Clara, I once worked with a guy (we were stagehands) who was this big, rugges, tattooed, gruff looking dude. He sometimes wore a kilt to work. Kind of badass in a very good way. He didn't wear it when there was a chance he would be in the rafters rigging the stuff that hangs in the air during a concert, thank heaven, but nobody ever said anything untoward about it. I haven't seen him in a few years (I had to retire from the business for health reasons) but I bet he still wears it regularly. In Shreveport, of all places.
So yeah, skirts on dudes, heels on dudes, no problem in a lot of places.