You are in charge of what you do. You decide how far to go and where and when to stop. So, it's entirely up to you.
My limit is, I don't want other people (other than my wife) to know that I am a crossdresser. That means when I am out as a male, I am all male. I do go out on occasion as a female, but in that case, I'm all female and I take care that nobody can see me leaving my house dressed as a female.
All dolled up and away from my neighborhood and usual hangouts, I am not recognizable as my male self.
