Ralph Lauren doesn’t consider himself a car collector. Yet, in an unremarkable warehouse around 40 miles from New York lie more than 100 automobiles. Lauren maintains the cars in working order so that he can drive any of them whenever he wants. He said that the purpose of restoring a vehicle is not to put it on display like a monument but to rehabilitate it to full working condition.

Lauren still owns the first car he bought new, a shiny 1971 Mercedes-Benz 280SE 3.5 Cabriolet. He has owned it for decades, but it is not his favorite car—none of them are. Ralph equates his cars to children, saying they all have different personalities. Therefore, he can’t have a favorite. The fashion designer owns some of the world's rarest and most expensive cars. Here are Ralph Lauren's 10 most expensive cars.

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10 1955 Jaguar XKD

Value $6 million

Jaguar built the XKD, or D-Type, to continue its dominance at Le Mans. Jaguar knew it would get swallowed up by the competition if it remained stagnant while others improved. The D-Type was a beauty carved by an aerodynamicist's scalpel. It featured a rounded nose, a long, swooping hood, elliptical body panels, a driver’s windshield, and a shark fin behind the headrest to provide stability.

Specs and performance

Further, the D-Type’s monocoque design reduced weight and improved structural strength. The D-Type lost to the Ferrari 375-Plus in its debut year. However, from 1955 to 1957, the D-type dominated at Le Mans, clocking speeds on the Mulsanne straight that other cars could only dream of.

Mike Hawthorne and Paul Frere came second overall in the 1956 Reims-Gueux endurance race, driving Ralph’s D-Type. In 1964, Patricia Coundley clocked 161.3 MPH in the car, becoming the fastest woman in Europe. A 1955 D-Type similar to Ralph’s sold for $6 million in January 2021. The vehicle’s value will keep rising, especially considering Jaguar built only 54 examples.

9 1930 Mercedes-Benz SSK

Value $7.4 million

Ralph Lauren’s SSK is perhaps the most famous of the 30 or so units Mercedes built in the late 1920s and early 1930s. The SSK (Super Sport Kurz) was a formidable racer. Ferdinand Porsche had, before he departed from the company, slashed the Model S by 19 inches to improve handling and agility. The car’s monstrous, supercharged 7.1-liter engine provided power. Despite the car’s weight, the combination of nimbleness and power brought racing success.

Specs and performance

Count Felice Trossi of Italy raced the SSK after buying it from the first owner. It’s unclear who came up with the design of the SSK Count Trossi’s incredible shape. Whoever did it built one of the most beautiful cars in the world. From the top, it looks like something Batman would drive. An ‘ordinary’ SSK sold at auction for $7.4 million. There’s no telling how much Ralph’s SSK Count Trossi would go for.

8 Alfa Romeo 8C 2300

Value $12 million

In the 1920s and early 1930s, Alfa Romeo won races for fun, primarily thanks to the design and engineering prowess of Vittorio Jano. Back then, the same vehicles were used in grand prix and endurance races. Installing headlamps and mudguards on the 8C 2300 turned it into a long-distance racer. The vehicle earned the ‘Monza’ moniker after Tazio Nuvolari drove it to victory at the 1931 Italian GP.

Specs and performance

Driven by future WWII hero Jean-Pierre Wimille, Lauren’s 8C 2300 Monza won the Lorraine GP in 1932. An Italian owner took it to Africa, where it stayed until 1962. From Africa, it went to the U.S., then to Germany, before joining Ralph’s collection in 1988. A Monza similar to Lauren’s sold for $11.99 million.

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7 1954 Ferrari 375-Plus

Value $18.3 million

The Ferrari 375 Plus shared several similarities with the D-Type it competed against in the 1954 Le Mans: a swooping body, a small driver’s windshield, and a stabilizer fin behind the driver’s headrest. Under the hood, however, things were a lot different. The 375 Plus used a 4.9-liter V-12, which produced 75 more horsepower than the inline-six engine in the D-Type.

Specs and performance

Ferrari’s 174-mile-an-hour rocket won the 1954 Le Mans race. Driven by its Argentine owner, Enrique Saenz Valiente, the 375 Plus Lauren would later win many races, including the Buenos Aires 1000-kilometer race in 1955. Ralph owns the fifth of five 375 Pluses Ferrari made. One of them sold for $18.3 million.

