Oprah in Rachel Roy

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1. Rachel Roy Post-Oscar® Dress
In 2007, Oprah wore a gown in a gorgeous shade of merlot to celebrate with Oscar winners like Forest Whitaker and Helen Mirren. "Rachel Roy made it for us, and it looked great onstage," Kelly says. "It was one of those times when everything works together—set color, lighting, hair and makeup and a great dress."
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