In the last year, Anna Wintour, the typically private Vogue editor, has submitted to a 60 Minutes interview; given a talk at the 92nd Street Y about her charity work; courted White House Social Secretary Desiree Rogers at Monkey Bar and boldly announced at a CFDA town hall meeting that she has friends in the White House. Just last week, Ms. Wintour devoted a few minutes to each reporter who had lined up along the red carpet at the premiere of The September Issue, a documentary by R. J. Cutler about her magazine, smiling and gracefully answering questions.
It is unclear whether Ms. Wintour is trying to soften her image, solidify her legacy or please boss Si Newhouse with this mountain of publicity—or all three—but whatever the reason, it came to an apex last night on CBS’s The Late Show, on which she appeared to promote the documentary.
Despite reports that she was strongly advised to leave her sunglasses at home, the Vogue editor entered the stage to Madonna’s “Vogue” in large black shades, a black-and-white floral, knee-length dress and a heavy necklace of yellow gems. She took the glasses off once she got to her seat. She was wearing heavy blush, dark eye makeup and deep pink lipstick.
“I see you have very interesting socks on,” she told host David Letterman, who wore a suit that was short enough to reveal white socks and black loafers. “There is a designer you should look into called Thom Browne. He cuts pants like really short so you can focus entirely on the socks.”
“Really?” asked Mr. Letterman. Ms. Wintour appeared serious, though Mr. Letterman seemed to think, understandably, that she was toying with him.“Yes,” she replied.
Ms. Wintour sat perched right on the end of her seat, legs crossed and hands neatly clasped. Her tense, forward posture said she was nervous, but for each question Mr. Letterman asked, she replied with quick, prepared answers that were funny and self-deprecating. She laughed at Mr. Letterman’s jokes and she laughed at herself. She laughed even when the comedian’s probing seemed to irk her.
He asked about her reputation. “I read in The New York Times this week that I’m an ice queen, a Sun King, I’m an alien fleeing from District 9 and I’m a dominatrix,” Ms. Wintour said. “So I reckon that makes me lukewarm royalty with a whip from outer space, what do you think?”
“Good gig!” Mr. Letterman replied.
He asked about The Devil Wears Prada, which was met with a slight eye roll. “Well, I seem to remember that the movie was fiction and we really like fiction at Vogue.”
“Right, right,” said the comedian. “Have you ever put anybody in a headlock?”
The lips parted and she shook a bit with laughter. “Maybe you?”
Mr. Letterman asked if it took money to be fashionable. Ms. Wintour used the opportunity to plug the Fashion’s Night Out shopping event on Sept. 10. But could someone be fashionable on a budget of, say, $20? Mr. Letterman asked. “Well, you can buy lipstick!”
The host gave up and decided to focus on the film. He said he was impressed that in the documentary, certain spreads were being re-shot less than a week before the issue went to press. Is this typical? he asked.
“Absolutely,” Ms. Wintour. replied. “As it is for a TV show. I mean, you guys didn’t even call me till Friday!”
“Wow. It takes you three days to get ready? Big deal!”
Ms. Wintour laughed at this, too, even though her smile went tight and not quite as toothy.
Mr. Letterman was also surprised that the main characters in the film were his contemporaries. “Vogue is not only run by senior citizens,” joked Ms. Wintour, essentially admitting her age (59). “We have a lot of younger people working at the magazine but the director in his wisdom chose to focus on the more mature people working there.”
Mr. Letterman’s next guest was Yankee first baseman Mark Teixeira . Before Ms. Wintour left the stage, Mr. Letterman said that they would hit some balls. “Oh, we are?” she said, and laughed some more. But she didn’t stick around.