Portrait of a Lady
It’s hard to make an entrance on Zoom, but Jenny Walton found a way. When I met the 32-year-old illustrator and designer in November for a virtual interview, she was wearing a beige Surrealist-inspired dress from Loewe’s Fall/Winter 2022 collection. It was printed with two black gloves, themselves adorned with crimson fingernails, that wrapped across the chest and hip in an arch re-creation of Boticelli’s Venus. Walton could have accessorized with some great earrings and called it a day, but no: She was sipping Diet Coke out of a vintage Coca-Cola goblet from Etsy, which she had selected specifically because the red lettering matched the nails on her dress. As a finishing touch, she pulled a biscuit stick from a cherry-colored box of Pocky. When she’d gone out to a deli that day to buy her soda, she’d noticed that the packaging perfectly mirrored the color palette of her dress, so obviously that was coming home with her too.
Walton was laughing while she told me all of this—and it is funny, in an If You Give a Mouse a Cookie kind of way—but finding beauty in the everyday is an earnest concern of hers. “That’s what I enjoy about life,” she says. “I’m drawn to trying to find nice moments.”
The nice moments that Walton documents on social media—Prada events and tennis outings with Miu Miu, heaping bowls of pasta and aperitivos in Verona, antique Italian furniture to fill her apartment in Milan—have earned her some 356,000 Instagram followers and made her one of fashion’s most intriguing figures. Influencers with beautifully appointed homes and luxury sponsorships are a dime a dozen, but the enthusiasm Walton brings to dressing up in elegant and somewhat anachronistic outfits makes her online presence feel shockingly fresh. “I’m so into her storyline,” the photographer Jamie Beck said on a November episode of the podcast A Thing or Two, speaking about Walton’s recent social-media output. “I find her more interesting than the Kardashians.” Beck is not alone: When Walton and her former fiancé, The Sartorialist founder Scott Schuman, broke up in May, Gawker published an item on it.
Over the past year, Walton has become something like fashion’s Emily in Milan. She’s living in the city with her two dogs, posting photos of Milan’s chic older women, and attending sparkling brand dinners, while her outfits are bolder and more glamorous than ever. Whether it’s Walton’s obsession with JW Anderson’s pigeon clutch or her documentation of party dresses gone awry, it’s clear that she’s having a ball with fashion. But who actually is the woman in the archival Prada?
Once you get over the volume of designer clothing in Jenny Walton’s closet, the first thing you’ll notice about her style is its ladylike precision. Walton dresses with a retro kind of formality. I don’t mean that she looks like she’s engaging in 1950s cosplay but rather that she composes outfits with a head-to-toe polish that was more common in our grandmothers’ generation than it is today. Walton isn’t just putting on a pair of pointy-toed slingbacks with her statement coat, she’s putting on the shoes and the pearls and big sparkly earrings, and then she’s styling her hair in old-school waves or sweeping it into an updo reminiscent of a Hitchcock blonde.
“There's a crispness about her style,” says Leandra Medine Cohen, the writer and Man Repeller founder, who got to know Walton when they lived on the same block in SoHo. “That's not true of mine. I’m really messy—I show the process—and there’s something quite put-together and neat [about her]. I think that contrast against her personality, which is so warm and nonjudgmental, is very seductive for a lot of people.”
Walton’s refinement works in large part because it doesn’t feel uptight. “She’s not snobby at all,” says Medine Cohen, who was just one of several people I spoke with who noted Walton’s kindness and good humor. “Play” is a word that comes up a lot when Walton describes getting into the zone with building an outfit. “I feel like an artist and each dress is a paintbrush or something,” she tells me. On Instagram and in real life, Walton projects a readiness to roll up her sleeves, whether she’s sharing hacks for re-creating Prada’s white-collared turtleneck sweaters on a non-Prada budget or, as she described to me in great detail, attempting to save multiple injured birds in New York by scooping them up in a scarf and taking them to a bird rescue uptown. (Walton, who named her JW Anderson pigeon clutch Peggy, as in Guggenheim, has always loved birds.)
There’s another reason why Walton’s look feels decidedly un-Stepford, and that is because it’s heavily informed by fashion’s foremost purveyor of twisted elegance, Miuccia Prada. Not only does Walton wear the clothes that Mrs. Prada makes—including a skirt suit from Fall/Winter 2007 with a wickedly warped texture and a pink satin miniskirt from Spring/Summer 2022 that makes the wearer look like a human pointe shoe—but traces of the designer’s personal style are evident in her affection for curls, headbands, and big earrings. “Everyone’s obsessed with her style, as well they should be,” Walton says. “I think she melds perfectly the artistic with the intellectual, and that’s something that’s very rare in fashion.”
