In ELLE’s Crime of Fashion series, we investigate whether clothes make the criminal—and talk with people who risked the slammer for a slice of glamour.
Five years ago, I investigated how society grifter Anna Sorokin, alias Anna Delvey, was getting Saint Laurent in jail. As it turns out, she employed a former fashion magazine editor named Anastasia Walker, who pulled off-the-rack designer looks and shipped them to Rikers Island, the holding facility reserved for New York’s most notorious criminals and Sorokin’s home for over a year. Walker told me that her client insisted on “timeless” pieces, given her trial style would almost certainly become tabloid fodder (it did) and feature heavily in Inventing Anna, the Netflix project about her life (it was).
But fashion was about more than just legacy. It was also a strategy: By dressing up, maybe she could distract the jury from the fact that her story was dressed up, too.
While at Rikers awaiting a verdict, Sorokin conducted other sartorial experiments. “The uniforms they give you [are] the same ones they give to men, the only difference is sizing,” she told me recently. “I wanted to make my uniform look a bit better, so I would put my pants or the shirt inside out and draw contours of my body.”
With a prison-grade sewing kit and basic skills picked up as a kid, she tailored the one-size-fits-all set. Guards forced her to “take [the stitching] out with my hands when they saw me in the hallway,” she says, but not before her work caught the attention of fellow inmates. “They would try to hire me to do their uniforms,” she says. “But I was like, ‘I don’t work for a jar of peanut butter.’”
Anna Sorokin closed out the SHAO show during New York Fashion Week.
Sorokin had her sights on something a little less gritty, but just as nutty: the world of New York fashion. On Wednesday, just shy of two years after being released on house arrest, she co-produced three Pornhub-sponsored fashion shows in Chelsea alongside PR shark Kelly Cutrone, who describes her partner in crime as “a genius performance artist” and “smart as fuck” on a phone call earlier this week.
This wasn’t Sorokin’s first fashion show, but it was the biggest, buzziest, and best-attended. Her Dancing With the Stars partner, Ezra Sosa, sat front row wearing a bedazzled ankle monitor in solidarity. Legendary fashion photographer Nigel Barker debuted his new line of pre-mixed espresso martinis backstage. And the crowd was packed with New York influencers and editors.
Sorokin with her DWTS partner Ezra Sosa.
In more ways than one, the spotlight is back on Sorokin, and the attention has some people contemplating the correlation between high style and low morals—and whether this kind of short-term shock value has staying power. One editor near me whispered: “My mom can’t wait to watch her on Dancing With the Stars, but like c’mon, Anna Delvey doing fashion week? Really?”
A lot of people have a lot of opinions about her return. Whoopi Goldberg certainly wasn’t afraid to voice hers earlier this month. “It really doesn’t matter to me,” Sorokin says firmly. “It’s great if they don’t like me, because I feel like they’re stupid.”
So, how did we get here? After years posing as a German heiress, Sorokin was sentenced to jail in 2019 for swindling Manhattan’s elite to the tune of $275,000. She bounced around different correctional facilities, before a judge put her on house arrest in late 2022.
Sorokin wore her signature Celine glasses a during her trial at the New York State Supreme Court in Manhattan in 2019.
It didn’t take long to come up with a new concept capitalizing on her crimes; in 2023, she formed a pop-up PR agency with Cutrone called “Outlaw” and invited editors, stylists, influencers, and other fashion people to the roof of her Lower East Side apartment building, where local designer Shao Yang debuted a collection. “Fucking Vanessa Friedman [fashion director and chief fashion critic for The New York Times] reviewed it and called it Off-White-meets-Gaultier,” Cutrone says. “We knew we were going to get press, but we didn’t think we were going to get that kind of press.”
Maybe it was the success of the show or the fact that her rent was $7,000, but Sorokin applied for an address change and moved into Cutrone’s house upstate five months later. They cooked, played board games, and hatched new ways to make noise together. “We’re in the same house, so it’s like a married couple who does a brand or something,” Cutrone says. “It’s not just a nine-to-five thing. It might be a Sunday in the dining room, and [we’ll say] ‘This would be really fun!’”
Cutrone hugging Sorokin after a court hearing this summer.
All that table talk led the unlikely duo to this: closing out NYFW with back-to-back shows for the brands Private Policy, Untitled & Co., and SHAO. Everything took place on the same day, at the same event space in Chelsea. When I arrived early for the SHAO show, the third and final one, Cutrone was overseeing a last-minute run-through wearing aviator sunglasses, leggings, an oversized hoodie, and black flip-flops. “They’re custom!” she chirped.
Backstage, Sorokin was mingling with the models, because, well, she was one. “I cast myself, so that’s great,” she had told me earlier. Then, the lights dimmed, and she walked the runway in a sharply tailored blazer and maxi skirt with a side slit showing off her ankle monitor. The crowd erupted in cheers. The clothes were beautiful, but it’s clear what everyone was there to see.
