I often see comments here saying they're okay with men wearing dresses or skirts, then everybody just mocks the next low-effort tranny literally only doing that, wear a skirt. Be more honest to yourselves: you're not okay with crossdressers either.
And you know what? That's okay. Skirts and dresses aren't tailored to the male body. I'll PL a bit but at high school I was really thin and androgynous, one day at drama class I tried on one of those maxi skirts because all the kids were just doing shit like that for fun and when I looked at myself in the mirror I immediately noticed how awful I looked. Why? Because despite being skinny and all I still had a male torso, male hips, male legs, etc, and the garment was simply not made with me in mind.
“But clothing is a social construct!! Men used to wear skirts and heels!!!” Yes, open garments tailored for men, like kilts. Notice how men don't look ridiculous wearing a proper Scottish kilt, but the moment they try a plaid skirt from Amazon they look like badly packed meat from the supermarket. Same with heels, men's dress shoes still have a heel, and the old-timey heel shoes for men were nothing like stilettos, which are an obviously femenine shoe.
The reason why women got away with wearing pants is because pants were baggy and sit at the natural waist. In the proper size, they looked great on women. But even today women's trousers are not made the same as men's. I've mentioned the rise—no matter how high or low it is, men's still have to take account for the balls. Pants made for women are usually also tailored to their hips, buttocks, etc. And skinny jeans are just awful, no matter the sex.
Anyways—sure, experiment with clothing, but you'll always look like a retard, no matter your sex, if it doesn't fit right. Just remember the awful suit worn by Ellen Page, she looked like a little boy trying on his old brother's hand-me-downs.