TabbyTurmoil:
One of the functions of gender in our current society is to signal who we want to attract, who we want to desire us (I agree with Andrea Long Chu on this, if not many other things). This man is straight so leads us to conclude that he is signalling either an attraction to himself in his skirts or , possibly, the enjoyment of sexual submission, both of which onlookers might prefer not to be privy to.
Interesting comment.
Or, here's an idea, he might hope to attract a woman that accepts and likes him the way he is - a woman who appreciates flamboyant, sartorially transgressive men. An oddball woman like me, for example. 
Believe it or not, some women are into this sort of thing. Though I appreciate we have the ontological status of Yetis... Honestly, the main thing that would put me off this guy is the baldness (and his age); I like longish hair on both sexes.
But isn't it good that this man is being upfront about what he likes to wear? If you're a man who likes to dress this way, the odds of finding a woman are stacked against you. So better get it out there from the outset. What you see is what you get.
A woman in a long-term relationship who is devastated by the discovery of her male partner's secret liking for tights and heels is a common story. No one is gonna go through that with this guy!
The extent to which people dress to attract others varies hugely. I can honestly say that I wear whatever I like, from dungarees to lace, floral, pastel maxi dresses. I also have hairy armpits, which I understand is unattractive to most people. But those people are not the right ones for me. I like my hairy armpits and, yes, I do find them quite sexy. If any man or woman should also like them, that would just be a bonus; it's certainly not my motivation. Maybe this guy feels the same...