Emmys 2017: The Biggest Risk Takers of the Night

Did these stars' bold style moves pay off? That's for you to decide!

01 of 13

WORTH THE GAMBLE?

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J. Merritt/Getty; John Shearer/WireImage; Frazer Harrison/Getty

From bold color choices to interesting dress silhouettes, these are the polarizing red carpet looks you'll be discussing all day Monday.

02 of 13

REESE WITHERSPOON

69th Annual Primetime Emmy Awards - Arrivals
John Shearer/WireImage

The Big Little Lies star switched up her style by eschewing a glamorous gown for a sleek silk Stella McCartney double-breasted tuxedo dress. Did her power suit make for a power move?

03 of 13

SARAH PAULSON

69th Annual Primetime Emmy Awards - Arrivals
J. Merritt/Getty

Sarah plucked her Carolina Herrera gown straight from the runway, but its puffy sleeves might convince anyone that it came from an '80s archive.

04 of 13

EVAN RACHEL WOOD

Evan Rachel Wood
Dan Steinberg/Invision for the Television Academy/AP

Evan's been continuously sporting suits on the red carpet, but this time, she went bold by playing up proportions in her three-piece Jeremy Scott tux featuring a teeny tiny jacket and extra wide-leg pants.

05 of 13

ARIEL WINTER

Ariel Winter
Jordan Strauss/Invision/AP

Ariel doubled the risk factor of having a serious wardrobe malfunction with her two thigh-high slits on her beaded black gown. "I usually do cleavage and not legs so I decided to switch it up," she told PEOPLE on the carpet.

06 of 13

ISSA RAE

69th Primetime Emmy Awards, Arrivals, Los Angeles, USA - 17 Sep 2017
Matt Baron/Shutterstock

Issa's asymmetrical custom Vera Wang Collection gown came with two unattached sleeves that could either look totally incomplete or completely cool. That's for you to decide!

07 of 13

KERI RUSSELL

69th Primetime Emmy Awards - Limo Drop Off, Los Angeles, USA - 17 Sep 2017
Invision/AP/Shutterstock

If there's a trail of black feathers down the carpet, you will most likely find Keri at the end of it in her J. Mendel gown.

08 of 13

MANDY MOORE

69th Primetime Emmy Awards, Arrivals, Los Angeles, USA - 17 Sep 2017
Rob Latour/Variety/Shutterstock

Does her black-and-white tulle gown have you smiling, or in tiers?

09 of 13

PADMA LAKSHMI

69th Primetime Emmy Awards, Arrivals, Los Angeles, USA - 17 Sep 2017
David Fisher/REX/Shutterstock

She debuted a new hairstyle to go with her old favorite silhouette: a curve-hugging, exaggerated mermaid gown.

10 of 13

AMANDA CREW

69th Primetime Emmy Awards, Arrivals, Los Angeles, USA - 17 Sep 2017
Matt Baron/Shutterstock

The Silicon Valley star's balances risqué (so sheer!) and modest (those long sleeves) touches, leading to a style statement that was decidedly mixed.

11 of 13

JULIE BOWEN

69th Primetime Emmy Awards, Arrivals, Los Angeles, USA - 17 Sep 2017
Rob Latour/Variety/Shutterstock

Her column velvet Alberta Ferretti is so sleek and classic. Are the origami ruffles exciting, or overkill?

12 of 13

NATALIA DYER

69th Annual Primetime Emmy Awards - Arrivals
Jeff Kravitz/FilmMagic

If Natalia gets sleepy during the ceremony, her skirt can double as a comforter for a quick catnap.

13 of 13

MACKENZIE DAVIS

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Frazer Harrison/Getty

Highlighter green is a hard hue to pull off, but when it's featured on a dress with an oversize bow at the waist, it makes it all the more polarizing.

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