She’s as famous as the stars she features in Vogue, but Anna Wintour prefers to hide behind her sunglasses — a look and a stance that doesn’t seem to impress Gen-Z
Iconic, feared and revered; Anna Wintour, the famously inscrutable editor of American Vogue, has always remained an elegant enigma despite being the most powerful woman in fashion. Her signature look, of heavy-fringed bob, dark sunglasses and graphic slenderness, is even recognised by people with negligible interest in fashion. Her consistency suggests that while Wintour may be the arbiter of taste and the one who decides who and what is in or out, she herself doesn’t succumb to transient trends. Her polished froideur is part of her brand, along with her fearsome reputation, formidable work ethic, dedication to micro-managing every aspect of Vogue and her refusal to do small talk. She is a busy career woman making thousands of decisions every week, who simply doesn’t have time to care what the rest of the world thinks. Or does she?
The recently released biography about Anna Wintour by Amy Odell has all eyes focused on her in a manner not seen since the novel The Devil Wears Prada, published by former assistant Lauren Weisberger in 2003. Odell’s book is exhaustively researched, containing over 250 interviews with family, friends and former colleagues of Wintour. But does it reveal the soul of the steely fashionista? Who is Anna? What price is paid in terms of maintaining her position as boss-lady for so long?
Somewhat surprisingly, Odell says of Wintour: “Despite living her life in the spotlight, Anna has never cared to be the centre of attention.” Indeed, she quotes Wintour saying to friends: “I’m so bored by me.” And this is the quandary for anyone seeking to explore Wintour’s personality from a distance.
She has fashioned herself as polished and impenetrable, a caricature that is much more simplistic than the complex person behind it. Her chilly demeanour and armour of hair and glasses conceal not only her face, but also her vulnerabilities. Can anyone definitively say if she is introvert or extrovert, rude or reserved, ruthless or merely a perfectionist? Could she even be shy, as some assert?
Wintour, now 72, used to believe that five years was the lifespan of an editor’s tenure at any title. In defiance of her own credo, she has been the editor of Vogue for 34 years. She has been artistic director of Condé Nast since March 2013 and was also later elevated to the role of global chief content officer for Condé Nast and global editorial director of all Vogue titles. She is also a dame commander (DBE) of the Order of the British Empire, a recipient of the French Légion d’Honneur, and was appointed by former US president Barack Obama to the President’s Committee on the Arts and Humanities. For someone who dropped out of school with no qualifications at 18, it has been a stellar career trajectory.
Her early life and childhood as the daughter of Charles Wintour — a newspaper editor with an equally chilly and exacting reputation — was privileged and comfortable. Although very bright, she wasn’t academic, preferring early jobs in retail at Biba and Way In at Harrods. As a fashion-mad teen in the 1960s, she adopted her signature style template of Twiggy svelteness and fringed Louise Brooks-style bob (initially cut by Vidal Sassoon). Aged 18 and keen to follow her father into journalism, she got her first credit as a fashion editor in Student magazine, owned by Richard Branson. A role at Harpers & Queen followed, where she spent five years gaining experience and proving herself as meticulously organised.
She started her career Stateside in 1975, freelancing in New York, before roles at Harper’s Bazaar, Viva and Savvy eventually led her to the job of fashion editor at New York magazine, which heralded her as a rising star. At that time, on meeting Grace Mirabella (then editor of Vogue) for an exploratory chat about joining the title, she was asked about the role she would like. She replied to Mirabella, simply, “Yours.” The meeting abruptly ended.
Before her ambition was realised, Wintour would be parachuted into Vogue as creative director by its publisher, Alexander Liberman in 1983, marry child psychiatrist David Shaffer in 1984, become pregnant and move back to the UK to helm British Vogue in 1985. Staff at British Vogue were reportedly shocked by their her management style — she sacked contributors, insisted on strict punctuality and swept aside its tradition of eccentricity (cultivated by former editor Beatrix Miller), in a blaze of efficiency.
Jane McDonnell, publisher of The Gloss, worked for Wintour during this period. She recalls: “The transition was challenging — out went the lovely British girls and their haphazard time-keeping and in with 6am calisthenics, an American go-getting mindset and no lunch. [Wintour] could be brusque, cold and dismissive, even to very senior editors. We called her Nuclear Wintour. But while she was extremely demanding, she paid extraordinary attention to detail, pushed everyone to their absolute limit and probably inspired a belief in how perfectionism can deliver beyond expectations. She detested excuses, and got bored easily. She was picky about everything. We breathed a sigh of relief when she went on maternity leave but she was back about a week later in heels and a figure-hugging YSL dress.”
