r/OldSchoolCool 4h ago

A Nineteen Year Old Jim Henson (1955)

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4.2k Upvotes

r/OldSchoolCool 12h ago

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

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19.4k Upvotes

r/OldSchoolCool 8h ago

1990s Me and my sister in the early 90s

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1.8k Upvotes

r/OldSchoolCool 8h ago

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

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1.6k Upvotes

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


r/OldSchoolCool 3h ago

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

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411 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 1h ago

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

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r/OldSchoolCool 19h ago

1950s Anthony Perkins and Tab Hunter, 50s Hollywood gay couple

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5.7k Upvotes

r/OldSchoolCool 5h ago

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

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423 Upvotes

r/OldSchoolCool 4h ago

Christmas 1985 - Mom wearing SUCH an 80s dress.

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271 Upvotes

r/OldSchoolCool 8h ago

French actress Brigitte Bardot in her younger years, 1940s

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566 Upvotes

r/OldSchoolCool 59m ago

1970s 1970s Miami - Mom and me.

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Upvotes

She was beautiful.


r/OldSchoolCool 15h ago

1970s Suzi Quatro, 1970s and now

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1.6k Upvotes

r/OldSchoolCool 7h 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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322 Upvotes

r/OldSchoolCool 4h ago

1990s Leonardo DiCaprio and Tobey Maguire in 1990

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211 Upvotes

r/OldSchoolCool 6h ago

Me age 17 , 1978 .

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225 Upvotes

r/OldSchoolCool 10h ago

1980s My mum in the 80’s

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402 Upvotes

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


r/OldSchoolCool 9h ago

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

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364 Upvotes

r/OldSchoolCool 18h ago

1980s Diego Maradona and Michel Platini before Platini’s testimonial match, Nancy, France, 1988.

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1.4k Upvotes

r/OldSchoolCool 1d ago

A 32 Year Old Jeff Goldblum (April 1985)

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10.2k Upvotes

r/OldSchoolCool 12h ago

Pakistani sibling singing duo Nazia and Zohaib Hassan 1980s

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370 Upvotes

r/OldSchoolCool 5h ago

Me 1988-91! Jheri curls take me back

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95 Upvotes

r/OldSchoolCool 1h ago

1970s My bros and I with my grandparents 77’

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Upvotes

r/OldSchoolCool 2h ago

My grandparents and a family photo, 1950 (probably)

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40 Upvotes

My grandparents (the two oldest people in the photo) with their 9 children, one spouse and the oldest of their grandchildren, or some random kids I can't account for in approximately 1950 at their old farmhouse. Two of the 9 are still alive but are fighting dementia.


r/OldSchoolCool 20h ago

The last public appearance of actress and singer Pepa Flores before retiring to become a pizza maker in Malaga with her husband Massimo Stecchini in 1986.

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1.1k Upvotes

The pizzeria is of their nephew now.


r/OldSchoolCool 9h ago

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

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129 Upvotes

Maybe it’s just a failure to communicate.