The September Issue (2009)

"There is something about fashion that can make people very nervous," says Anna Wintour in the opening scene of The September Issue. That something, she contends, is how very insider-y and decidedly undemocratic the world of high fashion feels. And Ms. Wintour should know. As editor-in-chief of Vogue since 1988, she has been the fashion industry’s giant-sunglasses-wearing chief oligarch for decades, recommending that Yves Saint Laurent’s designer add some colorful evening gowns to his collection, and that the Gap seek out young designer Thakoon to design its newest collection of white shirts. Unlike the many celluloid caricatures of her in the last 10 years, director R.J. Cutler’s documentary shows Anna is also a real-life woman. A mysterious, only occasionally vulnerable, but still real-life woman.

The September issue tells the story of the making of Vogue’s all-important fall fashion (in this case, 2007) issue. For those not in on the world of fashion or publishing, the September issue is not just any old fashion rag. It is the Superbowl of magazines, the foremost pile of ad and editorial pages to hit newsstands all year long. To understand just how much bank this single issue takes in, you’d have to flip past the two-hundred-some-odd pages of advertising, of which there were total of 727, before you got to the first actual story. The audience gets an intimate look into how Wintour and a cadre of editors, photographers, models, and assistants bring together the aspirational elements that will have laywomen and celebrities alike scrambling to get a hold of the "It Bag" or "Must Have Color" for the next six months.

How exactly does the magazine’s helmswoman do it? Mostly by charming the pants off of advertisers (though not literally), dishing out generous helpings of sometimes cold and unfeeling truth to designers, and silencing young staffers with withering stares. Although pretend fashion editors like Meryl Streep in The Devil Wears Prada, Vanessa Williams in TV’s Ugly Betty, and even Bebe Neuwirth in How to Lose a Guy in 10 Days have tried to perfect that last, no one does it with quite the economy and aplomb that Wintour seems to manage. At one point, when an editor is jockeying to get a less-than-groundbreaking accessories piece into the issue, Wintour gives her one of those looks and reminds her that this is the September issue.

According to Cutler’s storytelling, Wintour is not all blood and iron, though. In a few "confessional" scenes, she talks about how her British family sees what she does as so much folly. (Really? She’s Anna Wintour, guys!) And she has a surprisingly good sense of humor about it all. She dotes on her daughter, whom she describes as her greatest weakness, and she gets as close to giddy about beautiful things as her icy demeanor will allow.

It would also seem that the film’s crew felt the weight of the "September issue." The soundtrack with original music by Craig Richey evokes an idyllic bygone era of fashion — you know that time before economic recessions and ugly battles over universal healthcare — when hemlines, furs, and such things really mattered. Likewise, cinematographer Robert Richman’s shots of Marchesa gowns in the streets of Italy and of Vogue’s flame-haired artistic director, Grace Coddington, in the Tuileries are as lovely and romantic as any fashion spread the magazine itself has ever produced.

As pretty as the parade of clothes and celebrities (Sienna Miller is the issue’s cover girl), the real fun of the story lies in seeing Wintour’s often contentious but wholly symbiotic relationship with Coddington. Wintour knows the business inside and out and Coddington has an unmatched eye for beauty. Wintour is cruel — even if it is largely unintentional — decisive, and stalwart. Coddington, a former model forced into retirement by a disfiguring car crash, is warm, emotional, yet strong. Having started her career at the magazine on the very same day as Wintour, she is its unsung hero (not to mention the film’s unabashed star) and she knows it. After crying into her salad about Wintour’s killing page after page of her gorgeous 1940s-inspired fashion spread, she happily pushes back in her own surreptitious way: by calling the photo retouching department to undo Anna’s orders on another piece.

Like the film itself, it’s both deliciously catty and satisfyingly brilliant!