Everyone is talking about Oprah’s final two shows airing May 23rd, with whispers of a long list of Who’s Who in the entertainment industry givig the media queen her official send off. The latest issue of O, which hit newsstands yesterday, May 17th, features a rundown of Oprahs fashion hits and misses over the years, with commentary by O Magazine Creative Director Adam Glassman and Oprah’s show stylist for the past six years, Kelly Hurliman.

Wardrobe hit: Celine red suit

Adam Glassman: “That is my all-time favorite! It was from Michael Kors’s last collection for Celine. 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 war 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. When that picture was shown around the world, of her sitting on top of the car in the red suit, it was brilliant.”

Wardrobe miss: Long yellow jersey dress (“Schmatte”)

Oprah WinfreyAdam Glassman: “And then there was the infamous ‘after-school outfit.’ 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.’”