Agreed with Experimental, some of it has to do with how you carry yourself, the other half of the coin is whether or not you take any pride in the way you look. And yes, those white hats looked "pimp" to say the least.

Wearing the hat of kilter, isn't as popular anymore, partially because while it looked "cool" for a world war II film, doesn't look the part anymore, and yes, you probably would get laughed at behind your back. On the contrary, i'm doing my best to get my hat to do the 50 mission crunch, as i do still think that looks vedy nice.