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Oprah Winfrey's Stylists Weigh in on Her Fashion Hits and Misses

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She may be the reigning queen of talk, but even Oprah Winfrey has made some questionable fashion choices in her 25 years on air. So in the June issue of
O, The Oprah Magazine
, Winfrey’s pals Adam Glassman, creative director of the magazine, and Kelly Hurliman, her stylist for the past six years, weigh in on nine of the soon-to-be-retiree’s fashion hits and misses. The red suit (left) Winfrey wore on the 2004 season premiere — when she gifted the entire audience with new cars — won props from her fashionable friends. “That is my all-time favorite,” Glassman says in the mag. “It was from Michael Kors’s last collection for Celine.” However, not everyone loved the suit. “Gayle [King] 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,'” recalls Hurliman. “Oprah said, ‘I love this suit, it’s the right look, I’m not changing.’ When that picture was shown around the world, of her sitting on top of the car in a red suit, it was brilliant.” Not so brilliant? Her long yellow jersey dress (right), affectionately called a schmatte. “Between tapings she always put on something really comfortable,” Glassman shares. “But instead of sweatpants, this time it was a long dress.” And it stayed on through taping. “She felt cute in her schmatte and wanted to know why she couldn’t do the next show that way,” Hurliman says, recalling Winfrey’s words: “‘I’m comfortable … I feel like me.'” To see more hits and misses, pick up the June issue of O, on newsstands Tuesday.

Oprah Winfrey style
Courtesy O, The Oprah Magazine