Mike
Get ready for a blast from the past. We’ve gathered the coolest nostalgic old school pictures of past generations at the height of their swagger.
From slick hairdos and iconic fashion to classic cars and legendary hangouts, these snapshots capture the essence of what it truly meant to be “cool” back in the day.
Whether you’re reminiscing about your own glory days or just appreciating the vintage vibe, these pictures will transport you to a time when style was timeless and attitude was everything.
So, kick back, relax, and enjoy this trip down memory lane with the ultimate collection of old school cool.
1. Kamala Harris in the 80s
2. My 3rd Great Grandpa, sometime in the late 1800s.
3. My wife said i couldn’t pull it off (update 6 years in the making) circa 1990 and now.
4. Ella Fitzgerald arrested after singing to an integrated audience in 1955.
5. Parents first selfie on their new camera (1998)
6. On the Beach, Manhattan, 1977
7. First and only time it snowed in Miami, 1977.
8. My great grandfather in 1926, 23 years old. He snuck into America at age 12 by hiding in a barrel on a Canadian ship.
9. 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
10. Elizabeth Hurley, 1990s.
11. My wife when I got home from the Navy in 1994.
12. 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.
13. My grandparents dressed for Halloween 1967.
14. When Johnny Cash introduced the 13 year old singer, Dolly Parton, on the Grand Ole Opry in 1959, she got 3 encores.
15. Eminem and his crew, 1991.
16. Late 1980s. My parents were babes.
17. Mark Hamill and Annie Potts (1978)
18. Biracial Family circa 1900.
19. Hermosa Beach …. summer of 1978.
20. Debbie Harry, 1978.
21. 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.
22. The Estevez Brothers, Emilio Estevez and Charlie Sheen born (Carlos Estevez). Santa Monica High School. Class of 1980 and 1983
23. Ozzy Ozbourne , 1985 (growing his hair back after shaving his head)
24. Negotiations between the zoo director and escaped chimpanzee. Belgrade, Yugoslavia 1988.
25. Penelope Cruz & Salma Hayek at the premiere of Dogma, 1999.
26. Muhammed Ali walks from the courtroom after being sentenced to five years as a concientious objector to the war in Vietnam (1967)
27. Since it’s his birthday today, here’s a picture of 6 year old Robin Williams with his mother Laurie in 1957.
28. Shelley Duvall on the set of Brewster McCloud (1970)
29. An unusual couple on the New York City subway, 1980.
30. Racing Driver James Hunt with model Sue Shaw, November 1973.
31. Racing Driver James Hunt with model Sue Shaw, November 1973.
32. Carrie Fisher, Paul Simon, and Shelley Duvall, 1970s
33. Julia Louis Dreyfus with her mom and sister, late 1960s.
34. Chris Cornell with his 5 siblings, circa 1989.
35. My big sis about to head up to college in the family truckster, in 1982
36. Kyle McLachlan and Lara Flynn Boyle, 1990s.
37. Madonna (1995)
38. 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)
39. Ruth Bader Ginsberg 1953.
40. Christopher Lee with Peter Cushing in 1994.
