r/OldSchoolCool 3h ago

Princess Diana hugging a young fan in Birmingham,1995

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2.0k Upvotes

r/OldSchoolCool 8h ago

Paul Newman and his wife Joanne Woodward in 1958. They were married for 50 years, from 1958 until his death in 2008.

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4.3k Upvotes

r/OldSchoolCool 5h ago

1980s Harrison Ford, Carrie Fisher & Mark Hamill, 1980

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1.8k Upvotes

r/OldSchoolCool 4h ago

1980s A model promoting the DynaTAC 8000 cellphone in 1984

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1.1k Upvotes

r/OldSchoolCool 10h ago

1990s Kathy Griffin and Jack Black on a date in the 90s

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3.4k Upvotes

r/OldSchoolCool 6h ago

1920s Old Black Jewish Harlem in the 20th Century, 1920s - 1960s...

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1.5k Upvotes

r/OldSchoolCool 1h ago

1990s Gillian Anderson and David Duchovny by Mark Seliger for US Magazine, May 1997.

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r/OldSchoolCool 15h ago

1970s Sally Field in 1970s

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4.5k Upvotes

r/OldSchoolCool 5h ago

1980s Claudia Schiffer during fashion show (1989).

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614 Upvotes

r/OldSchoolCool 11h ago

1990s Son and mother on their way to a pride parade, 1993

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1.7k Upvotes

r/OldSchoolCool 12h ago

Led Zeppelin one month after forming, performing in Sweden 1968

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1.9k Upvotes

r/OldSchoolCool 34m ago

1990s Madchen Amick Serving Looks and Pie – Twin Peaks, 1990

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r/OldSchoolCool 4h ago

1940s Elizabeth Taylor, (1940s.)

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296 Upvotes

r/OldSchoolCool 16h ago

1990s Cameran electra 1998

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1.9k Upvotes

r/OldSchoolCool 1h ago

My Nana, circa 1950, making a Budweiser pyramid.

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Upvotes

r/OldSchoolCool 5h ago

1990s Thomas Jane, Philip Seymour Hoffman, and Mark Wahlberg on the set of ‘Boogie Nights’ in 1996

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247 Upvotes

r/OldSchoolCool 15h ago

1990s Vendela kirsebom 1995

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1.2k Upvotes

r/OldSchoolCool 3h ago

1980s Jackie Chan in the 80s

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114 Upvotes

r/OldSchoolCool 1d ago

1990s Denise Richards, 1998

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9.8k Upvotes

Wild Things


r/OldSchoolCool 9h ago

1950s James Dean photographed by Dennis Stock, 1955.

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363 Upvotes

r/OldSchoolCool 8h ago

1980s Arnold Schwarzenegger & Danny Devito on the set of "Twins" (1988)

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278 Upvotes

r/OldSchoolCool 23h ago

1990s Drew Barrymore, 1995

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4.1k Upvotes

r/OldSchoolCool 3h ago

My Grandfather, In Highschool 1951

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78 Upvotes

Guess his ethnicity 👀


r/OldSchoolCool 15h ago

Kylie Minogue and friends at Amsterdam Gay Pride, 21.06.2000

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771 Upvotes

r/OldSchoolCool 7h ago

1990s Rollerblades made me feel cool. 4th of July 1991

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143 Upvotes