The OP mentioned a couple of really interesting notions, not the least of which was:
This has some resonance with me, and might for some others as well. I have found that the more openly I wear skirts the more I integrate the overall look into something that is me instead of something hypothetical or contrary to who I am. As a guy, I do not particularly want to look like a woman. This is not to say that I do not enjoy the look of a skirt on women, for I do; however, the sort of look I put together for myself is not necessarily something that a woman could pull off well. "Vive la difference", I suppose. I suspect the guys that hide in the shadows or who only venture out "in character" may well tend to go "more femme" than those who actually get out and about in their rigs. This is not to say that practising before stepping out is a bad thing; I spent a couple of weeks learning how to deal with some of my looks before taking them out. Tripping over the hem is not a good way to make a good impression.Amplitude of desire for femininized style = 1/(openness of skirt wearing)

There's also:
which is dead on the money. The more time one spends out in public in a skirted rig the more natural it becomes, the more confident and comfortable one feels and that letter component just projects into the space around one. It also has the added side-benefit of exposing those around one to a "bloke in a skirt", and that he's the same bloke whether it's "one pipe or two".Amplitude of sensation of conspicuousness =1/(length of time spent openly wearing a skirt)