Visiting Cindy Sherman's New York apartment has a brain-addling effect. In one room, the trappings of domesticity: a washer-dryer, groceries, a pile of packages. In another, the studio in which Sherman creates her unsettling and subversive portraits, which for almost 40 years have recast culture's perception of women and men, heroes and victims, and the vastness in between. There are wigs everywhere, a rack of costumes, an intimidating computer, and pieces of notepaper on which are scribbled character clues like "coquette" and, most intriguing, "blueberry."

We're here because Sherman and Bazaar have been plotting. The idea: a satire of that storied—well, snapshot—species, the street-style star. We nicknamed it Project Twirl. "I just loved the description of these people," Sherman says, perched at her desk in a striped T-shirt and jazzy Prada pants. "These characters who go to the fashion shows—and twirl, as you talk about."

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Cindy Sherman

Who, me? Prada dress, $6,790, sweater-vest $1,190, skirt, $12,820, earrings, price upon request, neckpiece, $525, and boots, price upon request,prada.com.

This striving, posing, highly public land is a foreign one to Sherman, an artist lauded as much in fashion as in the art world (her first international project was 1994's postcard series for Comme des Garçons; since then she has starred in campaigns for Marc Jacobs and M.A.C., and collaborated with brands from Balenciaga to Louis Vuitton). While she characterizes herself as an occasional "extravagant dresser" ("Stores call me and say, 'We've got this for you.' When I say I'm too busy, they send them!"), Sherman does not live to be photographed. She's actually rather shy. If she's attending a fashion show, for example, "I kind of run in," she says. "I don't want to make eye contact with photographers. I don't want them to think I'm waiting for them to take my picture. Ooh, God, no."

Sherman, 62, is one of the world's greatest sociologists, so in a way, infiltrating the street-style species is a weirdly natural extension of her work. "You know, I never expected to be doing what I'm doing for as long as I've been doing it," she says. "Every time I start a new project, it's a new challenge, to try to think of new faces or new characters. Sometimes I feel I'm repeating characters that are poking out of these faces that I shot maybe eight years ago"—a fun exercise for Sherman nerds. "I take on projects like this when I'm starting on a new body of work because it inspires me, gets the juices flowing."

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Cindy Sherman

The nonchalance of squiggles. J.W Anderson top, $1,095, mytheresa.com, and pants, $630, Selfridges, bag, $1,680, mytheresa.com, and shoes, $1,065,j-w-anderson.com.

And this is a juicy subject, all right. Initially I'd given Sherman some names to follow on Instagram, and her reaction was visceral. "I was physically repulsed after looking at some of these accounts—thinking how this person travels with hair and makeup and a photographer and is just going to visit her sister in L.A.?" she says, sighing. "They're not even selfies; they're setups. Then some of them get paid to wear the clothes? I guess it makes sense—it's business, but there's just something dead about the whole thing. It's so self-involved."

Which makes Sherman's work on these pages more meta than meta. Alma-meta, if you will. "For a lot of the faces, I was inspired by real people I found online," she explains. "I didn't want it to be obvious, though. I'd change the hair color, style, something. But they still look like they're somebody—rather than just me with makeup on." She continues, "It was hard to capture the real twirling idea. I don't use flash, so it was a little slower. The times I tried to, it was all blurry. But I like limitations because they make you think of other ways of getting around that. Like the shadow in the Chanel image." After the post-validation orgasm, the cigarette? She laughs. "Exactly!"

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Cindy Sherman

Stack it on. Dolce & Gabbana top, $1,595, pants, $1,595, headpiece, $545, and bag, price upon request, 877-70-DGUSA.

Sherman was also quick to capture the disingenuousness of the whole posing exercise. Take the second spread of this portfolio, where she is splayed resplendently over the Palais de Tokyo in J.W. Anderson. "I had a few images, and then I realized that if I put them in a certain order, there was progression that implied, 'Who? What? Me? Really? Oh, my God!' " Oh, for a video camera at this moment: Cindy Sherman as Euro Valley girl.

