Adam Glassman: It's not easy to get someone dressed for five television shows a week—and make sure she's camera-ready from every angle, to boot.
Kelly Hurliman: And it's never been a relationship where I say, "You're wearing this today." Oprah knows what she likes, she knows her body. At the end of the day, what she's wearing always comes down to what she wants to wear. You wouldn't believe how often she's walked onstage having tried on something for the first time five minutes before.
Adam Glassman: Well, let's start with hits, like that Costello Tagliapietra dress she wore on a show about Valentino in 2009. We'd had it made for Oprah to wear on the cover of the April 2009 issue of O, the one with Michelle Obama. But even though it was a nice departure from her usual formfitting silhouette, we ended up needing bright colors for that cover, and didn't use the dress. Then one day I turned on the TV and was so happy to see Oprah wearing it! I e-mailed you to say how great it looked, and you replied, "Oh, Oprah hated it."
Kelly Hurliman: I thought it was so cute; she said it looked like a choir robe. But André Leon Talley from Vogue was on the show that day, and he said, "I love your dress—whose is it?"
Adam Glassman: And when André said he loved it, we were validated!