Would I? I get beef all the time from rude saps who think I dress too much like a man. Just because I don't ever wear yoga pants または those weird frilly scarves. Yeah, I wouldn't mind dressing like a man.
I always wear clothing of people of the opposite gender, so yeah I would!
One thing to keep in mind though is that all of the Colors(色) and designs I wear are gender neutral, even if they were made for a certain gender. So is it considered cross-dressing if あなた can't tell?
I like women boots, and coats(and underclothing), men belts and caps(and some pants), etc. I mix it up, I have never consider it cross-dressing または even realized it(until now) just whatever fits the best and is cheapest. But if someone called it cross-dressing I wouldn't mind!