The Queen of Vogue Goes Top-Down
When you think of Anna Wintour, visions of fashion runways, Met Gala gowns, and her signature sunglasses instantly come to mind. But behind that famously icy composure is a side few people know: Anna Wintour is a vintage convertible enthusiast. Her garage, tucked away from paparazzi lenses, could double as a museum of open-air automotive art. From refined British roadsters to muscular American cruisers, her cars tell the story of a woman who appreciates elegance not just in fabric, but in finely-tuned metal and chrome. Let’s take a top-down tour of her 25 vintage convertibles that prove her taste in cars is just as iconic as her fashion sense.
1959 Jaguar XK150 Drophead Coupe
A favorite among style connoisseurs, the Jaguar XK150 blends elegance with understated ferocity. Wintour’s example—a deep British Racing Green beauty—has a handcrafted walnut dash and buttery-soft leather seats. It’s the perfect car for someone who defines “effortless luxury.” The XK150’s purring inline-six engine is quiet power, much like Wintour herself.
Charles from Port Chester, New York, Wikimedia Commons
1964 Mercedes-Benz 230SL “Pagoda”
The 230SL is the epitome of minimalist chic. Nicknamed the “Pagoda” for its subtle concave roofline, this car radiates quiet sophistication. Anna reportedly drives hers through the Hamptons in late summer, the crisp air matching its pearl-white finish. It’s couture on wheels—timeless, graceful, and meticulously designed.
1957 Porsche 356 Speedster
Wintour’s Porsche 356 Speedster is proof she appreciates design purity. With its low windshield and stripped-down simplicity, it’s one of the most photogenic convertibles ever built. She calls it her “Sunday therapy,” driving it early in the morning before New York wakes up.
1966 Alfa Romeo Spider Duetto
The Spider Duetto is pure Italian flair—equal parts romance and rebellion. Famously driven by Dustin Hoffman in The Graduate, Wintour’s cherry-red model channels her bold side. It’s the car equivalent of red lipstick: daring, timeless, and impossible to ignore.
Tokumeigakarinoaoshima, Wikimedia Commons
1962 Chevrolet Corvette C1
Every collection needs some Americana, and Wintour’s C1 Corvette brings that with chrome-laden confidence. Its two-tone paint and tail fins scream mid-century optimism. The story goes that she bought it after a Vogue shoot inspired by 1950s Hollywood glamour.
Jeremy from Sydney, Australia, Wikimedia Commons
1955 Austin-Healey 100M
Light, fast, and distinctly British, the Austin-Healey 100M combines racing spirit with refined craftsmanship. It’s rumored Wintour keeps this one at her English country estate—a nod to her London roots. With its two-tone blue-and-cream finish, it’s as striking as any couture gown.
1970 Fiat 124 Spider
Playful yet stylish, the Fiat 124 Spider is a compact convertible that’s surprisingly soulful. Wintour reportedly drives hers through upstate New York with her daughter. Its Italian design flair pairs perfectly with her love for classic European elegance.
1963 Lincoln Continental Convertible
Few cars command presence like a Lincoln Continental with suicide doors and acres of chrome. Wintour’s black-on-black model feels presidential, yet relaxed—a ride worthy of Jackie Kennedy and her peers. It’s classic American prestige, Vogue style.
1958 BMW 507 Roadster
A jewel in her collection, the BMW 507 was famously loved by Elvis Presley—and now by Anna Wintour. With its long hood, subtle curves, and rarity (fewer than 260 ever made), it’s the automotive equivalent of haute couture: tailored perfection.
1965 Ford Mustang Convertible
Even the world’s most fashionable editor can’t resist the all-American Mustang. Wintour’s 1965 convertible, finished in Wimbledon White, perfectly balances nostalgia and freedom. She reportedly took it for a spin along the Pacific Coast Highway—sunglasses firmly in place, of course.
MercurySable99, Wikimedia Commons
1954 Cadillac Eldorado Convertible
Big, bold, and unapologetically glamorous, the Eldorado is a diva’s dream. Wintour’s pastel-pink model feels lifted from a Hollywood soundstage. It’s the kind of car that doesn’t whisper luxury—it sings it.
Alexander Migl, Wikimedia Commons
1960 MGA 1600 Roadster
The MGA is the picture of 1960s refinement. Small, nimble, and irresistibly charming, it’s a driver’s car with just the right touch of class. For Anna, it represents understated English design—subtle but unforgettable.
