Oscars 2017: The Biggest Risk Takers of the Night

The most polarizing looks from the night, which you'll be debating all day Monday

01 of 12

STYLE GAMBLERS

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Steve Granitz/WireImage;ANGELA WEISS/AFP/Getty;George Pimentel/FilmMagic

From dramatic ballgowns to surprisingly minimal dresses, it's up to you to decide if these risky red carpet moves paid off

02 of 12

JANELLE MONÁE

89th Annual Academy Awards - Arrivals

Janelle has worn so many show-stopping black and white looks throughout awards season, but she kept her most embellished, sheer, dramatic look (it's Elie Saab Haute Couture) for last.

03 of 12

DAKOTA JOHNSON

89th Annual Academy Awards, Arrivals, Los Angeles, USA - 26 Feb 2017
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When your dress draws comparisons to Sandra Bullock's hand-me-down wedding dress from The Proposal, it might be a sign you could have lost a layer or two (she's in Gucci, with Cartier jewelry).

04 of 12

NAOMIE HARRIS

89th Annual Academy Awards, Arrivals, Los Angeles, USA - 26 Feb 2017
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We love how much Naomie loves an avant-garde look, but was wearing a short strapless caped dress with a stomach cutout and mismatched shoes (all Calvin Klein by Appointment) a fun risk or fashion miss?

05 of 12

SCARLETT JOHANSSON

89th Annual Academy Awards, Arrivals, Los Angeles, USA - 26 Feb 2017
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Scarlett usually turns heads for her body-skimming designs. This year, we did a double take after seeing the sheer amount of fabric in her loose-fitting A-line Alaïa gown.

06 of 12

LESLIE MANN

89th Annual Academy Awards, Arrivals, Los Angeles, USA - 26 Feb 2017
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We can certainly appreciate anyone who experiments with a bold color on the carpet or a standout silhouette. But mixing both (in Zac Posen) can run the risk of being red carpet overkill.

07 of 12

MICHELLE WILLIAMS

89th Annual Academy Awards, Arrivals, Los Angeles, USA - 26 Feb 2017
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What's most shocking about Michelle's custom Louis Vuitton halter gown how much double-sided tape needed to secure that daringly low neckline.

08 of 12

JESSICA BIEL

89th Annual Academy Awards, Arrivals, Los Angeles, USA - 26 Feb 2017
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The Oscars statue seemed to be the biggest inspiration behind a lot of the night's looks, but did Jessica's very literal interpretation take it a step too far?

09 of 12

CYNTHIA ERIVO

89th Annual Academy Awards - Arrivals
Frazer Harrison/Getty

If there ever was a time to go bold with a floral-print and exaggerated circle skirt, it would be at the Oscars. But we're not so certain this look is coming up roses.

10 of 12

FAYE DUNAWAY

89th Annual Academy Awards, Arrivals, Los Angeles, USA - 26 Feb 2017
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Clearly Faye couldn't decide between a double-breasted tux or a ruffled, sheer gown, so she just combined the two!

11 of 12

BLANCA BLANCO

89th Annual Academy Awards - Arrivals
Steve Granitz/WireImage

Once you're done staring at those sculptural shoulder details, you'll probably start thinking, 'That slit is a wardrobe malfunction waiting to happen.' And if you did, you'd be right!

12 of 12

SOFIA BOUTELLA

89th Annual Academy Awards - Arrivals
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The actress's silver sparkly Chanel column dress with feathery flared hem gives us flashbacks to Katy Perry's Grammys gown from two weeks go. So Sofia was very brave to copy a look that was just compared to The Beauty and the Beast's Fifi the Feather Duster.

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