The fashion world adores Cindy Sherman. Designer stores call her when they get something in that might cater to her “extravagant tastes.” Raf Simons says she is an influence and hung a large work by her on the wall of his New York office. The artist sat front row at Simons’s debut Calvin Klein catwalk show in 2017, and he repaid the favor by dressing her in his exclusive Calvin Klein By Appointment collection for the annual benefit gala at the Metropolitan Museum of Art a few months later. At the fashion world’s most exclusive party, she was the epitome of uptown edgy chic in a floral two-piece trouser suit and heels. Sherman attended in company with Simons’s clique of supporters, including rapper ASAP Rocky and actress Gwyneth Paltrow. A member of fashion-and-art’s royal family, she designed a bag for Louis Vuitton in 2008 that sold quickly and is now a collector’s item. In 2011, she collaborated with MAC Cosmetics to create a selection of makeup including lipsticks called “Flesh-Pot Pale” and “Ash Violet.”
Getty Images: Rindoff Petroff/Dufour/Getty Images
Cindy Sherman, Paris Fashion Week, March 2014.
Sherman, born in New Jersey in 1954, has spent her life as an artist trying on clothes and morphing her looks with outrageous makeup, so it’s natural that her universe and fashion’s should convene. An artist who explores identity, she believes her compulsion to dress up stems from a childhood where she needed to remind her parents she was there—she was the youngest of five children. Yet there is no nervous ambiguity about Sherman’s personal style. She has worked and associated with fashion designers for more than thirty years, beginning with a series of images she made for Interview in 1983, in which she wore Issey Miyake, Comme des Garçons, and Jean-Paul Gaultier pieces from Dianne Benson’s boutique. The idea was to spotlight the expectations of the fashion world. Sherman was captivated by the outfits, saying in a 2016 Harper’s Bazaar interview: “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. I was fascinated by that.” Ten years later, in spring 1993, she was commissioned by Harper’s Bazaar to create a selection of self-portraits called “The Cindy Sherman Collection.” For this assignment she wore new-season outfits, including a patchwork ensemble by Dolce & Gabbana, and an evening frock by Vivienne Westwood; in one image she sported a pair of underwear on her head.
Molly Ringwald starred in Sherman’s 1997 horror film Office Killer, about a copyeditor who turns into a mass murderer after accidently killing a colleague.
Sherman maintains that her ideal epitaph would be: “She finally found the perfect outfit.”
These days Sherman counts Narciso Rodriguez as a personal friend; in a Harper’s Bazaar interview with Cathy Horyn, the designer commented that “it’s easy to talk to her about fashion, she knows so much.” For an artist who is intent on portraying the dilemma of image, confidence in her own look doesn’t seem to be a problem. Despite reservations about art being used as a “cool accessory” for the fashion pack, she is able to get right on board with elite labels and pick and choose what works for her. The first Parisian piece she ever bought, back in the 1980s, was a Jean-Paul Gaultier suit. But finding equilibrium in her personal identity has taken time. As Sherman said in a 2016 interview with the Observer (UK), “I think it took me a very long time to figure out who I am, what my needs were, and for a long time my characters were to ask those same questions: maybe this is who I want to be?”
When I was a kid—maybe ten years old—because I had a suitcase of old clothes, old prom dresses and things like that, I would play dress-up. Plus, I discovered some of my grandmother’s clothes somewhere in the basement—she had died years before, or maybe it was even my great-grandmother because they were really old clothes, from the turn of the century. I put them on, and I turned into this old woman. I have a photo somewhere. My girlfriend and I would turn into little old ladies, and we’d walk around our neighborhood dressed like this. But then I discovered that while all my girlfriends were turning themselves into ballerinas and princesses, I was more interested in turning into monsters or witches—ugly things.
—Cindy Sherman, System, 2014
Getty Images: Arnold Newman/Getty Images
Cindy Sherman with designers Azzedine Alaïa (center) and Nicolas Ghesquière of Louis Vuitton, Paris Fashion Week, March 2014.
I don’t think I can see the world through other people’s eyes, but I can capture an attitude or a look that makes others think I can. I have an appreciation for why people choose to look the way they do. But I can’t know what they experience.
—Cindy Sherman, Interview, November 2008
Sherman understands the complexities of innovative style. She was a fan of the amazing—but slightly awkward and tricky to wear—label Marni, when it was helmed by its founder, Consuela Castiglioni. You had to be confident to wear the collections Castiglioni designed before she left in 2016, which featured geometric shapes and prints, dusty colors, and difficult silhouettes. The intelligentsia loved them. Sherman’s idea of fun is “going to Marni and having four big shopping bags delivered the next day.” Labels of choice also include Prada, Stella McCartney, and Jil Sander—clothes for the thinking woman.
And Sherman most definitely thinks about fashion. In a 1994 New York Times interview, she said, “The way that fashion imagery in the industry has already directed our way of thinking so that we assume anyone who wears those clothes has to be thin or beautiful isn’t anything like reality anyway.” Her editorial work for Harper’s Bazaar in the current century includes “Project Twirl,” for which Sherman dressed up as a street-stylish blogger and wore clothes by Chanel and Miu Miu. She satirized the social media catwalk of Instagram but also revealed how much she enjoyed the clothes. Marc Jacobs’s boots were “amazing,” and she loved the green Gucci suit from the shoot, which was “so out there that it’s something I’d consider wearing. . . . There was a snake on the back that was really cool.”