Biggest Fashion Risk Takers

No one can accuse Lea Michele, Kristen Wiig, Zoë Saldana and these other stars of playing it safe. Tell us – do you love these looks or loathe them?

01 of 10

LEA MICHELE

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Kevin Mazur/WireImage

The color of the Glee greige Atelier Versace gown (worn with Lorraine Schwartz jewels and Casadei pumps) is on-trend, as is the up-to-there slit, but the highly structured cut (and conical chest!) left people divided.

02 of 10

KRISTEN WIIG

KRISTEN WIIG
Gilbert Flores/Celebrity Photo

Resurrecting a trend that hasn’t been popular since the early ’90s, Kristen turns heads by pairing a wide Fred Leighton choker with her Balenciaga by Nicolas Ghesquière halter gown.

03 of 10

ZOË SALDANA

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Jason Merritt/Getty

With a dagger-encrusted neckline (and matching daggers on the sleeves!), a bejeweled waistline and crystal-fringe, Zoë is certainly one of the blingiest stars on the red carpet in her Givenchy Haute Couture by Riccardo Tisci gown and Tiffany & Co. jewels. The only missing accessory? Her rumored beau !

04 of 10

KALEY CUOCO

KALEY CUOCO
Francis Specker/Landov

The actress arrives at the event with a bang – a big bang – in a Tiffany-blue, silk organza Romona Keveza gown (with matching Judith Leiber clutch and Martin Katz jewels), featuring a very voluminous skirt and a sweetheart neckline.

05 of 10

ROSE BYRNE

ROSE BYRNE
Dimitrios Kambouris/WireImage

The Bridesmaids star’s sparkly white Elie Saab jumpsuit (which she said she’s had her eye on for a few years) stands out among a sea of gowns – and lands her on our best-dressed list.

06 of 10

SHAILENE WOODLEY

SHAILENE WOODLEY
Kyle Rover/Startraks

Perhaps paying homage to the Hawaiian set of her movie The Descendants, the presenter and nominee chooses a floral-print L’Wren Scott in a simple silhouette, plus Irene Neuwirth jewels.

07 of 10

BUSY PHILIPPS

BUSY PHILIPPS
Kyle Rover/Startraks

Also taking a risk with patterns, Busy – who accompanied her nominated BFF – looks casual and summery in a hippie-ish tie-dye dress, Irene Neuwirth jewels and a front braid.

08 of 10

HEATHER MORRIS

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Jason Merritt/Getty

Glee cheerleader Heather breaks out of character and dons an edgy, off-the-shoulder mini with leather panels and a sheer overlay, plus high-impact danglers and hot pink eye shadow.

09 of 10

AMBER RILEY

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Kyle Rover/Startraks

There’s nothing understated about the very oversized bow Heather’s Glee costar wears on the front of her calf-length lace dress.

10 of 10

JANE KRAKOWSKI

JANE KRAKOWSKI
Stewart Cook/Rex USA

Eyes up here! The 30 Rock actress brings serious sex appeal to the red carpet in an embellished bustier and cap-sleeve number that accentuates her assets and drops a whole bunch of jaws.

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