Will dress drag down Giuliani's candidacy?

NEW YORK — It is difficult to shock New Yorkers, yet Rudy Giuliani teetered close to the line when he sauntered onto a stage wearing a platinum-blond wig, makeup, dainty white gloves and a frilly pink gown.

His appearance at an annual political roast was exactly 10 years ago, and at the time, the idea of the tough-talking mayor in a busty ball gown raised eyebrows but was mostly accepted as a good joke — adhering to an unwritten rule for the shenanigans that take place at the roast, known as the Inner Circle dinner.

Shortly after winning re-election that year, Giuliani took his feminine side to a national audience. While hosting "Saturday Night Live," he appeared in one skit as a bosomy, gray-haired Italian grandmother in lipstick and a flowered housedress, with stockings pulled halfway up his calves.

Now that Giuliani is running for the Republican presidential nomination, experts and political observers are wondering whether those well-photographed and widely documented performances — and others — could damage his campaign.

Political observers say many voters associate a macho demeanor with Giuliani's post-Sept. 11 image as a strong national leader in a time of crisis — an image that could lose its power if dressed in stockings and dancing the cancan.

Yes, there was another year when he wore fishnet hose and did high kicks with the Rockettes.

"People think of him as a leader and a tough guy, and he has this image as somebody who tamed the city of New York and made the trains run on time, and seeing him dressed up like a girl would run contrary to all of those things," said Neal Thigpen, a political-science professor at Francis Marion University in South Carolina.

South Carolina has one of the nation's earliest presidential primaries next year, and as the first Southern contest, it could set the stage for the region.

With conservative voters largely dominating presidential primaries, some experts say the footage of Giuliani cavorting about in women's wear could significantly damage his chances there and throughout the South. The images are already showing up on the Internet, including a mock campaign commercial on the popular video-trading site YouTube.

But others say the gender-bending gags won't matter.

In Nevada, another state with an early caucus, Republicans would be unfazed by the image of Giuliani in women's clothing, said Heidi Smith, chairwoman of the Republican Party in Washoe County.

Giuliani impressed Reno citizens in a campaign appearance there last month that included a trip to Costco during which he mingled with shoppers, posing for photographs and signing autographs.

"That meant more than seeing him in drag," Smith said. "If he wants to wear a dress, who cares?"

Giuliani's other Inner Circle characters included a 1950s greaser on a motorcycle, the Lion King and the Beauty's beast.

New York mayors have appeared in costume at the charity event for decades. David Dinkins once donned full cowboy regalia and entered the ballroom on a horse; Ed Koch wore a suit of glittering gold; and Michael Bloomberg has ridden a mule and pretended to smoke pot.

In 1997, the New York media had fun for a few days with Giuliani's first cross-dressing experiment — the Village Voice printed a favorable review by real drag queens — but it didn't appear to hurt him politically.

But for conservatives who already are leery of backing Giuliani for president because of his support for abortion rights and other positions on social issues, the feminine clothing could also remind them of his support of gays while mayor — even though the majority of cross-dressers are not gay.

Southern Baptist Convention official Richard Land said gay issues represent just one area of the problems religious conservatives have with Giuliani.

"There are so many deal breakers for Giuliani, it's difficult to know where to start," he said.

Asked this month about his theatrical past, Giuliani told Fox News that it shows voters another side of him.

"I think what they'll find out about me is I enjoy having fun. I mean, I really enjoy those Inner Circles. I made them fun, and I enjoyed them," he said. "And so you're going to get a couple of things people can interpret different ways, I guess."