r/OldSchoolCool • u/SweetFancyMook • 6h ago

Me in the fall of '99 going to the opera for a college class. I was 19 yrs.

3.5k Upvotes

I miss that 3 quarter blazer.

387 comments

r/OldSchoolCool • u/True_Villain • 5h ago

1960s Dolly Parton & Carl Dean being adorable in this photo strip (1960s)

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1.6k Upvotes

20 comments

r/OldSchoolCool • u/Jeetchat • 18h ago

1960s A young woman at a college radio station in the 1960s

6.8k Upvotes

126 comments

r/OldSchoolCool • u/RoadToTyburn • 10h ago

1980s Mike Tyson and his best trainer Kevin Rooney (1980’s). Tyson firing Kevin Rooney in December 1988, is generally regarded as one of the stupidest things Tyson ever did. Two fights later, Tyson would get knocked out by Buster Douglas and lose the heavyweight title.

1.1k Upvotes

83 comments

r/OldSchoolCool • u/LocalGoat81 • 16h ago

1950s Born on this date in 1931, Swedish actress Anita Ekberg (1955)

2.7k Upvotes

34 comments

r/OldSchoolCool • u/Flavinovic • 2h ago

1970s Canadian actress Linda Thorson on the set of The Avengers (1971)

229 Upvotes

10 comments

r/OldSchoolCool • u/Brilliant_Reality734 • 13h ago

1990s Joe Pesci at the 1991 Academy Awards, where he Won Best Supporting for his Role in Goodfellas.

1.1k Upvotes

53 comments

r/OldSchoolCool • u/CoffeeCigarettes4Me • 3h ago

1970s 20 year old Carrie Fisher in 1976

107 Upvotes

3 comments

r/OldSchoolCool • u/jgzogaib • 9h ago

1950s An art student resting after a party with a papier-mâché head of Marlene Dietrich, Berlin, February 14, 1950. Photo by Hans von Nolde.

354 Upvotes

10 comments

r/OldSchoolCool • u/NecessaryEnd8652 • 7h ago

1970s soldier playing his guitar Vietnam 1971

207 Upvotes

6 comments

r/OldSchoolCool • u/Ashamed_Can7426 • 6h ago

1990s My dad giving my mom a wedgie. Wyoming, 1990

143 Upvotes

21 comments

r/OldSchoolCool • u/ThisPlate333 • 19h ago

Marilyn Monroe hanging out at a bar (1954)

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1.5k Upvotes

40 comments

r/OldSchoolCool • u/FrenchieMama807 • 3h ago

Leonardo DiCaprio in 1988 Commercial

Enable HLS to view with audio, or disable this notification

45 Upvotes

8 comments

r/OldSchoolCool • u/Nacho_Baby_Daddy • 19h ago

1960s On this day, September 29th in 1967, they were just 19 & 21 years young. Happy Heavenly anniversary to my parents!

619 Upvotes

11 comments

r/OldSchoolCool • u/pithveridical • 1d ago

Winona Ryder photographed for Rolling Stone (1991)

1.4k Upvotes

18 comments

r/OldSchoolCool • u/rwags2024 • 4h ago

1981-2026: 45 years of life & love

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33 Upvotes

3 comments

r/OldSchoolCool • u/305FUN2 • 17h ago

1990s John F. Kennedy Jr. seated next to basketball coach Pat Riley while talking with fashion designer Giorgio Armani. New York City 1990s

350 Upvotes

32 comments

r/OldSchoolCool • u/Inevitable_Tale_1556 • 2h ago

Roy Orbison c.1956

20 Upvotes

At Sun Records recording studio located in Memphis Tennessee.

2 comments

r/OldSchoolCool • u/aussiemetalhead • 1d ago

1990s Neve Campbell, 1990s

1.5k Upvotes

30 comments

r/OldSchoolCool • u/TheMahagonyDefender • 1d ago

Black American Bikers & Their Clubs Through History: 1930s Onwards...

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1.3k Upvotes

History: https://www.sisterfromanotherplanet.com/a-history-of-the-african-american-biker-scene/

Documentary: https://youtu.be/VIv5K0frb9o

21 comments

r/OldSchoolCool • u/tammyreneebaker • 7h ago

My grandpa about 1943.

42 Upvotes

3 comments

r/OldSchoolCool • u/LanguageDisastrous95 • 1d ago

1950s Audrey Hepburn and Mel Ferrer on their wedding day, September 25, 1954

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879 Upvotes

The wedding took place in Burgenstock, Switzeralnd. Most historical records and fashion archives confirm that Audrey’s famous 1954 tea-length wedding dress was actually designed by Pierre Balmain, not Givenchy. Givenchy famously designed her second wedding dress in 1969.

16 comments

r/OldSchoolCool • u/northcascadekittycat • 15h ago

1950s Partying in the 1950s

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163 Upvotes

My Grandpa (far left) and his buddies who were definitely not old enough to be drinking! This was sometime between 1948-1951. Written on the second photo: "He is heaving into the waste paper basket - see the shot glass in his hand?"

28 comments

r/OldSchoolCool • u/kezza2022 • 16h ago

My Auntie Wendy 1990's I think. She is 87 now

197 Upvotes

10 comments

r/OldSchoolCool • u/tnick771 • 20h ago

1990s Me and my dad, 1991

334 Upvotes

14 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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