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Anna Wintour exposed her funny bone during her taping of “The Late Show With David Letterman” Monday afternoon.

ANNA AND DAVE: Anna Wintour exposed her funny bone during her taping of “The Late Show With David Letterman” Monday afternoon, appearing as a guest on the program to discuss “The September Issue” and promote the citywide retail event Fashion’s Night Out on Sept. 10. But even before Wintour stepped out in front of the studio audience (which included, for support, publisher Tom Florio and contributing editor William Norwich), Letterman was already working hard to warm up the oft-proclaimed “ice queen.”

“They say that she’s aloof, bitchy and mean to her staff,” Letterman joked during his monologue. “Oh, wait, that’s what they say about me.” He also said he was wearing a “Vera Wang hairpiece” in honor of the Vogue editor in chief.

As he introduced her, Letterman plunked a copy of the September issue of Vogue on his desk — that is, the September 2007 issue featured in the movie, not the current one with Charlize Theron on the cover.

Wintour, clad in a black-and-white Carolina Herrera dress, poked fun at herself, walking out in her trademark sunglasses but then removing them for the interview. She also played along with most of Letterman’s jokes. When Wintour described the scene from “The September Issue” that was to be excerpted during the program, Letterman said, “I heard it was a car crash and an explosion.” To which Wintour said, “That’d probably be better.” When Letterman asked if young people also worked at Vogue, after noting the magazine seemed to be run by editors his age, Wintour said: “Vogue is not only run by senior citizens.”

And later, when the talk show host said he was surprised at how certain parts of the magazine are still undecided within a week of close, Wintour said, “You do it, too — you only called me on Friday.” (That is, for the pre-interview, not for the actual booking.)

Letterman admitted he’d never been to a fashion show, but said they look like they are occupied by “beautiful women who look like the Neptunians have released them. But nobody buys that stuff, do they? Is somebody walking around like they’re from Neptune?”

“Lots of people,” Wintour snapped back, laughing.

She even dished out fashion advice. Wintour complimented Letterman on his “interesting” socks, and recommended he look into Thom Browne since the designer’s short-length suits show off fancy footwear. Asked if someone only has $20 in their fashion budget, what should they buy to still be fashionable, Wintour replied to audience laughter: “Well, you could buy lipstick.”

Nor did Wintour speed off in her Town Car immediately after her segment — she stayed to watch New York Yankees first baseman Mark Teixeira hit fastballs down 53rd Street while a few hundred Times Square tourists looked on. Letterman joked the Vogue editor “can throw a mean cutter,” but — unsurprisingly — she neither pitched nor swung a bat. — Stephanie D. Smith

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