Oscars 2017: The Biggest Risk Takers of the Night

The most polarizing looks from the night, which you'll be debating all day Monday
By Colleen Kratofil
February 26, 2017 11:59 PM

1 of 12

STYLE GAMBLERS

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

Advertisement
Advertisement

2 of 12

JANELLE MONÁE

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.

3 of 12

DAKOTA JOHNSON

David Fisher/REX/Shutterstock

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).

Advertisement
Continued on next slide.
Advertisement

4 of 12

NAOMIE HARRIS

David Fisher/REX/Shutterstock

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?

Advertisement

5 of 12

SCARLETT JOHANSSON

David Fisher/REX/Shutterstock

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.

6 of 12

LESLIE MANN

David Fisher/REX/Shutterstock

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.

Advertisement
Advertisement
Continued on next slide.
Advertisement

7 of 12

MICHELLE WILLIAMS

David Fisher/REX/Shutterstock

What's most shocking about Michelle's custom Louis Vuitton halter gown how much double-sided tape needed to secure that daringly low neckline.

Advertisement
Advertisement

8 of 12

JESSICA BIEL

David Fisher/REX/Shutterstock

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?

Advertisement

9 of 12

CYNTHIA ERIVO

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.

Advertisement
Advertisement
Continued on next slide.
Advertisement

10 of 12

FAYE DUNAWAY

Jim Smeal/BEI/Shutterstock

Clearly Faye couldn't decide between a double-breasted tux or a ruffled, sheer gown, so she just combined the two!

Advertisement
Advertisement
Advertisement

11 of 12

BLANCA BLANCO

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!

Advertisement
Advertisement

12 of 12

SOFIA BOUTELLA

Jeff Kravitz/FilmMagic

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.

Advertisement
Advertisement
Replay gallery

Share the Gallery

Up Next

By Colleen Kratofil