I’m gonna agree with what some others have said. You’re not wearing a woman’s clothes, you’re wearing your clothes. You’re not dressing like a woman, you’re dressing how you wanna dress. I think that’s fine.

A lot of the women in my family (and, my wife) buy clothes from the men’s department. I buy my young nieces, who are not old enough to have a differently shaped body than the boys their age, shirts from the boy’s section. When my youngest niece was six, the only NASA shirt was in the boys’ section. I think every kid should have a NASA shirt at some point, and it doesn’t matter if they sit or stand to pee. That became her favourite shirt for a while, until she outgrew it. We didn’t tell her it was a boys’ shirt. It was her shirt.

These days, skirts and dresses are definitively feminine clothing, especially in the west. In the east, men wear kimonos and yukatas (I think) and other such robes which are functionally the same as dresses, and they are considered elegant and formal. The problem with a guy wearing a dress is that dresses are tailored for women. They’re meant to accentuate and show off the breasts. Even a dress made for a little girl typically is cut the same way, and it’s fucking weird. If a tailor wanted to design a dress for a man, they would make the waist wider, and either it would stop at the waist, it would be cut to show off his pecs, or it wouldn’t show anything, but it would be almost a different garment. Take everything you know about “manly” clothing design, and say you want to put that into a dress. What would it look like? It could be denim, or flannel, or that rigid material Dickies are made from. I imagine it would be pleated and I imagine it would have long sleeves to keep you warm. Honestly, if I were a clothing designer, I would take this as a personal challenge to make a dress the manliest man would be proud to wear. But even the name “dress” is ingrained in our head as being a feminine article. Yet Scottish men wore kilts, which are totally not skirts. You wouldn’t say a man in a kilt is any less manly than a man in pants, so why do we assume a good past-knee-length skirt of denim or even a thick cloth is less manly than the kilt (which I think is about knee length)?

If you look at what is happening in the crotch with dresses/skirts, and pants, you might think, minus any social conditioning, that skirts and dresses are for men, to accomodate their external genitalia; and pants, with their tighter support in the crotch, are made for women, to help hold sanitary napkins in place. Since their genitals are internal, pants make more sense. But, both genders go the opposite way. Men hold their external genitals tightly in pants (even those of us who wear looser fitting pants and boxers, or boxer briefs), while women “let it all hang out,” though nothing hangs out. Boys on the school yard love to flip a girl’s skirt or dress up, showing everyone her underwear, but other than embarrassing a classmate, what’s even the point? Her genitals are internal, you can’t see anything but her white cotton panties. It’s not like if it were a guy, you could see a bulge.

I say fashion is backwards, which is why fashion makes no sense to me.

I still (47/M) wear pants, though. I would wear a kilt if I had one. Like, a nice kilt. Wouldn’t bother me in the least. They generally aren’t sold in stores (maybe in Scotland? but I’m not even part Scottish). I’ve seen them online but I’ve never thought to order one. I’d want to try it on in a shop first, decide if I like the feel. I’ve never worn anything like one. So I’d have to get used to it.