On Dressing Badly in a World That Champions Personal Style

unaesthetic life millennial pink man repeller


here was a moment, or a series of moments, in my young adult life when I realized I had forgotten to care about fashion. More specifically, I had forgotten to learn how to dress. It was like one of those dreams where I end up in public pantless, except I am wearing pants — they’re just very, very ill-fitting. How did this happen? And how does one exist, as a millennial woman in downtown Manhattan, when one’s idea of layering is inspired by the woman from “Feed the Birds” in Mary Poppins?

Growing up, I liked Vogue as an idea. I understood that it was supposed to be important. I even got my mum to put black-and-white pictures of Kate Moss in frames in my bedroom. I once, excruciatingly, described myself as a “fashionista” on (an early UK precursor to Facebook) without actually knowing what it meant. But this was tweenage folly; I was never a fashionista, or even the 13-year-old suburban equivalent.

In the mid-sized British town I grew up in, it was preferable to be as nondescript and conventional as possible. And while that appealed to me, I was never quite able to achieve it, instead diving headlong into whatever subculture interested me at the time. One memorable outfit featured a baggy Sex Pistols hoodie (I, of course, knew only one song) with a dark magenta underskirt, which I thought of as an Avril Lavigne-style tutu, but in hindsight made my lower half look like that of a 19th-century courtesan.

Only a few years later, I would wear head-to-toe Jack Wills (Britain’s answer to Abercrombie & Fitch) — striped shirts, v-neck jumpers, vests, soft tracksuit bottoms — such that I looked like a frat boy vacationing in Martha’s Vineyard with his emotionally removed father. Both these “looks,” by all accounts, were unendingly embarrassing. And yet, I look upon them now with a surprising sense of pride. Not because I looked good (I didn’t), but because I had committed to something I liked — to a version of myself that I felt happy with.

I haven’t been able to do that since reaching adulthood. Now that I am expected to get my clothes from more than one store, and lovingly curate outfits in a way that somehow makes sense for my body type, budget, attitude and local climate, I have become overwhelmed. Now that I am no longer in my socially hegemonic town, where the most sartorially rebellious thing people could think of doing was to be “emo” and wear a checkered sweatband, the opportunities feel endless. Now that I instead live in New York, where personal style is frequently mistaken for personality, the stakes feel too high.

The nuance of my unaesthetic life is that, on the one hand, I would love to feel confident and shiny, photograph well and avoid feeling genuine horror at the thought of scraping together an outfit for an evening out. But on the other, everything about me is in the way of that — whether it’s my less-than-perfect mental health, my body issues, my need to be pajama-level comfortable at all times, my lackluster finances, my sexuality, my unpopular opinion (shared by grumpy boyfriends the world over) that shopping is, in fact, boring… I always seems to have a reason not to invest time, money or energy into my personal style.

The other night, while getting ready to go out, I belabored how to wear the oversize black corduroy shirt, which doubles as my personal anxiety blanket, for over 30 minutes. I tried on several different pairs of pants and skirts but nothing looked right, which seemed logically impossible considering all my clothes are black. After that many outfit changes, I usually start to feel as though the human form is just an abstract concept, or a rumor made up by Nordstrom Rack.

It’s in these moments that I curse my inability to buy the right clothes. And yet, I still drag my feet whenever I have the opportunity. Shopping, it seems to me, seeks to sell me a new life by reminding me that my underwear is unflattering and that I didn’t shave my bikini line properly again. The act of pulling garments on and off, my skin pallid under the overhead strip lighting and body barely covered by the wispy changing room curtain — consistently half an inch thinner in width than it needs to be — is bad enough. Add in the self-esteem issues I’ve collected from the societal meat-processor that is female adolescence and the curse of having a perma-thin, beautiful mother, and the whole things turns into a cruel, Sisyphean task.

What’s a gal to do, then, but wear so much loose, black clothing that she begins to resemble Emperor Palpatine from The Empire Strikes Back? The unflattering cycle continues.

But there are greater implications to dressing badly than just toiling in front of my mirror and feeling awkward at parties. One’s style has crucial connotations — socially, professionally and romantically — that are not altogether frivolous, despite being culturally overstated. Ultimately, we see each other, we exist in the world, and it is commonly accepted that we will not be publicly naked. But in the age of Instagram and personal brands, looking the right way seems to be a perverse qualification in and of itself, even outside of visual pursuits like modeling or style blogging.

So how do I, despite my neuroses, dress in a way that will make people want to hear what I have to say? Make them want to hang out? Make them want to hire me? How does one exist and succeed in an increasingly visual world when one is style-blind?

I hope to untangle this eventually, like the windswept tassels on a poncho I shouldn’t have worn in 2007. And in the meantime, I suppose I’ll depend on my cinematic doppelgangers — be they turn-of-the-century pigeon wranglers or craggy defenders of the dark side — to help me make light of the visual world, sans an elusive look of my own.

Lizzi Sandell is a British writer who lives in New York City. She says “hi” to dogs she meets on the street. 

Illustrations by Amber Vittoria; @amber_vittoria

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