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The Best (and Worst) Oscars Looks of All Time, from Grace Kelly to Kerry Washington

You know you can't resist. See the greatest hair, makeup and fashion from the Academy Awards (plus a few looks that went horribly wrong)
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Oscar season brings out the inner critic in all of us. Whether you're throwing your own stylish soiree or kicking back in your comfiest Victoria's Secret sweats, you know you're going to witness fashion moments that make you cry with envy and with laughter (oh, Bjork -- will you ever live down that swan?). The award show may get a little (okay, a lot) boring and repetitive, but we never get tired of the perfectly tailored couture gowns and jewels so bling-y they come with their own bodyguard. We're counting down all of the Oscar looks, going way back -- like before E!'s GlamCam 360 back -- to give you the good, the bad and the Cher. (And on that note ... if you notice a conspicuous lack of great looks from the 80s and 90s, well, we'll let that omission speak for itself.)

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Best: Vivien Leigh, 1940
The side cutout and floral print dress was way ahead of its time when Leigh wore it to the awards for her Oscar-winning performance as Scarlett O'Hara in 1939's "Gone With The Wind."

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Audrey Hepburn, 1954
Hepburn attended the 1954 Academy Awards (straight after performing in Broadway's "Ondine," no less) in this lace Givenchy gown, where she won Best Actress for her portrayal of Princess Anne in 1953's "Roman Holiday."

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Grace Kelly, 1955
Famed costume designer Edith Head created this icy blue gown that Kelly would accept the Best Actress Oscar in for her performance alongside Bing Crosby in 1954's "The Country Girl."

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Sophia Loren, 1958
Loren presented David Lean with the Best Director award for "The Bridge On The River Kwai" in this classic cut floral print dress with diamond drop earrings and necklace. Loren would later win the first Oscar for a foreign language performance in 1961 for her performance in the Italian film "Two Women."

BY MARISSA DESANTIS | FEB 28, 2014 | SHARES
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