Ralph Lauren doesn’t just design clothes—he curates style, and that extends far beyond the runway. His garage reads like a greatest-hits album of classic performance and design. From rare Ferraris to legendary pre-war racers, his car collection is a masterclass in craftsmanship, history, and presence. These aren’t just collector’s items—they’re rolling works of art with real stories, horsepower, and soul. Whether it’s a one-of-a-kind Bugatti or a Le Mans-winning Ferrari, here’s a closer look at ten of the coolest cars to ever park under the roof of a fashion icon.

1938 Bugatti Type 57SC Atlantic

Only four were ever built, and Ralph Lauren owns one of the survivors. The Type 57SC Atlantic is a rolling art piece with its riveted dorsal seam and sleek aluminum body. Lauren had his restored by Paul Russell and Company—over 9,000 hours of painstaking work.

Originally built by Jean Bugatti, this pre-war icon packed a supercharged 3.3L inline-eight, making it one of the fastest cars of its time and easily one of the most visually dramatic.

1955 Jaguar XKSS

The Jaguar XKSS was basically a road-going D-Type, and it doesn’t get much cooler than that. Only 16 were ever completed after a fire destroyed part of the original production run. Ralph Lauren owns one of these ultra-rare survivors—once the same model driven by Steve McQueen.

Under the hood is a 3.4L straight-six pushing 250 hp, with disc brakes and lightweight construction. It’s race-bred, street-legal, and oozes vintage charm.

1962 Ferrari 250 GTO

Arguably the most valuable Ferrari ever made, the 250 GTO is holy grail territory. Lauren’s car is one of just 36 built, powered by a 3.0L V12 making 300 hp.

Designed by Giotto Bizzarrini and built for the FIA’s GT racing class, it dominated the track and redefined beauty in motion. Lauren reportedly picked his up in 1985—today, it’s a multimillion-dollar icon with pure racing DNA.

1964 Ferrari 250 LM

The 250 LM was Ferrari’s first mid-engine road/race car, and Lauren’s is one of only 32 built. It won the 1965 24 Hours of Le Mans—Ferrari’s last overall victory there. Its 3.3L V12 made 320 hp and pushed this lightweight racer to nearly 180 mph. With curvaceous styling and a bulletproof racing pedigree, it’s a high-octane reminder of Ferrari’s golden era.

1955 Porsche 550 Spyder

The 550 Spyder earned the nickname “Giant Killer” for how it punched above its weight in racing. Just 90 were built, and Ralph Lauren’s is one of them. This 1.5L mid-engine car made 110 hp but weighed just over 1,200 lbs. It was quick, nimble, and deadly serious on track. The same model famously took James Dean’s life in 1955, but its motorsport record lives on.

1960 Ferrari 250 GT SWB Berlinetta

Short-wheelbase, front-engine perfection. The 250 GT SWB Berlinetta came with a 3.0L V12 pushing 280 hp and a top speed near 150 mph. Ferrari only built 91 of them between 1960 and 1962. It wasn’t just a looker—it won races, too, including the Tour de France and Goodwood TT. With its balance of performance and elegance, it’s one of the most desirable Ferraris ever made.

1930 Mercedes-Benz SSK “Count Trossi” Roadster

With its long, swooping fenders and muscular presence, the SSK “Count Trossi” is pure pre-war drama. Powered by a supercharged 7.1L straight-six with 300 hp and over 500 lb-ft of torque, it was a rocket in its day. Built for Italian aristocrat and racer Count Carlo Trossi, this one-off design blends art and aggression like few cars ever have. Ralph Lauren acquired it in the ’80s, and it still stuns decades later.

1996 McLaren F1 LM

Only five McLaren F1 LM models were ever built, and Ralph Lauren owns chassis LM3. Powered by a 6.1L naturally aspirated V12 with 680 hp, it could hit 60 mph in under 3.2 seconds and top out near 225 mph. The LM was a stripped-down tribute to McLaren’s ’95 Le Mans win and featured that unforgettable center-seat layout. It’s a pure driver’s car—raw, rare, and built to dominate.

1958 Ferrari 250 Testa Rossa

With its pontoon-fendered body and blood-red engine heads, the 250 Testa Rossa is one of Ferrari’s most iconic racers. Only 33 were built between 1957 and 1962, and Lauren’s is a standout. Its 3.0L V12 cranked out 300 hp, helping it win three 24 Hours of Le Mans races. The styling was as functional as it was beautiful, built to maximize airflow and reduce drag on the track.

1938 Alfa Romeo 8C 2900B Mille Miglia

Built for endurance racing, the 8C 2900B Mille Miglia is a blend of Italian elegance and engineering grit. With a 2.9L supercharged inline-eight pumping out 180 hp, it was among the fastest pre-war sports cars. Only a handful were made, and Ralph Lauren’s car came from the estate of Alfa collector Bill Serri. With race wins and coach built curves, it’s a piece of Italian racing heritage.

*This article was developed with AI-powered tools and has been car-fully, I mean carefully, reviewed by our editors.