While its characteristics change over time, the concept of "coolness" remains constant: it's all about the attitude. Being hip requires personality; a bit of badassery will do the trick, and age need not stand in your way. If you're especially trendy, you'll be happening long after the moment is captured on camera, just like these 20th-century celebrities.
Just because they're in black and white doesn't make them any less cool. If anything, it's old school, which anyone will tell you is the best type of cool.
- 5384 VOTES
1957: Marilyn MonroeDoes this have the timeless cool factor?
- 6431 VOTES
1960: Muhammad AliDoes this have the timeless cool factor?
- 7353 VOTES
1964: Bobby FischerDoes this have the timeless cool factor?
- 8469 VOTES
1957: JFKDoes this have the timeless cool factor?