I think we are in a golden place in time in the UK. It is unremarkable now to see a man in a skirt on the street, but on the other hand you are an interesting person with style if you are out in a skirted outfit.
The other day I saw a man with a marvellous mohawk. It was bright red with black tips standing at lease 4 inches high from his forehead to his neck. He was just minding his own business on a tube train as I was in my skirt. We had both made choices which made us interesting, but we were both going about our life without a problem from the many other people on the tube.
I think we now have choice, but it requires confidence and bottle to take that choice. I guess the guy in the mohawk may get push back in some work spaces, however one site I work on, has a main contractor who has a small black mohawk going on, where I am at work in a toned down skirt outfit.
Looking back, I remember when I first started wearing a bush hat. There were no gender issues to worry about, but I was still making a choice which was not normal. I had my hair loss/headaches reason to wear a hat, but to the person in the street, I was just making a style choice. Sometimes I get asked about my "Cowboy" hat and where's my horse....it's a bush hat from Australia....shouldn't it have corks?....

Daily, a happy man in a skirt...