20 Vintage Photos of Peoples Cars In The Swinging Sixties

Last Updated on July 2, 2025 by Matt Staff

In this collection of 20 vintage photos, we take a nostalgic ride back to a decade defined by chrome bumpers, bold colors, and serious style. Buckle up, this is more than just a look at old cars; it’s a glimpse into the everyday lives, dreams, and driveways of the people of the swinging sixties.

1. Rocking the new three-wheeled convertible, 1961

A person smiling while sitting in a convertible parked by the seaside, with the ocean and cloudy sky in the background. The photo is in black and white.
nomadicearth/via reddit.com

2. “My grandpa proudly showing off his car after being hit while parked”

A man in glasses and a jumpsuit smiles and poses beside a vintage car with a damaged rear end. The car's trunk is painted with the words "CHICAGO OR BUST." The photo appears to be from the mid-20th century.
safe_net_9558/via reddit.com

3. A ’61 Buick Flamingo with a rotating front seat

A woman in a light coat and dress sits in a vintage pink convertible car with matching pink and purple upholstery, parked on grass. She rests her arm on the back seat and looks thoughtfully into the distance.
secretlakr/via reddit.com

4. Showing off her new Corvette Mako Shark II, 1965

A woman in a turquoise dress stands next to a vintage silver sports car with unique wheels, parked on a paved area with bare trees and buildings in the background.
yes-pranks/via reddit.com

5. A real passenger princess, Hollywood, 1961

A large dog sits upright in the passenger seat of a vintage convertible car beside a driver wearing sunglasses, as they travel down a busy city street with classic cars in the background.
lank_thompson/via reddit.com

6. Goodyear’s 1961 illuminating tires

A woman in a dark dress and heels leans against a vintage car with glowing whitewall tires at night on a city street, with historic buildings in the background. The scene is in black and white.
johnnylgarfield/via reddit.com

7. Someone’s grandmother, ditching a car for a horse, early ’60s

A woman in a light skirt stands beside a vintage silver Volkswagen Beetle, petting a brown foal on a grassy, sunlit field.
sharkdinner/via reddit.com

8. Bobby Darin standing next to his dream car, Hollywood, 1961

A man in a suit leans against a futuristic, sleek car with dramatic fins, parked in front of a building under construction with scaffolding and columns visible in the background.
skipperbob/via reddit.com

9. Cruising around in the long Cadillac Coupe DeVille, 1965

A classic black car with a driver wearing a hat is stopped at an intersection in a city with tall buildings and streetlights, giving a vintage urban atmosphere.
hesjuggernaut/via reddit.com

10. “My Dad with his MGA in 1964”

A young man in a white shirt and tie sits on the hood of a vintage convertible car, smiling. The black-and-white photo appears old and is visibly creased and worn. A building is seen in the background.
pilotdavo/via reddit.com

11. Rocking out in this Ferrari 250 GTO in Ohio, 1968

A man sits in the driver's seat of a classic sports car with the door open, parked on grass under large trees in a park-like setting. The car has sleek curves and wire-spoke wheels. The image is in black and white.
proscriptus/via reddit.com

12. This is what NASCAR looked like in the ’60s

Black and white photo of a crowded car race on a curved track, with classic stock cars and grandstands full of spectators in the background. Two lead cars, numbered 4 and 21, are side by side at the front.
hellvis_50s/via reddit.com

13. Annette Strøyberg and Roger Vadim showing off their Ferrari 250 GT, 1960

A woman sits casually on the trunk of a vintage convertible car, while a man in glasses and a t-shirt stands nearby. Trees and old equipment are visible in the background, giving a retro, candid feel.
dtewfik/via reddit.com

14. Muhammad Ali putting a vinyl record into his car record player, 1968

A young man sits in the driver's seat of a vintage car, looking toward the camera while holding the steering wheel. The car's interior and dashboard are clearly visible in the black and white photo.
fluffyfawnxo/via reddit.com

15. Getting ready for a day on the water with a ’61 Chevy Apache Suburban

A vintage light blue and white Chevrolet station wagon is parked on sandy ground near a river, with a man standing beside it. Industrial equipment and a barge are visible on the water in the background.
userdeleted/via reddit.com

16. Taking Dad’s car to prom, 1960s

A young woman in a white prom dress stands by a classic white car as a young man in a white tuxedo jacket and black pants holds the car door open for her. They are outdoors, smiling at each other in the evening light.
chaos_mom/via reddit.com

17. A family trip in the station wagon, 1964

A woman in a floral dress naps in the front seat of a blue car, while three children, two sitting and one lying down, rest or look away in the back seat during a sunny day.
samaelv/via reddit.com

18. Eddie Fisher and Elizabeth Taylor surveying the construction of a film set from Taylor’s Rolls-Royce, 1961

A woman in a pink headscarf and a man sit in a green convertible parked in front of a large building under construction with scaffolding. The scene appears to be from the mid-20th century.
butterfly69/via reddit.com

19. Cary Grant with his 1960 Rolls-Royce Silver Cloud II

A man in a dark coat and sunglasses stands next to a vintage gold and white Rolls-Royce car, parked by a calm lake with trees in the background on a misty day.
j3434/via reddit.com

20. Someone’s grandfather was working as a taxi driver in Brazil, 1961

A man in light-colored clothing and a hat stands with one hand on his hip, leaning against a vintage car parked on a cobblestone street in front of old storefronts. The photo is black and white.
arthur_rs/via reddit.com

Want to see more vintage car content?

Check out 20 of the Coolest Cars From the 1990s, or take a look at The 10 Best-Selling Cars of Each Year in the 1980s. Finally, if you want to see vintage photos of motorcycles from the past, check out 20 Vintage Photos Of Classic Motorcycles And Sidecars (1910s-1950s).

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