Oprah Winfrey

Photo: George Burns/Copyright © Harpo Productions, Inc.

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Adam Glassman: Now, Oprah rarely goes shopping, but when she does, she always finds something that works.

Kelly Hurliman: She was the one who found the outfit for the 2004 "Favorite Things" show—the silk top with a leather band and pleated skirt. It was on the mannequin at Hermès. She said it spoke to her.

Adam Glassman: Not everything is so effortless—like that dress last year that made you want to stop taping.