No way! You are talking to someone who had kids in high school where the football team dressed up as women to raise money for charity during homecoming and were crowned Miss BHS or whatever high school they attended. It was hilarious to watch these guys try to walk and dance in heels.
Anyone that would make it a negative for dressing like a woman in good fun for charity doesn't have a clue about most people in this Country. I have seen some of the funniest acts at roast for candidates and other events for charity and it is all in fun.
Peach lives in the South and her church raises funds in the same manner --- the men dress as women. HAR!
Perhaps you could compare the cause that fundraising was for to the cause Rudy cross-dressed for and get back to us.
Once again, if Rudy at the time harbored ambitions for office outside NYC, I have no idea what he was thinking when he did this.