I'm not a transvestite or a Scotsman. However, as a member of the Society for Creative Anachronism, I've often worn medieval costumes that include skirts. Actually, men's clothes from the 14th century resemble robes or short dresses, but they both have skirt-type coverings for the legs and not pant legs. I've found that they're a lot more comfortable than pants--and as long as the skirt isn't excessively long and narrow, you don't lose any functionality (although you do have to remember the maxim Dress like a man, sit like a lady. If I could get away with it, I'd happily wear kilts or other wide knee-length skirts all the time. For the time being, though, I'll just have to take advantage of my opportunities to dress in costume.