Crossdresser’s passing in public is a discussion that a great deal has been said about. This website would not be complete unless I said something also which is don’t worry about it!
Some think that they do but don’t and some might but most won’t. If you look close enough there will be tell-tale signs that give them away from large hands to the way they walk. I do not pass and don’t bother trying having given up years ago.
Crossdressing on the road
It is 2017 and most people just don’t care what you dress like. My friends and I have been to the top rated restaurants in San Francisco. We are not crossdressers passing and never had any problems because we behave ourselves and dress appropriately. Recently we joined a group of Vanity Club friends in Atlanta Georgia and dined at several very nice restaurants. One of the managers gave me some cards when she heard the were others in our group and encouraged me to pass them out. The Perimeter Mall was across the street and we shopped everyday trying on tons of clothes each day.
Once Caitlyn Jenner came out people seem to be more accepting or at least they are not shocked anymore so it’s old news.
If you are not out to shock people and dress pretty much age appropriate plus or minus a decade you should be fine. If you dress to shock you probably will. You will have to accept what comes with it but, you will not be a crossdrersser passing.
I think where you go is as or more important than what you wear. Is where you want to go safe? Restaurants and public places are probably better than dive bars or hidden away places. Think about how far you will have to run for safety or if they have security people to help.