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The 12 Biggest Fashion Risk-Takers

Red Carpet

JESSICA CHASTAIN

We can't deny the sea foam shade is divine on the actress (though, really, is there any color that doesn't look amazing on Jessica?) and that her Harry Winston jewelry is to-die-for, but we're on the fashion fence when it comes to the silhouette of this plunging Calvin Klein Collection dress.

Jordan Strauss/Invision/AP

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