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WATCH: Anna Wintour to Letterman: "I'm An Alien, Remember?"

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With Madonna‘s “Vogue” playing in the background and her signature dark sunglasses in place, Vogue’s infamous and iconic editor-in-chief brought high fashion to late night television with her first appearance on The Late Show With David Letterman. Anna Wintour took the hot seat to discuss the much-anticipated documentary The September Issue, which follows the Vogue staff as they put together the 840-page September 2007 issue with Sienna Miller on the cover. After gently ribbing Letterman about his socks and recommending that he look into cutting-edge menswear designer Thom Browne, Wintour settled into a chat about fashion, her persona and affordable fashion in these difficult economic times. Wintour showed her playful side by commenting that according to last week’s NY Times, “I’m an ice queen, I’m the Sun King, I’m an alien fleeing from District 9 and I’m a dominatrix. So I reckon that makes me a lukewarm royalty with a whip from outer space. What do you think?” She got more serious while discussing Fashion’s Night OutVogue and the CFDA’s huge N.Y.C-wide retail event on September 10 meant to create excitement over shopping and boost sales. And while most pieces in Vogue might be out of the average girl’s budget, Anna insists “what’s wonderful about fashion today is that it’s available to so many different people at so many different prices.” So if you had just $20 to spend on fashion, asked Letterman, how do you spend it? Anna says, “Well, you could buy lipstick.” Count us in. Tell us: What do you think of Anna Wintour’s appearance on The Late Show?

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