Consider the boss: The boss is terrifying; the boss is inspiring. The boss has the power to ruin your life. The boss has the power to push your life forward, through sheer force of will. She’s great and terrible. She’s great because she’s terrible. And no one is more of a boss than Anna Wintour, because she’s spent 28 years proving it, one binder-size glossy at a time.
A decade ago this summer, Wintour became a living, breathing avatar for a certain kind of boss — the terrible kind, with “great” a halfhearted asterisk. Though her notoriety was already well established in the media and fashion worlds, The Devil Wears Prada transformed Wintour’s image from that of a mere public figure into that of a cultural icon. “Anna Wintour” was still synonymous with razor-sharp bobs and weather-impervious eyewear. Now, though, she became every overlord you’d ever bitched about three drinks deep at happy hour, only to dutifully fetch her coffee the next day.
In 2016, though, we’re in a fully post-Prada era of Anna Wintour. To chart the Vogue editor’s cultural footprint over the years is to track our idea of what it means to be a boss — from a tyrant in chinchilla to an idol for the post-Sandberg age. Wintour isn’t just redeemed. She’s openly admired, Arctic chill and all.
In the hands of actress Meryl Streep, screenwriter Aline Brosh McKenna, and, of course, Wintour’s onetime assistant Lauren Weisberger, Wintour was reborn as Miranda Priestley, tyrannical editor of Runway magazine. Miranda is a woman with the power and influence to land her underlings any job they want — pending her approval, of course — with a wave of her manicured fingers. And thanks to Weisberger’s firsthand experience, thinly fictionalized (or so it was heavily implied) in the 2003 novel, Streep’s performance was taken as Wintour gospel. To The Devil Wears Prada’s massive audience, Anna was Miranda, and Miranda was Anna: equal parts terrifying and terrifyingly successful.
The Devil Wears Prada filters that success through the eyes of one of her employees, Andy Sachs (Anne Hathaway, in her first leading role targeted outside the tween demographic). Andy doesn’t have the fashion know-how to appreciate Miranda’s savvy, let alone her accomplishments. What she does have is the ambition — and self-respect — to know that hunting down unpublished Harry Potter manuscripts is not her preferred use of a bachelor’s degree.
The film is careful to reprimand Andy for thinking she’s above a job that, as she’s repeatedly told, “a million girls would kill for” in an industry she dismisses on principle. Miranda’s signature monologue, added to the script at Streep’s insistence, is a methodical takedown of Andy’s superiority complex. Behold the Cerulean Speech, abridged:
“This … stuff? Oh. OK. I see. You think this has nothing to do with you. You go to your closet and you select, I don’t know, that lumpy blue sweater, for instance, because you’re trying to tell the world that you take yourself too seriously to care about what you put on your back. … However, that blue represents millions of dollars and countless jobs and it’s sort of comical how you think that you’ve made a choice that exempts you from the fashion industry when, in fact, you’re wearing the sweater that was selected for you by the people in this room from a pile of stuff.”
And in case we didn’t get the message the first time, here’s the pep talk Stanley Tucci’s art director gives Andy when she’s reached the end of her rope not 10 minutes later: “Wake up, 6! [Andy is, horror of horrors, a size 6.] She’s just doing her job. … Where so many people would die to work, you only deign to work. And you wonder why she doesn’t kiss you on your forehead and give you a gold star for your homework at the end of the day.”
It’s an explicit acknowledgement that there’s a method to Miranda’s, and therefore her inspiration’s, madness. The demands she puts on her assistants aren’t arbitrary or cruel. (For the most part; that Harry Potter suicide mission was torture, plain and simple.) They’re an extension of the demands Miranda puts on herself, because being in charge of the most influential fashion magazine in the world is really fucking demanding. Miranda is responsible for protecting Runway — and, by extension, Miranda Priestley — from inertia, competition, and human error, and has prioritized her life accordingly. She’s not asking anything of her minions she doesn’t ask, and get, from herself.
But this isn’t Miranda’s movie. It’s Andy’s, and by the time its credits roll, that’s whose side it takes. Miranda throws a deputy under the bus to save her own job, Andy deems it a backstabbing bridge too far, and one wistful flashback to the-person-she-was-before-this-job later, she’s apologizing to her pious ex-boyfriend: “I turned my back on my friends and my family and everything I believed in, and for what?” So much for the virtues of fashion! Miranda/Anna is allowed to make her case, but in the end, Devil tells us, anyone who doesn’t want to either sell their soul and/or get railroaded by a taxi cab (shout-out Emily Blunt!) should get out while they still can.
Like any good makeover montage, fast-forward 10 years later and you’ll get a different picture of what it means to be Anna Wintour. It starts with her industry, whose continued struggles have only brought her accomplishments into sharper relief. The work-life balance of a handful of staffers seems like an increasingly petty complaint when held up against a readership that remains well into the seven figures and the undisputed edge in ad sales that comes with it. Wintour is seemingly the only person on earth who knows how to run a steady print operation in 2016, which both explains and is made all the more remarkable by her promotion to artistic director of the entire Condé constellation in 2013 — a title she’s taken on in addition to keeping Vogue on course.
