Shananigans, I tried to read most of your post, but you need to add some tl;dr's sometimes...
One point that it seems you overlooked is that women can take clothes from the mens' department wear those and not have it called crossdressing. That is where the double standard comes into play. On reddit there is a more active FTM community and you can read in some of their posts about how far they have to take crossdressing in order for people to realize they are trying to present a masculine image. If they do just a little it's so accepted that nobody realizes they are trying to make a statement about their gender identity.
