If you could ask Anna Wintour anything, what would it be?

Vogue’s current editor-in-chief – and subject of the upcoming documentary, The September Issue – has often been called the most important figure in the fashion world (when not being referred to as a “cold space alien”). In a year that has seen a huge downturn in the economy and an even huger uprising in online media, she is responsible for the monthly publication of Vogue, whose current issue is a 584-page fashion manifesto that will no doubt sell hundreds of thousands of copies. Like every issue, it is a collection of works by hundreds of editors, writers, photographers, advertisers, models, and designers. In other words: there are a hell of a lot of people who depend on Vogue, and consequently, Anna Wintour, for a job.

I surveyed some friends (and fellow Worn staffers) on what they would ask Wintour if they could. The answers were endless, subjects ranging from the relevance of fashion in today’s world, to what it’s like to be a professional woman in publishing, to the evolution of a trend, to the lack of diversity in Vogue. But rather predictably, her August 24th interview with David Letterman – her first media appearance since a 60 Minutes featurette last May – stuck mainly to the following points: Wintour’s reputation as an ice queen; Wintour as parodied by Meryl Streep in 2006’s The Devil Wears Prada; and, of course, some banter promoting both the documentary and September 10th’s Fashion’s Night Out, a shopping event in New York City.

Perhaps my expectations were set too high. After all, a ten-minute interview on a late night talk show is hardly the proper platform to get into a weighty dissertation on the significance of fashion during economic turmoil. Yet even amid Letterman’s typical playful teasing I became frustrated with all the focus placed on Wintour’s reputation. There’s the question that has been raised by others a million times before but has never actually been discussed at length, at least not in the mainstream media: if Wintour were a man, would anybody actually care about how straightforward and abrasive she is with her staff?

For somebody who is so often caricatured as a “bitch” (the critics’ words, not mine), Wintour certainly didn’t come off as cold and soulless. She sat mildly slouched in her chair, hands shyly folded in her lap, joking about Letterman’s socks and laughing along when he asked if she’s ever put any of her staff members in a headlock. She was a bit quieter than some of his usual guests (actors and entertainers), but ultimately was a good sport who was not afraid to poke fun at herself. It made me wonder – if this was the real life incarnation of an icy dictator, how would the magazine even manage to get published with a passive editor in the hot seat?

-Anna Fitz