What Do We Really Mean When We Say Something Is ‘Flattering’?

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Picture the last time someone told you an outfit was "flattering." Was it a sales associate? A mother or well-meaning aunt? A friend well-versed in glossy magazine wisdom and skilled at comparing torso shapes to pieces of fruit? Try to remember what, specifically, they pointed out. It may have been a cut that minimized your hips, a print that obscured your midsection, a tailored seam that made your waist appear smaller. Perhaps it hinged on negative space, making it appear that your body takes up less physical room than it does in reality.

Finding clothing that makes you feel good often has to do with calling attention to something you love about yourself. But clothing deemed "flattering" is often about hiding things, a Caravaggio-esque exercise in using shade, light, and strategically-placed seams to disguise our bodies as something they’re not. So often, it all comes down to making you less of yourself. Literally: Whether you’re trying to sneak a half-inch off of your thighs with vertical stripes or cinching your waist into submission with a carefully placed belt, the ultimate goal frequently comes down to minimizing the physical amount of mass that comprises our bodies.

It took a while for me to understand why I bristle when someone deems an outfit to be "flattering." Ultimately, no matter how benevolent that cooing sales associate’s intentions are, I hear code-speak for "that does a good job at hiding what’s wrong with you."

Sounds harsh and perhaps hypersensitive, but I don’t think I’m alone in this. I asked women I respect to tell me how they feel when someone drops the f-bomb on them. "It sounds innocent enough, but if somebody were to say it in a condescending fashion, I wouldn’t like it," says Sara Benincasa, a comedian and author who recently penned an eviscerating takedown of society’s obsession with weight. "A better thing to say is this: ‘That dress is lucky to have you in it.’" (Props for that.)

"I hate [the word] less coming from a friend who knows me and knows that I don't want to look like a maternity ad," my friend Natalie tells me. Natalie, who works as a producer for a news organization, is a stunning and super-fashionable woman who wears a size 16, rocks crop tops with the best of them, and, at one point in our chat, described herself as "a walking contradiction: A plus size woman who wears Spanx and crop tops simultaneously."

We both agree that "flattering" is a nuanced word — and how it’s interpreted comes down to the person receiving it as much as the person saying it. "If it comes from someone who knows me, I know they understand that I want to look nice, and that's a gentle way of saying ‘I know you hate your tummy/thighs/butt, et cetera, and I want you to know you shouldn't worry about it in this garment,’" she tells me. "But a salesperson saying it… that comes with a tinge — or a load — of condescension. If someone who doesn't know me says it, they're probably saying ‘you're fat, but it's not as noticeable here.’"

The definition of "flattering," and how much significance we ascribe to it, is different for everyone. For myself, and probably for many women, the word comes implicitly attached to a scroll of dos and don’ts passed down from generation to generation, from mother to daughter in fluorescent dressing rooms, from teen magazines and girlfriends and personal stylists and season after season of What Not to Wear-style programming on television. Whether the offender in question is peplum, oversized tees, or horizontal stripes, my hunch is that many women know the exact styles and garments that ring mental alarm bells, even if you — gasp — kind of love the clothes.

And it is so hard to unlearn these conventions. After spending years shopping and learning to dress ourselves, consciously and subconsciously taking notes on what worked and what didn’t as we sift through piles of garments in countless mall dressing rooms, each of us studying how different cuts and fabrics and washes reacted to the shapes of our limbs and the contours of our torsos, they are just as embedded inside us as the bones, muscle, and fat we try to mask, skew, and contort.

I’ve asked more than a dozen girlfriends and acquaintances whether they, too, have their own rule books buried deep inside their brains. Almost everyone does. A petite friend tells me she grew up with a litany of rules for dressing as a short, "pear-shaped" woman, including a hard no on longer-length skirts and dresses. I ask if she’s ever purchased an item that broke these rules. "A tea-length skirt. Vintage. It was gorgeous. I never wore it out."

I wanted to know more about how so many of us are on the receiving end of this messaging, and how it becomes so deeply internalized. So I asked Jennifer Ogle, a professor in Colorado State University’s department of design and merchandising whose research specializes in things like body image, media influence, and the psychological, social, and cultural aspects of dress.

"Various socio-cultural institutions — mass media, the fashion industry, families, et cetera — send clear messages about how to make bodies that diverge from narrow norms of attractiveness conform to these ideas," Ogle tells me. Media, of course, deluges us with these messages. The fashion industry has a Midas-like gift for turning these insecurities into piles of gold with various methods of minimizing and camouflaging (see: the $1 billion business of Spanx). Family members can play a major role in shaping how we dress ourselves — especially moms, who Ogle refers to as the "appearance gatekeepers" of the family.

All of these entities can, Ogle says, "convey cultural conventions about how to dress various body shapes so as to ‘hide’ culturally-constructed ‘body flaws’ and to create the illusion of a ‘perfect’ body, as defined by society. Similarly, media content may ‘instruct’ consumers in how to ‘dress the body’ so as to minimize so-called flaws and enhance features that are valued by society at this time/in this place." These messages train us to see the act of dressing as troubleshooting; a skilled game of strategy in neutralizing body parts arbitrarily deemed undesirable by society.

