Oprah's Style: 25 Years of Fashion Hits and Misses

Kelly Hurliman: That dress looked like it would do all the right things. It was a rust-colored A-line knit with a V-neck, all of which usually works. But you really have to try things on and take a hard look, head to toe—and of course, we didn't have time. The placement of the darts accentuated her chest, and the belt sat right underneath, so it looked like a shelf. When I glanced at the monitor, I said, for the first time ever, "Oh my God. Should we stop and have her change?" But before I finished that sentence, she'd started the show. I know that everyone has good and bad days, but unfortunately, our bad days were lived out in front of millions of people.