Old School Skateboarding Captured in 20 Vintage Photos

Sports March 27, 2025

Before there were big skateparks and sponsorships for those select skaters deemed fit for the life-altering moment, street skating existed as a raw and rebellious expression of freedom and creativity. In the early days of street skating, skaters would carve through city streets using all the curbs, staircases, and sidewalks they could as their playground. These vintage photos capture the infectious essence of those pioneering years of street skating.

1. Mark Gonzales, one of the pioneers of street skateboarding,(1984)

A skateboarder performs an aerial trick at a skatepark, holding the board with one hand. The skateboard has a graphic design on its underside. The scene is captured in black and white, with trees and a clear sky in the background.
internaloutdoors

2. 1980’s Tony Hawk at a local skate park

A skateboarder with a blue shirt and shorts stands by a chain-link fence holding a skateboard. The fence is lined with excited fans holding skateboards and clothing, reaching over. Grass and a clear sky are in the background.
redcobra762

3. Farrah Fawcett out enjoying her skateboarding

A person with wavy blonde hair is skateboarding on a road. They are wearing a red shirt, blue jeans, and white sneakers. Their arms are outstretched for balance, and they're smiling while looking back. The background shows trees.
tostost

4. Skateboarding in New York City, 1965

Four people skateboard down a city street lined with parked vintage cars on both sides. A truck is nearby. They appear focused and are enjoying the ride. The buildings in the background indicate an urban setting. The photo is in black and white.
redditsagranfaloon

5. Ellen O’Neill, champion freestyle skateboarder (1970s)

A person skateboarding on a sidewalk in a park setting. They are wearing a blue shirt and yellow shorts and are balancing on one leg while the other leg is extended. The background shows grass, a tree, and people in the distance.
denncity

6. Another shot of Ellen O’Neill just bringing the heat

A person skateboards downhill on a paved road. They have arms outstretched for balance, wearing a light blue sweater, floral shorts, knee-high socks, and sneakers. The background features dry, rocky terrain under a clear sky.
annamiapia

7. Kids skateboarding in New York City, 1965

A group of young people is skateboarding on a city street. In the foreground, a boy in a jacket crouches on his skateboard, while another boy in a sweater rides with him. The background shows a blurred street scene with parked cars and buildings.
morallycheck953

8. Skateboarding legend, Ellen O’Neal going freestyle (1977)

A person with long hair jumps over a high bar outdoors, with a skateboard below them. The background features a hillside and trees. The image is in black and white, giving it a vintage feel.
bossinternetking

9. Bam Margera riding his first skateboard (1988)

A young boy skateboards down a driveway. He is wearing a blue jacket, striped shirt, and jeans, with red Converse shoes. A white car is parked nearby, and there is greenery and a house in the background.
chrisburke

10. Freestyle skateboarding legend Kevin Harris showing off his moves to his family at his own wedding, 1983

A groom in a suit performs a skateboard trick indoors at a wedding reception. The bride in a gown stands nearby, surrounded by clapping guests. The setting is decorated with streamers, and there's an EXIT sign in the background.
raininkarpz

11. Tony Hawk, 1980

A skateboarder in a red shirt and helmet performs an upside-down handstand trick at a skatepark. The skateboard is held by one foot, with a clear sky and trees in the background.
tdognola

12. Jeff Jones jumping his skateboard over a Beetle in 1987

A skateboarder performs an aerial trick over a vintage car while a crowd watches. The skateboarder wears gloves and a tank top, and the crowd appears excited and cheering. A person in a cap gestures enthusiastically. A driver watches from the car.
northhiker

13. Clint Eastwood skateboarding through Rome in 1965

A person in a suit rides a skateboard down a busy street, smiling, with classic cars and a bustling city backdrop. The scene is in black and white, giving it a vintage feel.
farfarawayinrome

14. This dapper stranger is far cooler than the rest of us can ever hope to be

A person in a suit and sunglasses is skateboarding barefoot down a road, holding a briefcase in one hand. The background shows grassy and rocky terrain.
target2

15. Jodie Foster riding a skateboard in Paris in the 70s

A person skateboards on a path with the Eiffel Tower in the background. They are wearing a graphic t-shirt and jeans, balancing with arms outstretched. The scene captures movement and an iconic Parisian landmark on a cloudy day.
allgoodthings96

16. A skateboarder in Central Park, 1960

A man in a suit and hat skateboards down a tree-lined path. People gather on either side, some taking photos and others watching. The image is in black and white, giving it a vintage feel.
gandalfthegreat

17. Eazy-E skateboarding (1989)

A person skateboards at a busy outdoor skate park. They wear a dark jacket, light pants, and a cap, with palm trees and people walking and skating in the background. The scene is lively and energetic.
starkfr

18. Rodney Mullen, 1985

A shirtless skateboarder in floral shorts performs a trick on a wooden ramp. He wears knee pads and high-top sneakers. An old car and industrial buildings are in the background, with a clear sky overhead.
deleted

19. Skate scene in Croatia, Zagreb after the war

A skateboarder performs a trick on stairs in a lively urban setting, surrounded by a crowd of observers. Some people are sitting on a ledge, while others stand nearby. Trees and buildings are visible in the background.
barro79

20. Skateboarding in the shadow of the Eiffel Tower, Paris 1976

A black and white photo of a skateboarder performing a trick on a half-pipe in front of the Eiffel Tower. Spectators, many sitting on skateboards, watch the action. The sky is partly cloudy.
tg803
Tags:

About Author

You May Also Like

Left image: A man in a t-shirt sits and laughs, resting his arm on a chair. Right image: Two baseball players in Braves uniforms stand together, one wearing a hat, with a stadium crowd in the background.
Sports Celebrity
17 Photos of Home Run Hitting Legend Hank Aaron
Vintage Basketball photos - Left: A basketball player celebrates with arms raised, confetti around him, wearing a Texas Tech jersey. Right: Two basketball players walk together smiling; one wears a blazer, the other an NBA uniform with number 23.
All Nostalgia Sports
35 Vintage Photos From the Golden Era of Basketball