Who's the Man Behind the Tod's?

As CEO of a luxury Italian brand built from humble cobbler beginnings, Diego Della Valle is taking his company more global and more glam—while staying ever closer to home.

Diego Della Valle—the man behind the Tod's, Hogan, and Fay brands, the man who bought John F. Kennedy's 52-foot cruiser Marlin at auction, the man who keeps a photo on his office corkboard of himself standing next to the King of Spain, apparently in the act of sniffing the monarch's shoe—is in one of the regular style meetings held in his Milan offices.

"What's all that stuff on the floor?" he asks, looking disdainfully at some logo prototypes. "Is that ours?"

"Yes," a Hogan designer says nervously. "It's a pattern of 'H's."

"So where's the 'H'?" Della Valle asks. "If it's supposed to be an 'H,' I want to see it!"

"Okay," answers the unfortunate woman, who then attempts to fast-forward to a more promising topic. "We can look at the 'H's. Now I wanted to show you—"

"Don't treat me like a kid," Della Valle interrupts. And then he flashes a smile at his cowed collaborator. He wants her to know he bears her no grudges.

Il signore Della Valle, as everyone at Tod's refers to him, is the sort of success story that graduate business-school students write about in dissertations. Della Valle himself, however, never received an MBA. He never even finished his law degree at Bologna University. "I did four years," he tells me, "and enjoyed myself enormously, but I didn't have much sense of academic duty." That's why he's plain old signore, rather than dottore or avvocato or geometra or ragioniere or any of those other titles that Italians love to toss about.

Della Valle comes from Le Marche, the central eastern region of Italy known for its rolling hills, its Verdicchio wine—and its shoes. Until Tod's went exponential in the eighties, the Della Valle family business differed little from the hundreds of other small footwear manufacturers in the valley between Fermo and Macerata, providing employment for 35,000 people. Grandfather Filippo was a humble cobbler: His old wooden workbench and tools are displayed shrinelike just outside the prototypes section of the Tod's plant here. It was Diego's father, Dorino, who expanded the business, setting up a small factory that made women's dress shoes for, among others, Azzedine Alaïa.

Dorino—who, at the age of 81, rides his bicycle around the gleaming white corridors of his son's new headquarters and is the only person allowed to smoke in the building—wanted his eldest son to be a lawyer. Diego, however, had other plans. After bailing out of academia at 23, he flew to New York and organized a presentation of his father's shoes at the Hilton. Orders followed from several department stores that promptly relabeled the shoes as their own. But Della Valle wanted more. He wanted his own brand.

To do so, though, he needed a name and a big idea. The name J. P. Tod's (later shortened to Tod's) came from the Boston phone directory. The big idea came in the form of driving moccasins—worn by the likes of the late Fiat head Gianni Agnelli, who made the shoes part of the effortlessly relaxed Portofino playboy look he cultivated. For Della Valle, as for many young Italian entrepreneurs of his generation, Agnelli was a role model and an inspiration: "He was a symbol of luxury for us—and he was always surrounded by beautiful women."

Tod's was one of the first Italian brands, says Della Valle, to break down the division between work clothes and play clothes: He based its style on the fact that, according to him, all over the world lifestyles were getting simpler. "We just married this intuition with Italian taste and Italian quality," he explains. The results have been spectacular. At a time when many brands are struggling, Tod's has continued to post buoyant quarterly results. Its annual revenue of over $500 million in 2004 puts it up there among some of the biggest Italian fashion houses. Interim 2005 figures are even more upbeat, showing a 19.4 percent increase.

Steadfastly refusing to farm out production to cheaper labor markets such as China, Della Valle keeps ahead of the game by combining a flair for second-guessing consumer trends with an extreme caution in shifting the image of the brand and its products. It took Tod's five years to come up with a logo for canvas handbags. When the insignia was finally presented during Milan Fashion Week in September 2005, it was based not on the expected "T" monogram that had Tod's designers tearing their hair out for years as Della Valle rejected logo after logo but on a series of collages by Michael Roberts, fashion director of The New Yorker. Roberts's smart, ironic designs take the label's most famous product—the driving moccasin, with its rubber pebble sole—and use it in witty prints where the shoe becomes a New York taxicab, a box at La Scala, or a motorboat towing a water-skier. "It's not boring," Della Valle points out. "It changes every season. We believe this could be the next step in logos."

Another Tod's novelty, the brand's first clothing line, is equally low-key. "It's a small selection of cult products," Della Valle explains, "that I see more as wearable accessories than as clothes." Consisting of ten pared-down pieces—including a man's leather motorcycle jacket and a woman's suede skirt—the spring/summer 2006 collection is the work of up-and-coming Chinese American designer Derek Lam. It will be on sale in only 15 Tod's boutiques around the globe, among them the new Tokyo store by local architect Toyo Ito. An audacious concrete-and-glass structure on the chic fashion strip of Omotesando Dori, it resembles a tall box—that most ubiquitous of urban forms—which has been taken back to nature by a pattern of concrete branches traced across its façade. Up until now, Tod's stores have tended to be rather unshowy. But just as the brand is infusing more and more glamour into its shoes and accessories, so is it allowing more attitude in boutique design, logo development, and advertising. Its latest campaign, launching this spring, is edgier and shot in Los Angeles by Swedish fashion photographer Mikael Jansson.

