The Depths of Wintour

Harvard alum gains unprecedented access to the inner workings of Vogue

Among the capricious fashion cognoscenti, tastemakers can command respect and recognition for half a season or half a century. The once fabulous, now floundering House of Halston struggles to recapture its Studio 54 panache, while Chanel’s Karl Lagerfield still woos critics with slightly tweaked versions of a flapper’s little black dress.

Despite the rapid flux of the industry, R.J. Cutler ’83—director and executive producer of “The September Issue”—has managed to capture and eternalize an iconic moment in fashion history, and with it, an intimate look at the foremost fashionista of past 20 years. Amidst fashion’s pop cultural boom, awash with reality television shows and mediocre celebrity clothing lines, Cutler managed to wriggle his way into the offices of Vogue—the last bastion of classic luxury journalism—to chronicle the creation of a single issue in his new documentary.

At the helm of this extraordinarily influential monthly fashion tome is editor-in-chief Anna Wintour. Her ubiquitous sunglasses and the withering glare behind them provided fodder for “The Devil Wears Prada,” a book and major motion picture centered on an unnecessarily cruel caricature of a boss—one part business savvy, three parts bloodthirst. Yet “The September Issue” showcases a witty, driven businesswoman with a demanding work ethic, not unlike that of Cutler himself.

“My training was fairly intensive,” Cutler recalls of his involvement in the arts at Harvard during the 80s. Working towards a special concentration in Dramatic Theory and Literature, he cut his teeth as a director in a number of campus productions. “I directed a play or two every semester that I was an undergraduate,” he recalls. “And then after I graduated, I worked at the A.R.T. and taught at the Institute for Advanced Theater Training [during] its very first year.”

Further postgraduate endeavors led Cutler to produce “The War Room”—a documentary directed by D.A. Pennebaker and Chris Hegedus about Bill Clinton’s 1992 presidential campaign—followed by a string of other producing credits, including “Thin,” a 2006 documentary focusing on the rehabilitation of women with life-threatening eating disorders.

While the production of a magazine hawking $4,000 wool coats may seem like something of a departure from Cutler’s more serious subject matter, he insists that the industry is worth exploring.

“I’m really just telling stories about people,” he says. “Anna was a subject who struck my curiosity. [She’s] a remarkable figure not only in the fashion world, but in the business world.”

Aside from directorial and executive decisions meted out with even-toned precision, Cutler goes behind the shades to delve into Wintour’s personal life with interviews and visits to her home. “I was very clear from moment one that I was there to tell the story about Anna, what she does, how she does it, and who she does it with,” Cutler says. “But she knew that I was interested in who she was a person.” The film also focuses on Wintour’s infamous professional relationship with creative director Grace Coddington, a fire-haired industry veteran who harbors enough warmth and emotion to fend off nearly all of her co-worker’s stinging barbs.

Exercising “complete creative control” over the project, Cutler and his crew spent months in and around the Vogue offices during preparation for the September 2007 issue, which tipped the scales to become the largest magazine in history at over four pounds. The Fashion Bible’s glossy cover invited readers to partake in “840 pages of fearless fashion,” featuring a coquettish Sienna Miller clad in a feathered gown, her hair swept back in a severe, piecey bun.

“The industry was thriving, and everybody knew the industry was thriving,” Cutler notes of his time spent at Vogue. Since the publication of that sartorial magnum opus, the nearly 120-year-old magazine has suffered a downturn in size and ad pages, making “The September Issue” seem like an unknowingly somber look at an era of excess gone by.

Cutler insists that the ostentatious wealth was not a focal point during filming. “I think one of the things the film succeeds at doing is showing the incredibly hard work and artistry that is pervasive through the industry, even while it has a frivolous side,” he says. “If you were thinking about the cycles of boom and bust, you imagined that there would be a downturn at some time, but it’s not like people were smoking hundred-dollar bills.”

Like the ebb and flow of Vogue’s parent company Conde Nast’s bank accounts, it’s clear that Cutler’s newfound fashion industry fame will eventually wane. Even as he promotes “The September Issue” across the globe—backed by Wintour’s own support—he is already thinking ahead to future film projects, though he confesses to a certain lingering fascination with the glamorous life. “I remain curious about the work that [the Vogue editors] do, as well as this industry that I’ve come to know so well.” Such is the enduring allure of Vogue, which seems destined to preserve its relevance through whatever straits lay ahead.

—Staff writer Roxanne J. Fequiere can be reached at