This is one of those issues that I have also thought about.
If I relate it to others here, some of the language does seem rather blunt at times. I think I tried to raise it on a few occasions, possibly by thinking about the issues differently.
It was when I began to relate it to myself that it took on a rather different perspective.
The term guy in a dress is a presumption that a male is wearing a dress. But why should any male feel he can't?
We can think of George Cloony in a dress, for example. Or Sylvester Stallone. Our image is of these very male people, wearing women's clothes. But try to imagine, these men, or any other particularly male men wearing clothes that are simply different from the norm?
A good place to start is a kilt. Though it does tend to be associated with other notions of male assertiveness, beard for example.
Can I express who I am in my appearance? Can our society progress to the point where we can, express ourselves, with our appearance, without seeming to look as if we are faking or charactureing?
Many of us will remember a time when long hair on a man was an automatic indication of effiminacy. Yet short hair on a man was a military necessity, not a social one. One look at paintings of the American Founding Fathers, shows up a lot of long hair.
I've never heard of George Washington or Ben Franklin being referred to as drag queens.