No offense but you're worried about the wrong thing. There is nothing illegal about wearing clothes of any gender. If you're that worried about going through security, you're going to be miserable sitting in the waiting area and on a plane sitting 1 inch from someone who may be a religious nutcase or just an abject bigot. Security takes a few minutes in line and then a few minutes through. The flight takes forever and you are stuck with the person you sit next to.
