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> As an aside, I have said for a long time that I wish it was socially uncontroversial for a guy to wear a loose skirt or dress in public, and that if I found one I liked I would wear it all the time.

Yeah it’s becoming a bit less uncommon but not by much.

Maybe you could make up a Scottish heritage and wear a kilt? Other options would be overalls (there’s overall high-fashion) you might have the same shape issue as pants but they won’t fall down thanks to built-in suspenders (which you can play with e.g. cross, halves, …), or onesies (kigurumi) if you don’t mind being seen as a weeb.

Ugh, I'd say women's clothing is way worse than men's. No standard sizing, and too many faddish items. Women's clothes typically lack usable pockets and they are not as durable. Crappy fabrics that shrink and fade, horrible zippers that break...

That being said, you might want to go to Kohl's and try on Lee women's pants. Those aren't bad, although I hate the way Kohl's marks stuff up and then puts a normal price on it and calls that a sale.

> though it's a line to cross and somewhat of pill to swallow.

If the pants fit, I really don't think anyone is going to notice.

Avoid the pants with pink flowers on them.