Marlon Brando- the most macho of the Old Hollywood A-List, and probably the craziest too. Classically handsome, and physically large (spoiler alert- 90% of actors are miniature in real life), no one could make a dirty old tee shirt look so cool. Brando's masculinity shone through in all of his rolls, and in the way he wore clothes. His style still inspires designers today (hello anyone who's ever made a biker jacket) and can be worked into any man (or woman's) look.
Fun Hollywood story: I was pulling things for a shoot, and went to my friends at Schaeffer's Garment Hotel , who stock the coolest vintage biker jackets and raw denim around, and saw a hat in the case that I just had to have... "THAT ONE! Can I borrow it??" to which the shop owner, Robert, replied "No way, that's THE hat. Like, Brando's actual hat from The Wild Ones, and it doesn't leave the shop." The shop's milliner, Gunner Fox, is a third generation Hollywood hat maker, who's grandfather made the original. A great Hollywood moment... see the hat below.