With the ways we’re taught to dress being so inextricably linked to the ways we’re taught to see our own bodies, it makes sense that this kind of socialization could potentially have long-lasting negative effects on our own body image. I ask Ogle whether there is indeed a link. "Absolutely," she says. "In my own work, I have found that women and adolescent girls use clothing to emphasize features of the body that they like and to camouflage features of the body that they do not like, and doing so is a key ‘body project’ for them, or something that they work at and accomplish as part of their self-identity."

Of course, it doesn’t help that many of us are learning these rules in our ultra-vulnerable and prickly tween and teen years, too — when things that perhaps aren’t even meant to be criticism can be easily perceived as such, tucked away deep inside us until metastasizing into real-deal Body Image Issues we carry with us our whole lives.

"I remember shopping for a prom dress when I was 16 or 17 and probably a size 6," recalls Benincasa. "Some woman said to me, ‘Oh, we'll just get a control panty to hide your belly.’ Like bitch, what? I'm 16. I know this is the fancy mall, but get your life right with your projecting the bullshit onto a young lady."

"Projecting the bullshit onto a young lady" can be, psychologically speaking, hugely to blame for these messages taking root in our brains. Our sensitivities in this stage of our lives likely make this process of navigating the body, how we dress it, and how we see it even tougher. "Depending upon how the topic is broached, it seems possible that interpersonal instruction about how to camouflage a bodily flaw might be interpreted by a young girl as criticism upon her body," says Ogle. Cue the doubt, shame, and self-criticism setting up shop in her brain and camping out for a lifetime.

But what happens when we kick these conventions to the curb? After all, rejecting the notion of dressing as flaw-masking goes hand-in-hand with rejecting the idea of your body parts as flaws. I asked Ogle about the potential impact of spurning these rules. "I imagine it would depend on one’s motive for rejecting or defying the rules," she says. "Perhaps it could be experienced as empowering, if the rejection was on one’s own terms or as a means by which to reject cultural beauty ideals and assert the beauty of one’s own body." Anecdotally, I couldn’t help but notice a rise in my own confidence when I, a 5’0" and 140-pound woman with nothing close to a six pack, purchased my first crop top. It felt a little rebellious, like I was planting a flag in uncharted territory of a very public, performative kind of self-acceptance.

Tanesha Awasthi, founder of Girl With Curves, has built a brand out of inspiring her readers to wear whatever they feel good in. I ask if she, too, noticed a rise in her confidence once she started ignoring conventional wisdom about what looks good on her body. "Definitely," she says. "I love horizontal stripes, and it makes me feel amazing knowing that I'm inspiring other women to step outside their comfort zone and wear the skintight pencil skirt even though they have wide hips, or rock the polka-dot print dress simply because they love it. Forget fashion rules. To me, ‘flattering’ is what a woman feels her best in."

Benincasa, similarly, says she feels better when she throws the rules out with the garbage. "The rules I absorbed from popular culture were a constraint on my ability to have fun with fashion. Now that I wear what I think looks great on me, I feel better," she tells me. "I like to look the way I like to look. That doesn't mean skinny. So I'm dressing the body I live in." I ask her what some of her favorite "rule-breaking" garments are. "I love red," she says. "I look great in red. It doesn't make me look smaller."

In September, the stunning Dascha Polanco (from Orange is the New Black) positively slayed on the red carpet during New York Fashion Week wearing nothing but a bodysuit and a floor-length duster. She told Vanity Fair that the outfit was a deliberate choice that she and her stylist made, in part to look like a boss but mostly to help her work through her own body confidence issues: "[Stylist] Darius Baptist thought that I should wear a bodysuit and just show my thighs, since I’m so self-conscious about them. But fuck it, this is me, this is who I am, this is real. I was made this way."

"I'm all for making [women] feel confident and showing you can do anything that anybody else can do," her stylist, Baptist, tells me over the phone. "My train of thought is that you can do whatever it is that you want to do, just as long as you have the confidence to pull it off. That's, to me, one of the good things about fashion. It's meant to have fun, not to take it so seriously."

Daring to publicly wear an outfit that makes you feel vulnerable in this way is almost like method-acting your way toward self-love: You practice being comfortable with yourself, you practice projecting that image publicly, and eventually, it solidifies into something real.

Whether it’s a crop top or a curve-hugging dress or, hell, a super effective set of Spanx, it’s totally okay to like clothes that make you feel good, or that you think look good on your body. There’s nothing wrong with wanting to dress for your shape in a way that feels right to you. But where does that definition of "what’s right" comes from? Is something a perfect fit just because it tucks and nips in the right places, or uses a bit of tromp l’oeil to trick the eye into thinking your body is smaller? Or is something perfect because, no matter what the cut or shape or style, when you put it on you feel like a fucking queen?

"Most women know by a certain age which styles and shapes they feel best in, but the key is to try it on," says Ann Mashburn, an Atlanta-based fashion designer. "Take a hard look from a decent distance from a mirror with the right shoes. Do you love the way you look? Do you feel like the best version of yourself? If you take a lot of delight in Beetlejuice striped trousers, maybe you should listen to that sense of delight, regardless of how they make your thighs look."

Maybe in reality, the perfect outfit occupies that rare slice of the Venn diagram where the image we have of ourselves in our head overlaps with the image we’re projecting into the world — not because it’s a mask. Maybe the ultimate satisfaction can come from muting those dressing room alarm bells and listening instead for that sense of delight Mashburn’s talking about, instead of approaching the act of dressing ourselves like a game of body part Whac-a-Mole. Maybe, when we lose the narrative of minimizing ourselves, we have everything to gain.

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