These Are the 15 Coolest Coupés and Convertibles of All Time

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Imagine cruising down a sun-drenched highway with the wind whipping through your hair. That’s the joy of riding in a convertible! Undoubtedly, countless models have graced the asphalt throughout history, but which ones truly stand out as the coolest of the cool? From classic American muscle cars to elegant European roadsters, these 15 vehicles have combined design, speed, rarity, and overall appeal in the right mix to leave a lasting legacy.

1961 Ferrari 250 GT California Spyder

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Base Price New: Around $11,000
Average Price of a Vintage Model: $18 million

As one of the most sought-after and expensive cars, the Ferrari 250 California Spyder is an automobile icon. It is a luxurious and powerful open-top grand tourer produced between 1958 and 1966. Its sleek and curvy bodywork by Pinin Farina successfully grabbed the attention of famous people. Celebrities like Steve McQueen lusted after it, and today, these Ferraris are extremely expensive, seeing that the record price is over $18 million!

1965 Shelby Cobra

Base Price New: $7,500
Average Price of a Vintage Model: $2 million+

Ford and Carroll Shelby collaborated to produce a formidable roadster that conquered racetracks. Forget fancy interiors; they were all about performance. Shelby stuffed an exotic AC Cobra with a monstrous V8 engine, creating an insane speedster. As expected, these Cobras have become expensive and are worth millions because they’re rare.

1960 Mercedes-Benz 300SL Roadster

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Base Price New: $11,000
Average Price of a Vintage Model: $1.8 million

Nicknamed the “Gullwing” for its unique doors that opened upwards, the 300SL is one of the most recognizable cars ever. It wasn’t just cool; it was a game-changer! Its luxurious interior included premium materials and technology that were too advanced for the time. Owning this Benz was a status symbol back then, and today, they’re still multi-million dollar classics.

1967 Ford Mustang Convertible

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Base Price New: $2,376
Average Price of a Vintage Model: $36,995

The model came as a shocker because, despite being a sleek sports car, it was also affordable. Its long hood and short rear deck would make you think it’s all looks and no muscle, but don’t be deceived; this Mustang packs a powerful V8 machine. Alongside its timeless charm, it has a comfortable interior, smooth handling, and an open top, which is best for enjoying the road.

1959 Cadillac Eldorado Biarritz

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Base Price New: $7,401
Average Price of a Vintage Model: $268,800

The 1959 Eldorado Biarritz was a land yacht loaded with every imaginable luxury feature of the time! It had enormous tailfins pointing to the sky and a spacious interior fit for royalty. This two-door Cadillac came with automatic headlights and air suspension. It wasn’t just about appearance; drivers could enjoy comfortable, smooth rides.

1963 Chevrolet Corvette Stingray

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Base Price New: $4,252
Average Price of a Vintage Model: $69,900

The 1963 Stingray was a dramatic leap for Chevy as it had a significantly different build from the previous Corvettes. It ditched the round headlights, and for the first time, you could get a hidden headlamp option (think jet fighter!). The fiberglass hugged the curves, giving it an attractive look, and the rear window split in two. To crown it all, it had a powerful V8 that roared when cruising.

1961 Triumph TR3

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Base Price New: Around $2,200
Average Price of Vintage Model: $20,000 to $45,000

The TR3 is another affordable British speedster and an excellent choice for those who want a high-performing vintage piece in their garage without breaking the bank. The Triumph Roadster “TR” is a lightweight and elegant automobile with a long hood, a small grille, and wire wheels. The British manufacturers confirmed in an interview that it was built for people who love luxurious features.

1955 Ford Thunderbird

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Base Price New: $3,995
Average Price of a Vintage Model: $26,300

The 1955 Ford Thunderbird was a personal luxury car designed to compete with European grand tourers. Unlike the rough-and-tumble Corvettes, it was a smoother ride. It wasn’t the fastest, but it was comfortable, stylish, and perfect for cruising with a date. This two-seater became popular among wealthy people who wanted to announce their presence.

1962 Alfa Romeo Giulietta Spider


Base Price New: $4,000
Average Price of Vintage Model: $40,000 to $60,000

Here’s another masterpiece with attractive bodywork crafted by Pininfarina, the legendary car design company. The Giulietta Spider by Alfa Romeo was manufactured from 1955 to 1965 to drive on winding roads and cruise the Italian countryside in style. This majestic coupé is known for its responsive handling and an unusual shape that stands out.

1953 Chevrolet Corvette

Base Price New: $3,498
Average Price of a Vintage Model: $168,000

The 1953 Corvette was the first American mass-produced sports car, quickly symbolizing performance and style. This two-seater grabbed attention with its futuristic fiberglass frame, a radical departure from previous boxy forms. Power came from a throaty six-cylinder engine. Though not the fastest, it was a head-turner on the road. The Chevy wasn’t perfect, but it started a legacy that continues today, making it a true national icon.

1971 Plymouth Barracuda Convertible

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Base Price New: Around $3,500
Average Price of Vintage Model: $100,000

Unlike its hardtop counterpart, the 1971 Cuda is rare, as only 374 were manufactured. Therefore, finding one in good condition is hard, and a restored version could fetch well over $100,000. Muscle car enthusiasts of the period loved the Barracuda due to its massive engines and hidden headlights that flip up electrically, giving it an aggressive form.

1968 Pontiac GTO Convertible

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Base Price New: $3,666
Average Price of a Vintage Model: $64,995

Named Gran Turismo Omologato, the 1968 Pontiac GTO grand tourer was cleared to compete in sports car racing by the International Automobile Federation. It combines performance with luxury and is designed to cover long-distance trips quickly. This road racing vehicle has a long hood and wide stance that makes it impossible to ignore, a sought-after feature by drag and street racers.

1963 Studebaker Avanti Convertible

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Base Price New: $4,445

Average Price of a Vintage Model: $59,900

Seeing a vintage ride from an independent company other than the usual heavyweights was refreshing. Besides its chrome-laden curves, this luxury coupé had a fiberglass body with a sharp, pointed nose that looked like it belonged in a sci-fi movie! Sadly, Studebaker’s financial woes meant production was short-lived and became a commercial flop.

1967 Alfa Romeo Spider Duetto


Base Price New: $4,100
Average Price of a Vintage Model: $49,000

This little Italian beauty is a design success as Pininfarina’s work shines through its polished curves and striking look. Though launched in March 1966 at the Geneva Motor Show, Alfa Romeos continued their prowess on the road. They gained fame in the movie industry after featuring in the blockbuster film “The Graduate,” starring famous actor Dustin Hoffman.

1957 Chevrolet Bel Air

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Base Price New: $2,611
Average Price of a Vintage Model: $56,900

The Bel Air symbolized American prosperity and style, which most people, including celebrities, adore. The 1957 model was available in various body styles, including two-door and four-door sedans, hardtops, convertibles, and station wagons. However, the open-top has always been the most sought-after due to its tailfins, often seen in classic car shows and movies.

Written by grayson