When a customer showed up at the Phoenicia Diner with the diner’s logo—an illustration of a station wagon with canoes strapped to its roof—tattooed on her forearm, owner Michael Cioffi knew he had hired the right designer to rebrand his Catskills eatery. That someone would ink the logo on her skin seemed to Cioffi a high compliment, a sign of the diner’s successful reboot. 

This success was thanks to New York City–based designer Gabriele Wilson, who recently re-created the 50-year-old diner’s interiors and identity, designing everything from T-shirts to illustrated placemat menus that cleverly double as souvenir guides to nearby activities. Cioffi discovered Wilson after learning she was the mastermind behind the whimsical branding of Blue Marble Ice Cream and the trendy Brooklyn restaurant Buttermilk Channel. He hired her immediately after meeting her.

Whether or not you’ve been to the Catskills Mountains, in southeastern New York state, you’ve likely seen Wilson’s work. As a senior designer at publishing house Alfred A. Knopf for seven years, she created covers for nearly 1,000 books, from Michael Pollan’s best-selling In Defense of Food to a collection of jewel-like chapbooks, inspired by textile patterns, for the Poetry Society of America. In 2006, Wilson started her own studio, Gabriele Wilson Design, to try her hand at a more diverse range of projects. Since opening her own shop, she’s made restaurants beautiful, revitalized brands from natural personal care company JĀSÖN to shoe company Palter DeLiso, and designed lavish art books for publishers Rizzoli New York and Abrams. 

“All these new businesses I’ve worked with have become really successful—every single one,” Wilson says. “That’s been hugely satisfying.”

What’s her secret? Over green tea at Billy’s Bakery in the TriBeCa neighborhood of New York City, blocks from her one-room studio, Wilson talks about what makes a design successful. “Things that are done really well look easy,” Wilson says. “I’m a tennis player, and I recently saw Roger Federer play at the US Open. He looks like silk. He doesn’t look like he’s working. And he’s the top player. It’s the same for designers: beautiful design doesn’t look styled. I hate stuff where you can say, ‘Oh, that’s by that designer.’ It’s about not letting design overpower the concept and really getting at the heart of the problem.” While branding Phoenicia Diner, for example, she focused on one question: what did the diner really need? Classic black menu boards and an old-school stainless steel “DINER” sign paired with a sleek curved bar, elegant globe lamps, and uniquely illustrated coasters and matchbooks—the finished product struck a difficult balance, maintaining Phoenicia’s appeal to local regulars while also attracting flocks of tourists and foodies.

Instead of a signature style, what makes Wilson’s work unique is an elegance and wit that, like Federer’s smooth tennis playing, looks easy, even though it’s really not. “She operates well under an enormous amount of pressure—she understands perfectionism,” says Alice Quinn, the Poetry Society of America’s executive director. Wilson’s designs are also simple and understated, with a hint of playfulness. Blue Marble cofounder Alexis Gallivan says, “She doesn’t take herself—or the almighty design—too seriously.”

Growing up in Concord, Massachusetts, Wilson was surrounded by art and photography. Her mother was a painter; her father, a scientist who worked with artificial intelligence. The famous German cartoonist Loriot (Vicco von Bülow) was a cousin; her grandfather was head of Kodak’s chemistry lab. “It’s why I’m in this field,” Wilson says. “I was exposed to the photo industry early on, so I use a ton of photography in my designs. If I wasn’t a designer, I’d be a photojournalist.” In addition to design luminaries like Paul Rand and Alvin Lustig, she cites photographers and filmmakers—Horst P. Horst, Alfred Hitchcock, Wes Anderson—among her biggest influences. 

At the College of Wooster, in Ohio, Wilson studied English and fine art, passions she fuses in her design career. But it wasn’t until shipping off to teach English in Prague that graphic design entered her radar. “At the time, I didn’t know what graphic design was,” she says. “But in Prague, I started noticing poster and cover designs in antique bookstores. The Czechs have an incredible typographic sensibility.” She fell in love with the bright orange cover of the Czech novel Truck Stop Rainbows, by Iva Pekárková—so much so that she was motivated to get a master’s degree in design. Back in the United States, she did a stint as a “glorified secretary” at IBM while taking QuarkXPress classes at night and applying to art schools. Ultimately, she enrolled in Parsons the New School of Design’s associates of applied science in graphic design and completed the two-year intensive program in one year “to save money, which was a bit mad.” 

Immediately after graduating, Wilson cold-called Archie Ferguson, a cover designer she’d admired, and asked for an informational interview. Ferguson helped her land a job as a junior designer with book jacket designer Evan Gaffney. “He seemed like a god. He had done Bridget Jones’s Diary,” Wilson says of Gaffney. A year later, Ferguson called Wilson up and asked her to come into Knopf. After talking with Ferguson and art director Carol Carson—a “diva of cover design”—Wilson was offered a senior designer position at the storied publishing house. She was 23. 

