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
Louis Armstrong Playing At The Sphinx
Steve McQueen
Hugh Hefner
History’s Cool Kids: The Best Of Old School Cool
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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!

Alec
Alec is the founder of the PBH Network and has become lethal at Trivial Pursuit thanks to All That Is Interesting.
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