History’s Cool Kids: The Best Of Old School Cool

Published March 19, 2014
Updated July 13, 2020

From Mick Jagger hanging out with Andy Warhol to David Bowie's epic mugshot, enjoy this gallery of the best of old school cool.

While nostalgia for yesteryear can feel mawkishly selective, there is a certain je ne sais quoi appeal to fashions of decades past. Enter “old school cool”, a community on Reddit that catalogs some of the best photographs that capture the human appeal of our yesteryears.

From the vintage to the recent and the celebrity and the criminal, enjoy forty of the best photographs of old school cool:

Paul Newman Venice
Paul Newman boating in Venice, Italy during a 1963 film festival.

Louis Armstrong Playing At The Sphinx
Louis Armstrong serenades his wife at the Sphinx.

Steve McQueen
Steve McQueen rests after completing a 500 mile race in the Mojave Desert.

Hugh Hefner
Hugh Hefner in the late 1950s.

David Bowie Mugshot
The mugshot of David Bowie after being arrested for marijuana possession in Rochester, New York in March 1976.

Old School Cool Hippies
A high school student in Los Angeles in the late 1960s.

Tony Hawk In The Early 1980s
Tony Hawk in the early 1980s.

John and Jacqueline Kennedy take in the America's Cup.

Showgirls Playing Chess In 1958
Showgirls play chess before a show in 1958.

Ice Skating In New York
Ice skating in Rockefeller Center in New York City during the early 1930s

Arnold Schwarzenegger
Arnold Schwarzenegger poses with a glass of cognac in the early 1980s.

Audrey Hepburn
Audrey Hepburn

Phil Collins 1970s
Phil Collins in the early 1970s.

Eatmore Ice Cream

Jimi Hendrix
Jimi Hendrix

Princess Yvonne And Prince Alexander In 1955
Princess Yvonne And Prince Alexander of Sayn-Wittgenstein-Sayn, Germany, enjoy some mid-day activities in 1955.

Franklin D Roosevelt At Harvard
Franklin D Roosevelt takes a break during crew at Harvard.

Debbie Harry
Debbie Harry poses for the camera while driving in New York City.

James Brown In 1967
James Brown in 1967

Krazy Kat Club In 1921
A photograph from the Krazy Kat Club in Washington DC in 1921.

The Stoned Rollers
The coolest bowling team ever.

Muhammad Ali 1964
Muhammad Ali poses with $1 million during a photoshoot in 1964.

Susan Kare
Susan Kare, the graphic designer who created many of the interface elements and typefaces for the Apple Macintosh in the 1980s.

Skateboarding Central Park
Skateboarding through Central Park in the mid 1960s.

New York Subways In 1980s
Guardian Angels patrol the New York City subway in 1985.

Roadside Flowers
A woman sells flowers on the roadside of California in the early 1970s.

Sophia Loren Playing Pool
Sophia Loren lining up a shot in pool.

Filming Of Shining
Stanley Kubrick takes a selfie during the filming of The Shining.

Nikola Tesla
Nikola Tesla casually works in his laboratory.

Old School Computers

Mick Jagger And Andy Warhol
Mick Jagger hangs out with Andy Warhol in New York City.

Old School Cool


Old School Cool Biker Gang
A California biker gang member

Old School Cool Pictures

John Muir And Teddy Roosevelt
John Muir and Theodore Roosevelt at Yosemite in 1903.

Old School Cool Ditka
Chicago Bears coach Mike Ditka waves to reporters before a game.

Old School Cool Photographs
A woman poses for the camera on the Upper East Side of New York City in 1969.

Sean Connery Teaches Handstands
Sean Connery teaches handstands during breaks of shooting a James Bond film.

Old School Villians

New York City In 1982

Best Of Old School Cool
Waiting for a bus in Iran in the late 1970s.

Old School Cool Bernie Sanders
Burlington Mayor Bernie Sanders picks up trash in a public park after being elected in 1981.

Old School Cool Scooter

The Beatles Arrive In America
When the Beatles arrived in America.

Thanks to r/OldSchoolCool, Tumblr, and imgur for some of the images above.

And if you loved this gallery of the best of old school cool, be sure to see All That Is Interesting's other posts on the summer of 1969 in New York and fascinating photographs of 1960s Afghanistan!

Alexander is a cofounder of All That's Interesting with an undergraduate degree from the University of Virginia in History and Economics and an MSc from the School of Oriental and African Studies in Economics. He specializes in American history, the Cold War, and true crime.
Savannah Cox
Savannah Cox holds a Master's in International Affairs from The New School as well as a PhD from the University of California, Berkeley, and now serves as an Assistant Professor at the University of Sheffield. Her work as a writer has also appeared on DNAinfo.
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Baldwin, Alexander. "History’s Cool Kids: The Best Of Old School Cool." AllThatsInteresting.com, March 19, 2014, https://allthatsinteresting.com/old-school-cool. Accessed May 19, 2024.