The engines start up, and the conversation turns briefly to soccer, until Della Valle notices his publicist’s bag on the floor in front of him. “It’s beautiful,” he says, proudly caressing the off-white rounded calfskin D-Bag from Tod’s fall 2008 collection. As the head of a publicly traded, billion-dollar luxury empire—which also includes the Hogan, Roger Vivier and Fay brands and employs nearly 3,000 people— Della Valle is entitled to a bit of pride, particularly in view of his humble beginnings.
Della Valle was born and raised in Sant’Elpidio a Mare, a small town in the Marche region, a hub of shoemaking located a third of the way down the east coast of Italy’s boot-shaped peninsula. His grandfather was a cobbler, and his father, Dorino Della Valle, built a business making shoes for Azzedine Alaïa, Calvin Klein and Neiman Marcus, among others. Not wanting his children to follow him into the trade, Dorino sent his eldest son to a university in Bologna to study law. It didn’t work.
“I was a bit undisciplined,” Della Valle confesses. “Where there was a bit of fantasy, I did well. But when it came to studying math.... Well, anyway, I always wanted to have this profession. I was always hanging around the factory as a boy. I just liked being there. Even today when I go into the materials warehouse, which is the size of a soccer pitch, I’m like a kid in a candy shop.”
Della Valle’s early “mania” for shoes, as he describes it, led him to entrepreneurial ends. One afternoon he skipped school and took the train to visit the biggest supplier of molded plastic shoe forms in Europe, which happened to be in Le Marche. Despite being only 15 and arriving without an appointment, he asked the supplier to make a prototype of a shoe he’d designed. The supplier, who knew Dorino, was amused by the precocious teenager and conceded.
“He is single-minded and very determined,” says Della Valle’s brother Andrea, 43, vice chairman and managing director of Tod’s SpA and chairman of Fiorentina. “When Diego has a clear and precise idea of what he wants, he sees it through to the end.”
Diego may have closed his first deal with the plastic shoe-form supplier, but Dorino took more convincing. After his son spent many years sampling university life, mostly outside the classroom—at bars, playing billiards, chasing girls—the casinista, or rascal, as Diego describes his younger self, dropped out to join the family trade.
“I could have killed him,” recalls Della Valle senior a week later during his daily rounds at the firm’s shoe factory in Cassette d’Ete. Known affectionately as Signor Doro (which in Italian means “Mr. Gold”), Dorino shares his son’s passion. At 83, he often rides a bicycle around the sprawling plant to check on production, offering advice along the way. Like his son, he has an inimitable, though very different, sense of style, punctuated by a snowy mustache. Today, in a gray cashmere tracksuit, self-designed white leather shoes, and sunglasses and carrying a silver-handled black cane, he looks like a pimped-out Clark Gable. “The factory was supposed to stop with me,” he says. “But it was impossible to stop Diego.”