Step into a time machine and prepare to be wowed by the effortlessly cool vibes of past generations!
We’ve gathered the most nostalgic old school cool pictures that showcase people at the absolute height of their coolness. From slick hairstyles and iconic fashion to classic cars and timeless swagger, these nostalgic snapshots capture a world where style was king and confidence was off the charts.
Whether you’re looking to relive the good old days or just appreciate some vintage flair, these photos are a reminder that cool never goes out of style. So, sit back and enjoy a blast from the past that’s dripping with pure, unfiltered coolness!
1. Parents doing college homework together 1993
Old School Cool – Reddit
2. Prince William took this photo of his mom, Princess Diana, in 1989 when he was 7 years old.
Old School Cool – Reddit
3. My parents when they first started dating. Circa 1990
Old School Cool – Reddit
4. My Mother and Father, 1974
Old School Cool – Reddit
5. Is The “Dream Team” Still The Greatest International Basketball Team Ever Assembled? (1992)
Old School Cool – Reddit
6. Keanu Reeves hanging out with a homeless man in West Hollywood (1997)
Old School Cool – Reddit
7. My Great Grandmother (center) with some of her friends, Middle School, Illinois, 1956
Old School Cool – Reddit
8. Dance teacher Patsy Swayze, center, with her daughter-in-law Lisa Niemi and son Patrick Swayze, 1978
Old School Cool – Reddit
9. August 1995, croatian soldier Marijan Horvat and his then girlfriend, now wife, Ira
Old School Cool – Reddit
10. In 1994, Jim Carrey ruled the world. Can you think of any actor/actress in history that had a better year???
Old School Cool – Reddit
11. My wife and I in 1993 two days after we were married.
Old School Cool – Reddit
12. Johnny Depp’s notorious 90s rock nightclub “The Viper Room”
Old School Cool – Reddit
13. Arnold Schwarzenegger and Linda Hamilton posing their biceps (1991)
Old School Cool – Reddit
14. Sandra Bullock and Keanu reeves in 1996
Old School Cool – Reddit
15. “When I turn 33, I’ll retire. That’s the time when a man has to dedicate himself to other things. I don’t want to be a rock star all my life.” ~ Mick Jagger, 1972
Old School Cool – Reddit
16. Paramount Pictures, Hollywood Stars Group Photo 1987
Old School Cool – Reddit
17. Behind the scenes on the set of Dazed and Confused (1993)
Old School Cool – Reddit
18. Wes Anderson and Owen Wilson running out of the studio after signing the contract for their first film – 1992
Old School Cool – Reddit
19. Attractive parents? Here’s mine. Early 90’s.
Old School Cool – Reddit
20. Black and White, together, 1950’s.
Old School Cool – Reddit
21. George Carlin and Kevin Smith (1999)
Old School Cool – Reddit
22. My grandfather 16 years old.
Old School Cool – Reddit
23. Gillian Anderson, on the set of “The X-Files”, 1990s
Old School Cool – Reddit
24. This is what Las Vegas looked like in 1895.
Old School Cool – Reddit
25. Kate Bush, 1978
Old School Cool – Reddit
26. Sally Field, circa 1970.
Old School Cool – Reddit
27. John Candy and his daughter Jennifer, 1983
Old School Cool – Reddit
28. A rare photo of actress and inventor Hedy Lamarr at 55 years old, after her first facelift, 1968
Old School Cool – Reddit
29. Rhona Mitra posing as Lara Croft, 1990s
Old School Cool – Reddit
30. A customer using the Internet at Burger King, 1998
Old School Cool – Reddit
31. Dolly Parton in the 70’s, offstage, relaxed, and looking simply angelic.
Old School Cool – Reddit
32. Brad Pitt’s Senior Prom Photo at Kickapoo High School in Springfield, Missouri, 1981.
Old School Cool – Reddit
33. My aunt in 1972
Old School Cool – Reddit
34. On August 13th 1969
Old School Cool – Reddit
35. My dad drinking a cup of coffee from the thermos while reading the map to see where they should head (1991)
Old School Cool – Reddit
36.
Old School Cool – Reddit
37. My dad at his 20’s – 1990/91
Old School Cool – Reddit
38. Behind the scenes on the set of Dazed and Confused (1993)
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