I find the cousin theory interesting, that the distant cousin forced him to wear the clothes. I also agree it might have been to protect Brill from either mom or cousin's desire to see them in dresses. And my sister and I have a theory that the day Leah meet Roxy for the first time, he was wearing a dress to remember his mom who just died. And Roxy could've worn boys' clothes every time after that and Leah wouldn't have thought anything of it because Noah is her younger sister. I also 100% agree that the juxtaposition of his stoic response to being naked versus his response to finding out she remembered him a girl who cried a lot is hilarious. Roxy did already admit to her that he cried a lot when younger so I assume the girl part was the shock?