that's probably because some women are capable of doing man work and man work requires man clothes, for various reasons

idk, the other way around... high heels were initially a class thing and it was about the length of the heel for you to ride a horse (heels are for horses, and the legacy persists today in shitty sloped shoes) stockings were probably originally for men because women showing their legs is quite unchristian/jew/muslim

basically, "woman's clothes" is a category that largely used to be also men's clothes

short skirts? ever heard of a tunic? tall boots? just have a look at what firemen wear... short shorts? rugby uniform... cut off jeans? i am embarrassed to say that this used to be a woman thing and now is relatively common man thing

i think that such conventions outside the context of the use case of the clothing are stupid

you wear armor if you gonna swing a claymore, you wear a plate carrier if you gonna go out shooting bad guys, you wear stockings if you are cold