@Italiangreyhound
I totally agree with
Itisbetter
"Wear what you want is fine at home. Once you are at work I think it becomes less straightforward. I would not work with a nudist for example. I’d struggle with vest tops or short shorts. I don’t enjoy being close to others flesh."
I am sure there are quite a few outfits I'd find problematic if people wore them in my company at work. So when we as a society go out in public, we attempt to wear things that are not going to be very difficult for others. If we wear stuff others don't like fine. That's life.
If I worked with a guy who dressed like this I would accept his clothes style and not comment on it. But I'd definitely feel uncomfortable around a guy in high heels and tight skirts.
Right, so keep it behind closed doors. In other words, make sure it retains the status of a fetish/dirty little secret. Because men in skirts and/or heels aren't fit to be seen in public....! Sort of like the attitude many people had (still have) to any kind of PDA between men/gay people. "It's fine as long as I don't have to see it/hear about it."
If someone felt uncomfortable around this man because of his clothes, surely that would be their problem - not his? And surely it would have more to do with their own negative assumptions and moral judgements about him and the sort of person he must be than his actual clothes.
Of course most people will be challenged, confronted, made uncomfortable by anyone who radically departs from the status quo. People are, on the whole, extremely conformist. This thread demonstrates that amply.
Only a hundred years ago, women in the West wearing trousers was extremely scandalous, even illegal, and would have made most people "uncomfortable". It was often considered sexually provocative and kinky, as well. Let us all be grateful for the likes of Marlene Dietrich and Katherine Hepburn, who dared to make people uncomfortable and popularised trousers for women. We all need these daredevils and nonconformists.
Men still have a LONG way to go for equality in these matters.