You will need a silk-screening kit which which make it easy for you to begin T-shirt printing. If you go on ebay, you can get a great deal for the printer itself which varies from $2500 upward.
I know some guys that wear tight girl jeans and some tight shirts that are completely straight (the guys, not the shirts haha). And I know one person who has a studded belt too and he is not emo/punk. I don't know about a frilly shirt though... But I do know that girl clothes have been the fashion for guys for a while now. More than likely he gets it from all of the cool new bands that are out now. I keep seeing all the singers in the bands wearing girl pants and they are straight and not emo/punk.