As far as I know, no state or Canadian province has any law that says your clothing and outward presentation must match your gender indicated on your ID. I drive dressed all the time.
With all the pressure society places on a person to dress as a male or female, remember, there is actually NO DRESS CODE. The only laws about clothing are about public nudity. A man or a woman is entitled to wear a dress, wear makeup, have his hair grown long or anything he or she wants as long as they do not fall under the nudity laws.
However, when you talk to the police just admit to them you are crossdressed or a transexual and every where I have been, they're cool with it. However, if you have been picked up for DUI, request a jail outfit or the like before you are placed in a cell. Myself, I always carry a pair of sweat pants, a T-Shirt and some tennis shoes in the back of the car, just in case. As you don't want to be in the men's lockup wearing a dress.
Danielle.