As director John Huston once put it, Montgomery Clift "always held something back." He wasn't one of those what-you-see-is-what-you-get types. But there were a few things about him you could be sure of. He was tough without being macho. He was one of the first guys on the scene to get all moody (here's the guy Dean learned his game from). And his bad luck offscreen left him tortured as hell. But while his sensitive, anti-Wayne act kept you guessing, his style couldn't have been more clear: classic, clean, and American. Simply put, few folks ever looked as sharp as Monty with a slicked-back pompadour, a white oxford, and a pair of worn-in khakis.—ANDREW RICHDALE
* Proof that good style isn't always about the bells and whistles: an understated—but well-fitting—oxford of any shade is just as dashing today as it was in the '50s.