It seems like you are working toward revealing yourself to the world at large. I think it's great - and you are very brave for doing so. The law of averages means that eventually you will run into someone you know if you go out often enough. Even if you don't see anyone close by it doesn't mean you haven't been spotted.
I would just act as if it is an open secret. If I get questioned about my appearance I try to answer simply and honestly. If someone asked me why I was wearing a skirt or had on makeup I'd try to act as if it was the most natural thing in the world. Something along the lines of "...because I feel like it today." If you are out in the world and get approached in a friendly way by someone you know, it's a pretty good indicator that they will be ok with you as you are.
Easier said than done, right? I've run into neighbors as Lucy, but with the hair and shades etc. it's possible they didn't know it was me. I just walked on by. Where I live we generally don't talk to strangers - and I can be really strange!
