Perhaps you haven't thought of this, but women often wear what you might think of as "men's" clothes to work. Postal carriers, UPS and FedEx drivers, police officers and firefighters, etc.
As for my answer; It will never happen so why worry about it. While it might become acceptable someday for men to wear some sort of dresses or skirts and blouses it is never going to become acceptable for men to walk around in public wearing breast forms and hip and butt padding. Without the body enhancements, I have no real desire to wear women's clothing in public.
I do wear women's jeans in public but I've long ago thought of them as "jeans", not "women's jeans". Tome and others, they are just well fitting jeans.