Things to do before you die: ski Everest, hunt boar in Sardinia, and ride shotgun with Ralph Lauren. Preferably on a clear summer day in his silver stealth bomber of a 2007 Ferrari F430 on Old Montauk Highway, a single-lane ribbon of asphalt on the eastern tip of Long Island that gets significantly more tolerable at high speeds. Gripping the steering wheel with the fly-or-die Formula One hold he learned years ago at the Bob Bondurant racing school (hands at 9 and 3 o'clock), Lauren guns it to 60, then 70 miles per hour, shifting with wheel-mounted aluminum paddles that literally put the gears at his fingertips. Soon we're blurring along at 95, our backs centrifugally glued to the leather seats, and with the flick of a finger into high gear—rrrrrriiiiir—we're gone. With his faded military-green T-shirt, canvas cargo shorts, regally unkempt white hair, deep-fried tan, and aviator sunglasses, Lauren—a week into his monthlong summer vacation—looks like a helicopter pilot who crashed on the beach of a remote tropical island 30 years ago and has been living there ever since. "How do you like the sound?" he asks over the growl of the 490-horsepower engine, flashing a boyish grin. "Now you know why I don't listen to the radio in these cars."

Lauren rules the road the way he rules the American fashion industry: with steady vision, virtuosic (and absolute) control, prudent decision-making, headlong momentum, and an urge to throttle the competition. At 67, he's looking straight ahead rather than for an exit (or even a rest stop), expanding his $11 billion business into Europe, Asia, and even Russia. All the while, he's exporting his worldview—in which pastel is primary, good taste is dogmatic, and upward mobility is a force stronger than gravity—to the farthest corners of the earth. With Polo Ralph Lauren turning 40 this year (life everlasting for such a business) and Rizzoli publishing a lavish 500-page coffee-table retrospective, Lauren has become an ambassador of Americana in all its finest varietals, from Western to WASP. "I always resented the fact that people were so impressed with Europe," he tells me when we get back to his Montauk homestead, a low-slung shingled cottage that once belonged to John Lennon and Yoko Ono. His voice is soft, almost a whisper, but his message vehement. "I think I've built something beyond the fashion business. A way of living. It's about taste, quality of life, another dimension of your persona."

Lauren's car collection is another dimension of his own persona, and a watermark of his prosperity. An impossible lineup of 50-plus dream machines that have all been restored to glory, the convoy is a portal to the past, when guys drove their race cars home from the track at the end of the day and manufacturers—much like Polo Ralph Lauren—were the manifestations of their designers: Jean Bugatti, Enzo Ferrari, Ferdinand Porsche. "I love the technology of these cars, the smoothness, the speed, the precision," says Lauren as he walks among them in his garage, tracing their shiny metal as he would the hem of a blazer. "It's one of those things: Guys go to play golf, I drive my cars." His gateway drug was a white '61 Morgan convertible with red leather seats, which he bought in 1963—back when he was a traveling salesman for the Boston-based tie company A. Rivetz & Co.—and was later forced to sell when he couldn't afford a garage in Manhattan. Hooked on the novelty of wooden steering wheels and the like, Lauren eyed more purchases, some that he mulled over for 20 years before finding the exact model he was after. There's his silver 1955 550 Porsche Spyder (the same as James Dean's deathmobile), black 1979 Porsche Turbo ("My Darth Vader car—I darkened all the wheels"), 1957 Jaguar XKSS ("There was a fire in the factory, so they only made 16 of these"), 1929 Blower Bentley, one of just three in the world ("And they said I'd never get it out of England!"), 1965 Aston Martin DB5 Volante (James Bond's accomplice in Goldfinger), and a 1955 Mercedes-Benz 300SL Gullwing Coupe (a car that looks like it might take flight). "They all have personalities and they all have a moment in time of being the ultimate," he says wistfully.