“You’re too sexy for me.” Thus did Rod Stewart crush Alessandro Ristori’s dreams of a duet. They met backstage at Annabel’s nightclub, in London, where the Italian cabaret singer was a regular entertainer. Despite their three-decade age difference, it’s easy to see a kinship between the two singers. Ristori, whose repertoire relies on torch songs and lounge classics, dresses like Stewart in his heyday: bell-bottoms, open shirts, and double-breasted blazers, heavy on the polyester.

Stewart, though, is just one source of inspiration for Ristori. Think of the 41-year-old as an endearing mash-up of Julio Iglesias and late-era Elvis with a winking whiff of Austin Powers. His too-much-is-never-enough retro style has turned Ristori into a de facto mascot for the fashion world. His nickname is “Gucci Guy,” thanks to all the free clothes he’s received from Gucci C.E.O. Marco Bizzarri. Ristori is also the entertainer of choice for playboy Flavio Briatore, whose Twiga club and restaurant, in Forte dei Marmi, is one of his residencies. Accompanied by the Portofinos, his backing band, Ristori was also the wedding singer at the reception of Charlotte Casiraghi last summer. Call him kitsch, perhaps, but never inauthentic. “It’s not a project—that’s the secret,” he says, in Italian-accented English. “You’re believable only if you’re the same person onstage and off—and I am.”

Born in Faenza, in Emilia-Romagna, Ristori has been aiming for fame ever since founding his first band, a rockabilly tribute act, in his teens. A music producer he’d met encouraged Alessandro to enter an American Idol–like show in Russia. Ristori, long a fan of early-1960s easy listening, embraced his passion for singing lounge songs, placing third. It was a lucky break, as he explains, since Russians were primed to respond to his throwback dolce vita songbook. During the 1980s nadir of Communism, some Western television broadcasts were permitted, many from Italy, including the Sanremo Music Festival and movies starring singer-actor Adriano Celentano. “They remember it, like a good memory,” he explains.

“It’s not a project—that’s the secret,” he says, in Italian-accented English. “You’re believable only if you’re the same person onstage and off—and I am.”

That show didn’t lead to immediate stardom, though, and he began singing on cruise ships. It was only after one sailing contract was canceled at the last minute, five years ago, that Ristori booked a gig at Le Bar Américain in Monte Carlo. A growing cult following brought him to the attention of the wider 1 percent, including Briatore, who soon hired his fellow countryman to play his birthday party. Briatore has become Ristori’s biggest booster, getting him jobs at clubs such as Twiga and his Billionaire Porto Cervo, in Sardinia.

This year, for obvious reasons, has been different. Ristori spent much of it in lockdown with his wife, recording two EPs, titled Aperitivo Vol. 1 and Vol. 2. Each is filled with covers he sings in his shows, like “Un’estate Fa,” the Franco Califano classic with which he often opens the evening. The first is out now, and the second follows this fall; a full album of original songs—the entrée after the aperitivo—arrives next year.

As summer continues, Alessandro is playing concerts again, back on the same louche Mediterranean circuit, but he’s hoping to make the leap across the Atlantic soon. “Las Vegas is my dream,” he says, his voice speeding up with enthusiasm, “I hope to arrive there very soon—not like a star, but like a good artist, so everyone can come to my show.” Rod Stewart, are you listening?

Mark Ellwood is a journalist and broadcaster living in New York City