Because I already saw some great characters mentioned I'm gonna try to bring up some others
Arashi Narukami from Ensemble Stars (aka the queen and the love of my life)
Canonical trans woman
Richard III from Requiem of The Rose King
So I wasn't completely sure whether to include him, but I think he does fall under the trans umbrella and he is ge...... reply
grell from black butler and you can argue strongly for dororo from the original 60's manga. (as in dororo lives as a boy and gets angry when his gender is questioned. but you know... the 60's...) reply