The Thomas Crown Affair with Steve McQueen, and just about any French New Wave film. Try something by Jean-Luc Goddard. Breathless is a good starting point.
+1. I saw it in theaters and again the other night. Both times I had to tell myself to focus on the movie and not Pitt's badass wardrobe once he hits middle age.
I was watching "The Good The Bad and The Ugly" the other day and Clint Eastwood's raw denim jeans and leather cowboy boots were gorgeous the way he pulled it off.