In 1987, pregnant with her second child, Wintour returned to New York when she accepted the role of editor at House and Garden. Just over a year later she achieved her ultimate goal, the editorship of Vogue. After she had been deposed, Grace Mirabella described her successor as “cold, suspicious and autocratic, a vision in skinniness”.
Today, Wintour occupies a unique position of power and influence as probably the last old-school magazine editor and the absolute gatekeeper of fashion. She is both queen bee of the fashion clique and the personal incarnation of the Vogue title. As a mega celebrity, she is now equally as famous as the stars she puts on her covers. This is the contradiction that lies at the heart of the Wintour enigma. Despite being a household name, especially since The September Issue documentary and The Devil Wears Prada movie, she is an intensely private person.
She is extremely powerful but does not enjoy the limelight — the cool persona, the face-framing bob and the opaque sunglasses are tools to navigate the glare of publicity. (The perpetual dark glasses — which she even wore when seated beside Queen Elizabeth — actually have prescription lenses; as short-sightedness and light sensitivity are hereditary family traits.)
Notorious for her perfectionism, Wintour allegedly requested that a baby’s ‘fat neck’ be airbrushed, made Oprah diet before she could be a Vogue cover star and gave Hillary Clinton a thorough style makeover in advance of featuring in the title. At Condé Nast, her word is law and she is reputed to be an exacting and driven editor who pushes her staff relentlessly, often working until midnight in advance of publication.
Personally and professionally, she is extremely disciplined, starting her day at 5.30am. Odell claims that, in 2000, she even returned to her office, post a face-lift, with her bruises still visible. Yet, for all the negative gossip, she has many long-standing staff and commands both respect and admiration within the industry. Indeed, Wintour has stated: “I have so many people here... that have worked with me for 15/20 years and you know, if I’m such a bitch, they must really be a glutton for punishment because they’re still here. If one comes across sometimes as being cold or brusque, it’s simply because I’m striving for the best.”
One Irish person who has personally encountered Wintour is Debbie O’Donnell of Seahorse Media. O’Donnell interviewed Wintour for her 2020 documentary Fearless — about Glamour editor-in-chief and Corkwoman Samantha Barry — and found her to be a gracious interviewee. “After meeting her in person, I can see first-hand how much she champions women,” O’Donnell says. “She contributed to our documentary to support Samantha Barry and gave us 40 minutes of her time, which she could have cut short at any time. Each answer was considered and relevant. She was very generous with her answers.
“I can only speak from my experience, but the fact that she gave us so much of her meant a lot to me and elevated the documentary. It was more like an informal conversation rather than an interview. She was efficient and professional — exactly how I thought she would be.”
O’Donnell continues: “I talked to a lot of people around Anna who spoke of her wicked sense of humour, and how she’s great company and known for regularly entertaining at her home.”
She concedes, however: “You don’t get to a position in the fashion industry or indeed any industry like Anna has without having a steely edge, but from my experience at Condé Nast, I have no doubt that her passion for the publishing house and its people are at the forefront of her mind.”
Stories of Wintour’s legendary peccadillos — rare bloody steaks for lunch, a veto on sharing lifts and an inability to bother remembering minions’ names — all contribute to the legend. However, her longest collaborator at Vogue, the legendary fashion stylist Grace Coddington said of her: “I really respect her as an editor. And I don’t know anybody else that could do what she does... She has very high standards and it’s difficult, but apart from that she was always really fair and honest and straightforward with me.”
Wintour’s philanthropy is a defining part of her career: she founded the CFDA Vogue Fashion Fund post 9/11 and has also fundraised for Aids charities and the Democratic Party. And then, of course, there’s the annual Met Gala, which she has run since 1995, raising more than $200m for the New York museum’s Costume Institute in the process. To maximise its fundraising capacity, she has transformed the event from a discreet supper for the upper echelons of Manhattan society to a starry tribute to fame, excess and social currency that now overshadows the Oscars. As with the Condé Nast titles she oversees, she has navigated the event’s transition into the digital age with a live stream of the red carpet and online coverage.
