Well there IS one "skirt" for males. I think it might have come with store stuff. (it doesn't really look like a traditional kilt, so I'm calling it a skirt!)
Yes, I saw this kiilt impersonation and that's what spawned the idea of male sims in drag. Specifically, ala Rocky Horror.
When I first loaded up the game and saw the males now have the full range of makeup options, I knew someone would make crossdressing a possiblity soon enough. It's not really that "out of the norm". There were plenty of people making female to male clothing conversions for TS2, I don't see why TS3 would be any different.
Yes! I've used the makeup on a few male sims to fix oddly pale lips or add some color to an otherwise bland face. I know that the clothes present a possible issue with how they are overlaid onto the sim, but I'm hopeful that it will be an easy-ish time unlocking the sexes assigned to clothing.
I used to have TS2 installed on an older PC of mine ages ago and I do remember the clothing for men was awesome, but not as expansive as for women. I'm hoping that once someone figures out how to unlock said clothing, that I can make an Eddie Izzard sim. That and a fuggin' forehead slider for CAS.