Ralph Lauren's car collection

Chassis number 57591, known as the 'Pope Atlantic' after its first owner, British tennis player Richard B. Pope, is one of only three surviving examples of the four Bugatti Type 57SC Atlantics ever built. Lauren purchased it in 1988 and commissioned a full restoration requiring over 9,600 hours of labor by Paul Russell of Essex, Massachusetts, choosing to retain Pope's original EXK6 registration plate.

The car features a supercharged 3.3-liter inline-eight engine and its Art Deco body, shaped by Jean Bugatti, has earned it comparisons to the Mona Lisa among automotive historians. Autoevolution reports experts value each surviving Atlantic at north of $100 million, which would make it the most valuable car ever sold if it came to market.

Lauren owns two Ferrari 250 Testa Rossas, with the earlier example being chassis 0734TR, the 14th of only 34 cars built between 1958 and 1961. The model took its name from the red-painted cam covers on its 3.0-liter Colombo V12, which produced around 300 horsepower and drove a top speed of approximately 167 mph.

The Testa Rossa won the 24 Hours of Le Mans in 1958, 1960, and 1961, cementing its place as one of the most successful endurance racers of its era. Comparable examples have sold above $16 million at auction, with current estimates for pristine examples reaching well into the $40 million range.

The F1 LM was built as a road-legal tribute to the five McLaren F1 GTR cars that finished first, third, fourth, fifth, and fifteenth at the 1995 24 Hours of Le Mans, with only five customer examples produced. It is powered by a BMW S70/2 6.1-liter V12 producing 680 horsepower, surpassing even the race car's regulated 600 horsepower output, and the engine bay is lined with gold foil to manage heat.

Lauren has spoken publicly about the car's impact, describing it as unlike anything he had ever driven and comparing the experience to a hovercraft. Current market values for F1 LM examples are estimated between $20 million and $30 million by multiple automotive sources.

This roadster is one of only four team cars built jointly by Alfa Romeo and Carrozzeria Touring specifically for the 1938 Mille Miglia, where it was piloted by the Pintacuda-Mambelli pairing and finished second overall. Its teardrop-shaped fenders and twin-supercharged straight-eight engine place it among the most architecturally striking pre-war racing cars ever constructed.

Lauren reportedly acquired it from the estate of Alfisti collector Bill Serri in early 2004, and it was featured in the 2005 Speed, Style and Beauty exhibition at the Museum of Fine Arts in Boston. Multiple sources, including Carbuzz citing VINwiki's research, estimate its value at up to $20 million.

Commissioned as a one-off special by Italian racing driver and nobleman Count Carlo Felice Trossi, this roadster is built on the SSK platform but wears a dramatically swept, low-slung body that earned it the nickname 'The Black Prince.' Fewer than 40 standard SSK examples were built across the entire production run, making this unique commission effectively priceless in a conventional sense.

Lauren added it to his collection in the 1980s, and it won Best of Show at the Pebble Beach Concours d'Elegance in 1993. The supercharged 7.1-liter inline-six produces its full output only when the throttle is wide open, at which point the Roots-type blower engages with an unmistakable howl.

The XKSS was a road-going conversion of the Le Mans-winning Jaguar D-Type, and Lauren's example is one of the original D-Types returned to Jaguar and converted by Sir William Lyons to road specification. Only 16 of the planned 25 XKSS cars were ever completed, as a fire at Jaguar's Browns Lane factory in 1957 destroyed nine finished cars along with all the required tooling.

The 3.4-liter DOHC straight-six produces 250 horsepower and was clocked at 149 mph in a 1957 Road and Track test. Hagerty values the XKSS at approximately $7.8 million, while Ralph Lauren's own magazine has covered the car's history in detail.

Lauren's example is chassis 5500061, the 61st of approximately 90 Porsche 550 Spyders assembled, making it a rare survivor of Porsche's first purpose-built racing program. The mid-engine layout, lightweight aluminum body, and four-cam 1.5-liter flat-four engine made the 550 far more competitive than its displacement suggested, with the car famously defeating much larger Ferraris and Maseratis in period competition.

It was introduced to the public at the 1953 Paris Salon and directly influenced every Porsche racing car that followed, from the 718 through to the 917. Current market estimates for well-documented 550 Spyder examples range between $5 million and $7 million.

Lauren's D-Type is a factory racing car produced during the model's four-year competition run from 1954 to 1957, a period in which Jaguars dominated Le Mans. The 3,442 cc DOHC inline-six, fed by three Weber carburetors and paired with a four-speed manual, generated 250 brake horsepower and gave the aerodynamic aluminum body a competitive edge at high-speed circuits.

The D-Type's signature central fin and monocoque construction were years ahead of contemporary road car engineering. TopSpeed reports Lauren's example is valued at approximately $6 million, consistent with recent D-Type sales at major auction houses.