I live in a small, very conservative town. I went to my town's hair stylist. Confidence is key. Even though I didn't pass as a male to my hairdresser, my first time upon going in with my brother, I asked her, "I want the sides and back short, long on top, and straight sideburns." She says to me, "Oh, you want a boy's cut?" I pointed to my brother and asked to have my hair cut like his. And she cut it exactly the way I wanted. Now I go in and she knows how I like it cut, so all I have to tell her is "the usual" or "boy's/men's traditional cut please". Just be firm about how you want your hair cut, don't let them do it the way they want to, it is your hair afterall and you're paying for it. Maybe bringing a male friend/sibling with you will help too.