If you'd like to step into Oprah's shoes (or skirts or dresses or trousers...), here's your chance: She's putting some of her clothes and accessories up for sale in one giant eBay auction, with all the proceeds going to the Oprah Winfrey Leadership Academy Foundation. The fun starts on March 1; check it out at eBay. Happy bidding!

"Here is my favorite dress ever"—Oprah Winfrey's voice rises—"that I never once wore"—and it falls. She fans the cotton shirtwaist across her body, sighs and places it back on a rack filled with three dozen other dresses. It's the "I never once wore" part of her statement that explains why a few of Oprah's dearly beloved have gathered together on this breezy Saturday afternoon in Chicago.

Oprah is standing in her 19-by-26-foot closet at the soon-to-be-demolished Harpo Studios, attempting to do—albeit on a much grander scale—what we all try to do from time to time: clarify our needs, simplify our space and wave goodbye to some of our stuff. But how do you choose among literally hundreds of dresses, sweaters, skirts, pants, tops and shoes? Well, for one thing, you enlist helpers: Gayle King is here to provide her special brand of best-friend-ship; O's creative director, Adam Glassman, is here to supervise; O fashion editor Jenny Capitain and stylist Kelly Hurliman are here to organize the pieces Oprah keeps as well as the ones she lets go. Letting go confounds a lot of us, but over the years Oprah has learned a thing or two about spring cleaning.

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Photo: Jake Rosenberg of the Coveteur

"Spring is a time of transformation," she says. "It's about growing, which is the whole point of being on this planet." Handing a persimmon pump to Gayle, she adds, "If you stop evolving, then you've stopped being in tune with the music of your life."

Everyone is momentarily blinded by a neon magenta dress that Oprah drops like it's...well, like it's a neon magenta dress. "Over time, your tastes change, and that's fine," she says, motioning toward the eye-popping number. "I just don't need all this intense color, the embellishment, the heels anymore. When you're in front of TV cameras every day, you have to stand out, but I'm in a different place now, and those things no longer serve me."

Adam grabs a shoebox, and they dig in. "These would be perfect with Kirby's new Azzedine Alaïa dress," Oprah says, handing Gayle burgundy peep toes for her daughter. Next are stilettos that would best be described as lethal. "I wore these on an O cover," she says, and soon she and Adam are remembering the gown that didn't arrive, the mighty wind machine with a mind of its own, a second of synchronicity here, a moment of minicrisis there. The two have been in a lot of fashion foxholes together. Oprah plucks the perfect Manolo Blahnik from the pile, and Adam finds its match. "These are a keep!" they say, practically in unison.

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Photo: Jake Rosenberg of the Coveteur

The sorting continues in silence until Oprah smiles and says: "You know, Adam, you were the one who made me realize I was holding on to clothes that were all about a dream I had for myself. I chose them for this idea I'd gotten into my head of how someone like me was supposed to live, but they had nothing to do with my actual life. And that," she says, tossing a pair of leopard-print platforms into the donation pile, "changed me!" She moves to a stack of sweaters and continues. "I mean, I saw everything differently after that. I'm not just talking about my clothes—I'm saying you've got to make sure the exterior of your life reflects what you're feeling on the inside." Reaching into a rainbow's worth of cashmere V-necks, she says, "The same thing happened with my house. It was the place I thought you should have when you start earning money and can finally afford some pretty things. So you buy a silk sofa, but suddenly you can't let your dogs up on that sofa. And it wasn't just the dogs," she says with a laugh. "My butt kept sliding off those silk cushions!" Oprah pushes the entire leaning tower of sweaters over to Jenny. "I live in my true comfort zone now."

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Photo: Jake Rosenberg of the Coveteur

"So many women hold on to a look that they'll never wear again," Adam says, "things that have no real significance to them." Oprah pulls a turquoise print off the rack and winces ever so slightly. It's not the dress that isn't perfectly nice—it's just that it isn't her.

"If something is genuinely important to you, then of course you should keep it," she says. "But you should understand the reason it matters." She returns the dress to the donation rack and forges on. "I want to create a space that gives me access to the stuff that helps me, to things that hold a place of meaning for me. Because if you can't do that, then you're not using your things—your things are using you." Oprah gives the crowded rack a good strong shove out the door. She seems both relieved and exhilarated as it glides down the hall, and she turns back to see her once-crowded closet getting roomier. A number of pieces will go to auction, some for donation. Many, like the Chicago studio itself, will live in her memories. What remains will be the stuff that feels easy, soft, a little more subtle and a lot more liberating. They will be the clothes that match her current life. "Now that," she says, smiling, "is big!"

See more behind-the-scenes photos here.


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