60 Photos From the ’60s That Are Pure ‘Old School Cool’

All aboard! Our time machine is set for the 1960s! We’re going to be touring the entire decade rather than getting too focused on the summer of love or Beatles mania. We’ve assembled a list of what we think was extremely cool, stylish, or just undeniably 1960s. As always, we’ve included some celebrities, but we tried to share some of the focus on what life was like for ‘the rest of us.’ Buckle up, and I hope you enjoy it!

1. “Clint Eastwood circa late 60s”

A black and white photo of a man in a suit and open-collared shirt smiling as he walks down a busy street. Behind him, a man rides a Vespa scooter, and several cars, including a vintage Volkswagen Beetle, are visible. The street is lined with tall buildings.
u/GroovinWithaPict / Via reddit.com

2. “Debutante ball. Harlem, early 60s”

A black-and-white photo depicts a line of young men and women, dressed in formal attire, paired off and facing each other, holding hands. The women are in white gowns while the men wear dark suits and bow ties. They appear to be participating in a formal dance or event.
u/Big_Shot_Gangster / Via reddit.com

3. “A man being a man in the 60s”

Black and white photo of two men marching in the street wearing placards that read "I Am A Man." In the background, there is an armored military vehicle and several soldiers standing atop it. Additional onlookers and buildings are visible in the background.
via Imgur

4. “My mom’s senior picture in the late 60s.”

A black and white portrait of a woman with a large, voluminous hairstyle. She has a fringe (bangs) and is smiling. She is wearing an off-the-shoulder top with floral details. The background is plain and blurred.
u/ry_fi / Via reddit.com

5. “My uncle Jim showing off his Christmas present. Vinyl for a ’60s pop group.”

A young boy sits in a plaid armchair, smiling while holding a vinyl record album. Wrapping paper and opened presents, including clothes, surround him on the floor. Framed pictures decorate the wall behind him, and a coat hangs from the back of the chair.
u/Marty1966 / Via reddit.com

6. “A culture clash in London in the 60s”

A black and white photograph showing an elderly man wearing a bowler hat and using a cane, appearing to dance on a city street. Two young women, dressed in 1960s fashion, are smiling and enjoying his performance in front of a grand building with large columns.
u/chillin10101 / Via reddit.com

7. “My hippie mother holding someone’s pet raccoon sometime in the late 60s”

A smiling woman with long hair holds a raccoon in her arms. They are outdoors near a street with buildings and signs visible in the background. The woman is dressed in casual clothing, and the raccoon appears calm and content.
matthewsteez / Via reddit.com

8. “Johnny Cash, 1961”

A man in a black suit and white shirt stands outside, leaning on a wooden railing with a serious expression. A cross and part of a church with a steep roof are visible in the background against a clear blue sky.
Justsoinsane / Via reddit.com

9. “My mom sometime in the 60s”

A woman with dark hair stands outside in front of a bush and trees on a sunny day. She is wearing a sleeveless, floral-patterned dress and white knee-high boots. A quiet suburban street is visible in the background.
u/Mickey67Mouse / Via reddit.com

10. “Hippie Dad walking with his daughter. Amsterdam, 1968”

A man with long hair wearing a patterned vest and bell-bottom pants walks beside a young child with curly hair, who is holding a bottle. The scene is outdoors, with trees and bushes in the background. The image is in black and white.
Corpsman223 / Via reddit.com

11. “At the grocery store in 1962”

A smiling male cashier, wearing glasses and a white uniform, stands behind an old-fashioned cash register in a grocery store. On the counter are a large watermelon, a can of Jitney Jungle Coffee, two soup cans, and other items.
foofoofum / Via reddit.com

12. “Martha Stewart in the 60s”

A young woman with short brown hair is sitting and smiling while holding and reading a newspaper. She is wearing a light blue top and is seated in what appears to be a train or subway with a window behind her.
u/RickyKelley / Via reddit.com

13. “Disneyland used to have mermaids (1962)”

Four women dressed as mermaids sit on rocks in a body of water, smiling and waving. They have mermaid tails and are wearing tops that match the tails. In the background, a submarine with the name "Ethan Allen" can be seen near a rocky shore.
carmensax / via reddit.com

14. “Groovy 60s”

A group of women are standing and sitting on large concrete steps. They are dressed in various colored plaid skirts, knee-high socks, and solid-colored tops. Their attire and hairstyles suggest a vintage or retro fashion style. The setting appears to be an outdoor area.
u/userdeleted / Via reddit.com

15. “Louis Armstrong signs a teen with a mohawk in France in 1961.”

