I find Wintour to be truly fascinating. While everyone is discussing the death of publishing as we know it she secures herself an even bigger position of leadership at Condé Nast. At this moment it's not clear what this new position really means for publications like Wired, Epicurious or The New Yorker and I can not help but find myself very curious to see how her obvious influence will extend beyond the world of fashion.
In conversations I often compare Wintour to Steve Jobs. Most of us were willing to dismiss his most demanding character traits while acknowledging that he was a visionary genius, and yet similar behavior and success from Wintour results in her being branded a Prada-wearing devil.
I gained a better understanding of who Wintour is from a film, not that one, the other one. The R.J. Cutler directed documentary The September Issue (available for streaming in the usual places.) Cutler spent eight months following Wintour and filming over three hundred hours of footage.
While making The September Issue, I observed Anna Wintour day-in and day-out as she single-handedly commanded the $300-billion global fashion industry. In a business where last week's fashion shows are already old news, she has been at the top of her field (and the top of her game) for two decades and counting. Shortly after we began filming, I observed to a friend who asked what it was like to watch Anna work, "Well, you can make a film in Hollywood without Steven Spielberg's blessing, and you can publish software in Silicon Valley without Bill Gates' blessing, but it's pretty clear to me that you can't succeed in the fashion industry without Anna Wintour's blessing."
Cutler even learned four lessons in management by watching Wintour work.
Another reason to watch the documentary is to discover Grace Coddington. Every influential public figure always has a behind-the-scenes person who is equally, if quietly, influential to the work.