Ever wonder if your priceless exotic car really looks great?
Ralph Lauren knows which ones do.

He runs his own billion-dollar company, grew up in a middle-class neighborhood where the high school was an archetypal blue-collar 50’s “Grease”-era institution, and he started his business relying on his belief in his ability to turn normal schmucks into people who looked and felt like the world’s elite.

Every day in the late 1950s young Ralph Lifshitz did a double-take during his pedestrian commute in New York City to his job selling ties at Brooks Brothers as he passed import car dealer showrooms. His car nut side developed at that time, when he hoofed his way through Manhattan passing Jaguar and Morgan shops at a time when not many places in the U.S. had those rare imports on display. He thought the cars were beautiful.

Ralph Lauren - Looking Good

He was so smitten by post-war sports cars he actually purchased a Morgan while he was a working stiff in car-unfriendly New York City, yet had to sell it because he had no place he could afford to park it. The loss of the off-white Morgan drop-top was but one tough break for the budding clothes marketing genius until the late 1970s, when he finally started buying the cars he loved.

Lauren, who changed his name because he was teased about it in school, bought the cars he liked to actually drive them as commuter cars. Time magazine once quoted him about his name change: “My given name has the word shit in it,” he told Time. “When I was a kid, the other kids would make a lot of fun of me. It was a tough name. That's why I decided to change it.”

After the Morgan he deserted because of space issues in New York, he bought a Mercedes 280SE drop-top to use as a commuter in the city, never mind the impracticality of a soft-top car in New York City. As if that wasn’t impractical, he consecutively bought two Porsche 930s as get-to-work machines, not considering the rarity of these turbocharged supercars would work to transform them into the nearly unobtainable classics they are today. Both Porsches came black-on-black, the way the factory intended these devilishly fast faux-racers to be, but today the sinister color scheme elevates them to a level of fierceness of purpose that other Porsche colors can’t reach. Black 930s just look meaner than any other color. In the late 1980s black was the new cool. Ralph Lauren knew this long before. "I feel that cars in black are very weighty, they have a beauty and a shape and a sexy-ness to them," Lauren explains.

Ralph Lauren - Looking Good

Without aiming to become a deliberate car collector, the daily drivers in which Lauren shuffled himself around Manhattan were the exotics of the future, the inspiration for today’s Murcielagos, Diablos and Enzos. So like the hundreds of guys who owned Ferraris as just plain driving cars in the mid-1980s, Lauren liked his own cars because they were fun to drive and looked cool. That’s it. Lauren bought his Alfa Romeo 8C 2900, Mercedes SSK, Porsche 550 and Ferrari front-engine racers because he thought they were beautiful. He purchased street cars such as a 1955 Mercedes SL gullwing, a 1988 Porsche 959, and three McLaren F1 supercars powered by BMW’s race-derived 6.0-liter V-12s. He was a collector long before it became trendy for rich guys to buy their way into the exotic car market as a social hobby and an investment.

Lauren explains: "I never cared about being a collector. It was not my goal. Cars were always something that I loved. It was also about the famous owners and the men who built the cars. I was fascinated reading about what Enzo Ferrari was like, what Ettore Bugatti was about, and getting a sense of why they built these cars and what their lives were like. It’s the lifestyle, the romance, all those things together."

Ralph Lauren - Looking Good

Lauren’s people support the image that he collected some really nifty machines because of his elevated taste, using words like “pedigree” and “classic” and “timeless” to describe everything the man owns. “Cars have always been a source of design inspiration for me. The cars I collect have a message of timeless beauty,” reads his publicity material. However, he also has un-restored Jeeps and pickups that he thinks are cool because they’re in original condition, the kind that make you want to put one boot up on the dashboard while you’re driving it, envisioning 200 more miles of ranch road to cover before you get to feed to the cattle.

