well the first thought that we ("we" being inclusive of CD, TV, TS, etc.) obsess about is wondering what people will think. chances are, when you're out, most people will not notice you because they are too wrapped up in their own lives to care. this is especially true when going out dressed, driving around for a bit, and waiting at a stop light. I always obsessed and worried about what people were thinking, if I was being read, what they might say or do, etc. Finally I got tired of it and told myself "who cares what other people think?" that and "act natural Allie, this is nothing unusual for you. you're just going about your business as usual." and the always classic "stop looking around trying to figure out what everyone else is thinking! if you look suspicious or nervous people will pick up on it!"
so, in conclusion: try not to dwell on it, eventhough we all have, will, or do dwell on it. just remember that you're not doing anything wrong, illegal, or immoral. you're being yourself and you're expressing who you truly are, and there should be no shame in that. and think about those who are too scared/mortified/intimidated to do what you're doing. some of those people might be looking at you wishing they could do what you're doing. draw your personal strength from that.
...and when you do go out, be safe!