In Canada we don't have TSA but at security screening they don't ask for ID. You only have to present ID at the gate before boarding. I wasn't wearing any make-up or wearing a wig. (I am planning on growing my hair out anyway!!)
I guess I am just a guy in a skirt!

Although I do have what you in the US would call TSA pre-screen (using NEXUS) so they did ask for my ID but my thought is that they just want to make sure they name on the ID and boarding pass match. Can't let the everyone skip the security