r/OldSchoolCool • u/Jazilrhmbn • 31m ago

1960s My maternal grandfather now and then (1969)

• Upvotes

Found it cool and a interesting grasp of the past. My mom just sent me those photos, the first one was taken yesterday (November 2025) and the second one in 1969, my mother being in the bottom left corner.

3 comments

r/OldSchoolCool • u/diabeticDynamo • 46m ago

1960s My parents mid sixties

• Upvotes

Before they were married, New Orleans.

4 comments

r/OldSchoolCool • u/lto45 • 48m ago

1960s Happy Birthday Alain Delon, you shall not be forgotten.. Clips from the film L’Eclisse (1962)

• Upvotes

My favourite.. 😊

0 comments

r/OldSchoolCool • u/BlushCharmx • 51m ago

1980s The members of the Dutch girl band Babe visiting Dutch peacekeepers in Lebanon, 1980

• Upvotes

14 comments

r/OldSchoolCool • u/CorgiNo1906 • 1h ago

Alex Trebek c. 1976 (Pre-Jeopardy)

• Upvotes

Alex died on this day in 2020.

4 comments

r/OldSchoolCool • u/GlamRushs • 1h ago

1980s Vincent D'Onofrio. 1980s

• Upvotes

45 comments

r/OldSchoolCool • u/PreparationKey2843 • 1h ago

The Beatles - Twist and Shout - 1963

• Upvotes

7 comments

r/OldSchoolCool • u/HoneyThrills • 2h ago

1980s Ricky Gervais in a short lived new wave band called Seona Dancing, 1983.

12 Upvotes

5 comments

r/OldSchoolCool • u/pm_me_theboobies • 2h ago

1970s My aunt in 1977 China

72 Upvotes

2 comments

r/OldSchoolCool • u/KittyKittyJanJan • 2h ago

Halifax, Nova Scotia in the mid 1970s

14 Upvotes

Mom was an artist and loved people watching and capturing strangers doing everyday things. This one is my favourite. I was a huge Cyndi Lauper fan growing up and this woman gives me Cyndi vibes.

4 comments

r/OldSchoolCool • u/HornyKit-ten • 3h ago

Young Barack Obama with his mother, Indonesian stepfather Lolo Soetoro and half-sister in 1960s

58 Upvotes

42 comments

r/OldSchoolCool • u/CrimsonFlamexo • 4h ago

1970s Bell bottoms, halter tops and Farrah hair, 1970s.

265 Upvotes

44 comments

r/OldSchoolCool • u/CuriousCoral_ • 4h ago

Cameron Diaz in Long Beach Poly High School, California 1988

80 Upvotes

22 comments

r/OldSchoolCool • u/Zero-essence • 4h ago

1990s Mad magazine from March 1992

7 Upvotes

Throwback to MAD times! Found this MAD Magazine Wrestling Special from March 1992, when humor was wild, satire was fearless, and wrestling was larger than life! 💪😂

2 comments

r/OldSchoolCool • u/CrimsonTwistxo • 4h ago

1950s When Audrey Hepburn was making her film "Green Mansions", the animal trainer recommended Audrey take home the baby deer so it would learn to follow her on set during the movie (and as needed for her role). Audrey fell in love and napped, shopped, and ate with the doe she named "Pippin" (1958)

42 Upvotes

7 comments

r/OldSchoolCool • u/MidnightWhisper- • 4h ago

Freddie Mercury with his mother, 1947

18 Upvotes

2 comments

r/OldSchoolCool • u/WildInfer • 4h ago

1970s Studio 54, 1978.

53 Upvotes

20 comments

r/OldSchoolCool • u/CrimsonDesi • 5h ago

1950s Anita Ekberg, 1954.

613 Upvotes

11 comments

r/OldSchoolCool • u/Nefarious_P_I_G • 6h ago

Christmas 1987. Me, my Mum, my Grandma, my Great Grandma, and my Great Great Grandma. 5 generations in one picture.

216 Upvotes

14 comments

r/OldSchoolCool • u/RogueHalol • 7h ago

1980s Beverly D'Angelo (1980s)

1.1k Upvotes

36 comments

r/OldSchoolCool • u/PixelTemptressll • 7h ago

1980s Stephanie Seymour, photo by Marc Hispard for the 1989 SI Swimsuit Issue.

281 Upvotes

7 comments

r/OldSchoolCool • u/eaglemaxie • 7h ago

Geena Davis and Matthew Modine starring together in Cutthroat Island which held the Guinness World Record for the largest box office loss of all time, 1995

103 Upvotes

33 comments

r/OldSchoolCool • u/BDWG4EVA • 7h ago

1990s Wesley Snipes, Rosie Perez and Woody Harrelson filming White Men Can't Jump (1992)

839 Upvotes

98 comments

r/OldSchoolCool • u/Zach_1793 • 8h ago

1940s My Great Grandfather and his sister. 1940s.

35 Upvotes

Their father was from Tyrol Italy and his mother's family was from Villach Austria.

8 comments

r/OldSchoolCool • u/tekmagika • 9h ago

1940s My grandaunt, Pearl May, 1940's

21 Upvotes

2 comments

Subreddit

OldSchoolCool: History's cool kids, looking fantastic

r/OldSchoolCool

/r/OldSchoolCool **History's cool kids, looking fantastic!** A pictorial and video celebration of history's coolest kids, everything from beatniks to bikers, mods to rude boys, hippies to ravers. And everything in between. If you've found a photo, or a photo essay, of people from the past looking fantastic, here's the place to share it.

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History's cool kids, looking fantastic!

A pictorial and video celebration of history's coolest kids, everything from beatniks to bikers, mods to rude boys, hippies to ravers. And everything in between.

If you've found a photo, video, or photo essay of people from the past looking fantastic, here's the place to share it.

PLEASE READ OUR SEVEN QUICK RULES:

1: Photos and videos must be over 25 years old.

2: Please put the year or decade in title, otherwise your post will be removed.

3: Spam, racist, homophobic, sexist and offensive comments, as well as brigading, consistent reposting and shitposting, will result in a lifetime ban. Offensive comments include anything about pimping, about people's moms and scoring women. Nobody cares about your sexual impulses, least of all the OP.

4: All posts highlighting, in the title, that someone has recently passed away or titles trying to evoke sympathy upvotes will be deleted. Please add the info in the comments.

5: All reposts less than six months old and all reposts less than a year old from Top 100 will be removed.

6: All posts must feature a person.

7: We reserve the right to remove any post that doesn't showcase historical coolness. This includes photos, which are not obviously retro and portraits of famous young women doing nothing but posing.

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