
I bring you Princess Marco Turdina, from the show 'Star VS the forces of Evil' that ran from 2015-2019 on Disney XD, now streaming on Disney Plus.

It starts out as the male lead character needing a disguise to get into an all girls school/prison for wayward princesses but he keeps coming back to the same persona several times in the show, himself saying he looks pretty and "do I get to keep the dress".

He ends up inciting a rebellion with the slogan "individuality is not a crime" in the prison and the former principal hunts him down and as way of apology he dresses up and records a video for that antagonist, afterwards they sit down to play a board game with his family and he still had the dress on.

(Sorry for the quality on this one, screencapped this one form youtube instead of disney)
On the way back to the school to get a honorary degree as a princess he falls over in the carrage when it goes over a bump and we get to see that its indeed a pettycoat and that he even has purple heels to match(most times you see his feet they are in sneekers even in the dress). He also has makeup on in this scene, both eyeshadow and blush.

Later on he is back at the school and gets outed as a boy, and the princesses award him with a princess diploma and think its alright for boys to be princesses too.

I think I've got a new favorite Disney Princess anyhow. Would be a fun costume to make. I'm really surprised that the Disney execs let this one fly actually!

Found this one on pintrest, but its made by an artist that goes by Nintenderp. I thought it was cute.