Used to wear skirts back at University on a fairly frequent basis, usually with an eye towards hooking up with over-confident feminists (some of the best trysts of my life were initialized by ladies asking me what I was wearing underneath!). Have to admit it was also an exploration of gender identity. I'm not terribly interested in cross dressing, and I'm pretty happy being a masculine male, but I like to push social boundaries. Its fun to watch people squirm when you do things they don't expect... but that is probably a topic for a different forum.
I've never worn skirts since getting married 15 years ago (excepting a week at the Burning Man festival a few years ago), but I keep waiting for it to hit the mainstream. Hardly a day goes by with me thinking that I'd be much more comfortable in a skirt or kilt. I occasionally get a chance to lookup sites like this and check for news clippings... Wish I could say I'm still brave enough to lash out on my own and spit on public opinion, but these days keeping my job and cordial relationships with my conservative, beer drinking neighbors are higher priority concerns for me. Small town life kinda sucks that way.
Anyway, I'm glad to see a forum like this with so much activity. Maybe tides are finally turning....