Clinton was following a well-trod path. Since 1975, when Della Valle began running his family's 75-year-old shoe business, he has opened 50 J.P. Tod's stores worldwide (the newest in May on Manhattan's Madison Avenue). His signature style, the driving shoe—an updated version of a shoe Italian racers wore in the 1950s—has steered J.P. Tod's (Della Valle purposely chose an "English, easy-to-remember" name) into worldwide fashion consciousness and $500 million in annual sales. Characterized by 133 rubber bumps that cover the shoe's back and sole, the luxuriant loafers (priced from $325 to $1,700) have become a staple for screen sirens—Kim Basinger, Catherine Deneuve—and such Hollywood manly men as Harrison Ford and Denzel Washington.
"There truly isn't another shoe in the closet that I wear more," says Rene Russo, who with costar Pierce Brosnan sports J.P. Tod's in the upcoming remake of The Thomas Crown Affair. Even the Pope, it is whispered, wears Tod's. "But it is not a good promotion for us," jokes an employee, "because he wears long skirts."
Thrilled that the famous like his styles, Della Valle is quick to add that most of his customers "aren't celebrities—they are just people with good taste." But no one is more obsessed with his footwear than their maker. Though Della Valle attended law school in Bologna in 1970, he never planned on practicing. His soul belonged to shoes. Diego's grandfather Filippo Della Valle began cobbling prior to World War I, after which his son, Diego's father, Dorino, took over the business. Now 75, Dorino shows up to work every day, enjoying the title "super-supervisor." "We all live close, so it's easy to go to work," says Diego's brother Andrea, 33, who runs the firm's daily operations. (Sister Gisella, 40, is a design consultant.) In addition to a sleek new $46 million headquarters—with gym and child-care center for the 300 employees—there are five factories, all located near the family's hometown of Casette d'Ete, near Italy's Adriatic coast. A fourth generation is also involved: Della Valle's oldest son, Emanuele, 24, from his first marriage (which ended in 1979, after five years) works in the Manhattan office.
Now twice divorced, Della Valle lives with architect Barbara Pistilli, 40, and their 21-month-old son, Filippo, in a 22-room villa in Le Marche—complete with helipad—that they share with six Labradors and a beloved mutt. "In the summer when we have chairs outside I have to remember to bring my shoes in," or, he adds ruefully, "they destroy them."
His human customers accord his handmade products a bit more respect. The First Lady chose one pair of loafers—in beige fabric and leather. "She wanted to try them on," says the spokeswoman, "but unfortunately we did not have them in her size." Clinton had better luck with Tod's D bags, which were introduced in 1997 and later named in honor of Princess Diana. Though there is a three-to six-month waiting list for them in the U.S., Clinton took home two—a medium-size ($1,300) and a large-size ($1,450)—both in beige.
"She left with a big smile," says the spokeswoman, who promised to dispatch Clinton's size 39 (which is equivalent to an American size 8-9) shoes to the White House from a store in the States. Just the thing if she runs for the U.S. Senate in New York. The First Lady, better than most, knows that political survival often comes down to thick skin and soft soles.
Cathy Nolan in Casette d'Ete and Milan and Ulrica Wihlborg in Los Angeles