Cool Through the Ages: The Best Photos Ever Captured

A man and his beloved pet duck that he raised from an egg, 1994.

There’s “cool”… and then there’s the time­less old-school cool.

From the rebel­lious punks of the 1980s to the sharp-dressed sophis­ti­cates of the 1880s, every era has defined its own unique ver­sion of style, con­fi­dence, and atti­tude.

These snap­shots from the past remind us that true cool­ness nev­er fades—it only changes form. Whether it’s musi­cians break­ing the rules, movie stars redefin­ing glam­our, or every­day peo­ple cap­tured in can­did moments, each image car­ries a sto­ry of its own.

So let’s take a jour­ney back in time and cel­e­brate the rad, the bold, and the awe-inspir­ing fig­ures who shaped the mean­ing of “cool” long before hash­tags and fil­ters.

Susan Kare, famous Apple artist who designed many of the fonts, icons, and images for Apple, NeXT, Microsoft, and IBM. (1980s)
The Three Stooges vis­it­ing Yel­low­stone in 1969.
The Under­tak­er pos­es with an old­er woman, c. 1990s
Epic 80s moments
Uncle and Nephew play­ing pok­er, c. 1978
Dol­ly Par­ton, 1970s
Burling­ton May­or Bernie Sanders picks up trash on his own in a pub­lic park after being elect­ed in 1981.
Car­rie Fish­er feeds Meryl Streep choco­late cake, 1991
Sarah Jes­si­ca Park­er, Rob Lowe, and Robert Downey Jr. at the Gov­er­nors Ball, 1988.