Anna Wintour is the Sanest Person in Fashion, Says Simon Doonan

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Simon Doonan, creative ambassador for Barneys New York and self-described "bon vivant," was in Chicago last week to sign copies of his juicy new memoir The Asylum: A Collage of Couture Reminiscences... and Hysteria. We caught up with him—at Barneys, of course—to hash out insanity, sanity, and Jay-Z.

You write in your book about cities like Tokyo, that are just bursting with eccentricity. Now here you are in the Midwest. Is there anything crazy about Chicago?
I love Chicago. Chicago is like a mad, creative place. I have a lot of interesting friends here, like Chilli Pepper. Chilli Pepper is one of the iconic women of Chicago, one of the great, glamorous eccentrics of Chicago. She performs at The Baton Show Lounge, and she's an international legend. And she lives just down the street!

She's still here and performing?
Yesss, I just saw her this morning! Oh, I can't believe you don't know her, shame on you! [makes swatting motion.] She's very glamorous. But Chicago's always had a history of style and design. Just look at the fashion archive at the [Chicago History] museum. Women have always been stylish in the Midwest because they wanted fashion. They weren't in New York, they weren't in Paris, so they wanted it.

Who is the sanest person in the fashion industry?
It's probably Anna Wintour. She's an extraordinary, accomplished person, and she's achieved a whole new level of accomplishment at Conde Nast. To do what she does— like, to occupy this central role in global fashion— you have to have your act together. And also she seems able to multitask. She's attending the [fashion] shows, but she's also at the U.S. Open. I can barely do one thing in a day! And, she's always so beautifully pulled together. So maybe she's the sanest person.

Everyone's talking about Barneys' forthcoming collaboration with Jay-Z. Jay-Z has a lyric about being "crazy and deranged." So, is he?
Very, very creative people are often slightly unhinged. So yeah, he might have that.

Ok, your adoring fans are waiting for you to sign their books. So one last question: What drives you crazy?
What drives me crazy is I find that women in general tend to be too self-critical, especially American women. They're always flagellating themselves about not being thin enough or rich enough or whatever. And I found growing up in England, English women are a bit more casual and easy-going. American women tend to be too self-critical. I'm always encouraging them to be less masochistic and feel more free to be uninhibited, particularly with their sense of style. So that drives me crazy, people saying, "oh, can I wear this?" Wear it, for God's sake! That thing of being too self- conscious, too self-critical, women need to free themselves from that. Especially American women. As Tyra Banks said, "don't get it twisted."
· Simon Doonan [Official Site]
· Simon Doonan: San Francisco is the Center of the Fashion World [Racked SF]