Max Bernardini’s Luxury Vintage Collection

Max Bernardini has created an impeccably sourced gentleman’s quarters where everything is for sale. Crocodile flask included.

On a drizzly evening last November in Milan, not far from the Santa Maria delle Grazie church, whose rectory is home to The Last Supper, an improbable bacchanal was transforming Via Caradosso. A colossal tent stretched above the street, and nearly 800 revelers floated through a dreamlike atmosphere reminiscent of a Havana casino in the fifties. As waiters circulated Champagne and rum cocktails created by the legendary Havana bar La Bodeguita del Medio, the crowd of ordinarily staid Milanese (many done up in period attire) jockeyed for positions at roulette and blackjack tables and lined up to observe a master Cuban artisan named Eduardo—flown in from Havana for the occasion—rolling cigars. Not far away stood the man responsible for it all: Max Bernardini, a suave 40-year-old with a cigar in one hand and a drink in the other, dressed in a burgundy velvet jacket that could have come straight out of Marcello Mastroianni’s closet.

“It was like a time machine,” Bernardini said after the dust settled. (The party raged into the wee hours.) His era-defying Riviera Party—named in part after the famed Havana casino that closed down 50 years ago—was Milan’s social event of the year, bringing escapism into a season of tightened belts. It also provided the perfect manifesto for Bernardini Luxury Vintage, the antiques emporium Bernardini opened in 2005 on Via Caradosso as a salute to the lost art of genteel machismo. “The idea for the party was simple: Forget the crisis, have a mojito!” he says. “But if you want to buy something, I can satisfy your fantasies, from a thousand euros to a million.”

A visit to the establishment—which feels like a Deco-era smoking club and is staffed with a full-time bartender who knows his way around a Cuba Libre—reveals meticulously sourced goods, albeit at a price: a set of shiny silver Cartier bar accessories ($1,300); an eclectic selection of Dunhill lighters (from $1,430); and a canvas-and-leather Hermès suitcase from the fifties (from $3,600) that promises to make even a coach-class traveler feel like Cary Grant instead of a parcel in transit. If you ever found yourself wondering how to get your hands on, say, an Hermès silver magnifying glass from 1960 or the perfect marrow spoon, look no further. (Many items are now available at LuxuryVintage.net, a consortium of dealers from around the world that sell high-end vintage goods.) Bernardini’s negozio grew out of his father’s long-running antique jewelry business and expanded upon his two decades as a formidable dealer in Patek Philippe, Rolex, Cartier, and Audemars Piguet timepieces.

But the store’s real draw is its artful celebration of a bygone era. Take, for instance, the antique Louis Vuitton, Prada, Goyard, and Gucci steamer trunks in every permutation imaginable. There’s the wardrobe in ultra-rare orange Vuittonite that purportedly once belonged to a Romanov and which Bernardini won out from under the Louis Vuitton Museum at auction ($42,840), and a humble yet handsome Moynat trunk ($4,650) from the twenties. Many of these specimens—hunted down by Bernardini and his team of buyers in Europe and the United States—still have their original tumbler locks and vintage travel stickers.

A sharp eye at the casino party would have noticed a number of trunks and cases. Retooled by the boutique’s expert artigiano, these throwbacks to the heyday of transatlantic travel became roulette tables and humidors. “No matter how weird your idea, we can do it,” Bernardini says. Recent projects include trunks customized for high-end Linn audio components (from $20,000) and Nintendo Wii consoles (from $8,200).

Bernardini himself embodies both the modern and the vintage. He dresses bespoke, flows among Milan’s power elite, and quotes the Latin motto of the early-20th-century New York financier Henry Graves Jr.: Esse quam videri (To be rather than to seem). “In other words,” Bernardini says, “A gentleman is not supposed to show off.” But he is hardly an archaic dandy. He grew up traveling a lot (every January he spends at least two weeks in Buenos Aires and Mar del Plata, Argentina, “pretending to be a gaucho”) and collects guitars (including an old Rickenbacker that belonged to John Lennon). Along with rapid-fire Italian and Spanish, he speaks fluent frat boy. In other words, he knows how to have a good time while bringing gentility back to the work of being a gent.

“I’m not a brand,” Bernardini says. “I’m just a shop. And, really, it’s not a matter of money; that’s a vulgar consequence. When a client comes here, he has to live a dream. And we let him live that dream.”

Bernardini Luxury Vintage is at 2 Via Caradosso, Milan (39-02/481-8697; bernardinimilano.it).

Elements of His Style

A few of Max Bernardini’s favorite things

Hermès knotted yellow-gold cuff links ($2,300)

Gucci 1960s hunter’s thermos ($1,700)

Goyard 1930s case custom-made for polo clubs ($12,570)

Louis Vuitton Gin Tonic case ($17,140)

Rolex 1950s Oyster Perpetual Bubble-Back watch ($14,280)