No way. This is the Presidency of the United States we are talking about here. The leader of the free world. Nobody wants a cross-dresser in the White House. Once may be a good nature gag, twice is a big problem. He's done. That is a humiliating photo that will hang around his neck like a millstone.
Oh please, John Garfield owned an entire wardrobe of pink taffeta gowns that he would wear on holidays. President Taft had a fetish for high heels. LBJ often wore women’s panties and a bra. Its been rumored that Warren Harding had both male and female genetalia and used to conduct vivisection experiments on kittens in the oval office!
/sarcasm off
Actually it was more than once. If Rudy cross-dressed once for sweet charity, it would most assuredly be amusing. But one has to assume he kept doing it because he enjoyed it. This is significant because cross-dressing is very unusual behavior for a presidential candidate.
1) There was an appearance with Julie Andrews at a New York City Dinner
2) There was the SNL appearance.
3) There was the video'ed incident where Rooty dressed in drag, did a comedy skit with Donald Trump (in which Trump buries his face in Rudy's fake bosoms).
4) Rudy even offered to dress in drag for Showtime's Homosexual porn show, "Queer as Folk" (a show which promotes pedophilia)
5) Besides his famous pink gown and Marilyn Monroe wig, Rudy also cross-dressed as a chorus girl, and danced in a chorus line.