In addition to homes in New York and Jamaica, 68-year-old Lauren has a ranch in Colorado, and he gets around not just in his old pickups or Wagoneer, but in a ’57 Cadillac Eldorado Biarritz, in turquoise that’s been faded by the sun and weather, and is the equivalent of wearing a 1975 polyester leisure suit to the Oak Room today. If you can pull it off, that’s as cool as David Arquette wearing homeless-guy plaids on The Tonight Show. “I got hooked on European cars, though I love army Jeeps and pickup trucks and Woodies. They represent something that is beyond just the engine. The pickups represent a life, the farms, and the sort of utility I love. Jeeps, the same utility and sensibility. They were so stripped down, but they were so cool," says the master of looking cool. If James Dean were alive today he’d copy Lauren, who, of course, has a 1955 Porsche 550 RS Sypder--an edition of the James Dean death car. "I never liked big cars,” he offers. “I never liked the old American cars with the beautiful shapes. They are artistically beautiful, but they have no appeal to me at all.”

Ralph Lauren - Looking Good

Each week Lauren strolls through his collection of about 70 significant machines, which are kept in running condition at all times, ready for him to drive them to events, and on private drives. Most of the cars are in his secluded assemblage of three garages on Long Island. However, he’s building a new single garage to house all of the cars, in an artificially created mild climate friendlier than the ambient climate the East Coast provides, to help preserve them. Perhaps a quarter of the collection is not restored, and there are no plans to turn them into showpieces. These cars are at their coolest exactly as they sit. Screw the trophies.

The garage that’s under construction now has a library, which is where all of the memorabilia and trophies that the more famous cars have won will be displayed, not out in the main hall where the cars are. Most of the attention to the new structure was invested in climate control, and the space is kept deliberately sparse to focus visitors’ attention on the cars themselves. Visitors will be a rare occurrence, too, because there are no plans yet to open the structure to the public.

Friends of Lauren’s who will see the collection in its new habitat include Porsche competition phenom Brian Redman and America’s first world champion racer and notable car restorer Phil Hill, who know the cars intimately. Lauren needs such experts to begin to help advise him about additional cars to add to the unique and special collection, because one-of-a-kind supercars are becoming more difficult to find. Additions to the collection would be small in volume, says chief caretaker Mark Reinwald, “He specializes in quality, not quantity, and it’s getting harder to find the next spectacular car.”

Ralph Lauren - Looking Good

Lauren is a very private celebrity, and when anonymous purchases are made at the growing number of classic auctions in the country, his name emerges as a possible buyer. We may never know how many cars, and which super-rare machines he will ever own, although according to Reinwald, he favors driving the modern exotics and some of the older classics when he has a rare free weekend. Reinwald drives each car every six weeks, which he says is the best way to keep them in running condition. Each of the 70 machines is connected to a battery tender the rest of the time so the cars can be used anytime. During good Northeast weather, Lauren will grab one of the supercars, one of three ’96 McLaren F1s, the ’88 Porsche 959, or the Ferrari F40, and rack up some miles across the backroads. “Once you drive the McLaren, it's over. It's like no car I've ever driven. The McLaren is like Star Wars--a hovercraft. I feel like I'm not touching the ground. It's an experience I've never had before."

Ralph Lauren - Looking Good

"Strangely enough, I really don't like to drive the cars when people are around,” Lauren admits. “As it turns out, I don't really want to be seen in the cars. There's a part of me that likes the privacy, so the more garish the car, the less I want to drive it. On weekends, depending on the weather, I love the Jaguars, the XK120 or XK140. I love the Mercedes Gullwing and roadster and the Porsches.” In addition to the remarkable 959, he has a Carrera GT, too.

The non-race Ferraris, Porsches, and Jaguars see a lot of pedal time from Lauren. But he doesn’t ignore driving the race cars. However, he does drive them when his mood dictates and when the weather is cool enough that enjoyment in cramped, overheated cockpits is at its highest possibility.

For a guy who’s sweated out paying his Wall Street dues most of his life, you can forgive his desire to tear around in the air-conditioned comfort of a new Ferrari 599 instead of a 1958 Ferrari 250 Testa Rossa. Well, we can.