8 New Definitions Of "Flattering"

When someone scrunches up their nose and tells you that your outfit isn’t “flattering,” you typically know that it means one of two things: You're wearing something that either doesn't make you look taller or skinnier. Seeing style through that narrow lens is definitely a shortcut to whittling down the contents of your shopping cart, but we prefer to define a flattering piece as one that really represents the person wearing it. And, what does that say if we're all taking taller and thinner to mean better? 

Moving beyond those two definitions of “flattering” is an important step to harnessing the true joy of fashion. There's a whole spectrum of positive attributes your clothes could be delivering, and knowing what those are makes getting dressed more fun, and also much easier. Yes, that technicolored sack dress you love and your roommate hates is indeed flattering. Here’s the vocabulary you need to explain why.
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There's nothing wrong with subdued hues, but there's something very right about a colorful look. A bright outfit just says "Hi!" in a way that an all-black one never can. Bold, saturated colors project an approachable, lively disposition — even when you're feeling anything but vibrant. There are certain shades that are said to specifically complement your complexion (the old-school "winter" and "summer" colors come to mind), but we're of the mindset that liking it is all the reason you need.
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Even if you're not really a fan of oversized psychedelic daisies or pop-art hamburgers, there are certain prints that always makes you look more on. Dark, moody flowers, preppy pinstripes, spaced-out polka-dots, and leopard print often make a just-okay shape into something truly memorable.
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That midi-length pencil skirt and four-inch pumps might give you Gisele's silhouette, but that means nothing if you're relegated to the couch all night long because you can't move around for fear of face-planting. Heels that let you break into a sprint if you need to or a dress that looks best when you're twirling in it are flattering, because they help you be the energetic, joyful human you are.
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It's hard to explain, but you know it when you see it: A thick, sumptuous knit just looks better than its flatter counterpart. Price can play into textural richness (clothes with complicated textiles are harder to create, thus priced higher), but a textured, structural garment just plain looks more interesting. Of course, texture doesn't always equal flattering — it's all about striking a balance between softness, movement, and practicality. How to tell if you've struck that chord? If you're wearing something that people just want to reach out and touch (within reason!) you know you're doing something right.
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The concept of "flattering" has as much to do with how you feel in a garment as it does with how someone else sees you in it. And, when it comes to showing off, um, assets, not many people feel comfortable checking off every single box. Set that ratio for yourself — comfort leads to self-assuredness which is a straight shot to being flattered in your clothes. It might be long sleeves and a short hemline, or strategic cutouts on a maxi-dress, but a balance between revealing and hiding can be a lot more interesting than going all-in for either team.
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When everything about your outfit is way too perfect, it can be creepy in a Stepford Wife sort of way. Don't force it, of course — being quirky for the sake of quirk is generally a totally transparent move — but allow a dash of imperfection. Whether it's that denim jacket with the beyond-frayed elbows or the shoes that don't necessarily "go" with your suit, a little off-kilterness makes you look more human.
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There are certain trends, design elements, and graphics that are like a secret password — if you recognize an obscure Southern California skate logo on a stranger's jacket, or a tell-tale stitch on someone's bag (or four names on someone's shirt), the item automatically becomes 100% awesome. There's nothing more flattering than clothes that give you an automatic connection with other people. In many cases, these icons act as a built-in filter for the kinds of people you can attract.
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Dirty duds or clothes that have obviously been poorly taken care of aren't flattering to anyone (no matter how tall or skinny one looks in them). But, garments that have obviously been well-loved, often-worn, and tended-to have a certain charm that makes the wearer look like a Casanova, too.

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