Occasionally. Especially when I was younger. I remember dressing up for Halloween in an "army man" costume. My mom said that when we went door to door, everyone assumed I was a boy. At the time, my family thought it was funny.
A couple years later we went to Disney World for Christmas. I was wearing a sweater, jeans, and a cap with my hair pulled back in a ponytail. One of the workers said something to us and called me a "young man". I loved it (not knowing why), but again, my family thought it was funny.
As I got older, that happened less and less. Once, a younger kid asked whether I was a boy or a girl. I don't think I said anything at all; I was about 11 or 12. That's all I can remember right now for stuff before I started transitioning.