Strike a pose
Wintour finds power in privacy, personal opinions
An echo chamber of silence. That is the only way to properly describe the hush that falls upon the Four Seasons Hotel Toronto before Anna Wintour is presented with the inaugural Icon Award, a new honour formed out of a partnership between the hotel and the Toronto International Film Festival’s Share Her Journey campaign.
For a brief moment, more than 150 of the city’s most sociable and successful women go completely quiet, afraid that they might accidentally offend the editor-in-chief of Vogue and artistic director of Condé Nast. At times, it feels less like a chic brunch and more like a Sunday Mass.
It’s telling that at a film festival that draws such names as Meryl Streep (who played Miranda Priestly, a version of Wintour, in The Devil Wears Prada), Martin Scorsese and Christian Bale, Wintour is the most talked-about at parties, premières and other events.
When people speak of her, they go out of their way to affect an air of admiration, which often belies a sense of fear. They talk as though she’s not quite a real person, but rather — depending on your outlook — a larger-than-life deity or cartoonish villain.
It seems appropriate, therefore, that Wintour attended to accept the Icon Award. While the term is too often misused by entertainment shows and glossy magazines, in its proper function, “icon” refers to something that extends beyond fame or recognition. Icons are symbols of cultural movements, beliefs and values. As a fashion industry kingmaker, publishing titan and chairwoman of the Met Gala, Wintour is an undeniably important figure, but it’s the recognition she receives as a symbol of female empowerment that grants her an iconic status.
Of course, there is another side. Her reputation for intimidation is legendary. Her nicknames include “Nuclear Wintour,” “Wintour of Our Discontent,” “Fashion’s Ice Queen” and, of course, “The Devil Who Wears Prada.” In 2009, Morley Safer infamously asked Wintour on 60 Minutes if it’s accurate to say she’s a “bitch.”
For the record, I find Wintour perfectly warm and easy to chat with during an exclusive interview. She’s not curt, she doesn’t cross her arms and her tone never suggests annoyance or impatience. That said, I do get the impression she doesn’t suffer fools or take kindly to wasted time (she had nothing nice to say about Toronto traffic). There’s a reason chicken pot pie is one of her favourite foods: It’s efficient and gets the job done.
To understand why she may be perceived as aloof — or worse — one must remember she works in fashion, an industry often dismissed as inconsequential, silly and superficial because of its close association with femininity. In the documentary The September Issue, she reveals even her family doesn’t always take her work seriously (her father was editor of the Evening Standard and her siblings include the diplomatic editor for The Guardian and a human rights worker).
However, she thinks times are changing. Wintour’s Vogue is an advocate for women with brains, beauty and ambition, arguing these qualities aren’t mutually exclusive.
“There was a sense that women who were interested in and love fashion might not be substantial, which is of course a ridiculous thought. I think, actually, being proud of how you look and how you present yourself is very empowering in itself. Just because you love fashion and follow it doesn’t mean that you can’t care about the issues of the day,” she tells me.
Wintour took the helm at the American version of Vogue, the world’s most influential women’s magazine, just before the onset of third-wave feminism in the early 1990s. While many fondly remember Wintour’s first cover featuring a model in $50 jeans and a $10,000 jewel-encrusted sweater, fewer recall the cheekily subversive cover line “Men the new bimbos?”
While supermodels were once the lone denizens of its pages, issues under Wintour have featured politicians including Hillary Clinton, Theresa May, Kamala Harris and Alexandria Ocasio-cortez, powerful athletes like Serena Williams and global changemakers like Michelle Obama and Amal Clooney. “If those of us at Vogue can shine a spotlight on women like that who we admire and respect, but also love fashion, then that’s obviously important to do so,” she says.
Her Vogue also mixes fashion coverage with political coverage and cultural commentary. In 2016, Wintour sparked controversy when the magazine endorsed a political candidate (Clinton) for the first time in its history. Around the same time, sister publication Teen Vogue became a hub for progressive thought and activism.
There are critics who say political endorsements have no place in Vogue and voice concern over Teen Vogue aligning itself with a specific ideology. It does, after all, represent a shift from the traditional (and rather superficial, it must be said) “fashion reporting.” I can sense Wintour roll her eyes behind those dark frames when the subject of red carpet questions is broached. She tilts her head, laughs and sarcastically posits: “Like, ‘What are you wearing?’”
It’s clear, despite her love of fashion, she doesn’t think much of the typical reporting that takes place at movie premières, awards shows and film festivals. However, it’s TIFF’S and the Four Seasons Hotel Toronto’s history of championing women in film that convinced Wintour to make the trip. The Share Her Journey campaign is the festival’s five-year commitment to championing women in front of and behind the camera. It was founded in 2016 and includes the successful RBC Female Creator Initiative, a year-round program that provides emerging filmmakers access to mentorship, networking opportunities and skills development.
“I’m very impressed with the charitable work the Toronto film festival does in terms of empowering women and gender equality, which is so important to what we do (at Vogue),” she says.
In interviews over the years, Wintour avoids describing herself as powerful or an icon. She often claims to simply be doing her job. “It’s an honour to be at Vogue at this present time, when it’s a challenging moment for many of us, and it’s important to use that platform to bring change,” she tells me.
In a column for The New Yorker from a few years ago, cultural critic Jia Tolentino wrote, “An essential burden of womanhood remains that of being required, by everyone, to signify too much.” I can’t help but think this is yet another way Wintour represents the modern woman. She famously wears her tinted shades as a shield, not wanting to give away her every expression at runway shows. She doesn’t have personal social media accounts and shies away from the spotlight. Wintour may be on the forefront of another movement in her reluctance to give it all away and reclaim the right to privacy.
Of course, that shouldn’t be conflated with not standing up for what you believe. In her Icon Award acceptance speech, Wintour unapologetically shared political views, made her support of gun control known, touched on environmental destruction and applauded the growing number of women of colour in government.
She also praised females in the film industry, including Streep, Ellen Page, Rosamund Pike and Cynthia Erivo for their work and activism on and off the big screen. She knows first-hand carrying the torch isn’t all front-row seats at fashion shows and champagne receptions. “Standing for something is not always easy, but it’s a challenge I’m trying to set for myself as a woman,” she says. “In these times you can’t sit on the sidelines.”
Wintour has a firm grasp on how others see her. She understands that when people speak of her, they talk as though she’s not a real person. In this, we might find her greatest accomplishment: She uses her iconic position to promote her personal beliefs without fully embracing that status or entirely giving up her privacy. She understands she’s a symbol, but still manages to be her own person — a remarkable feat for anyone in 2019.
Standing for something is not always easy, but it’s a challenge I’m trying to set for myself as a woman. In these times you can’t sit on the sidelines.