Casette d'Ete, the village where Della Valle was born in 1953, has all but disappeared behind a sprawl of shoemaking factories and workshops. In fact, the only real evidence of its existence, for the passing visitor, is the sign telling you that you're entering and leaving the place.But this is an outsider's view—Della Valle considers home to be a village of the heart, as do many other Italians. He sums up the qualities of his native region as "good sense, a love of the quiet life, a lack of social barriers. It's a place where everything is based on solidarity, on community spirit." Social cohesion really seems to matter to Della Valle. It crops up again and again in our two encounters: the first in the meeting room of Tod's Milan HQ on the fashion artery of Corso Venezia, the second in the comfortable home that he and his third wife, Barbara Pistilli, have carved out of a medieval convent a few miles from the village.

"In a place like Casette d'Ete," Della Valle elucidates, sinking back into a well-padded sofa in his living room, "social rank is determined not by wealth but by whether you are perbene—Italian for a decent, upstanding citizen." It is telling that he uses the word without a trace of irony, when for many younger Italians the term has become infected by associations of stuffy bourgeois conformism. A hungry young Prada hound, for example, would never describe himself as perbene. Yet the word comes naturally to Della Valle; you feel that he really does believe in a benevolent meritocracy of polite, well-dressed citizens who appreciate the better things in life. (Much like the coterie of provincial-lads-made-good with whom Della Valle hangs out, including Luca Cordero di Montezemolo—a friend from his university days who is now chairman of Fiat and president of its racing and luxury arm, Ferrari—as well as Domenico De Sole, former CEO of Gucci.)

Della Valle is proud of the new Tod's factory and office complex, which lies just outside Casette d'Ete, within view of his hilltop demesne. Behind a long, low white marble exterior, clean white corridors are jazzed up with huge Day-Glo images of iconic Tod's products, while a futuristic undulating chrome staircase designed by Israeli architect Ron Arad leads up to the prototype lab on the first floor. Daylight streams in through floor-to-ceiling windows, some of which face the in-house nursery school garden. The nursery is not what Italians endearingly refer to as a "baby-parking" facility—it's a full-fledged kindergarten with trained teachers. When I enter, a father is picking up his three-year-old son, who gives Daddy a drawing he's been doing, apparently of fighter jets. "That's nice," says his father. "What is it?" "Shoes," his son replies.

Della Valle's younger son, Filippo, 8, was a pupil here until a few years ago and he now attends the local public elementary school. His father sees nothing strange in his mixing with the children of the workers who cut, glue, stitch, and assemble the 45 to 70 pieces that go into each pair of Tod's: "We all have different roles," Della Valle says without a trace of preachiness, "but that doesn't make us better or worse people." His 30-year-old son, Emanuele, has carved out his own role within the Tod's Group as director of Hogan and head of Forma Pura and Lightbulb Productions, creative agencies that handle everything from event organization to film production.

Still, it must be quite something for Filippo's friends when they come over to play. Not everyone's daddy has an indoor swimming pool underneath his country mansion, or a real soccer pitch on the grounds, complete with goals and corner flags. But then not everyone's daddy owns a soccer team either. Della Valle bought Fiorentina in August 2002, a move that surprised even his closest collaborators, most of whom were at the beach on holiday at the time. The team had gone bankrupt along with its previous owner, Italian movie magnate Vittorio Cecchi Gori, and was demoted to a minor league. But Della Valle's support enabled Fiorentina to obtain the players it needed to climb back to the top league, Serie A. In 2004 he passed on the presidency of the club to his younger brother Andrea, who is also vice president of the Tod's Group.

When I go to see Fiorentina in action, it's third in the league behind top-runner Juventus—the Turin team formerly owned by avvocato Gianni Agnelli—and the opponent on this day is Milan, which is in the hands of Italian prime minister and überbusinessman Silvio Berlusconi. Della Valle and his brother sit next to each other; beside them is Luigi Abete, president of Banca Nazionale del Lavoro and Cinecittà, the celebrated studios where epics such as Ben Hur, Cleopatra, and most recently HBO's Rome were filmed (Della Valle has a stake in both companies). Also with us is former Italian prime minister Lamberto Dini. Della Valle's son Filippo sits on his knee. When I ask him at halftime how his son is enjoying the match, he laughs and says, "He can hardly bear to watch." Della Valle is so obviously involved in the end-to-end that he is probably talking about himself, too, but for the finale Fiorentina powers through to win the game 3–1 and joins Milan in second place.

It's time for me to leave, but fog is creating trouble for the Ancona-to-Rome flights. No problema. Della Valle suggests I fly with him via Milan—first in the Della Valle helicopter, as it speeds over the patchwork fields and vineyards of Le Marche, then in the Della Valle jet, with its Tod's tan livery, as it ascends above the clouds from Ancona. This is a man who clearly enjoys prosperity and its fringe benefits. The only self-chastising notes are two books tucked behind the swing-out TV: an inspirational volume by the Dalai Lama and a handbook of irregular English verbs. But neither looks as though it's been opened. I ask him if "contemporary luxury"—the Tod's mantra, repeated in interview after press release—reflects his own lifestyle as well as that of the "cultured globetrotter," whom he identifies as his core customer. Della Valle thinks for a second, then decides that "the word luxury is becoming a bit obsolete. I prefer to talk about quality because quality is not just in things that cost a lot, it's something you get in a perfectly cooked plate of spaghetti, no?"