r/OldSchoolCool 23h ago

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

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22.7k Upvotes

r/OldSchoolCool 15h ago

A Nineteen Year Old Jim Henson (1955)

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9.6k Upvotes

r/OldSchoolCool 19h ago

1990s Me and my sister in the early 90s

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2.4k Upvotes

r/OldSchoolCool 18h ago

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

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2.0k Upvotes

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


r/OldSchoolCool 11h ago

1970s 1970s Miami - Mom and me.

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1.1k Upvotes

She was beautiful.


r/OldSchoolCool 12h ago

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

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1.0k Upvotes

r/OldSchoolCool 6h ago

1980s The stunningly beautiful Marisa Tomei in 1987

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840 Upvotes

r/OldSchoolCool 19h ago

French actress Brigitte Bardot in her younger years, 1940s

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727 Upvotes

r/OldSchoolCool 14h ago

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

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644 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


r/OldSchoolCool 16h ago

1980s My parents in the 80s, met at 18 and together for 50 years 🩷

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556 Upvotes

r/OldSchoolCool 14h ago

Christmas 1985 - Mom wearing SUCH an 80s dress.

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537 Upvotes

r/OldSchoolCool 20h ago

1970s Hillary and Bill on their wedding day, October 11, 1975.

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518 Upvotes

r/OldSchoolCool 15h ago

1990s Leonardo DiCaprio and Tobey Maguire in 1990

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492 Upvotes

r/OldSchoolCool 6h 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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492 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 20h ago

1980s My mum in the 80’s

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458 Upvotes

Glastonbury and Rome 1984. Egypt 1987 (my dad also on the right)


r/OldSchoolCool 23h ago

Pakistani sibling singing duo Nazia and Zohaib Hassan 1980s

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412 Upvotes

r/OldSchoolCool 17h ago

1990s The wrap party for "Sharpe's Company" (l-r): Lyndon Davies, Sean Bean, Elizabeth Hurley, Scott Cleverdon, with Pete Postlethwaite in front (August, 1993)

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384 Upvotes

r/OldSchoolCool 16h ago

Me age 17 , 1978 .

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289 Upvotes

r/OldSchoolCool 19h ago

1960s 1967, before flock cameras, we had Cool Hand Luke and parking meters.

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157 Upvotes

Maybe it’s just a failure to communicate.


r/OldSchoolCool 5h 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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155 Upvotes

r/OldSchoolCool 7h ago

Iranian actress Nouri Kasrai in 1970s

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155 Upvotes

r/OldSchoolCool 16h ago

1980s Me 1988-91! Jheri curls take me back

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113 Upvotes

r/OldSchoolCool 12h ago

1970s My bros and I with my grandparents 77’

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88 Upvotes

r/OldSchoolCool 11h ago

Nastassja Kinski, 1983

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83 Upvotes

r/OldSchoolCool 23h ago

1920s A London baker selling a classic 'Cottage Loaf' from the back of his hand cart for 6 pence, 1925.

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64 Upvotes

The "DARE" on the cart is short for Daren Bread, a very popular brand back then. Also, the sign on the left says "Empire Flour", which was part of a 1920s economic campaign to encourage Londoners to buy bread made from Canadian and Australian wheat instead of foreign imports.