There was a reality show on here in the US (I forget the name) that centered around an airline and all the things that go on at the airport. There was one episode where they would not let a crossdresser on the plane, but only for the reason that she was wearing a miniskirt so short it would make a prostitute blush. They explained that it wasn't a gender issue, just an issue of being inappropriate.
I have flown wearing all women's clothes, but i keep it to jeans and tees and no makeup. The only trouble I've ever had is that when my DMV photo was taken, my hair was very long and I look like a girl in it. They have to look up and down at me a few times, but it's never been a problem.
