Oprah's style experts breathe new life into Hillary's basic look. Tim helps Hillary choose a Diane von Furstenberg wrap dress and a pair of Manolo Blahnik pumps. "We took the classic black dress that every lady should have in her wardrobe and did this wonderful, high-spirited innovation of it," he says.

To complete the look, Rita warmed up Hillary's hair color with caramel highlights, and Bobbi used concealer to hide the darkness under Hillary's eyes.

Now, Tim says Hillary could pass for her teenage daughter!

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