My friend is a leader for the student LGBT community (and there are loads of trans people there). I think that by doing it he's unwittingly making a statement that transgendered people aren't serious about what they want. He scans as female less than 1/3rd of the time usually, but combined with women's clothing the scan probably goes the other way. I think it undermines his own best interest.
He should wait a couple of years to solidify his intentions before making people question them again.
And I know how upset he gets when people get it wrong.
But keep in mind that the reason I'm posting here is to dispel any fatal flaws in my own thinking first.
SpoilerJoke time: If a guy has been kicked out of both the male and female changing rooms in the clothes store what do you get?
SpoilerA cross dresser