The 1950s. A time when cars had style, presence, and the kind of design flair that made jaws drop and engines sing. It was the era when motoring wasn’t just a necessity, it was theatre. With tailfins sharper than opinions and dashboards like the bridge of the Starship Enterprise, these cars were art you could drive. And if you’ve got deep enough pockets and a decent garage, some of these beauties can still be yours.
Mercedes-Benz 300SL Gullwing - The German Wunderkind That Flew
Launched in 1954, the 300SL Gullwing was more than just a car - it was a technical ballet. Those iconic doors didn’t just look like something from a Bond villain's garage; they were born from necessity, thanks to the innovative spaceframe chassis that made conventional ones impossible. Beneath its long, sweeping bonnet was a 3.0L straight-six engine with mechanical fuel injection, a world-first in a production car.
This was a machine that could crack 160 mph back when most cars were still wheezing along in third gear. The interior was all leather and precision - Teutonic quality through and through. Today, you’re looking at around £800,000 to £1.2 million for a decent example. That’s a fair price for a car that looks like it should be hanging in the Louvre.
Ferrari 250 Testa Rossa - A Red-Headed Racing God
If the Gullwing was German order, the Ferrari 250 Testa Rossa was pure Italian passion. This wasn’t just a car - it was a predator. A snarling 3.0L V12 monster wrapped in a curvaceous body sculpted by Scaglietti himself. Its name, which means "Red Head", refers to the red cam covers, but it might as well describe its temperament.
It dominated endurance racing in the late ’50s, winning Le Mans, Sebring, and the Targa Florio. It’s brutally rare and ferociously expensive - some have sold for over £10 million. But what you get is not just a car, but a legend with pistons.
Porsche 550 Spyder - Lightweight, Lethal, and a Bit of a Rebel
The Porsche 550 Spyder might look like a toy from some angles, but it was a giant-killer in motorsport. With a 1.5L flat-four engine placed midship and a total weight that made most bicycles look heavy, it danced through corners like it was wearing ballet shoes.
It’s also famously known as the car James Dean was driving when he met his end - a fact that adds a layer of dark glamour to its mystique. With only 90 built, surviving examples go for north of £3 million today. It’s a piece of rolling folklore - just be careful if you're the superstitious type.
Jaguar D-Type - The Best of British with a Wing and a Roar
Now here’s a car that doesn’t need to shout. The Jaguar D-Type whispers, “I’ve already won.” And it had - at Le Mans, three times in a row from 1955 to 1957. The sleek, aerodynamic design was ahead of its time, complete with a stabilising fin behind the driver’s head that made it look like a Cold War fighter jet.
The 3.4L straight-six was powerful, but it was the handling and engineering that really set it apart. With values soaring beyond £15 million, the D-Type isn’t just a car - it’s a crown jewel in the monarchy of motorsport.
Aston Martin DB4 - Suave, Sophisticated, and Seriously Fast
Imagine if James Bond wore driving gloves - this is what he’d drive. The Aston Martin DB4 was introduced in 1958 and immediately made an impression. With its aluminium body designed by Carrozzeria Touring of Milan and a 3.7L inline-six capable of reaching 140 mph, it was the perfect blend of British class and Italian flair.
Inside, you’d find acres of leather and gauges you’d expect in a Spitfire. A proper driver’s car, with plenty of go and lots of growl. Today, a DB4 will set you back around £500,000, but you’ll never park next to another one at Tesco.
BMW 507 - The Roadster Elvis Couldn’t Resist
BMW's 507 was their swing at the American market - a svelte, sexy roadster that sadly cost too much to make. Only 252 were built, which is baffling when you see one. Long bonnet, short boot, V8 engine singing at your command - it was Bavarian beauty at its best.
Elvis Presley famously owned one, and you’ll need a rock star budget to do the same. Values today hover around £1.5-£2 million, which seems about right for a car that looks like it was chiselled by angels.
Chevrolet Bel Air - The American Dream with Tailfins
Ah, the Bel Air. This car didn’t just roll off the assembly line - it danced. Introduced in 1955, it became the poster car for post-war prosperity in the US. Chrome for days, bold two-tone paint jobs, and tailfins you could slice cheese with. The Bel Air was every teenager’s dream (myself included) and every dad’s pride.
Pop the hood and you could find anything from a modest inline-six to a throaty 265ci V8. It wasn’t about speed, though - it was about presence. Today, a mint Bel Air will cost you £30,000-£45,000, and it’ll win more hearts than a Ferrari.
Cadillac Eldorado – The Pink Dream I’ll Have One Day
If there’s one car that truly sums up the outrageous glamour of the 1950s, it’s the 1959 Cadillac Eldorado Biarritz. Forget subtlety - this was a chrome-drenched battleship on wheels, with those legendary rocket-inspired tailfins and an interior big enough to host a dinner party. It came loaded with electric everything, a 6.4L V8 under the bonnet, and styling that made every parking space look far too small.
And yes, if you're wondering - this is my dream car, preferably in pink, roof down, wind in my hair, preferably somewhere sunny but I’d take the English drizzle if it meant I could drive one.
Today, a mint condition '59 Eldorado Biarritz will set you back about £200,000, and frankly, that feels like a bargain for a mobile monument to American excess and design.
So, after all that, if your pulse is racing and your head’s full of tailfins and V8 rumbles, don’t just leave it there. We run Classic Car Driving Experiences across the UK, where you can slide behind the wheel of true motoring icons - no auctions, no shipping crates, just keys and an open road. Whether you fancy a track-day blast or a small escape with someone who understands why you keep talking about carburettors, we’ve got the perfect classic waiting.
