In the 80's when we toured the country one country bumpkin bar at a time, there was a different mentality of how to dress. We were the spillover from the previous generation that still would mix and match like wear a suit coat, t-shirt, then jeans. And sneakers. But we worked on making our hair look nice and our clothes were nice. At least for the nights we played, and the women who went to the clubs always looked pretty.
Today, especially today, there is a revolution of individuality going on. Sexuality, dress styles, music styles--it's all diverging into many different paths. Non-traditional lifestyles are fully "coming out" and claiming their spot on the stage. Honestly, with the audience anyway, it's hard from the back to tell the sexes apart from the rear. Mostly gone are all the raiments that definitely separated men from women. Women shave their heads and are often more tattooed than the men. They wear boots instead of pretty feminine shoes. Even the shoes have big toes and fat heels, buttons and sneaker laces.
So in order to be a crossdresser one would have to be somewhat of a "throwback" to older times when women knew how to really dress up in a feminine fashion. Many of the crossdressers today would look much more feminine than the females in the audience wearing boots and plaid shirts. This is just an observation of an oddity of culture.
Crossdressing will be much more accepted in larger cities than smaller towns the further inland you get away from the coasts. You will find many phobic personalities ready to belittle you, and sometimes instigate a fight. I remember one time we were playing in a small town in Montana and my guitarist buddy and I were both wearing black satin baseball jackets with Hall and Oates on the back and we had some guys come up to us at an A & W Root Beer drivein looking for a fight, because they thought we were "faggots" because of the jackets we wore.
The further inland you get the more provincial and ignorant the attitudes get.