but nobody “has to” wear pants. im not wearing any, and if I can do it anyone can

Tbf, regarding dresses, skirts and other gowns: Your legs never get pinched, you can just fold your legs up under you when sitting down, as a guy you can just lift it up to pee and don't risk getting your member stuck in the zipper, as a girl, if you have the proper underwear, you don't need to take of your pants, many long skirts actually come with pockets or you can mod pocket slits into them and wear historical pockets under them, you can have them in any length, some pants lengths are silly, skirts allow more air ciruclation, just wear them made of the weather appropriate material...

But honestly, as a guy who grew up doing late High Medieval Living History (about the time of Friedrich II of the HRE), dresses are frigging lit. Just pull it over, secure with your belt and pouch, put on your shoes, if it's cold get your cape. DONE. Go out there and look like the Anti-Christ, King of Jerusalem and "principum mundi maximus"

I would miss my pockets though. Can I just wear basketball shorts everywhere?

What kind of dreses should we wear as men, pretty pink maid outfits or black maid outfits?

Yea, but let's design some to work on male bodies. Dresses are generally built for female body shapes, and rely on curves most guys just don't have in order to complete the shape - so we end up looking like Graveyard Barbie in them.

Guys tend to be a lot more oblong, and the overall design would need a rethink in order to actively work with that shape, instead of unsuccessfully trying to compensate for it.

No, I don't know how to do this.