In Defense Of "Unflattering" Clothes

It’s my body, and I’ll wear a fashion potato sack if I want to.

A few weeks ago I was at a vintage store where I was supposed to be looking for furniture for my new apartment, but I inevitably ended up wandering over to the clothing racks. There, I found a truly incredible caftan. It was soft and swingy, covered in a repeating print involving sand and plants and the moon, swirls of beige and rust-red. I was about to leave for a trip to Joshua Tree, and this dress might as well have been tailor-made for strolling around weird sculpture exhibits and getting my mind blown at a sound bath in the desert. Plus, it cost $20. I had to have it.

Oversized, shapeless clothing has been having a moment lately, much to some people’s dismay, but I’ve waited my whole life to slip on a potato sack masquerading as a dress and feel on-trend. Some of these garments, desert caftan included, feel a little bit like the cotton nightgowns I owned as a kid, which were emblazoned with the faces of Disney princesses and probably the most comfortable things I’ve ever worn (granted, the lace around the wrists and collar itched a little). Sack dresses are cozy and comfy and sort of like wearing nothing at all, because they require little thought or care: You don’t have to pluck and pull at them, or worry about the hemline creeping too far up or the neckline creeping too far down. Your body is perfectly cocooned, encased in its fashion-sack for safekeeping.

These dresses can be simple, or they can have a whole bunch of stuff going on, fun colors or cuts, collars or prints. A sack dress could be a sleeveless mini — though it’s not really a sack, I practically live in this roomy Everlane V-neck dress — or, at the other end of the spectrum, you could go full-modest with sleeves and a floor-length hem. One subgenre of fashion sack in the latter category is the prairie dress, recently touted in a piece on the Cut.

Prairie dresses, like any iteration of the sack dress, are not for everyone. Scrolling through examples linked to in Lindsay Peoples’ post, I found some I loved and some that weren’t for me. But what I like about them as a category is that prairie dresses are risky and weird; they’re doing so much — the high necks, the voluminous skirts, the loud prints — that they inevitably inspire strong reactions.

Some of the strong reactions on Twitter in the wake of the Cut piece have included this one: that “thinking you look good” in a prairie dress could only come from “skinny privilege,” because you’d have to be conventionally attractive enough “that no one ever makes fun of you for dressing like a jackass.” Stella Bugbee addressed the topic in her June editor’s letter, in which she recognized “how alienating fashion can be when it comes to size and bodies,” but argued that fashion shouldn’t be limited to what’s technically flattering. “No one should ever call you a ‘jackass’ for trying a new look,” Bugbee wrote. “Life is short — take some risks. Or don’t. Whatever. Let me fashion in peace.”

The original Cut story prompted a strong reaction of my own: that prairie dresses, and sack dresses in general, appeal to me precisely because they’re not technically the sorts of things I’m “supposed” to wear. I’m between a size 12 and 14, and I carry most of my weight in my ass and thighs. In order for clothing to be flattering on me, according to fashion magazine logic, I should always emphasize my waist, where I’m smallest, to draw the eye away from where I’m biggest.

Is it actually a privilege to look good in those “unflattering” clothes? Sure, if we’re defining what looks good according to tired, conventional style wisdom.

Of course, what we’re really talking about when it comes to whether or not a clothing item is “flattering” or “looks good” is whether or not it can bring you any closer to the impossible societal ideal of the sexy — but hold on — not too sexy woman. It’s an ideal with which anyone who’s ever dabbled in femininity is well acquainted.

As someone who is white and nondisabled, with the very real privilege of walking into many nonluxury clothing stores and finding things in my size, my relationship with “unflattering” clothing is far from representative. Like millions of people, I hover somewhere between straight sizes and plus sizes, depending on the brand and however much I weigh at a given time. I'm also privileged in the sense that I get to choose when and whether to wear a smock dress, or something flowy and boho — unlike those who are size 16-plus, who are often limited exclusively to shapeless, structureless clothes. And just as the world might consider me in a sack dress differently than it would someone who’s a few sizes smaller than me, the same goes for someone who’s a few sizes bigger. I’m not subjected to the anti-fat stigma and oppression that befalls others in fashion, and far beyond it, every day.

So there’s certainly privilege involved when it comes to the way different bodies are treated in different outfits, including ones the fashion world deems unflattering. But is it actually a privilege to look good in those “unflattering” clothes? Sure, if we’re defining what looks good according to tired, conventional style wisdom — but that’s the same sort of wisdom that says skinnier people look better in everything, period. According to these sorts of rules, most of us can never win, anyway. So why subscribe to them at all?

Since I hit puberty, I’ve tried to balance the contradictory rules of girlhood: Be attractive, yes, but not so attractive that you slip over the razor-thin, practically invisible line into sluttiness. As a young person who prematurely developed biggish breasts and enormous hips, I was more than once reprimanded by a middle school teacher for the length of my shorts or width of my halter top straps and sent to the nurse’s office to change into more modest loaner clothing — baggy basketball shorts and T-shirts — even though my smaller, thinner peers got away with dressing much more scantily than I did. Eventually I learned to feel an overwhelming amount of shame for the inherent obscenity of my 12-year-old body, which led me to years of disordered eating, one trip to the ER, and body image issues, which, while they’ve since significantly lessened, snuck with me into adulthood.

