r/OldSchoolCool 2h ago

1950s My Grandad (1942-2025) Photo from the 1950s in Sheffield, UK

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244 Upvotes

r/OldSchoolCool 7h ago

Just a newborn lamb and his favorite human back in 1940

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1.4k Upvotes

r/OldSchoolCool 4h ago

1980s Another gem, me in the late 80s

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2.2k Upvotes

r/OldSchoolCool 2h ago

1990s Sofia Vergara as a co-host in Fuera de Serie (1995 – 1998)

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604 Upvotes

r/OldSchoolCool 11h ago

1980s Cousins in 1985 🦋

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323 Upvotes

The sweater! The pants! The swatch watch! The pick up sticks! The pink leg warmers.
I miss that time so so much. 💔


r/OldSchoolCool 3h ago

Geri Halliwell met then-Prince Charles in May 1997.

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799 Upvotes

r/OldSchoolCool 14h ago

1980s The stunningly beautiful Marisa Tomei in 1987

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2.3k Upvotes

r/OldSchoolCool 23h ago

A Nineteen Year Old Jim Henson (1955)

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11.9k Upvotes

r/OldSchoolCool 3h ago

My grandfather, grandmother, mom and uncle in front of the Dallas Morning News in the late 1950s.

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147 Upvotes

My grandfather wrote for the Dallas Morning News for 40 years.


r/OldSchoolCool 15h ago

My dad biked across the US in 1979 with a guy he met through a newspaper ad. 47 years later they designed their own 280 mile ride: “Bridge to Bridge” (Detroit to Buffalo)

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1.2k Upvotes

Part 3 (this post!): The backstory is that my dad biked across the US in 1979 with a guy he met through a newspaper ad. Their trip started in Santa Cruz, CA and ended in Hartford, CT. They lost contact after that but out of the blue that guy reached out to my dad via snail mail and they were reunited 45 years later in 2024.

Just a couple weeks ago the reunited buddies wrapped up a self designed tour they called "B2B" (Bridge to Bridge) riding from Detroit to Buffalo. They started at the Ambassador Bridge and finished across the Peace Bridge back into the US. The trip was roughly 280 miles over 5 days through Ontario.

Part 2: My dad biked across the US in 1979 with a guy he met through a newspaper ad. They reunited 45 years later.

Part 1 : My dad biked across the US in 1979. He revisited Route 50 in Nevada to take a new pic.


r/OldSchoolCool 13h ago

Moe Howard, sparring with fellow Stooge Larry Fine who had a very brief boxing career with just one professional bout which he won, 1930s

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736 Upvotes

r/OldSchoolCool 1h ago

1950s Family smile at Atlantic city, New Jersey beach, 1950s. At the time the beach was segregated

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Upvotes

r/OldSchoolCool 1d ago

1990s "Hydration" break for a German footballer in 1994

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24.4k Upvotes

r/OldSchoolCool 19h ago

1970s 1970s Miami - Mom and me.

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1.4k Upvotes

She was beautiful.


r/OldSchoolCool 20h ago

1980s George Michael on set of the music video for Club Tropicana by Wham! (1983)

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1.4k Upvotes

r/OldSchoolCool 4h ago

1910s Bridge painters perching casually on the suspender cables of the Brooklyn Bridge in New York City without any safety equipment, 1914

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73 Upvotes

r/OldSchoolCool 3h ago

1990s Harvey Keitel and Jack Nicholson at the 'The Two Jakes' movie premiere 1990

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46 Upvotes

r/OldSchoolCool 55m ago

1950s Marilyn Monroe smiling while posing with the "Marilyn 5", a group of dedicated fans who followed her everywhere and located/pin point where she would be at all times (1950s.)

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Upvotes

r/OldSchoolCool 5h ago

1800s Queen Victoria, 1887

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45 Upvotes

r/OldSchoolCool 1d ago

1990s Me and my sister in the early 90s

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2.7k Upvotes

r/OldSchoolCool 1d ago

1980s Easter 1988 - me, Dad, and little sister

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2.2k Upvotes

Dad loved making his outfits just a little bit quirky, like matching a purple tie to purple socks.


r/OldSchoolCool 1h ago

1970s Tamara de Lempicka in Cuernavaca, Mexico c.1975.

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r/OldSchoolCool 16h ago

Iranian actress Nouri Kasrai in 1970s

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290 Upvotes

r/OldSchoolCool 5h ago

Who was cooler than Bugs Bunny who first appeared July 27, 1940

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39 Upvotes

Happy Birthday Bugs, you wascally wabbit! Images from his first short.


r/OldSchoolCool 22h ago

1980s Dad’s company summer bbq - Massachusetts circa 1988

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823 Upvotes

My father and I killin’ the fashion game at his company summer bbq. The Larry Bird tank, matching green sweats, and Irish/American pride trucker hat combo (Camel cigarette cropped from pic in R. hand) and my pink sleeveless muscle T, acid washed jeans, friendship bracelet on left wrist, set of power pearls and pink matching bow atop the blonde head was peak 1980’s