I know a number of fellows around the country who wear those, and a number of others who wear tartan kilts to Scottish events. There's a picture in a fashion layout in the new Spin magazine, featuring a male model in a woman's skirt that's been accessorized so it appears to be a kilt.
I myself have worn a kilt as a part of various period costumes, and I like them, but the feeling is not the same as wearing women's clothing. A kilt is man's clothing. Ditto for the hakama I wore some years ago for a martial arts demo. It's considered to be a split-skirt, but it's still part of a man's costume. I get the same feeling from togas, dashiki, caftans and sarongs (unless I'm wearing the last over a swimsuit
). I do enjoy the occasional departure from conventional male dress, but these items were still made for men, and feel like men's clothing to me.
Even if kilts go mainstream, I don't think that will have much effect on the issues of crossdressing and transgender behavior.
The most common form of despair comes from not being who you are. - Soren Kierkegaard
Then there's always the matter of leg hair. 
