I don't understand the trend to wear clothes with dead celebrities on them. I'm a pretty conservative dresser (which is code for meaning I have no sense of style), so I am not a fan of T-shirts with silly or cocky messages written on them, let alone clothes with images of actual people on them.
Some of the more popularT-shirt images I've noticed people wearing over the years include:
When I was a teenager, an older lady in my neighborhood asked me why I advertised for companies for free. It took me a minute to realize that she was talking about the Nike Swoosh logo on my shirt. Ever since then I have decided to stop leaving money on the table so I got a sponsorship with Nike. Just kidding, apparently they only pay famous people for wearing their logo, the rest of us pay them in order to to wear their brand.
I'm guessing this T-shirt trend is probably just a form of idol worship (not the kind like lighting incense to Baal, but like wearing a team jersey with the number of your favorite athlete). If you really are a hard core fan of a celebrity, then go ahead and wear their T-shirt, but if you've never seen a James Dean movie, but you wear the shirt just because you think it's hip, then I feel bad for you.
The one I really don't get is Che Guevara. I can understand if you were a huge Lohn Lennon fan or if Bruce Lee was your martial arts mentor you looked up to, but I would venture to guess that most of the college aged kids wearing Guevara shirts are not Marxist revolutionaries. They are probably just trying to be rebels or be a little edgy. How come we don't see those same people wearing Stalin T-shirts?
Anyway, when I die, I hope you will all buy my T-shirts that feature my pensive countenance since it will probably be a cultural icon for generations. You will also be guaranteed to be cool if you do.