Dear Jen,
Long ago I learn that fear is the child of ignorance.
I explain myself because many people get the word ignorance as an insult.
We all ignore what the future will bring. We can do plans, dream or fear about the future but we don't know what will happen. We can predict the daily future will repeat as it has been happening but to change any important element in the scenario creates a bigger uncertainty and for many is a cause of fear and all the feelings you can imagine.
To go out dressed as a woman change completely our scenario and our instinct of survival makes fear it but those are just instincts. We can carefully plan, as thieves planning an assault to a bank all the possibilities, that will give us some "knowledge" in the future.
Applying the last, you have yo thing when and where you will go dressed. That attire yours is ok if you go to the office on a weekday, or your a business woman, what in the area I live I'd not common and you would call the attention. That's a very important point. In the first outs you don't want to call the attention but just fit in the multitude to "learn" what happen, so stop being ignorant of what's going on when you are like a woman. May be just some jeans and a normal blouse or tee would be better but remember that's my appreciation of your enviroment..
Go out as a male in a day like when you plan to go in femme, to the place where and see what women oof your age dress.
Finally just going out will teach you, believe me, that nothing will happen. Today so many people know something about transpeople but just try to blen with them.
Knowledge will kill the ignorance and she will have no kids.
Mho.
Devi