I’m far from unique here, obviously. Many women and gender-nonconforming people are taught to hate their bodies. And that hate is often complicated by the fact that we can never quite keep tabs on what, exactly, about ourselves we’re supposed to be hating. Are my thick thighs too sexy, or are they too fat? Some days I feel gross because I’m force-fed cultural signals that I am too big, too much, and other days I feel gross because yet another man is shouting disgusting things at me on the street. Give me some clearer signals here, patriarchy!

The sack dress trend — and more broadly, the normcore-y trends of mom jeans and big sweaters and formless, blobby clothing — has been such a relief to me because it’s lessened the competing signals blaring in my head about how I’m supposed to look and be. I’ve long coveted shapeless clothes because of their comfort and simplicity, but worried that, because of my body type, they’d just make me look like a fat slob. Nothing about my body, or the way I look in these clothes, has significantly changed. But because they’ve become such a staple in today’s fashion landscape — and, perhaps more importantly, because I’ve seen women and gender-nonconforming people of all sizes looking incredible in them on my social media feeds — I’ve decided not to give a shit about the fact that they are not, technically, flattering.

It helps that I’m gay and in a relationship with an assigned-female person. Even though I’m still steeped in the soup of cultural misogyny, like everybody else, it’s easier not to care about What Men Think on a larger, more systemic scale when I don’t have to care about how any one individual man considers my attractiveness, or lack of it. Queer people are used to dressing and performing gender outside the bounds of social norms — in fact, we excel at it. Lesbians and other queers have been at the vanguard of gender neutral, frumpy-chic style since time immemorial. Straight people just think it’s cool now.

Damned if you do, or don’t. But at the very least we can like the clothes we like, and like the way we feel in them.

My partner is a masculine-of-center nonbinary person, who’s subjected to a bunch of crap for performing gender the “wrong” way; they’re the last person who’d turn around and tell me that my own version of lazy femininity doesn’t cut it. (And I realize that, yes, plenty of people’s male partners support them in this way too, but lesbians have always been particularly good at loving each other’s bodies, even and especially when, according to conventional norms, they are imperfect; let us claim a sort of privilege here.) I don’t need my partner’s stamp of approval on every outfit, but it’s still nice to know that they’re attracted to me despite the technically unflattering clothing I wear all the time.

And sack dresses aren’t the only technically unflattering things I love. Oh, no. Wide-leg crop pants started showing up everywhere last year and are still going strong; I own four pairs of them, even though they make my butt and legs look enormous. I like that they’re loud, that they take up space, that I don’t have to squeeze my legs like sausages into skinny jeans anymore. If I’m not in wide-legs or a sack dress, I’m probably in high-waisted “mom” or “boyfriend” denim (what do these words mean???). Low-rise jeans will come back in style one day, but you won’t catch me going anywhere near them, ever again.

Having these clothes at my disposal is also great when it comes to experimenting with my gender presentation and identity. Don’t get me wrong; there are plenty of times, when I’m feeling more feminine, that I want to wear traditionally flattering clothes (dresses belted at the waist, A-line skirts). But whenever I’m feeling more androgynous, I love a good shapeless sack. At times, when I’m undergoing the occasional bout of dysphoria, they make me feel more at home in my body. Men are less likely to sexualize me in public (though of course, nothing truly stops them; I’ve been catcalled while in a sleeping bag–style winter coat before). I’m more likely to be read as queer by other queer people, and my presentation more accurately reflects whatever way I’m feeling, genderwise, that day.

I am wary of buying into the tenets of consumer empowerment feminism — style can be liberating, yes, but you can’t really divorce most store-bought clothing from the patriarchal, capitalist, anti-fat value systems that produce it. Nobody’s getting dressed in a vacuum. And yet, of the questions we should be asking ourselves about the clothing options made available to us, I don’t think we should place too high a premium on “how flattering is this?”

When figuring out how to clothe my flesh chamber every day, I’d rather focus less on the way fashion decision-makers would think I look and more on the way I feel. There’s only a certain extent to which we can control the way we’re treated in an inequitable world — either we’re showing too much of our bodies or we’re showing too little of them. Damned if you do, or don’t. But at the very least we can like the clothes we like, and like the way we feel in them.

There's nothing at all wrong with enjoying 'flattering' clothes — I like them plenty! — and it's high time that the fashion industry stopped making excuses for why there aren't more non-sack clothing options made available for the 68% of American women who are size 14 and above. We deserve options, and we also deserve to do whatever we'd like with them. We should buy the loud, tentlike desert caftan and/or the revealing crop top; indulge in the occasional wacky trend we’ll look back on in horror 10 years from now; refuse to follow fashion rules that might make us more desirable but less comfortable, less memorable. Less ourselves. ●

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