Damn. When I was in high school, we had a Sadie Hawkins dance (where the roles are reversed: girls ask boys, they pay for the tickets, etc) each year, along with homecoming and prom for the seniors. My senior year, a classmate told me that she had always wanted to go to said dance with a guy who would dress as a girl, so I immediately offered to do it because I thought it’d be fun.
Aside from a couple chaperones and the principal avoiding eye contact with me at all costs, no one said anything bad. The other guys thought it was either whatever or funny, and the girls didn’t give a shit.