Despite her success at Vogue, Wintour’s career has had its controversies. These include her stubborn championing of fur, giving Asma al-Assad (wife of dictator Bashir al-Assad) a gushing Vogue profile in 2012, accusations of racism and discrimination concerning the staffing of the group’s titles after the Black Lives Matter protests, her friendship with the disgraced Harvey Weinstein, accusations of fostering elitist attitudes, the closure of Men’s Vogue and Vogue Living in the financial crash, and former colleague André Leon Talley’s bitchy memoir The Chiffon Trenches. She has also incurred the wrath of designers by denying them editorial coverage, including Armani (who reportedly withdrew advertising) and the now deceased Geoffrey Beene and Azzedine Alaïa, who both stopped inviting her to their shows.
Through most of these, Wintour didn’t complain or explain. She did notably, however, issue an apology in the wake of the death of George Floyd for Vogue’s complicity in racism (despite being the first editor to put a Black model on the cover of the September issue in 1989); stating that the magazine had “not found enough ways to elevate and give space to Black editors, writers, photographers, designers and other creators”.
Power in the fashion world is fleeting: to have been as successful as Wintour is for so long is remarkable. She is the last remaining editor of the golden era of publishing (budgets today are down, ditto readership and advertising) and it’s unlikely that there will ever be a figure as singularly powerful as Wintour again. It is too easy to caricature her as just a bitchy boss — her career achievements bear witness to talent, ability and determination. When she does retire from Vogue and Condé Nast, her legacy will be immense. Wintour has transformed the profile of Vogue, made fashion more culturally relevant, mentored talented designers and effectively fostered a bridge between the creative and the commercial aspects of fashion. She has proved that liking fashion does not make you dumb. As yet, she still shows no sign of hanging up her Manolos and her point of view is still the one that counts.
Anna Wintour is still the boss.
By Orla Dempsey
In November 1988, Anna Wintour splashed onto the global fashion scene by putting a model wearing jeans on the cover of her first ever issue of Vogue. At the time, this was fresh, innovative and exciting. Unfortunately, I don’t think that you could describe Wintour’s covers of 2022 in the same glowing terms.
Today, she adorns her covers with the same nepotism babies — a collective term for the children of celebrities, models and industry players, as well as those hailing from privileged backgrounds, who are now famous in their own right — that have already oversaturated our social media feeds and TV screens. Gen-Z wants new faces who have worked to earn their spot in the limelight and can bring something unique to the table. We are only one empty-eyed Kendall Jenner cover away from an entire generation screaming: “Eat the rich!”
Wintour has attempted to appease the youth by featuring TikTok stars such as Addison Rae and Dixie D’Amelio — even going as far to invite them to the Met Gala. However, the online mobs deemed their presence, and their looks, unworthy of the event’s red carpet. I would tend to agree with the critics on this one: given the Met Gala is such an important event that is rooted in fashion and art, why invite two people who copy dances online for a living? There are plenty of more original creators deserving of an invite. Did Wintour and her team make this decision purely based on followers and stats, wanting the top-earning creators in attendance regardless of who they were?
Wintour’s own Met Gala looks have also been roasted by Gen-Z YouTuber HauteLeMode, stating she doesn’t lead by example. “This is your event, why not go for it?” says Haute, “Give the girls something to say oh… that’s how I have to do it.” If you’re going to spend a year making a guest list and choosing the theme, you need to show up and wow the masses. A bob and oversized glasses does not an icon make any more.
Wintour’s downfall is that she is no longer willing to take risks. She appears to be looking at Vogue as a business rather than a creative space. She seems to cherry-pick popular ‘It girls’ without questioning what they do for fashion or how they will inspire her readers.
With Wintour resting on her laurels, is there a future for Vogue? I suggest she takes a page out of British Vogue for inspiration. Although Edward Enninful’s magazine is still a fan of the odd nepotism baby, the editor, pictured below, brings diversity and excitement. Much like Wintour in her early days, Enninful isn’t afraid to push the envelope. Whether it’s putting a temporary tattoo on Rihanna’s face, honouring NHS workers or supporting activists, he has a clear, concise message and Gen-Z is receiving it willingly. If Vogue is to make it in the future, it needs a new outlook and new blood.
Sorry Anna, it’s not Vogue, it’s you.