6 1938 Alfa Romeo 8C 2900 Mille Miglia

Value $18.9 million

Phil Hill, a future Formula 1 champion, was a young racer when he laid years on a brown and cream(!) 8C 2900 Mille Miglia in Los Angeles after WWII. Before the war, the car had finished second in the brutal Mille Miglia, driven by Carlo Pintacuda. Hill bought the car and swiftly repainted it red. He won a race in the 13-year-old Alfa during the 1951 season.

Specs and performance

Despite his love for the car, Phil sold it and used the money to purchase a Ferrari. The vehicle changed owners several times before joining the Ralph Lauren collection. It is one of the four convertible 8C 2900s built for the Mille Miglia race. One Alfa Romeo enthusiast bought a long-wheelbase Mille Miglia for $18.9 million.

5 McLaren F1 LM

Value $19.8 million

Ralph Lauren seems to have an affinity for cars that won the Le Mans race. McLaren entered the 1995 race as an outsider for victory. The manufacturer surprised itself, and everyone else as the McLaren FI GTR took four of the top five places, including first. To mark the GTR’s stunning success, McLaren built five unique F1s named the LM (Le Mans).

Specs and performance

The LM was essentially a GTR for the road. It featured a high-downforce package and an unrestricted V-12 producing 680 horsepower. The drag added by the downforce package made it slower than the F1, despite having more power; it topped out at 225 MPH. McLaren built five LMs: the Sultan of Brunei owns three, Ralph Lauren owns one, and the other was sold to an American collector for $19.8 million.

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4 McLaren F1

Value $20.46 million

The McLaren F1 was miles ahead of its time. The world’s fastest naturally aspirated car was powered by a remarkable 6.1-liter V-12 engine by BMW. The F1 could have gotten a Honda engine. Gordon Murray, the vehicle’s designer, asked Honda, the F1 team’s engine supplier, to build the F1’s engine. Honda declined, missing out on an opportunity to make history.

Specs and performance

The F1 was the fastest vehicle in the world for several years and featured futuristic tech. It had three seats, two on either side of the middle driver’s seat. McLaren F1s have exploded in value in recent years. An example that had only done 242 miles sold for $20.46 million, $0.66 million more than the much rarer F1 LM.

3 Bugatti Type 57SC Atlantic

Value $34 million+

The 57SC Atlantic was a special car based on Jean Bugatti’s Aerolithe concept, which the public received poorly. The most striking aspect of the Aerolithe concept was the use of external rivets to connect body panels. Jean’s use of flammable magnesium panels forced him to use external rivets. Bugatti could have avoided the external riveting when building the aluminum-bodied 57SC Atlantic, but the manufacturer chose not to.

Specs and performance

Rivets hold together the 57SC Atlantic’s long, beautiful, and curvaceous body. Ralph Lauren owns one of the four Type 57SC Atlantics Bugatti manufactured. One sold for over $34 million (some outlets quote $40 million). The one Jean owned, the 1937 Le Mans victor, got lost during the war. Its estimated price is in excess of $100 million.

2 1958 Ferrari 250 Testa Rossa

Value $40 million

The 250 Testa Rossa was the first car raced by Ferrari following a mandate that limited the engine capacity of cars in the highest racing class to 3.0 liters. The restriction was implemented to slow cars down after disasters at various racing events. Ferrari named the car ‘250’ after the engine’s 250 cc cylinders and ‘Testa Rossa’, Italian for ‘red head’, as a nod to the engine’s red camshaft covers.

Specs and performance

The Testa Rossa was dominant. Ferrari had an advantage over other manufacturers, having already developed a 3.0-liter V-12 engine. Therefore, it didn’t start from scratch like its competitors. Ralph Lauren owns #14 of the 34 Testa Rossas built. Dealer Tom Hartley sold an unrestored 250 Testa Rossa for a reported $40 million.

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1 1962 Ferrari 250 GTO

Value $48.4 million

250 GTO designer Sergio Scaglietti didn’t consult a wind tunnel when designing one of the most beautiful cars ever. Regardless, the car sliced through the air like a bayonet through butter. The GTO came in second in its first race, going on to win three consecutive championships for Ferrari in the early 1960s.

Specs and performance

Ralph’s GTO is special, as it won its first race; Pedro and Ricardo Rodriguez drove it to victory at the Montlhery 1000. U.S. racing legend Roger Penske drove Ralph’s 250 GTO to many victories. Scaglietti’s design was featured in 30 out of the 36 GTOs that were manufactured. One of them sold for $48.4 million.