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The 15 Riskiest Oscar Red Carpet Looks of All Time



Photo: Getty

Charlize Theron in Dior, 2011

We always look forward to seeing what fashion risk-taker Charlize is wearing come Oscar night. She must’ve known she’d be sending mixed fashion messages with her rosey-bossomed Dior gown in 2011, but she had the guts to rock it anyway. When the fit of a gown (and of course, the wearer) is this flawless, you can get away with some unconventional details.



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