Oprah Winfrey

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

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Kelly Hurliman: I also liked that fitted red suit....

Adam Glassman: That is my all-time favorite! It was from Michael Kors's last collection for Céline. Oprah wore it for the season premiere in 2004, the Pontiac giveaway.

Kelly Hurliman: Gayle and the producer came to us right before the show started and said, "We don't think she should wear that. It's not fun enough." Oprah said, "I love this suit, it's the right look, I'm not changing." She knew everyone in the audience would be receiving a key ring with a red bow. And when that picture was shown around the world, of her sitting on top of the car in the red suit, it was brilliant.