I don't know about this. I mean, I get it that the OP feels that seeing men in skirts in ST "was silly," but really as far as human fashion is concerned, men-in-trousers is a relatively recent dress code and its use was limited to northern European climes for a long period.
Historically, the Romans managed to run a relatively successful and millennia-lasting republic and empire with their soldiers in skirts and senators in gowns and all other men wandering around shamelessly in at-the-knee shifts; the Greeks before them in their chitons (below the shin for older men, and at the knee for young ones) and mantles (gowns sometimes worn off one bare shoulder), and even gadding about in an chalmys when the mood took them; the Egyptians before them with those linen towels slung round their hips and the bare-chestedness of it all.
Even today, where the West dictates what's in and what's not in all things, including dress-code, there are still many regions of the planet that feature "men in gowns" as the fashionable norm.
They seem to manage ok with their sense of masculinity intact, i.e. without feeling "outright silly."
There's no historical basis for thinking that what is considered utilitarian dress in the future for males should be fixed to our current cultural fashion comfort zone, is there?