He might be an ally. I know a few transwomen and they all say the TRAs do not speak for them. They don’t use women’s spaces at all, i.e. they will research gender neutral toilets to use and one is disabled so she uses a disabled loo.
He could simply be gender nonconforming ally and not agree wearing a long tunic (dress) makes him a woman. Men wore tunics that length in our culture 700yrs ago…also with a belt round the waist. Go to any Viking re-enactment camp and lots of men in “dresses” running amok with axes and swords.
Or maybe I am being too optimistic. There’s certainly a bit of mutual assessing going on between him and the woman in the hoodie.