While this doesn’t specifically have anything to do with men in skirts, it does relate in that it shows how gender norms are just social constructs that can be entirely different in other cultures.
It also, in my opinion, shows just how subjective and fluid these concepts can be. Men wearing gender-non-conforming clothing is just one way these mainstream social constructs can be challenged.

Japan’s gender-bending history
In Japanese popular culture, new trends come and go. But the Japanese have toyed with gender norms for generations.
https://theconversation.com/japans-gender-bending-history-71545
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What i always thought when I went to Japan (or anywhere in Asia) is how well dress the punk/grunge dressers were. Clothes where clean and very neat.
They are always very well dressed! I noticed that as well when I was in Japan.
So much has changed in Japan, culturally, since I started working there in the 1980’s. Back then kids were punished just for lightening their hair from the universal near-black to a medium brown! And we rarely saw any variation from almost 1950s style dress in the cities or rail stations. I think the past “Lost Decade” economically and the huge demographic shifts there have broken through many taboos.
A lot has changed, even since I lived there for a year in 2005-2006. It was already more acceptable to lighten their hair and wear clothes that don’t conform to the norm, but it will still pretty strict and it was still mostly ok for women to do that. Not so much for men.
I always have problem when it comes to Japan. On first sight, they seem to really not care about gender, clothes rules and stuff like this. On the other hand, all this workaholics, hikikomori, suicides make me wonder why there is such a contrast in best and worst things over there. I sometimes hear from older people that too much freedom is bad, but even if considering it true, how one can measure such thing? There are some economical freedom indexes, but for a more context-based calculations I don’t think there’s a good way to validate it.
Japan definitely is not without its problems. I personally wouldn’t want to live there anymore for a number of reasons I experienced while I was living there, but their view in gender is interesting on the one hand. On the other hand, their traditional views on it has been westernized to the point that their modern perspective is very 1950s. That’s changing again now, but slowly.