Anna Delvey and Kelly Cutrone’s Latest Project? Their Bucolic Life Upstate.

“Hellooooo!” Anna Delvey belts as she opens the front door of Kelly Cutrone’s Hudson Valley home, her court-ordered ankle monitor visible as she walks into a living room full of mismatched furniture and a quartz altar surrounded by more than a dozen crystals. Above the mantle of the maroon-floral wallpapered fireplace, decorated with various sculptures, hangs a photograph of Indian yogi and philosopher Sri Aurobindo and Mirra Alfassa, a spiritual guru known as “The Mother.”

In the kitchen, Cutrone, 58, is making couscous in a black jumpsuit, her signature long jet-black hair hanging down her back. Next to the stove sits a glass of white wine on a counter cluttered with spices, utensils, and ingredients as Adele’s “Someone Like You” plays on small speakers nestled among the mess. Here, Cutrone welcomes me with a hug, the opposite of the curt greeting she gave Lauren Conrad ahead of a 2006 fashion show in the debut season of MTV’s The Hills.

The homey scene is striking considering Cutrone and Delvey, 33, only met months prior.

At the time, Cutrone, whose stints on The Hills and The City made her out to be “the boss from hell” (Kell on Earth was the name of her own short-lived show), was debuting a young designer during New York Fashion Week and needed a way to make headlines. So it made sense to team up with Delvey—who was under house arrest in her immigration case after being convicted in 2019 on eight charges, including grand larceny, for duping friends and financial institutions while posing as an heiress—to host a rogue fashion show on the tar rooftop of her East Village apartment.

What Cutrone could not have anticipated, however, was that her idea to collaborate with Delvey (born Sorokin) on a pop-up fashion PR company they named the Outlaw Agency would spur a deep friendship. And she definitely didn’t envision that, for the last seven months, Delvey would also become her housemate. Now, the duo is producing three NYFW shows in partnership with Pornhub, and with the added pressure to kick-start Delvey’s reentry into a world she literally committed crimes to be a part of, the stakes have never been higher.

“We were like frontline soldiers together. We’re bonded now in trauma and dreams and redemption,” Cutrone tells me during dinner at her eight-acre property near the Hudson Highlands. “We became like Ab Fab meets Thelma & Louise meets Batman and Robin.”

About five months after the pair pulled off their show for that young designer, Shao Yang, Delvey filed for an address change in her immigration case and moved into one of Cutrone’s spare bedrooms in Cold Spring, a two-hour drive north of New York City.

Since then, the duo has used Delvey’s Manhattan federal court hearings as guerilla fashion hits—all while quietly becoming the picture of domestic bliss inside the confines of Cutrone’s home.

At home, they cook meals together, hatch new business ideas, and feed the 13 goats Cutrone shares with a neighbor. (“Some people compost, we feed goats,” Cutrone says.) After Delvey “destroyed” her at Scrabble, Cutrone pivoted to Words of Wonders, an online puzzle she plays daily under the alias “Mommawolf,” and in which she was ranked second in the world at the time of my visit.

My afternoon with the pair coincided with Delvey’s first full day back on social media in 22 months amid her ongoing fight against deportation to Germany. It was just weeks before their three Outlaw Agency x Pornhub shows—which Cutrone describes as a fashion “turducken”—at the Altman Building. (Cutrone is the publicist for Pornhub.)

“Anna looked up to Kelly as the person she wanted to be when she came to New York, and as soon as Kelly met Anna, she basically fell in love with her,” Yang tells me over the phone days after my visit. “I think having them two together is, like, literally a powerhouse.”

And the fashion industry seems to be taking notice. “I think what they’re doing is interesting and admirable,” Fern Mallis, the creator of New York Fashion Week says. “They’re a match made in heaven for the moment.”

