35 Nostalgic Throwback Pictures That Define What It Means To Be “Old School Cool”

Dive into the timeless allure of “old school cool” with our collection of nostalgic throwback pictures. These snapshots transport us back to the defining moments and iconic styles of bygone eras, from the elegance of 1950s Hollywood to the rebellious 1970s punk scene, and the vibrant 1990s hip-hop culture.

Each cool image captures the essence of hipness, showcasing fashion, attitudes, and moments that broke ground and continue to influence today. Get ready to revisit the charm and charisma that made these times unforgettable.

Join us on this nostalgic journey, where true coolness is eternal and every photo tells a story of groundbreaking style and unforgettable personalities. Welcome to a celebration of the classic moments that define “old school cool.”

1. Me (far right) and my clique. Florida, USA, 1988.

2. My mom, my grandparents, and my uncle fully embracing the 1970s.

3. Mona Lisa of the Deep: A perfectly preserved daguerreotype of an unknown woman was found in 2014 in the wreck of the SS Central America, 7,200 feet beneath the ocean surface off the coast of South Carolina. The ship went down in 1857 carrying nearly a billion dollars in gold and silver.

4. My grandparents going on their honeymoon in the 50s looking like movie stars.

5. My dad and Steve Martin, Abquaq Saudi Arabia (late 1990).

6. Photo of my dad from the late 70’s, early 80’s? Can’t figure out what his shirt says though!

7. AlanisMorisette & Dave Coulier c. 1992

8. Watkins Glen concert (1973)….not even a broken arm could stop this woman from attending the rock festival in New York.

9. Christie Brinkley & Billy Joel, 1983.

10. Wife with Mid 80’s ski look.

11. My grandmother knew how to party in the 60s!

12. Ryan Dunn and Bam Margera in their High School yearbook, early 90s

13. My Great Grandmother in 1910 at the beach. She was about 28 years old here.

14. My parents before I was born, mid 1980s Arkansas.

15. Kurt Cobain with his girlfriend Tracey, 1980’s

16. This absolute unit of a jawline from Hugo in a 1942 yearbook I found.

17. 40 Years Later – and that’s my original high school jeans jacket.

18. My mom got dressed up and had her cousin/roommate take this photo before her first date with my dad (1981)

19. Hippie dad walking with his daughter. Amsterdam,1968

20. These are my mother’s parents in China around 1948. She married my father and came to America just before Mao Tse-tung took over China. My mother never saw her parents again. They could only write.

21. My grandma as a frog, Halloween 1977 atop her Chrysler Cordova.

22. This is my dad at 18 ,in Vietnam.

23. Sigourney Weaver and Mel Gibson in 1982

24. My 17 year old uncle’s junior yearbook photo in the late 70s.

25. Dick Cavett interviews Raquel Welch on his show in 1972

26. 1987 ski race attire. I was the man! ( or not)

27. Princess Grace of Monaco visits John F. Kennedy at the White House, May 24, 1961

28.

29. C. 1950s. I have been told I look like my grandmother…

30. My grandmother and her ( much younger) boyfriend, 1975.

31. Prince, standing victorious over Charlie Murphy during a game of basketball (1985).

32. GF’s senior prom 1980

33. Heath Ledger’s Polaroid selfie with Larisa Oleynik, Joseph Gordon-Levitt and Julia Stiles on the set of 10 Things I Hate About You. (1999)

34. Me in 1982 at 17 years young

35. My wife in 1984

Mike

Mike Primavera

Mike Primavera is a Chicago-based comedy writer even though he doesn't HAVE to work. He lives comfortably off of his family's pasta fortune. Follow him on all social media at @primawesome