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?

By [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.

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