Walton didn’t grow up with much in the way of spending money, and today she funnels her income from sponsored content and brand-illustration jobs into her closet, which has spilled out of her bedroom in Milan and into her kitchen cabinets. “Essentially, that is where all my money goes,” she says. Walton is a longtime vintage shopper, and she uses a variety of websites and apps (Vinted, Vestiaire Collective, Poshmark) to track down her treasures. Some of the best deals come from sellers who don’t know what they have, she tells me, which means that clever search terms won’t always help you. “The best thing you can do is just search Prada and do the whole fucking thing. You need a lot of patience and time,” Walton says. “However, this is my pastime.”
Fashion is full of small-town kids with a deep hunger for visual thrills, and Walton is one of them. The middle of three sisters, she grew up in South Jersey in a quiet town that bored her, in an old Dutch Colonial house that abutted a Christmas-tree farm and peach orchards. “She used to go back there and climb into a tree or a deer blind and paint and read,” says her mother, Trish Walton. Fortunately, creativity was encouraged in the house. Trish, a German teacher, is an expert quilter and a fan of old movies, and she taught her daughter to sew and embroider and introduced her to actresses like Barbara Stanwyck and Joan Crawford. On weekends and summer breaks, the family would make trips to flea markets, estate sales, and thrift shops, where Trish scouted for inexpensive wool to use in felting projects and Jenny scoped out 1950s Pyrex dishware and old smoking pipes.
Walton draws a direct line between these early experiences—of vintage shopping, distant glamour, and suburban boredom—and her prevailing aesthetic interests. After high school, she moved to New York to study fashion design at Parsons. When she graduated in 2012, she moved into an apartment in Park Slope with her classmate and friend Trevor Houston, now a footwear consultant and the curator behind the Instagram account @OldPrada, and the two spent their off hours watching old movies together. They found a shared language in the fashion and strength of the women they saw onscreen. “I feel like those actresses, they were going to give everything,” Houston tells me. “Their performances were radiating out of them.”
Walton entered the workforce during what was arguably the golden age of Instagram, a less professionalized era of social media when connecting with others, rather than hawking one’s lifestyle, felt more like the point. After college, while working as an assistant designer at Calypso St. Barth, she started to amass a following on the platform, where she posted her fashion illustrations—confident slashes of ink that could be seen as charmingly analog at the dawn of the selfie age. “My favorite part of the day slowly became this hour-long train ride to and home from work, where I’d just sit and listen to music and sketch. And then at the end of the train ride, I’d post the sketch,” she says. In 2014, Walton quit her job when a brand offered her $750 per in-store illustration, though she continued to pick up freelance design work as a financial hedge while she pursued illustration.
Around that time, Walton also started dating Scott Schuman, the photographer behind the popular street-style blog The Sartorialist. The two cut a striking figure: With his streamlined suiting and her eye-catching dresses, they looked like the ultimate fashion insiders. Though Walton had her own projects, she started working with Schuman too, eventually becoming fashion director of The Sartorialist. Standing outside the shows at Fashion Week, she became a frequent photographic subject not just of Schuman but of the other street-style photographers present. Tommy Ton, one such photographer, remembers taking notice of the way Walton put together vintage pieces and the poise with which she carried herself. “She’s always had this ability to understand her body language, in the way she crosses her legs or folds her arms,” Ton says.
Walton and Schuman got engaged in 2017 and moved together to Milan in the fall of 2021. The city is full of the kind of midcentury architecture and aesthetic details that capture Walton’s imagination; its local breed of refined older women, known as the sciura, has become an influence on her style, with their tonal dressing and wire-haired dachshunds. (Walton’s dog Baffi, whose name is Italian for mustache, is a wire-haired dachshund.) “Milan is endlessly inspiring to me,” she says. “All the tiny little moments: people’s terraces … the tiling of the buildings, the entryways.”
The narrative took an abrupt turn in May, when Schuman and Walton posted to their respective Instagram accounts that they had broken up. “We have been a great team for the past 7 years, have had many great experiences, and wish only the best for one another going forward,” Walton wrote in her post. Offline, she found herself another apartment in Milan, an old place with parquet floors and tall windows, and moved in with Baffi and her beagle, Charlie. Didn’t she consider hightailing it back to New York? “I’d been in New York for 15 years,” Walton tells me. “I really wanted a place where I could walk down the street and have no idea what was down it.”
But a breakup is a breakup, even in Italy’s capital of design. For the first few weeks in her empty new home, Walton was exhausted, mentally and physically. “I mainly just stayed in the house, cleaning and putting things together. I didn’t get dressed up at all, because I didn’t even have the energy for that,” she says. Bit by bit, though, she started to rekindle her spirits. Every single morning, Walton made a point of getting dressed up in an outfit she loved and walking into the city center with her dogs to get a caffè macchiato. She wore an old Prada banana-print skirt with a woven basket, an icy-blue Phoebe Philo–era Céline slipdress with dainty slingbacks, a showstopping leopard-print dress with a wide neckline. She remembers telling herself, “I’m going to do that every day, to keep going, to try to keep myself going.”