Sorokin getting ready backstage for SHAO.
New York Fashion Week has always been full of novelties. This year, Susan Alexandra featured dog models, Wiederhoeft marched 26 brides in matching corsets down the runway, and Area’s show went full troll. It’s not enough to just debut collections anymore; staging viral show moments is as integral to the process as making the clothes. For some emerging and independent designers, causing a scene is one of the best ways to be seen.
That’s where Cutrone thinks Outlaw can carve out a niche. “Who’s going to help these [young designers]? How do we open up the doors for them to thrive and give them a way to shine?” Cutrone says. “Anna and I have a lot of experience between us. I mean she’s done jail time.”
Former Cosmopolitan.com site director Amy Odell, author of the Anna Wintour biography Anna: The Biography, thinks the industry has long fetishized people and trends that are “deeply flawed.” Using Sorokin to sell clothes “seems like par for the course,” she adds, at least for now. “It’s likely when this ends a lot of us won’t even remember it in a year,” she says. “I think saying it signifies anything for the future of New York Fashion Week would be giving it too much credit.”
For Carrie Crecca Maitoza, the brand consultant behind popular fashion PR meme account @miss_pr_piggy, the virality of this moment reminds her of Lindsay Lohan’s very brief, very controversial stint as artistic advisor to the house of Emanuel Ungaro back in 2009. “That’s what this is giving to me, but for the PR world,” she says. “And I’m not saying it’s a bad thing.”
Whether you think she’s a criminal mastermind or, like Cutrone believes, a marketing maven, Sorokin certainly understands how clothing can be a tool for manipulation. When I ask about her future in fashion though, she is cautious. “I’m working on something, I’ve been so busy, and I don’t really talk about it publicly until I have everything figured out,” she reveals. “It sounds preposterous, considering the past events, but I’m happiest when I have a company to run.”
What she can say is that the business, which is separate from Outlaw, will be fashion-oriented. “I was offered [to do] The Masked Singer for a lot of money, I was offered a dating show while being on house arrest… but I don’t think I want to do much in entertainment at all. It’s just something that I don’t have the personality for,” she says. “I never wanted to be famous, [although] people love to say that. If you look at my old Instagrams, it’s just boring pictures of art, pretty much. There was no ostentatious display of wealth or whatever.”
Before the Private Policy show, Sorokin posed for photos and took selfies with attendees.
Fashion, she says, is and will remain her top priority. “It’s the corniest thing you can say, it’s so trite, but I think it just comes naturally to me,” she explains. However several industry insiders I spoke with were skeptical about her ability to parlay a criminal record into whatever it is she’s plotting next. “I did my time and paid my restitution,” Sorokin insists. “So it’s like, what else would you like me to do, kill myself?”
Cutrone says “there aren’t enough fashion people that could possibly hate Anna to keep her from not being successful.” And Fern Mallis, the creator of New York Fashion Week, adds that “Anna did her time, and should be allowed to do whatever she wants to do.”
Sorokin arriving to a court hearing in May.
One of the twistiest plot lines in Inventing Anna follows former Vanity Fair photo editor Rachel DeLoache Williams, who was forced to front a $62,000 hotel bill while on vacation with Sorokin in Marrakesh. A few years back, I asked DeLoache Williams during an interview whether she’d seen the viral Instagram account celebrating Sorokin’s courtroom looks.
“Yes, it’s like a big ‘Watch the birdie,’ that old magician’s trick,” she told me at the time. “Like, you’re paying attention to this, so you don’t see what I’ve actually done here.”
“But it didn’t work,” I posited. After all, Sorokin was found guilty and served jail time.
“No, it did work,” DeLoache Williams said. “Look at the way she was applauded in the court of public opinion, like that Instagram account. It’s frustrating, because I understand her appeal, and I certainly don’t blame anybody for finding it amusing. I probably would have too, had I not been taken advantage of by her, and had I not seen her for who she is, a despicable narcissist.”
After leaving the SHAO show, I walked by Motel Morris, a cute bistro across the street with outdoor seating. I noticed a man with short brown hair drinking wine with a woman wearing an Aimé Leon Dore sweatshirt. He hadn’t been at the show, but he looked familiar. It wasn’t until I got home that I realized it was Billy McFarland, the infamous Fyre Festival founder once dubbed “the poster boy for millennial scamming.”
A quick Google search revealed that he, too, was back in the spotlight. Earlier this week, McFarland appeared on the TODAY show to tout tickets ranging in price from $1,400 to $1.1 million for Fyre Festival II, taking place next April on a private island off the coast of Mexico. One thing about a scammer, they’re not afraid of a comeback.
Rose is the Senior Editor of Features & Special Projects at ELLE.com overseeing features and projects about women’s issues. She is an accomplished and compassionate storyteller and editor who excels in obtaining exclusive interviews and unearthing compelling features.