Most short people who have other shortcomings will always try and find ways to make themselves feel bigger. In Pitt's case, it makes him look like an idiot because he doesn't have a clue as to how to dress himself. Not to mention, if he had the talent to back it up, he wouldn't find the need to hide his shortcomings. There are plenty of other entertainers who are short but appear largest because they are extremely talented, and are secure with themselves. Hell, look at the guys in Lord of the Rings who played the hobbits they weren't any taller than Pitt.