I guess it would depend on if he was doing it of his own free will or not. If it was say, a lost bet or dare or something like that, and was obviously meant to be a joke, I would probably laugh, but not mainly at him if that makes sense. But if they were doing it because they wanted to, I would probably compliment him. People should be able to wear whatever they want to and feel comfortable in.
Well he's a human too! If he is serious I about wearing one I'd say go for it, and if he looks good I'd even compliment, but if it was for a joke and he was trying to get a laugh then I'd probably laugh with him about it
I would never laugh or make fun of someone because of that. That is so rude. I won't lie and say I've never laughed at a guy but he was a (gay crossdresser) friend of mine who told me he loves wearing heels but I didn't rudely laugh, more like a giggle because it was cute funny to think of that. If he really rocked whatever he was wearing I'd be like yeah btch you go btch