I can kind of relate to your post. My therapist says I am in a sprint. I am telling more friends about it and I dont care to go to my shed in a skirt (I want the neighbors to see me!!!). I BBQ now on my back deck in full atire and I dont care what they think, I am sick of living two lives and I do what I want (to a point).
I have gone to my therapy sessions twice fully dressed, only once had I ran into someone else (older lady = friendly smirk). I've left my beauticians in a skirt, a few cars drove by and must've seen me. I think I got a rush out of it more than being worried who saw me.
I too live in a small town (12,000 people) and most of them are older generation thinkers (working at a mine doesn't help). However I have confronted my boss and head HR about it and we have a plan to make it work with sensitivity training to other employees. I just wish I could skip it all and show up tomorrow in my skirts (but the mine is closing in 2 years and I don't want to burn any bridges... )
Just be true to yourself. If you cannot handle other peoples opinions or unable to ignore them, you might want to re think what you are doing. I however want to be seen, I want to be myself; however I will not go to a shopping mall dressed as I do not want smaller children to wonder why a man's head is on a woman's body ...lol (not sure why)... None of my neighbors have small kids so I don't care.