Although fluent in digital mediums, Wilson has never abandoned the handmade approach that her fine art and photography background instilled in her. This fealty to old-school methods—“tactile weirdness,” as Wilson puts it—is part of what makes her work so original. In a landscape of designs slapped together in Adobe Illustrator, she works in analog mediums—original photography, found objects, illustration by hand—as much as she can. 

“I don’t have ideas when moving things around on a computer,” Wilson says. Her work is fueled by adventure: she’s climbed Mount Kilimanjaro, she runs several miles a day, and every morning, she bikes on a three-speed from her home in Cobble Hill over the Brooklyn Bridge to her TriBeCa studio. “That’s when I have ideas—running, climbing, biking.” 

The poetic cover for William H. Gass’s novel Middle C offers a case study of how Wilson works. “With a piano key, I wanted to personify the main character—show his loneliness, his mediocre, middle-C tone,” Wilson says. Unable to find a satisfactory photo of a piano key, Wilson called piano makers Steinway & Sons and asked them to send her a middle-C key. They obliged, and the resulting book jacket is an evocative, slightly mysterious photograph of the keys C and C sharp against a giant turquoise Pantone chip. “Her cover for Middle C is an absolute masterpiece,” former colleague and renowned designer Chip Kidd says. “I hated her when I saw that. But just a little bit.” 

Many of Wilson’s cover designs are products of such elaborate scavenger hunts, though the average bookstore browser has no way of knowing it. “The covers I’ve done that have had the most legwork are always the most interesting,” Wilson says. For the Lolita Cover Project, in which dozens of designers were commissioned to create new covers for Vladimir Nabokov’s iconic novel, she visited Manhattan’s quirky Fountain Pen Hospital, where all manner of vintage pens are restored, and tracked down the exact pen model that protagonist Humbert Humbert uses in the book. Instead of recycling sexualized Lolita clichés—bobby socks, heart-shaped glasses—she had a friend, designer Peter Buchanan-Smith, write the name “Lolita” over and over (“I wanted male handwriting,” Wilson says). The resulting book jacket is a subtly chilling depiction of male obsession.

Wilson believes such field trips are often essential to solving design problems. For The Third Plate: Field Notes on the Future of Food, Wilson photographed actual dirt from the farm of the book’s author, chef Dan Barber. For The Toyota Leaders: An Executive Guide, by Masaaki Sato, she found a Canadian origamist online and had him fold a tiny paper Prius. For Lynne Cox’s Grayson, she searched through an antiques store to find a paper whale that, to her, “was the character—I chose him from many other whales.” The images on these covers have stories of their own, stories that echo the tales in the books’ pages. Such particularity and tactility lend mystery and meaning to her images.

“Gabriele’s designs always deliver a kind of joy,” says Carson, Wilson’s former boss. “Certainly wit. And always sublime color. That may seem a strange thing to say, but just look sometime in a bookstore or online and compare the effects. There is a lot of the expected, formulaic and mundane.”

Wilson expertly avoids the formulaic and mundane. “For me, the adventure and the research that go into the process of designing—interviewing the client almost like a journalist, listening carefully, reading carefully—are more exciting than the designing itself,” she says. 

This adventurous personality is key to how Wilson runs her studio, which is growing and currently employs a few junior designers. Before leaving Knopf in 2006, “I saved as much money as I could and took the leap, trusting it would all work out,” Wilson says. “A year later, the recession hit, but I made it through.” Her business savvy, whether it involves communicating with clients or juggling multiple projects, matches her creative skills. “She is a living example of the fact that it’s possible to be a brilliantly talented designer and also one of the nicest, most heartbreakingly lovely people you will ever meet,” Kidd says. “I have yet to achieve this—and don’t hold your breath.” 

Crucial to her business (and sanity, Wilson says) is choosing clients who put design first. She knows from experience that good design is essential to a company’s bottom line. “The clients I’ve had who really respect design make everything better for everyone,” Wilson says. “It might seem like a micro thing, but a logo can make or break a company.” She believes designers belong in the boardroom right next to business execs, a tack more companies are starting to take. “It’s huge for business-people to incorporate design into company decisions, instead of being, like, ‘Oh, the designers are over there at Kinko’s.’ I don’t want to work with clients who put design second.” Part of her ability to guide businesses in the right direction comes from a resistance to trends in the design world (“I can’t believe that the ‘artisanal branding’ trend is still a thing”). Her maverick sensibility, intense thoughtfulness and attention to problem solving make her work timeless and captivating. 

As to what’s coming next for her studio, Wilson says she’d like to try her hand at branding an airline. “I’m looking to scale up with fewer and bigger projects that have longevity and contain more elements beyond print and web,” she says, “whether that means uniforms, interiors or patterns.” None of her clients or coworkers seem to doubt her ability to take on such a challenge, however new or global it may be. “I believe the scope of her work is unique and lasting, whether for an interior design book, a novel or a restaurant identity,” Carson says. “She will be remembered for making the visual world a finer place.” ca