Will society ever come to be so unconcerned with gender identity that males who don a feminine garment will be viewed no differently than females who wear men's items?

Inspired by this question and particularly the answers so many of our distaff jellies gave. Lots wear male boxer underwear. Who cares? But let a man don panties. He’s immediately lumped with RuPaul or labeled a pervert. How long till we are all cool about the continuium we all lie on, somewhere between Rambo macho and Marilyn Monroe fem? Will tomboy always be a compliment and sissy a slur? Isn’t this just playing into male superiority?