IT'S A GRAY OCTOBER DAY in Le Marche, the region of central Italy where about 90% of the country's shoes are made in nonescript industrial factories that dot the velvety, verdant landscape. The iffy weather and impending rain don't bother Diego Della Valle, 52. As the president and CEO of Tod's S.p.A., he's used to climbing into his silver twin-engine Dolphin helicopter after lunch at Villa Brancadoro—his 17th century hilltop residence in the town of Casette d'Ete, where he lives with his wife Barbara Pistilli and their son Filippo, 8—and zipping over to Ancona, where he usually boards his Falcon 2000 and jets off to Paris or New York City or maybe even Tokyo.
But bad weather makes Diego's younger brother Andrea Della Valle, 40, vice president of Tod's S.p.A., very nervous. Even after the elicottero has floated up several hundred feet and the 100-acre estate below—tennis court, boccie court, soccer field, man-made lake, lemon and olive groves and church included—has receded into the distance and there's not much left to view except gray fluff, Andrea keeps a watchful eye out the window. It's not surprising, given the family dynamic. Andrea plays the goalie to Diego's striker, the introverted, behind-the-scenes power broker to Diego's extroverted, genial public persona. (A recent cover story in Capital, an Italian business magazine, was titled "When the Secret Is Your Brother.") While Diego will make headlines sparring in the press with Italian Prime Minister Silvio Berlusconi or hobnobbing with high-profile friends like Ferrari CEO Luca Cordero di Montezemolo, Andrea is content to talk soccer scores and sneaker styles with production managers back at the factory—many of whom have known him since he was 5.
Together the two brothers have built Tod's S.p.A. into a global luxury group with $450 million in annual sales that includes Tod's, the high-end leather-goods company; Roger Vivier, the legendary Parisian shoe brand; Hogan, a sporty sneaker and handbag brand; and Fay, a casual weekend clothing line. Four years ago, the Della Valles bought the Fiorentina soccer team, a move that has made them famous in a whole new arena—especially among young boys. It helps that the team, which was at the bottom of the league when they bought it, has since risen in the standings. All of this, of course, started with shoes. And shoes still account for 70% of their business.
Shoemaking in Italy—like fashion—is a family business, a craft handed down through generations. And nowhere is that more evident than at Casa Della Valle. (Diego's eldest son Emanuele also works for the company, as do two cousins.) But you won't see Diego hand-stitching the driving shoes himself. Many of the families in his factory have been with the company for several generations, at least since Dorino, Diego and Andrea's father, set up shop in Casette d'Ete in the 1940s and later began manufacturing shoes for private-label department-store brands in addition to designers like Calvin Klein and Azzedine Alaïa. Dorino's father Filippo was a local cobbler whose workbench still sits in a corner on the second floor of the factory as a kind of reminder of the family's more humble beginnings.