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Reese Witherspoon, 2002

Reese Witherspoon stole the spotlight at her Academy Awards debut, thanks to a Valentino makeover. "It was her first time presenting and Reese wasn't as established back then. People thought of her as cute, but not glamorous," the designer told InStyle. "We thought she could be the new Grace Kelly and made a gown that was romantic and fresh—as if she were starring in a brand-new movie."

(CREDIT: Ron Galella/WireImage)
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