A black and white photo of two men. The man on the right, dressed in a suit with a bow tie, appears to be drawing on the shaved head of the man on the left with a writing instrument. The man on the left leans forward, smiling. People are in the background.
Mademma12 / Via reddit.com

16. “Nasa before PowerPoint in 1961”

Six men in white shirts and ties are positioned around a large blackboard filled with complex mathematical equations, diagrams, and formulas. Three sit on stepladders, two stand on ladders, and one kneels on the ground.
Via imgur

17. “Dolly Parton in the late 60s”

Black and white photo of a woman with styled wavy hair, smiling directly at the camera. She is wearing a light-colored top with a patterned design and earrings. The background features vertical drapes.
u/and-thats-the-truth / Via reddit.com

18. “My dad and his pet monkey in Vietnam, 1966.”

A shirtless man, smiling, holds a small monkey in his arms. The man appears to be outside, standing in front of a tent and various items including a chair and a pile of sandbags. The environment looks like a camp or outdoor site.
matthewlarn / via reddit.com

19. “1962, my first day of Kindergarten and I was very nervous!”

A young boy stands on brick steps in front of a house. He's wearing a short-sleeve shirt, cuffed jeans, and sneakers. His hair is neatly combed, and he has a slight smile on his face. The background includes part of a wall, a doorway, and some foliage.
cwaqers / Via reddit.com

20. “Linda Ronstadt in 1968”

Black and white photo of a young woman sitting on a bed, smiling and holding a cup. She has long hair and is wearing a short dress, large hoop earrings, and tall boots. Behind her, there is an old-fashioned TV.
OneLaneHwy / Via reddit.com

21. “A selfie from 1966 of George Harrison in India”

A person wearing sunglasses and a light pink shirt takes a selfie in front of the Taj Mahal. The iconic white marble mausoleum and its symmetrical minarets are visible in the background, with a reflective pool and surrounding gardens in the foreground.
MissLouisiana / Via reddit.com

22. “Bruce Lee with his master Ip Man in the 60s”

A vintage photo showing two men standing side by side. The older man on the left wears traditional loose-fitting, light-colored Chinese attire, while the younger man on the right wears a short-sleeve, button-up shirt with dark trousers. They are posing against a plain backdrop.
u/userdeleted / via reddit.com

23. “London Pub in 1967”

A stylish woman in a pink skirt and knee-high boots drinks beer by a bar's window. Nearby, two women and a man enjoy drinks at a small table. Another woman stands and chats with a man by a doorway. The scene captures a vintage, lively social atmosphere.
deathakissaway / via reddit.com

24. “The Supremes in 1968”

Three women are seated on a green sofa in a room with a curtained window. The woman on the left wears a yellow dress, the middle one a light blue outfit with a white beret, and the right one a black and white checkered dress. They all have stylish hairstyles.
Admiral37 / Via reddit.com

25. “Cashiers at the Piggly Wiggly supermarket in Encino, California in 1962”

Black and white photo of a grocery store with multiple female cashiers in uniform standing behind registers in a row. The store has a high ceiling and appears spacious. A sign reading "PASTRIES" is visible in the background and there are shoppers in the distance.
wearethebaddies / Via reddit.com

26. “Audrey Hepburn, 1961”

A woman with long hair smiling gently while holding a fawn close to her face. The fawn is nuzzling against her, and the scene is illuminated softly, creating a warm and intimate atmosphere. The image is in black and white.
princessbananas85 / Via reddit.com

27. “Hotdog stand in New York in 1963”

A man in a white apron and white attire stands in front of a makeshift food stall decorated with colorful bunting. Behind him, a person is seated and another is partially visible. Crates of Pepsi surround the stall. The background shows a busy street and buildings.
sussouththemoon / Via reddit.com

28. “Betty White’s smile in 1963”

A woman with short brown hair in a colorful floral dress sits smiling behind a desk on a game show set. To her left, a man in a suit is partially visible. Nameplates in front of them read "BETTY WHITE" and "GEORGE KIRGO.
dittidot / via reddit.com

29. “Tim Burton’s Halloween costume in 1967”

A person in a vintage skeleton costume stands outside on a sunny day. The costume features a black outfit with white bone designs and a round, pumpkin-like head with painted eyes, nose, and a mouth. Trees and a house are visible in the background.
kyleskate / Via reddit.com

30. “American Airlines stewardess in 1967”

A flight attendant in a vintage uniform sits on a chair inside an aircraft. She wears a white dress with rolled sleeves, a stylish belt with red and blue stripes, white shoes, and a small pair of wings pin on her chest. Her hair is tied back with white hair accessories.
onepersononeidea / via reddit.com