In August, about 10 days before I arrived at Cutrone’s home, a judge reinstated Delvey’s access to social media and revised her house arrest to a 75-mile radius. Nine days after that, Delvey posted a 10-photo Instagram carousel with images of herself sitting next to hydrangeas, a sculpture, and inside an old Jeep. The caption: “Stockholm syndrome.”

Cutrone’s home could make anyone forget about the outside world. Behind the house, a large creek rushes among trees and blooming hydrangeas. Inside, it’s clear that Cutrone has carefully curated the artwork, crystals, and furniture. In the kitchen sits another altar that I later learn is dedicated to all the spiritual mothers and features a mason jar with ex-husband (and Andy Warhol protégé) Ronnie Cutrone’s ashes and two corn husk dolls that she and Delvey made one night while babysitting a reporter’s kid.

Cutrone says that two archaeologists previously owned the idyllic property she moved into in 2010. That same year, she left MTV to star in one season of her own Bravo reality show, Kell on Earth, before appearing as a judge on America’s Next Top Model for five seasons. Around the same time, she wrote two books: the New York Times bestseller If You Have to Cry, Go Outside: And Other Things Your Mother Never Told You and Normal Gets You Nowhere. While she was successful in the fashion industry, launching her company People’s Revolution in 1995 and representing high-profile designers like Vivienne Westwood, Paco Rabanne, and Donna Karan, the entrance into reality TV made her a household name, and as a result, a target of mass scrutiny.

“People see me on TV, like, that was a fake show. Whitney Port and Lauren Conrad never worked for me,” Cutrone says. “Like, we’d be sitting there looking through boxes of Jimmy Choo shoes that we were buying when we were making tons of cash. And they would be like, ‘Kelly you’re going to be very upset today, things are bad.’” (Reps for Conrad, Port, and MTV did not immediately respond to a request for comment.)

“At that time, when I got on TV, people were like, ‘Oh my god, she’s a witch, she’s a witch,’ because most of the women on TV are ripping out each other’s hair extensions, or half naked,” Cutrone says. “All of a sudden, I was a woman on TV who doesn’t wear makeup, doesn’t brush her hair, who says ‘fuck’ all the time.”

The show inspired Delvey, who was born in Russia and lived in Germany as a teen, to move to New York in 2013. “I always wanted to be in fashion. I grew up watching MTV, and I thought that fashion PR was just the coolest thing,” Delvey said in a March 2022 episode of the Call Her Daddy podcast, which was recorded while she was incarcerated. “I remember watching Kelly Cutrone.”

The podcast episode was released nearly four and a half years after Delvey’s arrest outside a California luxury treatment facility for allegedly swindling more than $200,000 from financial institutions, hotels, and individuals as she masqueraded as a German heiress eager to open a private arts club. Dubbed a “fake heiress” and “SoHo grifter” by the press, Delvey’s courtroom fashion dominated headlines before ultimately pivoting to her 2019 conviction. In February 2021, Delvey was released from a New York state prison. Weeks later, she was detained by ICE for overstaying her visa, landing back in prison for another 18 months. She was released on a $10,000 bond in October 2022, immediately put on house arrest, and banned on social media. Delvey is set to head back to court in October for a status hearing on her immigration case. Until her case is resolved, she is required to show up for monthly check-ins with the Department of Enforcement and Removal Operations and adhere to the conditions of her house arrest.

In all, Delvey has been in seven jails and jokingly tells me that Rikers was “obviously” her favorite.

Delvey’s detailed descriptions of her criminal case (which is currently under appeal) and her deportation fight is the first time during my visit she is animated while speaking in front of Cutrone—and Cutrone isn’t cutting in. She explains how, after getting out of jail (again), she moved into a 470-square-foot apartment on the fifth floor of an East Village walk-up, where she began producing a podcast from her living room, inviting reporters inside to chat amongst her stacks of newspapers and books, and working on her ongoing docuseries. She huffs as she explains that, despite her various business ventures and eagerness to move on from her “mistakes,” she cannot escape the “fake heiress” moniker.

