Not the cover of Vogue or any other distinctly "fashion" magazine, Vogue Editor-In-Chief graces the cover of Wall Street Journal Magazine shot by Mario Testino. While not as household a name as say, Martha Stewart with homemaking or Oprah with everyday lifestyle, Wintour is just as much of a powerhouse in fashion as the aforementioned women in their industries. It's interesting that of all publications, Wintour chose to grant the rare interview with WSJ magazine. Being that she is the top dog in fashion, it makes sense that she can only choose publications that are relatively unrelated to the industry. I expect WSJ will get into the actual business, power dynamics and possibly the financials of her work instead of her opinions on fashion. The issue will be on newstands March 26.
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The only other cover that Wintour has appeared on in recent memory (and what a Google search could find) was the premiere issue of fashion magazine Industrie in May 2010, knocking out rumored model Daria Werbowy. Difference being, this shot is likely from a photo site like WireImage or Getty and not an official shoot with Wintour like what WSJ has.
With copies, homages and parodies across all types of media, one of my favorite representations of Anna Wintour is from drag couture magazine Candy. They did a fashion editorial with two male models flawlessly dressed as Wintour and Vogue Creative Director Grace Coddington. The whole shoot is cheeky but lovingly done, albeit hilarious at points (Wintour grimacing at the cat). There's even a drag version of blogger phenom Tavi Gevinson.