31. “Jeff Goldblum on a family vacation in Miami in the early 60s”

A young person with glasses, wearing a navy blue t-shirt and checkered shorts, sits by a decorative pond with a fountain. In the background, there are palm trees and a building. The day appears sunny and bright.
dobbyisafreepup / Via reddit.com

32. “Dr. Martin Luther King Jr. in Jamaica in 1967”

MLK Jr. standing in a swimming pool with water up to his chest. He has a relaxed expression and appears to be enjoying the water. The pool water is clear and blue. The background shows part of the pool’s edge.
Blunt_Force20 / Via reddit.com

33. “New York, 1961”

A black and white photograph depicts a stylishly dressed woman and man crossing a busy urban street. The woman wears a fitted dress and hat, accessorized with gloves and a bag. The man, wearing a suit and hat, holds an umbrella. Vintage cars and buildings are visible.
Harambememberberries / Via reddit.com

34. “My mum market shopping in Hong Kong in 1966”

A woman with red hair, wearing a blue sleeveless dress with white trim and a pearl necklace, pushes a white frame overgrowth of potted plants. A young girl with blonde hair is beside her, and a woman with dark hair stands behind them, partially visible.
barriedalenick / via reddit.com

35. “Bobby Fischer playing 50 opponents simultaneously in 1964.”

A man is playing multiple games of chess simultaneously in a large, crowded hall. Numerous spectators and players are gathered around several rows of chess tables, observing the intense match. The room is filled with focused attention and strategic gameplay.
via imgur

36. “The inventor of the Lava Lamp with his wife in 1963.”

A man and woman stand beside a yellow van that has an advertisement for "The Sensational Astro Lamp" printed on its side. The man, dressed in a suit, has his arm around the woman, who is wearing a fur coat. The van’s license plate reads "845 RHY.
userdeleted / Via reddit.com

37. “Steven McQueen in his Jaguar in 1963.”

Black and white photo of a person driving a vintage convertible sports car, with text "JNH 809" on the license plate. The person is wearing sunglasses and looking back over their shoulder. Buildings and an external staircase are visible in the background.
via imgur

38. “My grandfather in 1967 with the 101st Airborne Division”

A soldier stands in front of a U.S. Air Force aircraft, wearing a helmet with the number 119 and a parachute on his back. He is dressed in military fatigues and looks into the camera, his right hand holding a strap of his gear. A "101st Airborne" patch is visible on his sleeve.
userdeleted / via reddit.com

39. “Daniel Elmore, a 72-year-old handyman, being congratulated by two of his daughters on graduation. All 10 of his 10 children got college degrees. 1964”

A black and white photo shows a graduate, wearing a cap and gown, being hugged by two women on either side. They all smile joyfully. The background is plain and a white chair is partially visible behind the woman on the right.
Ninjakick / Via reddit.com

40. “My brother dressed as a robot in February of 1965”

A black-and-white photo from February 1965 shows a child in a homemade robot costume. The outfit consists of a bucket helmet, cylindrical arms, and body made from tin cans and other metal parts. The child stands with arms raised in front of a house with a brick wall and bushes.
Geo-USA / Via reddit.com

41. “Stephen Hawking and his wife in 1964”

A man with glasses and a dark blazer stands next to a woman dressed in a black dress with a red long-sleeve shirt. They are holding hands and smiling while standing in a doorway. The setting appears to be the entrance of a brick house.
arsenalFC8 / Via reddit.com

42. “Disneyland ticket booth in 1962”

A group of people stands in line at an outdoor ticket booth. One person is purchasing tickets from the clerk behind the booth window. A price board lists different admission and ticket book options for adults and children. A bridge structure is visible in the background.
foofoofum / Via reddit.com

43. “Frank Sinatra exiting a helicopter with a drink in hand in 1964.”

A man dressed in a suit and tie steps out of a helicopter, holding a drink in one hand and the helicopter door in the other. He is smiling, and the helicopter is parked on a rooftop with various industrial structures in the background.
grizzly_atoms / Via reddit.com

44. “7-year-old George Clooney in 1968”

A black and white photo shows a man, a woman, a boy, and a girl sitting together at a table. The man and woman are smiling at the children. On the table are some plates and a glass. The family seems happy and engaged in conversation.
towhomnotwho / Via reddit.com

45. “My dad working at the original Tower Records in Sacramento, California in 1964.”

Black and white photo showing a woman and a child at a record store counter. The woman is in a patterned dress, the child looks towards the camera, and the clerk is a man in glasses and a plaid shirt. The store has shelves of records and some hanging clothing.
via Imgur

46. “You’ll never be ‘John Glenn just orbited the earth and landed in the Atlantic Ocean’ cool. 1962.”

