Probably the biggest hurdle to getting out in public cross-dressed is stepping out the front door. Being out and about can be intimidating in itself but at least there is a comfort in the anonymity of it. However, leaving the house and neighborhood, where people know who lives where and who drives what cars can make getting out stealthily quite a challenge.
One option is to leave in guy mode and find somewhere to transform. Some people will use a hotel room, a friend’s place, or even do it in their car. I prefer to transform at home first so that I have all of my wardrobe, accessories, etc at my disposal.
Once I am made-up, dressed and satisfied with my look I deconstruct a little to make my exit. I take off the wig, ear-rings, lipstick, breast forms and shoes. I put them in a duffle bag to bring with me. I then put on baggy clothes over whatever I am wearing and sneakers. A pair of sunglasses and a baseball cap seem to adequately conceal the makeup.
I go out to the car and drive out of the neighborhood and find a quiet place to reassemble. It feels a little awkward until the wig is back on but it only takes a few minutes to get put back together. After being out in public dressed as a woman for a while I have to remind myself to transform back before returning home. If I think that I might need to, I sometimes bring makeup removers so that I can completely transform back to guy mode, but I usually just do the same deconstruction and cover back up with the baggy clothes.