MercurySable99, Wikimedia Commons
1971 Citroën DS Décapotable
Trust Anna Wintour to own a convertible as avant-garde as the Citroën DS. Known for its futuristic suspension and aerodynamic design, it’s been called “a car from another planet.” Wintour’s silver model is a masterclass in French chic—a car that floats rather than drives.
1969 Jaguar E-Type Series II Roadster
Enzo Ferrari once called the Jaguar E-Type “the most beautiful car ever made.” Wintour clearly agrees. Her gunmetal-gray Series II combines speed and sensuality. With its elongated bonnet and perfect proportions, it’s pure art on wheels.
1957 Thunderbird Convertible
Wintour’s Ford Thunderbird proves that luxury can be playful. Its turquoise paint and round headlights evoke 1950s optimism, while its V8 engine provides more power than anyone expects from a fashion editor’s ride.
1972 Mercedes-Benz 280SE Cabriolet
This full-sized Benz convertible is refinement embodied. Hand-built, stately, and timeless, the 280SE Cabriolet fits perfectly in Wintour’s world of tailored taste. She reportedly calls it “the Hermès of cars.”
1961 Triumph TR3A Roadster
Compact but spirited, the Triumph TR3A is a British sports car legend. Wintour’s model, finished in racing green, captures her love for classics with personality. It’s small, quick, and surprisingly fierce—sound familiar?
The Car Spy, Wikimedia Commons
1968 Alfa Romeo 1750 GTV Convertible
Wintour’s affection for Alfa Romeos doesn’t end with the Duetto. Her 1750 GTV packs more punch and flair, offering an exhilarating drive wrapped in gorgeous Italian design. For a woman who lives and breathes aesthetics, this car is a natural fit.
Lothar Spurzem, Wikimedia Commons
1970 Chevrolet Chevelle SS Convertible
When Anna wants muscle, she doesn’t settle. Her Chevelle SS packs a 396-cubic-inch V8 that rumbles like rock ’n’ roll. It’s a bold choice that shows even fashion royalty has a wild streak.
1953 Aston Martin DB2/4 Drophead Coupe
Before James Bond made the DB5 famous, there was the DB2/4. Elegant and exclusive, Wintour’s deep navy model feels like it belongs outside a countryside estate, not a photo shoot. But that’s the charm—it’s sophisticated power, dressed to impress.
Rex Gray from Southern California;Cropped by uploader Mr.choppers, Wikimedia Commons
1969 Fiat Dino Spider
A collaboration between Fiat and Ferrari, the Dino Spider has a heart of Italian passion. With its V6 engine designed by Ferrari, it’s a car that whispers luxury but roars performance. For Anna, it’s another love letter to design that dares to be different.
Lothar Spurzem, CC BY-SA 2.0 DE, Wikimedia Commons
1950 Bentley Mark VI Drophead Coupe
Nothing says old-world glamour quite like a Bentley Mark VI. Wintour’s champagne-colored model features wool carpets and wood veneers that could rival any couture atelier. It’s dignified elegance, made for slow Sunday drives with purpose.
1971 Saab 99 Cabriolet Prototype
This one’s an oddball—and that’s why Anna loves it. The Saab 99 Cabriolet prototype was never mass-produced, making hers a true collector’s item. It’s Scandinavian design at its quirkiest, proving even the fashion elite enjoy the unexpected.
Staffan Vilcans, Wikimedia Commons
1965 Sunbeam Tiger Roadster
A British sports car with an American V8 heart, the Sunbeam Tiger was built for those who appreciate refinement and raw speed. Wintour’s cream-colored Tiger is deceptively fast—like a model in heels sprinting to a runway show.
1960 Maserati 3500 GT Spyder Vignale
Perhaps the most exotic in her garage, the Maserati 3500 GT Spyder is a rare blend of Italian craftsmanship and luxury. With coachwork by Vignale, it’s as beautiful as anything to grace a Vogue cover. Wintour’s example in sky blue exudes timeless poise.
1958 Rolls-Royce Silver Cloud Drophead
If there were ever a car that matched Anna Wintour’s reputation for grace under pressure, it’s the Rolls-Royce Silver Cloud. Elegant, serene, and effortlessly commanding, it’s the four-wheeled version of her editorial authority.
Beyond The Runway—Anna’s Timeless Ride
For a woman who’s built a career dictating the future of fashion, Anna Wintour’s love of vintage convertibles says something profound: timeless design never goes out of style. Her collection isn’t just about horsepower—it’s about heritage, craftsmanship, and beauty that endures. Whether she’s gliding through London in a Jaguar or coasting down the Hudson in a Mercedes, Wintour proves that real elegance—like a perfectly tailored coat or a perfectly tuned engine—is forever.
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