Before I say anything else, I want to make it clear that I am not against men wearing traditionally female clothing, and in fact this post is intended to be the exact opposite. Don't just read the title and jump to conclusions.
Fashion is something I do not completely understand. The way people chase certain brands and styles isn't something that I follow, and I don't think most people do either, but there seems to be certain things relating to clothing and fashion that seem socially universal (at least here in the UK, where I live) that make even less sense to me, and one of these is "crossdressing".
If a girl wears traditionally male clothes, it is thought of as normal, nobody even notices. If a man wears a dress however, it's called "crossdressing", and he is treated differently (depending on the situation, sometimes very negatively in comparison) to everyone else, just because of this.
This is one of those things that is totally nonsensical when you think about it, yet most people would still treat a man wearing a dress differently to a man wearing jeans, as if there is some kind of implicit social "wrongness" about it. This is partially as it is unusual to see a man wearing female clothing in public, but this seems to be mostly as men who would otherwise be doing it are not as they are afraid of prejudice.
I hope that in the near future "crossdressing" will be understood as being what it is for most people who do it - a style choice, and nothing more.