Oprah on the March cover of O magazine
Photo: Ruven Afanador
Oprah is fanning her face. "I'm having anx-i-e-ty," she says, singing that last word so it hangs in the air for a few seconds. She's looking over the dozens of shoes and three racks of clothes that O's creative director, Adam Glassman, has pulled aside and put into the "potential giveaway" pile in her Chicago closet—all deemed inessential because of poor fit, outdated style, or some other imperfection.

"Let's just start with the shoes—they're the easiest," Oprah says. "And I can see that this closet cleanout is going to give me a headache." She spies a pair of chunky-heeled, green suede oxford shoes. "Forget about them! I got those when I used to wear pants." Gone.

Adam holds up a pair of ivory lace knee-high boots. Oprah quickly comes to their defense. "Those I can't get rid of! They're beautiful. They're like sculpture!"

"Will you ever wear them again?" Adam asks.

"I never wore them ever, but I still can't get rid of them. They're closet jewelry. They make a closet look good." Onto the keeper pile they go.

Ditto a pair of silver lamé Gianfranco Ferré mules with rhinestones (Oprah calls them "amazing"), a beaded Ralph Lauren skirt ("Why would we get rid of that?"), a shimmery Calvin Klein top ("I can wear it with jeans and a blazer or dress it up all fancy-dancy").

Next in Adam's sights: a peach chiffon skirt having a froufrou moment among Oprah's unfussy everyday clothes. "When would you ever wear this?" he asks. "I'm going to wear this in the spring, when everything is lovely and gay," Oprah replies. Adam stops mid-organizing to consider that idea. "When you shop, sometimes you have an idealized version of yourself in mind, don't you?" he asks. "Yes. I'm picturing myself in a bonnet in the spring," she says. "Or at a lunchtime garden party." The skirt stays.

Adam pulls out a gold jacket by Ferré, one of Oprah's favorite designers. "I wore that to Quincy Jones's 71st birthday party," she says. "I just walked into the store and picked it up." Adam thinks it still looks stylish. "You could actually wear this jacket now," he says.

"Oh my God, I'm shocked you want to keep something!" Oprah says, laughing. "There was a time when I had to budget for clothes, and I still do so subconsciously. Early in my career, when I was an anchorwoman, I had a beige suit, a navy suit, and a black suit. Period. And I would just interchange them. Even now, wasting money on clothes makes me crazy."

Adam gets it; he really does. "It's difficult for anyone to toss something they've spent their hard-earned money on," he says. "My suggestion: Some things are classic, and you can keep those. But anything that's trendy? Let it go."

Oprah acquiesces, particularly after Adam suggests that the donated items be auctioned off on eBay. "The money should go to OWLA," Oprah says, referring to the leadership academy she opened for South African girls in 2007. "That sale would make all of this worth it."

With that settled, the process suddenly becomes easier. Flipping through one long rack of everyday dresses, Oprah pronounces: "These are all fine to get rid of." Next up: handbags. Oprah likes them spacious and sturdy, like the roomy tote she carries back and forth to her office. So she has no trouble saying goodbye to a number of tiny leather and crocodile bags acquired during her self-described "ladies who lunch phase." Then she spots a small beige clutch with a gold chain strap. "It's fantastic." She slings it over her arm, walks a few paces—and changes her mind. "It's just so not me." Off to eBay it goes.

By day's end, Oprah has put more than 150 items on the auction list, designated a few untouchables, and even developed a new perspective on her own style: These days comfortable classics win out over straight-off-the runway looks. "In the past, I've gotten talked into a lot of trends," she says. "But I don't have to be on anyone's best-dressed list. I'm really just trying to become more of myself."

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