@roundsquare you may suppose all you want on which came first here, the “not wanting to wear a skirt (because I’m afraid of people’s reactions)” or “feeling like if I wear a skirt I will be a social outcast (and therefore ‘not wanting’ to)”, but if you look at some of the things men do wear (and do) in public, then you might realize that they don’t give two hoots for “society’s approval”:
baseball caps worn at all angles, in all company, and in any place, no matter how stupid-looking
pants worn so low as to make a mockery of ‘modesty’
wife-beater t-shirts with nothing covering
facial hair that defies all convention (and sometimes physics and biology)
ponytails, and shaved heads
earrings, necklaces, bracelets, piercings of all styles (the only jewelry that women wear that I haven’t seen duplicated on men is “brooches”—maybe that’s just because I haven’t looked hard enough)
And as commonplace as some of those things are, if you’re as old as I am you realize that these things were NEVER seen (at least in the USA) at one point. Imagine the Michael J. Fox character going back to 1950s USA and replicating any of the ‘looks’ above.
I still say that if men want to do it, then they will. Personally, I like pants.