“I hate it,” Delvey says of the title.

The mention of the negative public perception immediately perks Cutrone’s ears, seemingly spurring her maternal instinct to protect Delvey. From her spot behind the kitchen counter, Cutrone likens the online hate to tartar on your teeth that “takes extra cleaning” to get out, increasingly less manageable and harder to cleanse with every passing jab, false narrative, and social media roasting that fuels the controversy.

As Cutrone continues her diatribe, Delvey sits back in an attentive silence.

Soon, it’s time for dinner. On the menu: large plates of seared scallops, mashed sweet potatoes, and an arugula salad with peaches grown on the expansive property. Over passed dishes and refills of wine, the pair finally details how they met. Cutrone takes the lead, leaning forward in her chair as Delvey delicately places two scallops on her plate along with a dollop of sweet potatoes. After initially hearing about Delvey mentioning her on Call Her Daddy from her daughter Ava, Cutrone says they met when one of her former business partners approached Cutrone about a possible collaboration.

At that time, Cutrone had met Yang, a Taiwanese immigrant who specializes in bespoke corset and tailored suiting, through fashion photographer and fellow America’s Next Top Model alum Nigel Barker. Impressed by her talent, Cutrone convinced Yang to start her own brand. Her excitement about the young designer, however, was quickly replaced with the harsh realization that she felt responsible for giving Yang a big solo debut.

Then, after a phone call—and then a FaceTime—with the homebound Delvey, Cutrone had a brilliant idea: throwing a fashion show at the convicted criminal’s apartment. After all, Delvey had already proven she could drive a fashion news cycle, producing splashy events like her dinner parties without leaving her living room.

“I thought, [Delvey is] the smartest, coolest person I’ve met in a really long time…. And I knew that I had enough experience to pull the rest of the shit off,” Cutrone adds, her three teal nicotine vapes lined up next to her on the table. “What I didn’t know at the time was that it was impossible, because [her apartment] was too small.”

Putting together that unorthodox show in just eight weeks was an arduous game of Whac-A-Mole. Cutrone describes the process, saying that it involved hiring off-duty NYPD as security guards, planning an afterparty at a neighboring pizzeria, and arranging for party buses to transport the models. But in the end, their gamble on harnessing curiosity and novelty seemed to pay off.

“I didn’t give a fuck about people’s perception, positive or negative, about Anna. I knew she was great, and I knew this was the right thing to do,” she says. “We rode it like a crazy wave in an ocean with a big wind. It’s like, let’s go surfing, and it’s [a] tsunami.”

A New York Times story about the event detailed how VIP guests like Purple editor Olivier Zahm and Lady Gaga collaborator Nicola Formichetti were among the approximately 100 people who packed onto Delvey’s roof. Guns N’ Roses blared from speakers while models posed against the egress door. The minute the show ended, Cutrone and her team ushered people out of the building to avoid the cops responding to multiple noise complaints.

Not everyone in the fashion world bought into the Outlaw Agency’s PR strategy. “I feel that the fashion show did not get the right coverage it was supposed to,” Hanan Besovic, a fashion commentator known online as @ideservecouture, tells me in a statement. “The headlines were only mentioning Anna and Kelly because they are the big names people recognize. While I hope that wasn’t their intention, the designer got the shorter end of the stick.”

Yang, however, didn’t seem to mind taking a back seat. “Kelly and Anna are celebrities, right? Everyone flocks to them, and I usually like to be in the background. I usually don’t like any attention, so I really enjoyed that. And I know that sometimes that’s what we need to do to get the brand out there,” she says.

The show solidified Cutrone and Delvey’s working relationship—and propelled a more personal alliance as fellow “soldiers.” As the pair talked about future projects, Cutrone began to notice the reality of Delvey’s life under house arrest, which included a constant revolving door of guests looking for an after-party, Zoom meetings with potential collaborators, and walking to her ICE check-ins to get some fresh air. Not to mention, her fridge was mostly filled with Spindrift seltzers, and her diet was primarily takeout.

