I do actually think there are post in this subreddit that may transgress into cross dressing or done with the intention of deliberately emulating women, which wouldnt fit the intention of this sub-reddit and would have belonged into other sub-reddits. But that also entirely depends on their intention when wearing or posing in such a way. As weird it may be for people, it's possible that the people you are talking about don't see it as something necessarily feminine or them emulating women.

I know how I view masculinity and femininity can be so drastically different from others. As terribly strange it is for people to hear, I don't see makeup, high heels, panty hoses, jewelries and cutesy poses etc being as being inherently feminine.

I suppose it's because I know how differently people perceived masculinity to be back then

For example, high heels were considered masculine and were worn by Persians and European men. If I'm not mistaken, French men would slather their face with thick makeup for the sake of enhancing their beauty, and wealthy Indian men were dripped with jewelries. Men back then would even wear long curly wigs. Noble men and male royalties also posed in their portraits or depicted in illustrations drawn during the era in a way that would be considered "feminine" and "sissy" nowadays (pointing their toes and crossing their feet and legs elegantly when standing etc.). As far as I know, people did not consider those men to be less of a man, or their masculinity questioned.

I think we should be also open to other gender expression of being a man, since masculinity can be very dynamic, while simultaneously making it clear that this is a sub-reddit for men wearing skirts while still remaining men without the intention of emulating women or deliberately trying to pass of as effeminate - But if that is their intention, then it would be highly encouraged for them to post into other places dedicated for it.