It’s surely against whatever rules of retail that remain to open a store simply because the building itself is, as the shopkeeper says, “so beautiful, especially at dusk, that it breaks your heart.” But when the shopkeeper is Massimo Alba, one understands. And when the shop is a small chalet in Courmayeur, a winter holiday spot for the Milanese cognoscenti high in the Italian Alps that loom on the horizon north of the city, it all makes sense.

Ever since he started his own line in 2006, after stints at Malo and other labels, Alba has been one of the fashion world’s most treasured designers, something of a secret. An ursine, shy man, the 59-year-old possesses a lack of cynicism and an open-mindedness that inform his clothes. No wonder Daniel Craig has been seen wearing an Alba corduroy suit while filming No Time to Die, the next film in the James Bond franchise—it’s a suit that embodies Alba’s aesthetic: refined but with an artist’s ruggedness, and just the right dose of smarts.

Alba has always followed his own path—which explains why over the past few years he has opened small stores not where data tells him to be but where his heart and curiosity lead him. Venues such as the 16th-century Palazzo Coronari, in Rome; or Taormina; or Sestri Levante, in the Cinque Terre. A year ago, he came across the small chalet in Courmayeur, and, as he says, “it felt right.”

Inside, the walls are lined with pages from Victorian-era books.

He says he sees a store as “an extension of my home—my own furniture is there, my paintings, my photos.” Indeed, each of his shops has the feeling of his atelier in Milan, a place filled with objects that inspire him; where his grandfather’s 1930s white tie and tails hang from a shelf, alongside rare midcentury Italian lamps, books, and photographs: large Lillian Bassman prints; Esko Männikkö’s portraits of Scottish factory workers. The walls are covered in pages from Victorian-era books.

Inside the Courmayeur chalet you’ll find clothes that are romantic in just the right way, pieces that have the relaxed but smart vibe of an artist. He’s known to splice lines of poems by his beloved Whitman or Bukowski onto a shirt. Or, as he did this season on a handkerchief, write Understand ME beneath a photo of Innocenzo Fraccaroli’s statue of a wounded Achilles. It’s this sort of effortlessness that has attracted not just Craig, but also Leonardo DiCaprio, Ian McKellen, Stanley Tucci, and soccer coach Pep Guardiola.

“I’ve been thinking a lot about vulnerability,” Alba says. “We’re terrified by it. But it’s what makes us human. It’s certainly what makes Achilles human, more than his rage.”

There’s an innocence about Alba, a lack of cynicism that’s rare in fashion. Whatever he casts an eye on—a line of poetry, a vintage watch or camera, the label design for an obscure brand of British gin, the ancient Loden overcoat on an even more ancient gentleman he runs into on the street—he brings a sense of “seeing it new.” When it comes to design, an important source of inspiration is one of his assistants—Jasper, a yellow Lab as quiet as Alba, with a penchant for staring, intently, puzzlingly even, into people’s eyes: “Nothing is uninteresting to Jasper,” Alba says. “It’s one of the great lessons he taught me.”

Every once in a while, Alba takes a meeting with one of the hedge funds forever interested in buying his brand. “They’re all very nice to me, but there’s always just one topic, really: money.” Alba, however, says he is more “interested in beauty,” even if he realizes “it’s sort of against the rules—but then the rules have been designed for people interested in winning, and I’m not sure I’m interested in that. Maybe I’m more interested in coming in second. Who knows?”

Matteo Persivale is a writer based in Milan