Now a Free Woman, Chelsea Manning Is Redefining Her Style on Her Own Terms

While still incarcerated, Chelsea Manning organized her thoughts about fashion—women’s fashion—and specifically what she imagined could work for her body and her life when she eventually walked free. Manning had for seven years worn prison coveralls, and prior to that she had lived quietly as a man who had only occasionally experimented with non-normative garb.

She measured herself with a makeshift tape measure composed of strips of 11-inch notebook paper. She noted that she was petite, perhaps a size 4 or 6, with a flat stomach, great legs, and curvy hips; she observed that she was a “pear shape.” She kept a detailed, opinionated tally of her preferences, both good and bad: jeans (boot cut, yes; acid wash, NO); denim (“yes, but careful, it’s not the ’90s”); prints (“it’s a matter of discretion . . . no animal print leggings, no puzzle pieces”); shorts (“not low around the hips and not high-rise like a lot of shorts are now”); colors (yes to black, naturals, pinks, purple, blue; no to white, green, citrus, metallics, red); yes to pencil skirts, but no to minis or midis or anything longer than a cargo short. And she assembled a folder of runway and editorial inspiration: professional looks (mostly from Maria Grazia Chiuri’s first collections for Christian Dior) in which a sharp-shouldered tailoring anchored flowy, distinctly feminine separates. She was smitten with a David Sims image of a pinstriped ensemble from Michael Kors on Pinterest “but couldn’t find the damn suit itself anywhere for purchase.” She clipped an image of two women leaping in print-on-print, slightly retro sweater vests and pleated skirts, and dubbed the look “hipster” (“NOT THESE COLORS—Ick!”) If one were to try to sum up Manning’s fashion sense behind bars by reference to a current icon, one’s thoughts might turn to Amal Alamuddin (pre-Clooney and red carpet foxy), who as a young barrister managed to look dead serious yet utterly stunning exiting the High Court with Julian Assange.

I received this fashion dossier from Chelsea Manning’s representatives in the months before she was released. I found it terribly moving in ways I am still parsing. Fashion and notions of style are so often disparaged in contemporary discourse, or reduced to a trifle, a hobby, a sort of forum for misplaced vanity and guilty pleasures. And, of course, they are anything but. How we explain ourselves to ourselves, first, and to the world, second, is fundamental to our ability to be in this world. And clothes play a defining role in the creation of that narrative. That Chelsea Manning, who lived for seven years in punitive and inhumane conditions, had found some hope, some comfort, by pondering the beauty of a Dior jacket or the hideousness of jigsaw print leggings? This wasn’t the leak I might have expected from Manning but, for me at least, it was revelatory.

And so when Manning was released from a military prison in Kansas, she was met by her devoted legal team from the ACLU, a barrage of media speculation and public adulation/consternation, and a small bag of women’s clothing, accessories, and cosmetics. I sent the bag—that is myself and my colleague Jorden Bickham. Jorden and I had pruned our closets, called on the kindness of a few like-minded pals in the industry, and assembled a small capsule wardrobe for the former private. We focused on ease and discretion. We believed that after seven years of incarceration one might want to wear tactile clothes with as little hardware or closures as possible: featherweight knits, pull-on trousers, yoga pants, backless mules. And we kept all her preferences front of mind limiting prints to stripes, the palette to black/navy/chocolate/cream. The only red in that bag was a lipstick. When Manning posted her first selfies to Instagram and we saw first the Everlane top and then the Gabriela Hearst dress, we were thrilled.

A few weeks later, Chelsea Manning came to the Chelsea Hotel for the first of two fittings with Nile Cmylo, the designer and alterations guru who works there in a studio with a leopard-print floor, deep purple walls, lashings of glitter, and Barbies galore. Manning was polite, direct, and most interested in talking about the history of fashion and the societal context of, say, the New Look; Cmylo commented later that she had clearly studied up for the fitting, that she showed an interest in fashion and a respect that was rare in a celebrity. Manning wasn’t especially interested in designer versus non-designer garb, and was quick to make clear that she was very happy to shop at Target (and indeed had just found an excellent swimsuit there). When I asked her what she would choose to wear daily at that time, she said khakis and a nice shirt or jacket, something appropriate and to blend in, but that she didn’t want to look like a Fed or a job applicant. I pointed out that on West 23rd Street in New York City in the year 2017 that look would be regarded as deeply subversive. Some combination of D.C. provincialism and the Rip Van Winkle effect of seven years behind bars would have to be overcome. We fitted her with tailored pieces and knit frocks by Gabriela Hearst, shirt dresses from Joseph Altuzarra, couture-ish pencil skirts from Jonathan Cohen, cool suiting from Rag & Bone, knits from Alabama Chanin, polar fleece from Dosa. Marc Jacobs (who Manning admires and once caught a glimpse of years ago in Provincetown) sent over purses, tees, and a little black tent dress that Manning cinched with her own black tactical belt. What I recall most from these mornings was the element of surprise, delight even, that can occur when you try on that thing you swore you’d never wear. Manning had professed a wariness of prints and volumes, yet she literally jumped for joy in a floral corset laced sundress with a tiered skirt by Rodarte because she’s a video gamer at heart and it touched her inner Daenerys. She felt powerful. Getting dressed is an uncanny business.

