16 Fashion Risks That Seriously Paid Off

Photo: Carly Otness/BFA NYC.
There's a fine line between a risk-taking red carpet look that works — and one that's a worst dressed contender. Toeing that line takes the right combination of daring, flair, and next-level styling finesse to pull off. In other words, making a kooky outfit work ain't easy. But, without fashion risks, these bright-lights events would devolve into a bunch of pretty ladies in designer dresses — and where's the fun in that?
So, we're paying tribute to 16 celebrities who got the risk-to-reward ratio right and actually owned their offbeat outfits. Ahead, proof that fashion favors the bold.

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Photo: Rindoff/Dufour/Getty Images.
Miroslava Duma's solution for a ho-hum chambray-and-skinny-jean outfit? Throw a big ol' fashion blanket over it. Done.
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Photo: David M. Benett/Getty Images.
We know a lot of folks still side-eye the overalls trend. But here, Hanneli Mustaparta proves that a dark wash and a close fit are all you need to take them from down-on-the-farm to up-in-the-club.
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Photo: Neil Rasmus/BFA NYC.
Vogue.com's Chioma Nnadi proves that any outfit, no matter how fancy, is instantly freshened up by a pair of unpretentious white kicks.
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Photo: David X Prutting/BFA NYC.
We're not sure if Lauren Hutton is over heels, channeling John Lennon, or just taking the stuffing out of an ivory dinner suit with her slightly grubby white sneaks, but we do know we like it.
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Photo: Laila Bahman/BFA NYC.
Musician Natalia Kills proves that sequin-pocket pants, a crop top, and monster platforms practically command attention — bonus points when you add a wide-brimmed black hat that doubles as your own personal dark halo.
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Photo: Carly Otness/BFA NYC.
All hail Jenna Lyons, queen of the quirkified basic. Her denim jacket? Ruffly and peplum-hemmed. Her white T-shirt? A tad longer than most. Her chinos? Ever so slightly drop-crotch. She is the patron saint of maximal minimalism.
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Photo: Joe Schildhorn/BFA NYC.
Leave it to Leandra Medine to freshen up the trend du jour, the all-white outfit, with massive proportions. We don't know if men are repelled by the double bell-bottom look, but we're intrigued.
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Photo: Matteo Prandoni/BFA NYC.
The shredded knit on Natalie Joos of Tales of Endearment makes us wish we hadn't tossed that top the Grumpy Cat in our life destroyed.
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Photo: Carly Otness/BFA NYC.
We're used to seeing Kenzo prints as part of a fancy-pants ensemble, but artist and director Vashtie Kola took hers all the way downtown with her black Timbs and gold jewelry for a new spin on the girly matching set.
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Photo: Joe Schildhorn/BFA NYC.
As founder of Avenue32, Roberta Benteler has a literal store full of luxe designer goods at her fingertips. What charms us so much about this look is the winsome way she styles it — the '40s housewife headscarf, the cropped, wide-legged pant — so it looks retro-charming, and not just chi-chi.
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Photo: Billy Farrell/BFA NYC.
Alexa Chung Ellen-izes a trim navy suit with the normcore sneaker of choice, the New Balance 574.
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Photo: Joe Schildhorn/BFA NYC.
Harley Viera-Newton proves that all see-through everything can be ladylike, with her demure, knee-length skirt. (We also love the granny-panty realness she's serving.)
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Photo: Madison McGaw/BFA NYC.
A lesser supermodel would have done miniskirt and sexy sweater, and left it at that. But this is Joan Smalls, so she threw on a dad-sized jean jacket over the whole shebang for a layer of vintage-inspired interest that cleverly doesn't distract from the mile-long-leg look she's got going on.
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Photo: Matteo Prandoni/BFA NYC.
Taylor Tomasi Hill, queen of all tricky trends, ably pulls off the only puffy shirt that doesn't give us Seinfeld flashbacks, and the only square-toed shoes that don't make us think of Pilgrims. Props.
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Photo: Angela Pham/BFA NYC.
There are a few fine examples of the lady suit represented here, but Tao Okamoto makes hers next-level by wearing a shape even most dudes are afraid to tackle: the double-breasted jacket. Proof positive that you don't have to be this guy to rock one.
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Photo: Joe Schildhorn/BFA NYC.
We bet you haven't even thought about wearing a handkerchief top since summer camp, 1997. We also bet Karlie Kloss is making you reconsider right about now.

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