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Anna Wintour facing her biggest challenge yet

Issued: 2018-03-31

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By Alexandra Steigrad

March 30, 2018 | 9:52pm | Updated March 30, 2018 | 10:31pm

Anna Wintour can certainly use a win.

The legendary Vogue editor-in-chief, who is celebrating her fifth anniversary as Condé Nast’s artistic director, is under pressure as the company enters an important chapter in its 109-year history.

One of the most influential magazine editors of her generation, Wintour, 68, has been a force in the fashion industry since she took the helm at Vogue 30 years ago — often dictating international fashion trends and making or breaking designers.

But as the magazine business has evolved to encompass digital, video and live events — and rely less on print — Wintour has found herself in unfamiliar territory. Her beloved Vogue, some believe, wields much less power than it once did, while as artistic director at Condé Nast Wintour has overseen some high-profile misfires, including:

“Anna’s got a gun to her head,” said a Condé insider, who noted the string of Wintour misses.

That pressure will no doubt mount in the wake of her latest hire — Samantha Barry, the vivacious 36-year-old social media guru plucked from CNN to revive Glamour, once Conde’s cash cow and one of its most profitable titles.

Barry, with no experience leading a magazine, will have her hands full. Glamour’s financial state has slipped significantly over the last five years, which happen to coincide with Wintour’s reign as artistic director.

For the last three decades, Wintour has been fashion’s ultimate power broker. Known for sporting a pair of oversized Chanel sunglasses and her precision-cut bob, Wintour has been able to stoke fear in the heart of a designer, photographer or model with a mere unshielded glare — a supposedly bitchy persona captured in the 2006 movie “The Devil Wears Prada.”

Wintour brilliantly brought Vogue acclaim by using its covers to reflect pop culture: mixing high and low fashions, tapping lightning-rod celebrities such as Kim Kardashian and Kanye West, and highlighting a class of up-and-coming social-media-friendly models.

While life inside Condé has been tough and is testing Wintour, her brand outside of the magazine is still rock-solid.

Wintour is still a premium A-lister, hobnobbing with Hollywood elites, Washington power brokers and even British royalty. Witness the cool calmness in the photo of her and Queen Elizabeth at a recent London fashion show.

Of course, as chair of the Met Gala she took a onetime sleepy event and masterfully turned it into the most coveted ticket of the Big Apple’s spring social season.

Despite her successes outside of Condé — she was even whispered to be on the short list of possible ambassadors to the UK — critics worry that Wintour’s knack for incisive decision-making isn’t what it used to be, and that she “has too much power” at the company.

Missteps during Wintour’s artistic director reign include the appointment of Eva Chen to helm Lucky magazine, which shuttered in 2015 after an unsuccessful stab at e-commerce, as well as the hire of Joyce Chang to run Self.

Condé folded Self’s print edition in 2016.

With Wintour looking over their shoulders, both editors were blamed for making their magazines look too much like Vogue.

Another flub that took place on Wintour’s watch was the death of Condé execs gave Wintour control of the fashion site’s content, folding its traffic into Vogue Runway, a Vogue offshoot, so that the international division could turn the site into an e-commerce play.

That venture cost Condé Nast about $100 million before it decided to throw in the towel, closing last summer.

Wintour fans inside Condé — and there are plenty — insist the recent difficulties at the company do not reflect her shortcomings but rather the revolutionary whipsaw of the magazine industry.

Wintour wields tremendous power inside Condé, and yet no new ventures have emerged under her watch to light a fire under Condé’s bottom line.

Wintour, through a spokesperson, declined to comment for this story.


Wintour’s big hire of Barry to lead Glamour comes after the company shook up its editorial ranks, with longtime editors Cindi Leive of Glamour and Graydon Carter at Vanity Fair exiting.

Heralded by Wintour as an editor who “comes from the future,” Barry — known by her peers by the nickname “Social Sam” — arrived at Condé with no traditional print journalism experience, an anomaly for an editor-in-chief. With the pressure on Wintour to produce a tangible success, the hiring of Barry is Wintour’s boldest move yet.

But Barry’s unusual resume raised many a perfectly tweezed eyebrow among the staff.

“She comes from the future — I really can’t speak to that comment. I don’t even know what that means,” one source sniffed. “I think it means we’re taking a new approach.”

That approach includes a focus on digital growth. In the last year, Glamour’s website averaged about 7.3 million monthly unique visitors, which is about one-quarter of the traffic of Refinery 29, Glamour’s biggest digital rival. Barry, who specializes in using trending news and audience-driven data to inform coverage, seems well-positioned to grow web traffic, even if the process of making a magazine is foreign to her.

Critics at Glamour have already noticed Barry’s “complete lack of strategy” and knowledge regarding “how to put together a magazine.”

That kind of criticism is par for the course at Condé, which is known for its “Mean Girls”-style hazing culture.


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