I think it's cute. When we were in high school, my best friend used to dress kind of androgynous (I had to show him how to shave his legs once), and we'd have fun little photoshoots in the park and at the mall. We thought it was hilarious to confuse people walking past and staring at us. Our other female friends were terribly jealous of his sexy legs.
Actually, I had a lot of guy friends in high school who had no problem wearing skirts, or strange things, or shaving their legs, or wearing makeup to school. One of my other best guy friends still wears makeup sometimes when he goes out.
Also, guilty of once "stalking" (read: following around the mall for an hour being too weird and shy to actually say hi) a cute androgynous guy my friend and I spotted this one time when we were like 15.
It takes a pretty confident dude to want to crossplay, and that's highly commendable. There's such a double standard in gender roles, and the ways people make assumptions of sexual orientation based on what someone else is wearing, that you have to be comfortable in your sexuality (whatever it may be) to be a guy willing to wear a dress or something non-masculine.
Costume Con - Kili in a dress
Atomic Lollipop - Come visit me at the Make-Your-Own-Button free craft booth!
Polar Chill - check out my costume DIY panel and workshop
FanExpo - Iron Man Mark VII version 2, Pacific Rim Jaeger pilot?
FanExpo - fem!Iron Man Mark VII - The Iron Man Armor Project
Atomic Lollipop - Vanellope von Schweetz; raver!Sailor Mars