns, but they just seem so loud on me! And I’m desperate for a new bag; I like your toiletry bag suggestion, now I just need to stop being so picky and buy something!


  15. Whatever the answer is, it’s not in Redbook. I find that picking a celebrity whose style you like, then choosing key pieces from their wardrobe to accentuate stuff you already own, is a good move.

    Disclaimer: My celebrity style of choice is David Bowie from 1974.

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