Middle age white chick here - might depend on the crowd you are around. I have a lot of friends who wear kilts (as in most of the men I consider friends, including the 6.5ft 400lb giant of a man. Just totally happens to be that way, they don’t know each other for the most part, and I find out years after becoming friends) and they don’t seem to have any trouble getting laid (not all of them are strictly into women, but they get teh secs so whatever floats their goats). But kilts aren’t the only counter-culture they actively and clearly participate in, both aesthetically and personally. That might make the difference; that’s just who they are and they are comfortable with themselves enough to do whatever.

If I saw some dude in a kilt and leggings I’d be super amused and chat with them, but I’m asexual so I also wouldn’t be interested, but I’d be interested in you, the person. The same way I’d be interested to talk to a dude in a prom dress or whatever. If their spine is so shiny they can rock that shit in public, I probably want to know them.