r/OldSchoolCool • • 3h ago

1990s Myself and wife around a year after we met 1992

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1.1k Upvotes

r/OldSchoolCool • • 3h ago

1940s My father and his best friend enjoying the outdoors - 1946

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851 Upvotes

r/OldSchoolCool • • 12h ago

1950s Paula Chandoha photographed by her father Walter in 1955 at their Long Island home.

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1.9k Upvotes

r/OldSchoolCool • • 11h ago

Actress and inventor Hedy Lamarr posing beside a silver-grey granite bust of herself, sculpted by artist Nina Saemundsson, 1939

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1.0k Upvotes

r/OldSchoolCool • • 6h ago

1990s My high school graduation photo, 1997

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364 Upvotes

I spent the night before trying (and for the most part, failing) to sleep with big velcro rollers in my hair. I don't recommend it.


r/OldSchoolCool • • 1h ago

1970s Our engagement party, 1973

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• Upvotes

r/OldSchoolCool • • 1d ago

1990s My wife and I back when we were dating in 1995

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8.0k Upvotes

r/OldSchoolCool • • 10h ago

Sandra Bullock @ the 1994 MTV VMAs

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510 Upvotes

r/OldSchoolCool • • 7h ago

My wife with our first child Maggie - 1995

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277 Upvotes

Maggie, AKA the Magpie, Magger Daggers, the Mags. Pound rescue and the smartest dog I've ever seen.


r/OldSchoolCool • • 15h ago

1990s Danny Trejo and Antonio Banderas on the set of Desperado (1995)

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1.3k Upvotes

r/OldSchoolCool • • 5h ago

1990s Third Grade 1998-First year w/ glasses

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135 Upvotes

r/OldSchoolCool • • 7h ago

1980s Over 1000 demonstrators organized by Act-Up and Gay and Lesbian Alliance Against Defamation protest the attack of 2 gay men by a group of teens on Broadway which led to numberous arrests of protestors on August 30, 1988

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197 Upvotes

r/OldSchoolCool • • 13h ago

Back in the 1980's...

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487 Upvotes

We were cool back in the 80's.. Almost 40 yrs later, we're still kinda cool.!!


r/OldSchoolCool • • 13h ago

1980s Andre the Giant and Fred Savage during the making of ‘The Princess Bride’, in 1986.

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472 Upvotes

r/OldSchoolCool • • 8h ago

1990s Anonymous woman playing Playboy flipper in Paris, early 1990’s

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135 Upvotes

r/OldSchoolCool • • 1h ago

My dad 1957 Indian Lake Ohio

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• Upvotes

r/OldSchoolCool • • 17h ago

1940s British factory workers on a Cornish beach, Sept 6th, 1943

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525 Upvotes

r/OldSchoolCool • • 1d ago

1982 - my great grandma playing Astrosmash on the Intellivision

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1.5k Upvotes

r/OldSchoolCool • • 2h ago

My journalist mom in the 80s

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26 Upvotes

r/OldSchoolCool • • 1h ago

1991 Top Ten Car Craft car of the year. Clock Work Orange.. 57 Sedan delivery.. and me all proper. Dad built this car..

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• Upvotes

r/OldSchoolCool • • 1d ago

1980s My Mom & Dad around 1987

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4.5k Upvotes

Mom & dad out on the boat about a year before I joined the party.

Obligatory PSA: drunk boat driving is NOT cool, even though my dad made it look very cool.


r/OldSchoolCool • • 7h ago

A teen girl's style in the 1990s

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62 Upvotes

r/OldSchoolCool • • 6h ago

1980s Another candy-sorting photo, Halloween 1982

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48 Upvotes

r/OldSchoolCool • • 8h ago

1980s My Halloween costumes 1979 to 1988

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73 Upvotes

r/OldSchoolCool • • 4h ago

1980s Dad in the early 80s

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35 Upvotes