There have been a bunch of times that Jimmy Olsen has gone in disguise in drag (mostly in his own comic), and there was a hilarious issue of Supergirl where Ambush Bug thought Supergirl was Superman who had been transformed.
James Olsen was very young at the time and puberty fully so he was able to pass as a girl when dressing up and putting makeup on (no hormone pills required).
Ambush Bug was never too smart lol
Hadn’t hit puberty is what I meant.
Jimmy could be argued as genderfluid!! (all star superman)
Going as a woman in disguise doesn’t mean he was LGBT. Not to mention I doubt DC is real proud of those issues now.