When Ralph Lauren began sewing neckties out of a cramped rented space in the Empire State building in 1967, little did he know that he would end up with a garage full of some of the most exotic cars ever produced. That’s alongside a massive fashion empire that’s successfully given the all-American label a respectable spot in the upper echelons of menswear. Four years later, he had to his name, purchases such as a 1971 Mercedes 280SE 4.5 convertible, and a 1979 Porsche 930.

Today, Ralph Lauren’s personal collection has burgeoned to over 70 cars, and is reportedly one of the highest-valued in the world, well worth at least US$300 million (S$404 million). “I’ve always seen cars as art. Moving art. While friends of mine were into paintings, I somehow felt that the real beauty of owning a rare and magnificently designed car was the fact that you can use it,” he once famously mused.

Of course, an estimated net worth of S$8.35 billion would guarantee you access to plenty of the rarest, limited edition, or one-of-a-kind vintage race cars — often with victory tied to their seats. A 1938 Alfa Romeo 8C 2900 Mille Miglia and the 1929 Bentley 4.5-liter ‘Blower’ which raced in the 24 Hours of Le Mans in the ‘30s are but two of many.

The American stalwart didn’t limit the collection with his adoration for vintage designs. His less-than-modest mix also included modern supercars with cutting edge technology, which provided the perfect backdrop for his latest New York fashion week show. Drop by his private garage upstate in Bedford, N.Y., and you’ll find a drool-worthy collection which includes a Ferrari LaFerrari, Lamborghini Murciélago Super Veloce, Bugatti Veyron, and McLaren F1.

But we’re just skimming the surface here. Read on to find out five of Ralph Lauren’s most exotic cars to date.