Actually some girl clothes are very practical and fit better. Guys don't have the selection girls have. Women have robbed the entire men's side of the wardrobe and have gotten away with it but men are still stuck in a non changing fashion and are just now beginning to realize there are choices. Best example are girl's stretch jeans...they fit great on a guy and most girls like the look. (win win for the guys. At least for the real guys who are man enough to try them).
Many have predicted skirts will become mainstream for men VERY soon and when you think about it WHY NOT? More practical than jeans or shorts in hot weather. Amazing how closed minds work (or don't work)!
This has nothing to do about being gay. It has everything to do with being a individual not subject to peer pressure.
So is school fun night the way for cross dressers to ask about clothes now? It always used to be I lost a bet and have to dress like a girl.
Wear whatever you feel comfortable in.