This is the Anna Wintour of The September Issue, the R.J. Cutler documentary released three years (and filmed just one, perhaps not coincidentally) post-Prada. Chronicling the run-up to the 2007 edition of its namesake, September is 85 uninterrupted minutes of Getting Shit Done, soundtracked by quotes like “She’s not warm and friendly. She’s doing her business.” At its heart is a constant push-pull between Wintour and creative director Grace Coddington, a self-described romantic in love with the transformative world-building of fashion, if not the practicalities of getting said fashion to the masses. (Coddington left Vogue at the beginning of this year.)
Cutler presents the two women as the magazine’s yin and yang, two opposite halves of an inseparable whole. Coddington orchestrates brilliant, dreamlike shoots; Wintour curbs her excesses and edits things down. Though Wintour’s ultimate authority is self-evident, this isn’t a Prada-style reign of terror. It’s a partnership: Wintour needs Coddington’s vision, and Coddington needs Wintour’s oversight. The friction is mutual, not a one-way demand, and it’s the chemical process that results in the magazine.
A similar image comes through in the more recent, if less successful, The First Monday in May. Like The September Issue, First Monday is a countdown clock to one of the fashion year’s federal holidays: the annual major exhibit at the Metropolitan Museum’s Costume Institute, and the orgy of celebrity, paparazzi, and extremely expensive clothes that marks its opening. The parts that focus on the exhibit and curator Andrew Bolton are the weakest, too grounded in the subject’s perspective and unwilling to express skepticism toward either the theme (China: Through the Looking Glass) or its contributors (like John Galliano, whose passing reference to being an “outcast” in the fashion world goes entirely unexplained).
The parts dedicated to Wintour and the gala she spearheads are, predictably, much more interesting. She is credited with transforming the Met Gala into a cultural and financial juggernaut, so much so that the institute’s space was renamed in her honor two years ago. (At a ribbon-cutting ceremony hosted by Michelle Obama, Wintour visibly, though still discreetly, teared up.) Once again, we see Wintour’s commitment and attention to detail — right down to the spacing between tables, which she adjusts by mere inches on a day-of walkthrough — yield results; once again, her reputation is dismissed as part persona, part trade-off. This time, though, filmmaker Baz Luhrmann adds a new spin: “Let me say something about the dragon-lady image. … A lot of it is absolutely true, but I do think if Anna was a man, there might be less focus on that.”
The Devil Wears Prada pays lip service to the idea that maybe, just maybe, sexism plays a role in Miranda’s, and thus Anna’s, notoriety. Of course, Devil didn’t just reinforce that notoriety — it made millions of dollars off of it, making Andy’s offhand “If Miranda were a man, no one would notice anything about her except how great she is at her job!” difficult to take at face value. It’s hard for our culture’s most indelible portrait of a domineering bitch to subvert the whole idea of a domineering bitch.
Which brings us to another seismic shift in What It Means to Be Anna Wintour. We live in a time when a leading candidate for president proudly ships out an actual Woman Card to her supporters. When Nicki Minaj will not drink pickle juice. When Beyoncé flat-out says, “I’m not bossy. I’m the boss.” And as the world’s most prominent example of a female boss for three decades and counting, no one has benefited more from that term’s gradual recalibration than Wintour.
The question of whether any given celebrity is “feminist” makes me want to douse myself in lighter fluid and take a hike on a volcano. Still, it’s obvious that the current, uh, vogue for feminist ideas has had an effect on how we view women in power, Wintour among them. Take the contrast between Miranda Priestley and a more recent fictional power editor: BoJack Horseman’s Amanda Hannity, chief of Manatee Fair and a clear Wintour analog. Hannity’s commanding, of course — sample quote: “No. Yes. Turtleneck. You’re fired!” — but she’s also the only member of the media willing to print allegations against Hank Hippopopalous, BoJack’s cross between Bill Cosby and David Letterman. “When we know what we know about a monster like that and we still put them on TV every week,” she says, “we’re teaching a generation of young boys and girls that a man’s reputation is more important than the lives of the women he’s ruined.” In the end, corporate overlords intervene, though “capitalism got in the way” is barely failure by BoJack standards. But more to the point: A scripted stand-in for Wintour wouldn’t have made that speech 10 years ago.
It seems that Wintour is aware of this change, and, in the bossest of boss moves, possibly helped to engineer it. Wintour doesn’t use social media, but she’s taken nicely to the spirit of creating, and playing with, your own image that comes with the age of Facebook and Twitter: doing an installment of Vogue’s not-even-trying-to-be-unscripted “73 Questions” series; performing stand-up in a (equally staged) Amy Schumer life-swap situation; stopping by Seth Meyers, her daughter’s workplace, to explain how the Kardashians (briefly) left her stranded at the Life of Pablo reveal. Here is a video in which Anna Wintour allowed a bucket of water to be poured on her head for charity. It’s the sort of playfulness — or better yet, canny performance of it — that comes with knowing your legacy is secure enough to take some stretching out.
Imagine that at Runway. At 10 years old, Miranda Priestley is iconic but ever-so-slightly out of date. Anna Wintour is still the boss.