A person wearing a NASA uniform and sunglasses relaxes on a chair aboard a ship, with legs crossed and feet propped up on a railing. They hold a cup, leaning back comfortably. In the background, there's part of the ship and water.
frankie_fresh / Via reddit.com

47. “My excited grandmother kissing her ticket to a Beatles concert in 1964”

A woman with blonde hair holds a ticket close to her face, partially obscuring her mouth. She is wearing a light-colored top and a coat, and she has a radio or similar device strapped to her shoulder. The image has a vintage feel.
toledoheelock / Via reddit.com

48. “The Paramount Pictures logo on the day it was originally painted in 1965”

A man stands beside an easel holding a completed painting. The painting depicts a serene landscape with a towering snow-capped mountain reflected in a tranquil lake, surrounded by rolling green hills under a sky dotted with fluffy clouds. The man has curly hair and wears a striped shirt and apron, with arms crossed.
userdeleted / Via reddit.com

49. “It was 1965. I was 21, and I had a hot new Mustang. I thought I was cool.”

A man squats next to a red vintage Ford Mustang car on a residential street. He is wearing a green cardigan over a striped shirt, dark pants, and brown shoes. Trees and houses are visible in the background. His expression is contemplative.
La_Lanterne_Rouge / Via redit.com

50. “Paul Reubens (PeeWee) in 1967”

Black and white portrait of a young person with short hair, wearing glasses, a dark suit jacket, and a tie. The expression is neutral, and the background is plain. The photo appears vintage, likely from the mid-20th century.
Inglorious / Via reddit.com

51. “My parents in 1963”

Two black-and-white portrait photographs side-by-side. The photo on the left features a person with short, dark hair touching their face and wearing a light-colored coat. The photo on the right shows a person with short, dark hair wearing a dark suit and tie.
Sticky-Wicked / Via reddit.com

52. “Man experiences irony in 1966”

A man sits on the rear of an overloaded pickup truck, which is stacked high with a large, tightly packed collection of tires. The truck appears weighed down, with the rear end near the ground. The scene is set on the side of a rural road with open fields.
act1989 / Via reddit.com

53. “Farmer in South Korea in 1965”

A person stands facing the camera wearing a large conical woven hat that obscures their face, a dark robe, and a light-colored undergarment. The background is a rural landscape with blurred, thatched-roof structures and greenery visible.
Kornichon / Via reddit.com

54. “My grandfather embarrassing my grandmother in 1965”

A man in a suit stands with one hand on his chest and the other arm extended, speaking or singing passionately in a room with several seated people. Two women cover their faces while another man and woman look on. Bottles and glasses are on the tables in front of them.
J_P_Olofsson / Via reddit.com

55. “Date night 1960. Mom and Dad at 22-years-old”

A sepia-toned photograph shows a man and a woman. The man, dressed in a suit and tie, is smiling and facing the woman. The woman, wearing a light-colored dress, is smiling at the camera. They are indoors, and there are plants in the background.
llamadogmama / via reddit.com

56. “My grandmother as a teenager, posing on a motorcycle in the 60s”

A woman with long hair, dressed in a red jacket and white pants, is sitting on a vintage Honda motorcycle. The background features a dirt road, an open field, and a distant cow. The scene appears to be a sunny day in a rural area.
AtypicalAshley / via reddit.com

57. “Ray Charles and Stevie Wonder in Detroit in 1962”

Two men in suits and sunglasses stand together, smiling and holding hands. One man is holding a pair of drumsticks, while the other wears a suit with a contrasting lapel. They appear to be enjoying each other's company in a well-lit, indoor setting.
tonyiommi70 / Via reddit.com

58. “A skateboarder in Central Park in 1965”

A man in a suit and hat skateboards down a park pathway. He is balancing confidently while the skateboard tilts to the left. In the background, a crowd of people stands and sits on the grass, watching him. Trees line the path, and it appears to be a sunny day.
Gandalf_The / Via Reddit.com

59. “Patrick Stewart at the age of 23 in 1963”

A man in a suit and tie is working with an electronic device, holding a tool and what appears to be a spool or component. There is a clothesline with hanging laundry in the background. He has a serious expression and is positioned in an indoor setting.
K1nsey6 / Via reddit.com

60. “Down on his peanut farm, future-president Jimmy Carter (1960)”

A black and white photo shows a smiling man in a flannel shirt sitting on a tractor, holding the steering wheel. Two boys stand behind him, one on each side, both dressed in casual clothes. They are outdoors with a wooden structure and trailer visible in the background.
act1989 / Via reddit.com

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