His explanation involved feeling pretty in summer dresses

This part always bugs me. Does this mean that Ancient Roman soldiers were "feeling like a women" when wearng dress-like army outfits? And Scottish warriors in kilts are just transwomen? And Ancient Greeks? And European aristocracy? Jesus? Alice Cooper? All glam-metal bands? This always made no sense to me.

It is not really fitting the topic, but I have a short story about the dresses and men. During time when I was active participant of LGB protests in my country. During summer time I was wearing Greek Toga cloths, because it was way too hot to be in "what men must wear" and I dislike shorts. People were so shocked by that, they were so agressive towards me, everyone was asking "Are you gay or something?" (and back then I was thinking I am straight or bi-sexual), I was even beated once by "christian life defenders" for wearing it. That was more than 10-12 years ago. It wasn't very hot here until recent years, and last year I went in Greek Toga-like stylized cloths to a LGBTQ meeting/protest in my regional center. And this time I felt myself again uncomfortable, as I was bombarded again such questions "Are you transwoman?" and "Are you a Gay?". But this time LGBTQ folks were asking this. I just answered to them that I have a freedom to express myself regardless of who I am and those questions are both transphobic and homophobic, because they are assuming who I am just on "role I must play if I wear such cloths", I was dissapointed, but, gladly, they seems to understand my position. Time is passing by, history is repeating itself.