In late June I went shopping with Manning for vintage clothes. She is very aware of herself as being a millennial, and millennials like a touch of ’90s tat (also a major dollop of irony: She wears a necklace of a tiny gold hashtag that we had made for her; that and Jorden’s lace-free Vetements Dr. Martens are probably the two most-loved things we contributed to her wardrobe). At this time, perhaps, six weeks into her life as a free woman, Manning was wearing khaki blazers over soft jersey dresses, and yoga pants with Tor Project T-shirts, Docs, and Chucks. She resembled a version of the person she imagined in the prison notebooks, but with a cooler, more streetwear edge. (Utility is prized—from a website called 511 Tactical she buys tops and pants with “lots of pockets and secret places to put things; keep IDs, credit cards, thumb drives”—and being hands-free is essential. Her backpack is black, heavy, omnipresent, and technical.)

At Screaming Mimi’s in Chelsea, a New York vintage institution for cool streetwear from decades past, she is helped by Legs, a young woman who takes her fashion cues from the 1995 film Hackers. (Manning to Legs: “It is a terrible movie. For technical reasons we laugh at it.” Legs to Manning: “But Angelina wears white leather all the time and there’s a love story!”) Legs points Manning to a black leather pencil skirt from Vivienne Tam; a black jersey minidress (yes! Mini!) with a hood lined in a psychedelic print; a sculpted denim jacket from Jean Paul Gaultier Jeans (it’s not the ’90s but it works); and an extraordinary lip print tee from Vivienne Westwood. Manning demurs when shown a very cool denim all-in-one from the ’80s: “I’ve already worn a jumpsuit. Might be a sore subject for me.” We head off to 10 Ft Single by Stella Dallas, a Williamsburg warehouse of America-via-Tokyo well-traveled and yet often curiously never worn workwear. It’s as hip and vernacular as one can get. Manning hunkers down and starts flipping through the hundreds of discarded message tees of other political and social movements and revolutions. She unearths one that reads Bankers Do It With Interest and a second in red (yes, red, that no-go color) with a giant thumbs up from something called Histacount. Her intention, being a millennial, is to wear vintage message tees with her pencil skirts and chicer trousers. A hi-lo sensibility is intuitive.

I spent a lot of time with Manning that day, and I found her endlessly surprising, candid, and clever. Her style role models are Queen Elizabeth I of England (“unquestionably feminine and unquestionably strong at the same time: She defeated the Spanish Armada!”) and Marie Antoinette (“she broke a lot of French high-fashion norms . . . terrible in her politics”). She has an issue with certain older women who wear the trousers (“unfortunately a lot of women try to project their strength through pantsuits, which are just hideous. It’s about projecting confidence not masculinity”) and certain older trans women who favor a more fetishized idea of womanly glamour. “I have myself figured out,” she says. “I’m not trying to be feminine or masculine in look.” Manning says she aspires to “live beyond definitions.” Now that is a challenge for anyone, and especially someone whose personal choices and public persona have come to mean so much to so many for all different sorts of reasons. Let’s face it: Manning is herself a definition of sorts to the right and the left, the trans and the cis communities. But in her personal life and her dealings, she is very clearly and thoughtfully her own person. When she gets dressed—in her Docs or her frocks or whatever—she isn’t trying to play the role of the girl or the boy; she’s just trying to be herself, and to be comfortable and efficient in her daily life.

When I spoke to Manning recently, we talked about how her personal style has evolved in the three months since her release. She is amused by how often she wears dresses. For a woman who once told me that “your so-called millennial pink is not for me; I have pink on my computer screen but I won’t wear it; such a frilly color,” she is surprised to find herself reaching for a certain pink frock from Kate Spade. (She was wearing it while building a computer on the floor of her apartment when we spoke.) She was looking forward to spending this fall in a “Johnny Cash suit from Theory, femme Johnny Cash.” And she has been wearing a lot of black: “It has this rebellious cyber punk element to it as well. Very Blade Runner. Very Matrix.” Also very Hackers (hello, Legs!). She still wears khaki slacks (from Banana Republic) and shirts, and possibly it is in this get-up that she snaps the sly pics of federal office workers that occasionally appear on her Instagram feed. “I am very careful to fit my style into the social norms of a particular situation,” says Manning. “I can violate some minor rules and expectations. The hashtag necklace, or boots not shoes. I can be subtle in my subversion of social norms.”