here's my 2 cents :
hats like that can be pulled off however, one must observe a certain set of rules...
1. you gotta have the right swag for it
if you dont look like jossi wells, aren't incredible at surfing and/or don't have tatoos on at least 15% of your body chances are you'll look like an idiot.
2. buy a quality hat
don't buy that shit
instead, buy that shit
3. one hat per crew
if you disregard that rule, you and your friend will look like you have sexual intercourse with each other on a regular basis
4. don't wear it all the fuckin time
like boy george