It'll be pretty obvious as soon as you start encountering people...I used to wear sunglasses on the sidewalks of Chicago so I could look at people without making eye contact to see if they were staring at me, making funny faces, pointing and laughing, whatever. If you're not getting any double-takes, that means you have the physical chops to pass. The next step is when you start interacting with strangers, like ordering at a restaurant or shopping at the mall...if your mannerisms and voice are such that you're treated like a woman, you're there.