Born to Ride: 20 Vintage Motorcycle Photos That Define a Generation

The 1900s were a transformative time for motorcycle culture as the open road became a symbol of freedom, rebellion, and individualism. The rise of biker gangs and the evolution of custom chopper designs marked the beginning of a cultural movement that would resonate for decades. Through these defining moments, the motorcycle became more than just a mode of transportation, it was a statement of independence and a testament to a lifestyle driven by passion, grit, and adventure. This era captured the spirit of those who sought to live on their own terms, forming tight-knit communities and embracing the thrill of the ride. Get ready as we take a look at 20 photos that embody biker culture.

1. Barefoot on a bike, 1977.

Two people sit on a motorcycle in front of a brick wall. The person in front wears sunglasses and is holding the handlebars, while the other person is behind, arms around the first. Both are casually dressed. The scene has a vintage feel.
u/culraid/via reddit

You’d have to be an absolute beast to ride a bike barefoot.

2. He’s riding a bike in a suit, 1950.

A person in a suit is riding a vintage Ariel motorcycle on a city street. The background shows old buildings and a parked car. The motorcycle has a visible license plate with the code "PBH 743." The photo appears to be black and white.
u/careful-prior9639/via reddit

I don’t think a 3-piece suit would give much protection during a fall.

3. The Chosen Few biker gang, 1972.

A group of eleven men wearing leather jackets and hats, posing together with two motorcycles. The men display various expressions and poses, with some wearing patches or badges. The scene is in black and white, suggesting a vintage photo.
via reddit

I love how a few of the guys didn’t get the “be serious” memo.

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4. The Sons of Silence in Colorado, 1971.

Black and white photo of a group of leather-clad bikers posing in front of a worn wooden building. Some sit on the porch steps, while others stand or lean against the walls. A "Friskies" sign is visible above the door.
u/art-man_2018/via reddit

These guys were enemies to the Hell’s Angels.

5. Adeline and Augusta Van Buren, 1916.

Three women pose with vintage motorcycles. Two wear leather riding gear and boots, while the third stands between them in a lace dress and pearls. The image has an old-fashioned, sepia tone, with motorcycles marked "Indian" in the background.
u/eaglemaxie/via reddit

They were the first women to travel across the country on two solo motorcycles.

6. That puppy looks sad that he can’t ride with them.

A vintage photograph shows a smiling woman sitting on a motorcycle with a sidecar, holding a child. A man is seated in the sidecar. A dog sits nearby on the dirt road, and a girl stands in the background near a house surrounded by trees.
u/itsdanbull/via reddit

The guy in the sidecar does not look too pleased.

7. The Tweety bird makes this photo even more menacing.

A man and woman pose confidently next to a motorcycle outside a building. The motorcycle features a cartoon duck on the fuel tank. Both are wearing glasses and casual clothing. The man has a beard and cap, while the woman wears a patterned shirt.
u/4melookc/via reddit

This photo was taken in the ’80s.

8. This biker gang was formed in the 1960s in Oakland.

A group of bikers posing in front of Helen's Bar-B-Que. They are dressed in leather jackets and standing with their motorcycles. A Coca-Cola sign is visible on the building's facade. The ground is dirt, and the atmosphere is casual and lively.
u/anyapetrova/via reddit

The East Bay Dragons MC started as a car club but switched to bikes because they were cheaper.

9. Bikers at a flea market in Buffalo, 1950s.

Two men in vintage clothing sit on classic motorcycles parked outdoors. The man on the left wears a leather jacket and boots, while the man on the right is in a cap and light-colored jacket. Cars are visible in the background.
u/eatnerdlove/via reddit

The HRD bike he’s riding was produced in the 1920s.

10. Biker girls, 1960s.

A black-and-white photo shows a group of people sitting on a row of motorcycles parked on the street. In the foreground, a woman with styled hair sits on one of the bikes, looking at the camera. Others are casually seated, facing right.
u/timtankard/via reddit

The way they’re laying makes it look like you could sleep on your bike.

11. Glasgow bikers, 1970.

A group of people sitting on motorcycles in front of a store with a "Dairy & Groceries" sign. The scene appears vintage, with the riders dressed in casual, retro attire, and the motorcycles parked in a line on the street.
u/sidandfinancy/via reddit

I always thought dairy was considered a grocery.

12. That’s definitely a crew I wouldn’t mess with.

A group of people sit on motorcycles gathered in front of a building. The scene includes individuals with long hair and beards, wearing casual clothing like denim and graphic tees, evoking a biker culture atmosphere.
u/donnydiamondazoff/via reddit

I can’t look at this photo without wondering how much oil was spilled in front of this restaurant.

13. Eddie Davenport is celebrating the 4th of July, 1947.

A man sits casually on a motorcycle in a street at night, holding a bottle. Broken glass is scattered on the ground beneath the bike. Another man stands nearby, leaning against a building with striped awnings. The photo is in black and white.
u/forbuss903/via reddit

Sources say that the antics of bikers this weekend were the reason for the Marlon Brando film ‘The Wild One’.

14. Taking a break in Baltimore, 1973.

A group of five young men pose with motorcycles in a shaded outdoor area. Some are shirtless, and two are seated on bikes. Trees and parked cars are visible in the background. One motorcycle helmet has an American flag design.
u/taxitaxitaxi33/via reddit

That’s too much cool to put into one photo.

15. Martha Stewart on her bike, 1990.

A person with short hair sits on a Harley-Davidson motorcycle, wearing a black outfit. They are parked on a gravel path, with a brick wall and open gate in the background, and trees surrounding them. The sky is clear and blue.
u/yacineyahioune/via reddit

Martha has a swagger that no one else can match.

16. Funny Sonny flying his patch on the back of an Outlaw’s bike, 1965.

Two people ride a motorcycle. The front rider wears a helmet with a spike and has a dark vest. The back rider is looking back, smiling with an exaggerated expression, wearing a similar vest. The background shows a grassy area and people in the distance.
u/ryansmith/via reddit

It’s a risky business, flying a patch like that.

17. Biker rally in Los Angeles, 1949.

Three people in a vintage setting: two sit on motorcycles while a woman in a bikini top and shorts stands smoking. The scene is outdoors with bikes and people in the background, suggesting a biker gathering.
u/matteljones/via reddit

How do bikers find out about rallies? Is there some biker call list or something?

18. Some members of the most notorious biker gang ever known, 1967.

A group of seven people posed with motorcycles against a plain background. Some are sitting on the bikes, while others are leaning or standing. They are wearing casual, rugged clothing and sunglasses, exuding a rebellious, laid-back attitude. Black and white photo.
via reddit

The oil coming out of that pan is diabolical.

19. Now, this is a gang that would make me walk the other way.

Three kids wearing sunglasses ride bicycles on a city street. They are dressed in denim and appear playful and confident, striking cool poses for the photo. The background features buildings and parked cars.
via reddit

That one guy on the right is ready to throw a punch.

20. A biker gang riding through Tokyo.

A young man and woman ride a motorcycle on a city street, both wearing leather jackets. The woman sits behind, holding onto the man. Other motorcyclists are blurred in motion, indicating speed. Buildings and a fence line the background.
u/eaglemaxie/via reddit

The guy’s legs look like his passengers.