I agree that much of it depends on the environment. It is more than your social circles, coworkers, and neighbors, but the general political climate of your area.
In South Dakota, a very Red State, I experienced a lot of anxiety going out for simple errands like shopping or appointments. As the political rhetoric increased, so did the hostility, not at me directly, but in general. My reaction was to not go out unless I absolutely needed to or if I was headed for the forest, where I seldom encounter people.
Since moving to southern Colorado, that has shifted dramatically. In this area, my neighbors are supportive or neutral. I have trans and bi- friends and neighbors. I often see cashiers wearing pride pins, supportive bumper stickers on cars, and people wearing pride colors just running their own errands.
What that has done for me is remove the worry that I may not pass. I just be myself. When I notice someone wearing a pride pin or colors, I mention it to them and show them my pride pin. I feel it is important to let people know that they are not alone, that we are allies, and that we are members of this community.
There is strength in numbers. I witnessed this during our local Pride celebration. Hundreds, if not thousands, of people were out having a good time. Some dressed in drag, many wore Pride colors, but almost as many just showed up as supporters in their everyday clothes. There were people of all ages just having fun. There was no police and no protestors.
If you live in an oppressive area, be safe. Seriously consider relocating to a more accepting community if you are able to.
If you live in a good and supportive community, be sure to let people know that we are here supporting each other.