Trying to look cool ends some time after highschool or before it.
I think that soon the cool look is the profecional clean cut look. The look that will win you a job.
With the way the economy is going, it is going to be harder and harder to get jobs, so thus the cultural look will be the profecional look, maybe.
Anyways, for me, I just look how I like, and never care what others think.
I have a lot of shirts with skulls on them. It isnt to look cool, it is because for some reason I like skulls. I dont know why, I just do.
I wear jeans, because they are comfortable.
My shoes are white, because I just like having white shoes.
I used to try and look cool. A long time ago.
I am someone that really doesn't care how people see me, unless it is someone I am trying to impress, meaning someone that might hire me for a job or something. And I try to look formal and profecional with that look.