The clothing, of course, allowed Sherman to become lots of girls. "I am not at all a sample size," she says, citing the Proenza Schouler look—a short skirt on a model but "mid-calf" on her. She was wild about Gucci's green suit. "It's so out there that it's something I'd consider wearing! Except for maybe the eyeball or the mouth. But there was a snake on the back that was really cool." Of the mad Chanel watercolor look, she says, "Oh, that girl was fun. There was so much to inform that character—sunglasses, jewelry. It's funny with the pants under the skirt. It looks like I'm wearing those braces that people with foot injuries wear." Marc Jacobs: "Other than being superlong, I kind of liked this look. It's so wacky with all those scary faces, and the boots are amazing." Dolce & Gabbana: "This lady may or may not get on the Métro. She might just stop in front of it, waiting for someone to take her picture. I loved those giant silk pajamas." Miu Miu: "Yin and yang!" And Prada: "I liked the way it looked on the models, but it was so unflattering on me." For this image, Sherman went full method, down to the gold lipstick worn at the show. "But I put glitter powder on top of it."

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Cindy Sherman

Marc Jacobs jacket, $10,000, bag, $1,700, and boots, $1,130, marcjacobs.com.

Sherman was one of the first artists to work with high fashion. "But hang on, didn't Dalí do some stuff?" she says, laughing. "One of my first projects was in the early '90s, for Harper's Bazaar, actually. They sent tons of clothes to my studio and said, 'Do what you want.' That got me started on looking at magazines. I've always been interested in fashion photography."

Of course, fashion is the most basic tool of transformation, one that Sherman jumped on. "In the mid-'80s, I did some stuff for this boutique in SoHo, Dianne B. It was really early Comme des Garçons, Castelbajac, Gaultier. It was the weirdest stuff, especially the Comme. I was like, 'This looks like bag lady clothes'—holes in it, ripped up, pirate-y. Kind of ugly, jolie laide." Sherman taps her jolie laide Marni shoe. "I was fascinated by that. It didn't seem like people were as obsessed with labels like they are now. That started in the '90s."

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Cindy Sherman

Twin set. Miu Miu top, $1,445, sweater-vest, $865, shirt, $640, skirt, $1,200, and tiara, $595, mimiu.com.

Sherman started much earlier. She began shooting portraits in the mid-'70s, while her landmark series, "Untitled Film Stills" (69 works in all, in which she embodied female stereotypes), was created between 1977 and 1980. The youngest—by many years—of five siblings, Sherman says her motivation to make portraits was a very basic need for attention. "They were already established as a family by the time I came along," she recalls. "It was a way for me to say, 'I'm here, you guys, don't forget about me!' Or 'Maybe if you don't like me this way, you'll like me this way!' Or 'I can do this!' "

Sherman's parents weren't as prone to introspection as their daughter. "I think they thought it was cute or something," she says. "I know they didn't think it would really turn into anything. When I went to college, my mother was always like, 'Take some education courses just in case so you can always teach.' They did see the early days of success; I think they started to realize it was a tangible thing for me." She adds, "I still don't think they really had a clue what I was doing."

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Cindy Sherman

Gucci jacket, $3,990, shirt, $750, pants, $2,150 and tie, $895, gucci.com.

Today, Sherman could very much rest on her laurels. In 2012, New York's Museum of Modern Art hosted a retrospective, and in 2011 one of her works, 1981's Untitled #96, sold for $3.89 million at Christie's (then a record for a photograph at auction). Ask if she's still ambitious and she replies, "I want to continue to be happy with what I'm working on because that's the biggest challenge. I'm hard on myself, but everyone is always waiting for someone to fall. That's a common problem for artists. They fall into a mold of their greatest hits and just repeat it. WhenI feel that I'm repeating myself, or about to, it's time to move."

But when the work is done—new characters born, new realities created—Sherman exhales into her life. She'll ride around Manhattan on her retro Pashley bicycle, or head out to her house on Long Island to collect her chickens' eggs. Sometimes, when she's feeling spent, she jaunts to a deprivational German health spa. Unlike the subjects of this series, she doesn't live in the middle. "I don't take selfies," she says. "I hardly ever use my phone for photographs. It's really hard to remember to even take a picture of something." She shrugs. "Usually the moment is gone. I just don't think about it."

One day, if Sherman plays her cards right, she could become a bona fide street-style star. "Like, if people will give me comments or likes, or something like that?" She grins. "And followers. I just want lots of followers."

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Cindy Sherman

The Twirl.Chanel sweater, $1,400, skirt, $5,500, pants, $1,450, hair band, $1,450, sunglasses, $525, bag, $3,100, bracelet, $575, and sandals, price upon request, 800-550-0005.

COLLECTOR'S EDITION COVERS

Cindy Sherman's original artworks for Harper's Bazaar appear on the covers of five limited-print March issue subscriber editions. Buy one at random for $5.99 plus shipping, or the collector's set of all five for $29.95 plus shipping, here while supplies last.

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