FWIW, it took me several years to get to the point of feeling halfway comfortable going out "dressed." I started by walking into town at 4:00 a.m. I graduated to going to a nearby supermarket right at opening time, when there weren't many people up and about, so I'd actually interact with people dressed. And so on. Each step made me very anxious, and it took a lot of times to get the anxiety down to reasonable levels.
It helped that nobody gave me a hard time about it. I've had maybe 2 or 3 negative reactions in almost 10 years. By now, I take the train in and out of NYC, ride the subway and the bus, go to chorus, all while I'm dressed. It almost feels normal....
BTW, I don't pass at all. My approach has been to "own" it, and work my way up to things slowly so I can at least fake confidence at any point.