I remember clearly being at a princess & pirate dress-up party with one of my girls. One of the boys there was absolutely in love with the idea of dressing up in the princess gowns. There was a moment where the party organizer hesitated — shouldn’t he wear the pirate costume? Would the parents object?
In the end, he got to wear his gown, he didn’t attract any undue attention from the grown-ups, and the party was a success. Sometimes society is weird, and we need to push back a bit. And I think the best chance we have of raising healthy children — whatever their gender/sex orientation — is letting them explore different roles in the safe environment of play. They’re discovering who they are. If we criticize or censor, we teach them to hide parts of themselves, but we don’t change who they are.
(Disclaimer: Not meant to sound like a lecture. You are a super-involved parent and I’m sure you’re making the right choices! But your comment reminded me of a moment that, on greater reflection, seems pretty significant and I wanted to share it with everyone.)