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Ralph Lauren’s lifestyle epitomizes his brand.

A stable of more than 50 classic cars with their own full-time curator; a mouth-watering collection of antique watches; a Hawker Siddeley jet to travel between his five residences in the Caribbean, Colorado and New York: Even by Billionaires’ Club standards, card-carrying member Ralph Lauren has it pretty good. Not that the boy from The Bronx is one to forget for a moment how far Round Hill, Jamaica, is from his old neighborhood, even though his ride from tie salesman to head of a $4.3 billion empire has been as meteoric as a drive in one of his nine red Ferraris.

“When you’re not born with money and you have to go out and work to buy a shirt or a pair of pants, you take nothing for granted,” the 67-year-old designer writes in the hefty new tome celebrating his 40 years in business, published by Rizzoli. “I think I’m still that boy standing in front of the window filled with the same excitement, yearning for something just out of reach.”

Of course, even though the enthusiasm of his young self might live on, almost nothing is really out of reach anymore.

With all those toys, it’s no surprise Lauren likes to stay home rather than diving into the social swirl of the fashion world. “I don’t live in that world of ‘Daaahling!’ I can’t stand it,” he told Time magazine in 2001.

Instead, he spends his free time with his wife, Ricky, and their three children, Andrew, David and Dylan, either at his Fifth Avenue duplex; his beach house in Montauk, N.Y. (which once belonged to Yoko Ono and John Lennon); a 283-acre Bedford, N.Y., estate; the sprawling Double RL ranch near Telluride, Colo., or in Round Hill, Jamaica, where he has two residences.

“I go home at night. I’m a normal person,” Lauren told W in 2000.

Indeed, his son David recently told The London Sunday Times, that a Saturday night in Bedford when he was growing up might include Ping-Pong and a milk shake-making contest judged by their dad. In fact, when he won the Lifetime Achievement Award from the Council of Fashion Designers of America in 1991, the designer celebrated with hot-fudge sundaes and his family rather than a Champagne-soaked bash.

This story first appeared in the October 15, 2007 issue of WWD.  Subscribe Today.

It might be that Lauren is simply reveling in the realization of his greatest dreams. The 14,000-acre Double RL ranch — a working farm with 1,500 head of cattle complete with an 1890s-era guest cottage called The Little Brown Cabin — could be the incarnation of the young Lauren’s passion for Westerns. “I wanted to be the cowboy who rode the horse,” he once told Vogue. Now he is, taking daily rides with Ricky when they are there in the summer. (An avid exerciser, Lauren also runs daily and plays tennis and basketball.) “Before I had a home in the West, I lived there in my heart,” he says in the Rizzoli book. “Eventually…the dream became real — I was the cowboy.”

As for his Jamaican residences, as he tells it, the Laurens went for a vacation almost 30 years ago and were so enchanted, they ended up moving in — buying first High Rock, an Anglo-Indian style house built in the Fifties in the posh resort overlooking Montego Bay and surrounded by the rain forest. In 1996, he added Cottage 26 for his children. Fittingly, the oceanside house was built by the late William Paley, founder of CBS and one of Lauren’s role models. “In Jamaica, I have no obligations,” Lauren told Architectural Digest recently, though he obviously hasn’t acted like it: For his support of local charities and his promotion of the island itself, the grateful government bestowed an Order of Distinction with the rank of commander on the designer and honored him with a commemorative stamp.

But it’s while he is in New York, Bedford and Montauk that Lauren gets to play with his museum-worthy car collection. “Cars are like a work of art,” says Lauren in his book.

The car collection was exhibited at the Museum of Fine Arts in Boston in 1995. (There are motorcycles, too, like a Ducati Monster and 996 S-series, but those are off limits ever since one crushed Lauren’s ankle.) But from his first love — a white 1961 Morgan convertible with a red leather interior from which he sold his innovative wide ties — it’s been cars that enthrall Lauren. It’s no unrequited affair, as he drives them all. The collection includes a 1938 Alfa Romeo 8C 2900 Mille Miglia (prize winner at the 2005 Pebble Beach Concours d’Elegance), a Bugatti Veyron, a 1929 Blower Bentley (one of only three), a 1955 550 Porsche Spyder, same as James Dean’s, and a 1955 Mercedes-Benz 300SL Gull Wing. Like everything in Lauren’s life, they’ve found their way into his various Polo collections: from a chair inspired by his three 1996 McLaren F1s to the all-black luggage and clothing line born from the black interior of a 1979 Porsche.

For now, Lauren has stopped adding to his toy pile. “I feel we have too much,” he said recently to the London Sunday Times. “I don’t want any more.”

And why should he? As he said to W in 2000, “I’ve achieved dreams in a real world.”

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