Ok I’m going to go against the grain here. I think men can wear what they like. A dress, knickers, tights etc. All the clothes that are generally for someone female, according to society rule. It doesn’t make them a woman - they are just a man in a dress.
People can dress how they want, as long as it is appropriate and they still allow for single sex exemptions in changing rooms etc. By appropriate, I mean they should not wear crotch hugging lurex to go shopping, but at home, or a likeminded party, why not? The whole point is, that their right to do so, shouldn’t threaten. If a man is wearing what looks like very uncomfortable knickers, as long as he doesn’t flash them inappropriately- so what.
My great grandmother bought men’s long johns many years ago, to cycle in. She went to a menswear shop with her sister to choose them. Later, she took to wearing her brothers trousers as far more practical - it caused a bit of a scandal . If women can wear trousers, men can wear dresses. There are women who wear boxers, and men who wear knickers.
I think the sooner gender stereotypes of dress (or anything) are dismissed by everyone, the better.