Though the end of Walton and Schuman’s relationship resulted in some rubbernecking from those well versed in fashion and media, it also added a new layer to the way Walton’s followers related to her. In her Instagram posts about hunting down vintage Italian furniture to fill her apartment, it was possible to catch a glimpse of a woman refashioning her life in her own image. Her first purchase for her new home was a wooden sculpture of a nude woman, which she placed in her entryway because, as she tells me, “I want it to be known when you come into my apartment that there is strong, proud, female energy. Me and both of my dogs are female, and this is our place.” Walton’s presence on social media wasn’t just interesting because of her clothes anymore; it had become a case study in self-determination through style.
Over the summer, Walton started receiving supportive messages from strangers, particularly women—a show of kindness that she appreciated but that started to bring out a codependent streak in her. In August, she took a two-week break from Instagram. “My therapist in Milan is like, ‘You have to treat it a little bit more like a business, because it’s just too much,’” she says of the platform. “I fight with that constantly because I feel lucky to have that. It’s what’s given me my whole career.”
Walton sees her trajectory on social media as a gradual build, accented by major achievements: a photo shoot for J.Crew in 2015, a Miu Miu event where she was hired to sketch store customers in 2018, an invitation to her first Marc Jacobs show in 2019, Prada’s offer to dress her for its show in February 2022. Without question, though, her career has shifted into a new gear in the past three years. “There was so much disillusionment around fashion during the pandemic, and I think she was, for a lot of people, a very safe way to stay connected,” says Medine Cohen. At a time when self-presentation had never felt more tenuous, or more pointless, Walton’s enthusiasm for fashion pulled double duty, reassuring clotheshorses that it was okay to seek solace in great outfits and reminding those of us who had forgotten how to dress that it was also okay, and maybe even healthy, to try.
As time went on, the way Walton embraced her budding life in Milan provided a dose of escapism and motivation as her followers considered the shape of their own lives post-lockdown. “It’s a bit like cinema … this woman living her life in Europe in this fantastic setting,” says Guillaume Lavoie, the proprietor of @WhatMiuccia, an Instagram account dedicated to the personal style of Mrs. Prada. “It’s making people dream.” The refinement and extremity of Prada’s clothing requires something of a performance from the wearer, Lavoie tells me, and as Walton’s life in Milan took shape, buttressed by archival pieces from the brand, she seemed to be radiating a performance not unlike those of the Old Hollywood actresses she and Houston loved so much.
When Walton returned to social media after her self-imposed break in August, she did it with aplomb. She had attended the Venice Film Festival premiere of Luca Guadagnino’s Bones and All as a guest of Mo?t & Chandon and walked the red carpet wearing a floral, full-skirted Prada dress from Resort 2008. “It was made for her. She looked like Grace Kelly,” says Ton, the photographer. Years ago, Ton had purchased the dress on eBay for roughly $250 and, after discovering that Walton was obsessed with that specific collection, gave it to his friend in exchange for two large houseplants. (These plants would have been very expensive at retail, Ton clarifies to me: “It’s not like I randomly took two small, little plants.”)
Who wouldn’t have a good time walking a red carpet in proximity to Timothée Chalamet, enjoying a glass of expensive champagne, and watching a cannibal romance film? But reflecting on that moment and that dress, which Walton had originally envisioned for a courthouse wedding, she sees it as a case of fashion pulling her out of an emotional rut. “I guess because it’s so inspirational for me on a personal level, it actually does have the power to make me feel better,” she says.
When we spoke in November, Walton had just hit another bump in the road. She’d come back to New York to apply for an Italian visa but learned that the process would take much longer than expected; she couldn’t return to Milan full-time until January, when her permitted number of days in the country as a tourist reset. For the time being, she was living in her younger sister’s apartment in Brooklyn, sleeping in the same bed, just like they did as kids. Walton was feeling dispirited, frustrated that her momentum had slowed. But, she tells me, “So what if it takes one to two years of a bit here, a bit there, to fully make it happen? That’s okay.”
While she waited, Walton was studying Italian with a tutor and with the staff at a local Italian restaurant who let her practice with them when she came in for coffee. She was hankering to acquire a couture piece designed by Cristobal Balenciaga, who is, with every bit of respect to Mrs. Prada, her all-time favorite designer. She was writing and painting and plotting a full-scale mural in the spare bedroom in Milan that she uses as a studio. She was, her sister Annagrace informed me, constantly upgrading household items around the apartment, having already repainted the cabinets. She was taking the financial leeway that comes with Instagram sponsorships and pursuing smaller projects that felt special and significant.
“I'm moving with a lot more intention,” Walton says. “I’m solo driving, and I love that. I know what I like, and I know what’s important to me. That’s not an issue.”
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