Jeez, what a non-issue.
Every school I ever attended, 3 high-schools, 2 junior highs, 3 elementarys, in Iowa, Louisiana, Kansas, and DoDDs-Germany, had “spirit days” for Homecoming week, and every one included a cross-dressing day. There was nothing “gay” about it — it was all in fun.
Especially when the football team would dress up as cheerleaders, and vice versa.