Known for her trademark pageboy bob and dark Chanel sunglasses, Anna Wintour has a signature look that has often served as armor, hiding her emotions from the cameras and press that often follow one of the most powerful women in media. Yet, ever since Wintour’s former assistant, Lauren Weisberger, wrote the 2003 best-selling roman a clef, The Devil Wears Prada, the longtime Vogue editor-in-chief and artistic director of Conde Nast has been taking off the glasses -- and letting audiences peek inside her world.
She is more than “the dragon lady,” as she was described in the book (and later in the 2006 film starring Meryl Streep and Anne Hathaway), and The First Monday in May, which opens the 2016 Tribeca Film Festival, is the latest film to expose the many sides of Wintour.
The First Monday in May (2016)
Directed by Andrew Rossi, the new documentary focuses on one of Wintour’s biggest legacies outside of Vogue: the Costume Institute Gala. Also known as the Met Ball, the annual fundraiser benefiting the Metropolitan Museum of Art’s Costume Institute in New York City has become a major social event since Wintour became chair in 1995. The film looks specifically at planning 2015’s event, China: Through the Looking Glass, which saw Wintour and museum curator Andrew Bolton navigating cultural sensitivities and trying to secure Rihanna as the event’s marquee entertainment.
Highlight: Seeing Wintour implore Rihanna to lower her performance fee and make sure she stays on brand with the event’s theme.
The Fashion Fund (2016)
Now in its third season (the first two aired on Hulu and Ovation TV), the Amazon reality series follows 10 designers vying to be named Designer of the Year by the CFDA/Vogue Fashion Fund competition. However, the real draw is seeing Wintour and members of the board -- designer Diane von Furstenberg and J. Crew president Jenna Lyons -- discuss the merits of each designer. The show itself is less of a Project Runway-inspired reality competition and more of a look behind the process of awarding a legitimate fashion prize.
Highlight: Watching Wintour chastise Furstenberg for her unbiased comments during a panel interview and complaining about the applicants’ repetitive videos.
73 Questions… (2014)
While this is technically a web series, 73 Questions has become a viral hit for Vogue with Victoria Beckham, Nicole Kidman and Iggy Azalea all answering a list of seemingly random questions -- 73 to be exact -- from Joe Sabia, digital artist and Head of Development at Conde Nast Entertainment. Over the course of five and a half minutes, Wintour shares whom she wants to play tennis doubles with and her least favorite word in fashion.
Highlight: Watching the growing disdain on Wintour’s face as she participates in her magazine’s own web series.
Various: Dior and I (2014), The Last Impresario (2013), In Vogue: The Editor's Eye (2012), Venus and Serena (2012), Bill Cunningham New York (2010)
Following The September Issue (see below), Wintour embraced her life as a talking head and fixture among various fashion documentaries. While these stories don’t get into her life, they do offer a glimmer of appreciation she has for the world surrounding her. “We all get dressed for Bill,” she famously told director Richard Press in the 2010 documentary about the New York Times photographer.
Highlight: Aside from her now-famous quote about Cunningham, seeing which documentaries she appears in with or without her trademark shades.
The September Issue (2009)
The most famous look into Wintour’s world has to be this 2009 documentary about the making of Vogue’s largest, annual issue. The film, directed by R.J. Cutler, is part of a zeitgeist moment for Wintour that followed in the wake of The Devil Wears Prada. It offers a look at her role as editor-in-chief and navigating the big personalities of her staff (creative director Grace Coddington and editor-at-large Andre Leon Talley) and even bigger expectations that weigh heavily on Wintour.
Highlight: Watching the symbiotic relationship between Wintour and Coddington unfold as they battle over photo shoots and layouts in the September issue.
Watch a clip from The First Monday in May, which will hit select theaters on Friday, April 15.