Esquire

YOU SHOULD HANG ON TO THAT

BRUNELLO CUCINELLI WAS HAVING A DRINK AT MANHATTAN’S Odeon bar in 1989 when he spotted twenty-eight-year-old John F. Kennedy Jr. among the patrons. They didn’t speak, but Cucinelli, then thirty-six, observed the young Kennedy. He noticed his shoes—they had been resoled. His sweater had patches on the elbows. “Clearly, he could have easily bought a new sweater,” Cucinelli says now. “I thought that was very chic. So I went back to Italy and put suede patches on the elbow of my new sweaters. It didn’t make sense to some, but the customers loved it.”

It’s a charming anecdote that reveals why Cucinelli remains a singular presence in the fashion world today. There’s the ability to anticipate what his wellheeled clientele will want to buy. There’s the appreciation for the “sense of ease” (his words) that separates the sincerely stylish from the try-hards. And there’s the belief in the value of clothes—a value beyond fashion—that stems from a different world altogether.

Cucinelli grew up in a farmhouse without electricity in

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