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:

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!

author
Alexander Baldwin
author
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.
editor
Savannah Cox
editor
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 August 16, 2025.