Pride and PrepBenetton's Glory DaysAlessandro Benetton, heir of the legendary Italian fashion brand, is the subject of a new book, AB: A Playlife Story, which is brimming with iconic images. Isabel WilkinsonMisty White Sidell04.23.13 2:07 PM ETBenetton Group chairman and heir Alessandro Benetton reexplores his family business’s brightest moment with AB: A Playlife Story, a vibrant coffee-table book due out in May. The title is a window into the handsome multitasker's life inside one of Italy's most dynastic apparel families, including Love Story–esque imagery from his ’70s school years at Harvard and behind-the-scenes takes of the Benetton Formula One racing team. There's even a brief thank-you note to the family's private pilot, who would quietly fly Alessandro to London overnight for secret rendezvous. See the highlights. At age 8 in 1972, the first and only time Alessandro has posed for a family campaign. Benetton with his mother, brother Mauro and sister Rossella. Alessandro with brother Mauro at a parish youth club in the mid-’70s. The two brothers are dressed in matching ensembles—a tradition Alessandro grew to detest. "At some point, I rebelled and stopped wearing the same clothes," he explains in the book. The "inseperable" Alessandro and Mauro pose with a sled at the beach. Benetton, age 15 here, was a "flirtatious, restless" teenager, according to the book. mauropagani Benetton windsurfing in Sardinia at age 15. Alessandro takes a photo with his father at his 1991 graduation from Harvard Business School. Benetton modeled briefly in the 1980s. "I lasted a season and had no fun," he says. "It would take hours just to get one shot!" At left, a shot from his comp card. (He kept his hair long until he began working at Goldman Sachs.) Benetton heads to Rome on a Vespa with his friend in the ’80s. Benetton is a big collector of cowboy boots. Here, a pair, from his closet, that he bought used in Arizona. The first Benetton aircraft, the Citation II, photographed in 1982. In one of the book's passages, Alessandro thanks the aircraft's pilot, because "without his help, I could never have flown in the middle of the night in a private airplane to London without anyone knowing. I admit that now the gesture seems somewhat over the top, but at the time it was impressive and when a beautiful woman's involved, as they say, anothing goes." Alessandro recently photographed in a pair of his favorite cargo pants, which were purchased at a military surplus store in the mid-’80s. Alessandro, pictured kite-surfing in Kenya. Alessandro collected many unique items in the course of his extensive travels. At left, a silver belt buckle he bought off a fisherman in Mexico. Benneton marries wife Deborah in the summer of 2008. The pair were originally due to marry in 1999, but "there was too much pressure. Paparazzi followed us everywhere ... The situation got out of hand ... We decided to let it go." Many years later on a family trip to New York, the pair married in the suburb of Tuxedo "with just us and the kids." A recent Benetton family portrait. Alessandro is surrounded by wife Deborah and their three children. Alessandro meets with members of Playlife's design team. The room is scattered with bits of preppy memorabilia. Benetton's "indestructible" L.L. Bean hunting boots, which he purchased over 30 years ago in Freeport, Maine. Benetton's time studying in New England proved to be a strong reference point for all of his design endeavors. A Guanaco blanket that Alessandro acquired on a trip to Argentina. Alessandro leaving his London office with Formula One race-car driver Michael Schumacher's helmet under his arm. Benetton served as the chairman of his family's Formula One racing team.