I was lucky in that my middle school/high school years were in the 1980's. The androgynous look was in then, so it was unisex/male rugby shirts and button down oxford shirts for the women. I was never feminine, but with the style of dress being more unisex than female, I didn't stand out in high school either.
Church was different, however. Until high school, I was expected to wear a dress or shirt. Thank God my mother let me wear pants to church by high school, but for the annual church photos, I had to wear a dress.
A couple of weeks ago I was over at my mom's house. She still goes to that same church and she said that a guy who knew back then thought he saw me at a restaurant (he would have seen me 4 years ago at my father's funeral where I was dressed in my usual male clothing). She pulled out the annual church photo books for us to go through because I wasn't certain of the name of the person and I was wondering who she was referring to. I couldn't help but look at the photos of our family in these church photo books. I didn't want my girlfriend to see them though! My mother was like, "why don't you want her to see them?" We have been together for 5 years, but I don't want an image of me in a dress burned into her brain!!