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

HITS!

For the past six years, Kelly Hurliman has dressed Oprah for her show; Adam Glassman styles her for O.

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!

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.

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.

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.

Kelly Hurliman: Which brings me to the Alexander McQueen plaid skirt. I wasn't even going to show it to her because I knew plaid wool probably wouldn't look great on TV, but she saw it and loved it and said, "Let's wear it on today's show." And it wound up looking like a fringed sofa blanket.

Adam Glassman: As if she had wrapped herself in it to watch TV, tucked it around her waist, then gotten up to tape her show. Oh, and then there was (next) the infamous "after-school outfit."

Kelly Hurliman: Yes!

Adam Glassman: Between tapings, she always put on something really comfortable. But instead of sweatpants, this time it was a long dress.

Kelly Hurliman: She felt cute in her schmatte and wanted to know why she couldn't do the next show that way. "I'm comfortable, I feel like me!"

Adam Glassman: Sure, go do it, go look like a shlumpadinka.

Kelly Hurliman: It was fine when she was sitting, but this show required her to stand, in her bright yellow jersey schmatte. I just put my head in my hands.

Photo: Courtesy of Harpo Studios

Adam Glassman: Sometimes there's nothing you can do. I mean, the show started in the '80s—big hair, bright makeup, jackets with huge shoulder pads. Everyone was guilty, but that was the style.

Adam Glassman: Even now, no one gets it right all the time. Like this year's Australia show, when Oprah wore that looong skirt. She loves a billowing blouse and skirt.

Kelly Hurliman: Great for hosting a party, not so great for TV. But she wanted to promote an Australian designer.

Adam Glassman: I was more concerned that the outfit was a lighter color on the bottom than on top. That's generally a no-no. And when the wind came, it looked like Oprah was about to sail away, right over Sydney Harbor.

Kelly Hurliman: Plus, she was standing next to minuscule Nicole Kidman. Afterward she said, "I now have no ego because I was onstage wearing a balloon next to Nicole Kidman."

Adam Glassman: She laughed about it. She'll never let any of us live it down, but she can laugh.

PERFECT FIT!

Adam Glassman: Still, for every mishap, there was a flawless hit. Remember the gray Carolina Herrera dress she wore to announce the end of The Oprah Winfrey Show? Gayle had said to me, "Don't you think she should wear color?" And I said, "No, this is perfect." It was serious, which was appropriate for the occasion.

Kelly Hurliman: We bought it off the rack at Saks, although not with the intention of using it for such an iconic moment. It was the right dress at the right time.

Adam Glassman: She's had a lot of magic moments. Even though the show wasn't about fashion, whatever Oprah wore had a way of creating buzz. And I think that has as much to do with her as it did with the clothes.

Oprah and Gayle sit down to talk about the end of The Oprah Winfrey Show