Photo: Jake Rosenberg of the Coveteur
Down, Girl!
"I never walked out of the studio in my stilts. As soon as we finished taping a show, the crazy heels came off and the soft slippers came on."
Photo: Jake Rosenberg of the Coveteur
A Shoe In
"I was about to give away these Ralph Lauren spectators, but you know what? I love them! If I still really respond to something, I keep it."
Photo: Jake Rosenberg of the Coveteur
Smitten Kitten
"I say out with the old, in with the Jimmy Choo! His kitten heels give me just enough lift. Meanwhile, Gayle's never met a heel she didn't like. Luckily, we're the same shoe size.
Photo: Jake Rosenberg of the Coveteur
She's Pushing It!
"Some people wonder if I'm putting the cart before remorse, but I know I'm not going to end up missing any of this stuff. When I'm sure something of mine is going to someone who will really use and appreciate it, I'm completely fine with letting go."
Photo: Jake Rosenberg of the Coveteur
French Dressing
"When I moved to Santa Barbara, I met a lot of fancy ladies. They were all in haute couture, so I thought it was the thing to do. I went to Paris in 2004 and had the Chanel couture experience. Now I have to keep this piece no matter what because it was roughly the same price as my first home!"
Photo: Jake Rosenberg of the Coveteur
Fond Farewell
"I got so tired of the whole jeweled-collar thing. This sweater is Oscar de la Renta, and it's beautiful. But Oscar's gone, and it's time to let this go, too."
Photo: Jake Rosenberg of the Coveteur
Throwing Shade
"Look at this lipstick red jacket—it gets there about ten minutes before you do!"
Photo: Jake Rosenberg of the Coveteur
At Least It Wasn't a Bikini
"I guess we've all got that one pair of jeans stashed away waiting for a diet miracle. Mine are the size 10 Calvins I wore in 1988, when I dragged 67 pounds of fat onstage to show the world I'd finally conquered my weight. It was iconic television, but what was I thinking?"
Photo: Jake Rosenberg of the Coveteur
New Rule
"If a skirt makes me look like I'm about to take flight, it needs to go to somebody else's nest. This thing is light and breezy, and neutral to boot, but I never felt great when I wore it."
Photo: Jake Rosenberg of the Coveteur
You're the Top!
"I will never give away my white Ferré blouses because nobody made a white shirt like Gianfranco Ferré! They were very architectural, so not everyone could wear them, but they worked for me no matter what size I was."
"I will never give away my white Ferré blouses because nobody made a white shirt like Gianfranco Ferré! They were very architectural, so not everyone could wear them, but they worked for me no matter what size I was."
Read more about how Oprah cleaned out her entire closet
here.
