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10 Cool Classic Cars That Will Never Go Out of Style

The 2019 Amelia Island Auctions in Florida tells us that millennials entered the car collector market with a bang and a growing nostalgia for autos they saw in their favorite action movies and TV.  

But the range of cool classic cars dates much further back than when these 20- and 30-somethings enjoyed their favorite entertainment staples.

And if you’re into collecting cool old cars, the melting pot is vast, fast, and stunningly gorgeous. It’s also more accessible for everyone as younger vintage cars mix with the truly iconic to make best classic car lists and still be affordable and upgrade worthy.

We’ve come up with a guide of 10 of our favorites to give you a snapshot of what’s out there. Take a moment to check out these game-changing, seriously cool classic cars that will never go out of style.

1. 1955 Citroen DS

Unveiled at the 1955 Paris Motor Show, this beauty departed from pre-WWII designs with its futuristic look and innovative mechanical design. A rare collectors’ car in the U.S., it’s nicknamed the “Goddess” (Déesse) in its native France.

Of course, the design-famed French made it a streamlined looker. Flaminio Bertoni fashioned the gorgeous design that looked like nothing else at the time. Mr. André Lefèbvre, an aeronautical engineer added to it with a focus on aerodynamics. Ahead of its time, the DS is made of plastic and aluminum, still used today in car manufacturing. 

2. 1957 Mercedes 300SL Gullwing

Fly, fly, fly away down the road in this gullwing-door original. A coupe and then roadster, the 300SL debuted in the Big Apple instead of Europe at the 1954 International Motor Sports Show. 

But what is gullwing, you ask? Think Back to the Future but with panache.

3. 1959 Chevy El Camino

A car-truck hybrid designed for Sunday family outings and a trip to the farmers market all in one and inspired by the original car-truck, the Ford Ranchero, the original El Camino boasts vintage muscle design. Chevy discontinued the El Camino after a few months and brought it back in 1964, the true muscle car of the 60s and 70s.

A two-door with Bel Air exterior, the El Camino was Chevy’s first steel-bed floor pickup, floorboards removable to reveal the Brookwood foot wells underneath. 

4. 1963 Corvette Sting Ray

Looking good on the outside and in, and by in, we mean: Look at you with your glamorous shades, wind in your hair and on your face, gliding down the road, happy, listening to your favorite tunes, enjoying the desert scenery or curvy cliffs overlooking the Pacific.

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The first real looker in the Corvette series, the 1963 model also boasted better handling with all-wheel independent suspension, a lighter body, and sleeker nose (with pop-up headlight charm) than previously seen, making it an automotive darling for touring adventures then and now. 

When was the last time you went touring? We go as often as we can and have some driving-spot favorites. Learn more about that before your next excursion. And when you go, be sure to take pictures and show off to your pals, and us!

5. 1964 Aston Martin DB5

Martini stirred not shaken as post-cruising libation suits this sleek British auto and 007 just fine. Bond’s most leaned-upon speedster for espionage (read: Goldfinger plus), you can rely on it to turn heads and your adventurous spirit. 

6. 1969 Boss 429 Mustang

Hot on the outside and the inside, literally, because the engine is so big there’s no air conditioning. It’s also loud as heck.

So roll down the window and enjoy the roar of the wind and your iconic muscle-car engine as you feel the rush of power. Built to compete with the muscle of Chrysler’s Hemi at NASCAR, the Boss 429 made it onto the streets thanks to NASCAR’s rule that to compete, Ford had to sell 500 cars with the same giant racing engine to the public for it to be eligible to compete. 

This classic is as American as apple pie, so when not barreling down the road with your loud engine, it’s the ideal beaut to take to your local diner for a slice. Don’t forget the vanilla ice-cream before you hit the pavement again with your energetic engine that feels just like your sugar rush.

7. 1969 Toyota 2000GT

Not your typical Toyota-practical vehicle, this long-nosed classic speedster earned its spot as most-desired sports car fast and not just for its gorgeous looks.

With an inline-six engine’s hand-built Yamaha twin-cam cylinder head, 150 horsepower with 130 pound-feet torque, and four-wheel independent suspension, this ultra-low coupe with X-shape backbone frame performs and handles like a dream. 

It also fulfilled its acting-role dream, starring with Sean Connery in You Only Live Twice, racing the British agent around the Japan location shoot.

8. 1969 Dodge Charger

We have another star in our midst with the iconic Dodge Charger, a muscle car that starred on the American TV series The Dukes of Hazzard from 1979 to 1985 for the shows entire run.

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The car named “General Lee” belonged to the Duke brothers, Bo and Luke and sported a horn that played “Dixie” and doors welded shut so the guys had to jump in and out. General Lee played in all episodes but one!

Originally, designed to take NASCAR from the Hemi, Dodge made it happy with the Charger “Daytona” and Bobby Isaac at Daytona. It boasted new fuselage styling, arced glass on the back, as well as a three-foot wing, and a longer nose cone in front.  

9. 1969 Ferrari Dino 246 GT

The soft-lined beauty of this Italian classic matches the beauty of its story. Designed by Enzo Ferrari himself in honor of his son Dino, an auto engineer who passed away at 24, the Dino resulted after Ferrari saw the success of the Porsche 911 which proved that a mid-engine roadster met the needs of his Ferrari buyers. 

A romantic at heart, Ferrari released the Dino as its own brand, sporting a descendant of the V6 engine designed 12 years earlier by Dino and another Ferrari engineer, Vittorio Jano. The Dino didn’t wear the Ferrari badge, rather a Dino brand badge on the back and front. 

The sleek stunner embodied the new offshoot brand vision, while the norm for Ferrari was a bigger engine than the small aluminum V6 with higher MSRP. Enzo Ferrari’s romantic notions paid off as the Dino competed with other lower-priced sports cars. 

10. 1971 Volkswagen Beetle

The car made for regular “volks” (folks/your average Joe, and Johann) way back when, and the classic for regular collecting-folks’ budgets today. Volkswagen added independent rear suspension in 1969 and in 1971 the famed 16000CC engine and the super beetle. It’s a smart initial-low-investment car that’s prime for a stellar makeover to transform your ride as you go.

We’re thinking: Baja bug anyone?

Which Cool Classic Cars Are You Eyeing?

This is just a smattering of the cool classic cars out there. But we hope you’re inspired to go for that iconic wonder you have your eye on. 

Take a tour with a vintage rental to get the feel for your new darling and know that you can take a lower-cost classic and work on it to make it sing to your personal specs. 

Need a bit more of a nudge or some practical financial advice? Read on to learn about how to make an expensive classic find its way into your life.