Bro that's to much to read. I just read the first paragraph so I'm answering that.

There is statics things like jilbab ad the style. It's only for women. You have a thobe and a litham that serve the same purpose but look different.

The former is for women, the latter is for men

But for other things depends on your environment. It's called 3urff in arabic.

That's why colored abaya/hijab are haram in saudi arabia. But halal in qatar.

Or ear pricing for men and so on.

For me for example. A man Wearing a girl summer dress or a an abaya with hijab. Is imitating a woman.

Same logic with imitating disbelievers. Hope i answered the question.