45 Nostalgic Old School Cool Pictures Showing Off Past Generations Height Of Coolness
OldSchoolCool is where the internet goes to collectively say, “Damn, my grandpa was hotter than me.”
It’s a popular subreddit dedicated to vintage photos of people looking effortlessly cool—before smartphones, before filters, before anyone said “vibe check” unironically.
So if you’ve ever looked at an old family photo and thought, “Why did everyone used to dress like a movie star?”—yeah, this is that. But better.
1. “Princess Grace of Monaco visiting JFK at the White House, 1961.”
2. My 3rd Great Grandpa, sometime in the late 1800s.
3. “Mississippi’s First Interracial Couple August 3, 1970”
4. My wife said i couldn’t pull it off (update 6 years in the making) circa 1990 and now.
5. “Pedro Pascal with his family in 1991”
6. Ella Fitzgerald arrested after singing to an integrated audience in 1955.
7. Parents first selfie on their new camera (1998)
8. On the Beach, Manhattan, 1977
9. First and only time it snowed in Miami, 1977.
10. My great grandfather in 1926, 23 years old. He snuck into America at age 12 by hiding in a barrel on a Canadian ship.
11. “Pee-Wee Herman in high school, the 1970s”
12. Queen Victoria photobombing her son’s wedding photo by sitting between them wearing full mourning dress and staring at a bust of her dead husband, 1863
13. Elizabeth Hurley, 1990s.
14. My wife when I got home from the Navy in 1994.
15. Susanna Hoffs of the Bangles with her husband Jay Roach (director of the Austin Powers movies) in 1993 and 2020. They have been happily married for 31 years.
16. My grandparents dressed for Halloween 1967.
17. When Johnny Cash introduced the 13 year old singer, Dolly Parton, on the Grand Ole Opry in 1959, she got 3 encores.
18. Kamala Harris in the 80s
19. Eminem and his crew, 1991.
20. Late 1980s. My parents were babes.
21. Mark Hamill and Annie Potts (1978)
22. Biracial Family circa 1900.
23. Hermosa Beach …. summer of 1978.
24. Debbie Harry, 1978.
25. Found in a stack of family photos from the 1970s. No one has a clue who he is and he’s not in any of the other photos.
26. The Estevez Brothers, Emilio Estevez and Charlie Sheen born (Carlos Estevez). Santa Monica High School. Class of 1980 and 1983
27. Ozzy Ozbourne , 1985 (growing his hair back after shaving his head)
28. Negotiations between the zoo director and escaped chimpanzee. Belgrade, Yugoslavia 1988.
29. Penelope Cruz & Salma Hayek at the premiere of Dogma, 1999.
30. Muhammed Ali walks from the courtroom after being sentenced to five years as a concientious objector to the war in Vietnam (1967)
31. Since it’s his birthday today, here’s a picture of 6 year old Robin Williams with his mother Laurie in 1957.
32. Shelley Duvall on the set of Brewster McCloud (1970)
33. An unusual couple on the New York City subway, 1980.
34. Racing Driver James Hunt with model Sue Shaw, November 1973.
35. Racing Driver James Hunt with model Sue Shaw, November 1973.
36. Carrie Fisher, Paul Simon, and Shelley Duvall, 1970s
37. “At my desk hardly working, 1984”
38. Julia Louis Dreyfus with her mom and sister, late 1960s.
39. Chris Cornell with his 5 siblings, circa 1989.
40. My big sis about to head up to college in the family truckster, in 1982
41. Kyle McLachlan and Lara Flynn Boyle, 1990s.
42. Madonna (1995)
43. The Black Panthers protesting outside the California capital. Days later, governor Ronald Reagan would sign the most restrictive gun control laws in US history (1967)
44. Ruth Bader Ginsberg 1953.
45. Christopher Lee with Peter Cushing in 1994.
