It really depends how much you want to go into it, because if you do cross dress regularly you will get into some flack and life will in general be harder for you, unfortunately that's just the way it is. My suggestion would be to only cross dress with those you trust and know will accept it, like friends and so forth, it doesn't matter if you're in public because they will support you. I wouldn't cross dress ALL THE TIME unless you really want to, as it's part of your gender identity or something like that, so just consider the fact that if you cross dress it's gonna be hard, but you can do it.