People.com Lifestyle Style 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 Published on February 26, 2017 11:59 PM Share Tweet Pin Email 01 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 02 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. 03 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). 04 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? 05 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. 06 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. 07 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. 08 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? 09 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. 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! 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! 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.