The only times I have really dressed in public were at gay pride festivals. The gay and gay friendly people at the festival were very accepting and kind to me. I got nice compliments and the second year I dressed in public, my trans friend said “you have really gotten the hang of this”…meaning, I looked less awkward, had better hair and makeup and carried myself better as a girl.
However, when I was leaving my hotel for the festival, in the elevator and in the hotel lobby, regular straight people looked at me strange, like I was an alien. I understand that it was their own issues that made them see me as weird but I really had to suck it up and be strong until I got somewhere more comfortable.
The experience made me think I’ll never feel comfortable dressed as a girl in regular crowds of straight people but I also learned that I can deal with that discomfort just fine.