TJ, I agree with dressing for the environment you are going to be in. If you are going to a pride event, the pink and blue wig will blend in just fine. I think at pride and comicon, anything goes. 🙂
I don’t pass, but like to at least not be noticed from a distance. If I’m going to walk trails at the park, then I love my short denim shorts, t-shirt, and cap. People watching at the place you are going to go in advance is great advice.
Wherever you go and however you dress, just go with confidence that you have just as much right to be there and dress however you like as anyone else does. Like Holly said, if anyone has a problem with your appearance, that’s their problem. We don’t have to, and shouldn’t, change our gender identity or presentation just to make other people comfortable. Wear whatever makes you happy, and don’t let anyone else take your happiness away from you.