After Delvey moved in—and out—of a friend’s house upstate, and another Manhattan apartment fell through in January, Delvey took Cutrone up on her open invitation to stay at her Cold Spring home.

Since February, Delvey has been the most permanent occupant of the house, as Cutrone and her daughter are often traveling or staying at their apartments in the city. While I tease that there must be a rotating cast of characters, Cutrone insists that they are “very private,” before listing off half a dozen people who regularly come over. Among the list? Delvey’s boyfriend (that she skilfully evaded further questions about) and Kelly Osbourne.

Still, even though Cutrone is “protective” of her private space and hasn’t lived with anyone besides her daughter in years, cohabitating with Delvey became second nature. “There’s an innate understanding of who we are—and we’re weird…. So I have a big circle line around me, she has one around her, and sometimes we meet like the Olympic circles,” Cutrone says, interlocking her fingers to form a Venn diagram.

Delvey has a more straightforward way of describing their friendship: They are able to sit in comfortable silence next to each other for long periods of time. “It’s not high effort,” she tells me a few days after my visit. “We never feel the need to restart the conversation, it’s always ongoing.”

Despite their bond, the two have obvious differences. Delvey is a notorious convicted felon, for one, but also a millennial well-versed in the art of social media. Cutrone is a divorced mother who has had a legendary reputation in the PR world since Delvey was a child. The contrasts are the most salient after dinner, when Delvey suggests we take group photos outside. She confidently poses in front of a large hydrangea plant, while Cutrone eventually plucks a flower to use as a prop.

“We only need to entertain each other when we take total pity on each other,” Cutrone says later in the car as we head to a nearby bar. Upon arriving, Cutrone slides onto a stool at the bar and orders a cocktail of her own creation: “Two ounces of vodka, one ounce of St-Germain, and the squeeze of one whole lemon…. It’s very refreshing.” For Delvey, an espresso martini.

Between drinks, Delvey and I discuss her continued efforts to stay in a country that seems hell-bent on throwing her out. “Nobody gives me credit for, like, sticking it out,” Delvey says.

With her first taste of freedom, she is ready to move on to her post-prison ambitions; most immediately, competing in the upcoming season of Dancing With the Stars, and one day, becoming CEO of her own company. Those dreams are about to be placed under a microscope as the Outlaw Agency coproduces three fashion shows with Pornhub—but it’s something Delvey says she can handle with Cutrone by her side.

“I’ve learned so much from her. For example, we’re planning a fashion show, and [she] obviously had so much more experience than I do,” Delvey explains. “We built on our relationship, as opposed to it being transactional…. Kelly doesn’t need me. Her world is not going to end if I’m not in it…. It’s not forced.”

Mallis, who is affectionately known as “fashion’s godmother,” thinks Delvey is uniquely equipped to make the pivot. “I think that Anna should have every opportunity…to do whatever she wants to do next. Prison is not the handicap it used to be. Martha Stewart did just fine,” she says, adding that Cutrone has “always taken on underdogs and young emerging designers, and she’s always been very supportive and embraces them more than almost anybody I know in the industry.”

Their upcoming back-to-back September 11 shows are for three designers: Private Policy New York, Shao New York, and Untitled&Co., and will feature makeup by MAC Cosmetics, vegan treats, and Nigel Barker’s new vodka brand, The Barker Company. The next day, Delvey is set to participate in a live Pornhub podcast panel, discussing censorship and free speech alongside Stormy Daniels.

As Delvey expresses her excitement about getting back to New York and producing the shows, we realize that I’m about to miss the train to the city and rush out of the bar. As our car screeches to a stop at the station, I ask if there are any last words.

Cutrone responds: “You fuck with Anna, you fuck with me.”