Anna Wintour’s Successor: A Tip Sheet

Will she stay or will she go? We mean Anna Wintour, of course.

While the Page Six item in The New York Post that Wintour will step down in July as artistic director of Condé Nast and editor in chief of American Vogue after her daughter Bee Shaffer’s wedding has been firmly denied by Condé — and dismissed by many others — other sources tell WWD that the speculation might not be totally fanciful and that, indeed, Anna could be eyeing the exit. But only she, the Newhouse family and perhaps a handful of others know for sure.

Regardless, the item immediately sparked a wave of speculation and, inevitably, comments among the back-biting fashion world ranging from “It’s about time” to “I never liked her anyway” and “Oh, Vogue is so bo-ring” (said only the way a fashion person can, as a word of six syllables).

And while some observers have painted Wintour’s departure — whenever it comes — as apocalyptic in nature along the lines of, say, the disappearance of ice cream or chocolate (what will the fashion world do without her? Um, survive and prosper would be the answer), there is no doubt that even she will step down one day.

So who might succeed her? (Not that anyone ever could, naturally.) Here, WWD handicaps the candidates:

Edward Enninful

In some ways, he is Anna Wintour’s most logical successor. At least his name is getting bandied about quite a bit. There are those who believe his British Vogue gig was always going to be an internship for the top job in New York, a city that Enninful knows and loves from his styling days at W Magazine. That said, we would preach caution on this one: Enninful’s first ABC numbers aren’t out until mid-year, and he also happens to be a man in a #MeToo world, which could seriously scupper his chances in America.

ODDS: 15 to 1

Amy Astley

There are a slew of candidates for Wintour’s throne who were mentored by her at Teen Vogue but Astley is the OG. The teen title’s founding editor, she was tapped by Wintour in 2016 to helm Architectural Digest — an indication of how much she is in Anna’s favor. Astley has long been seen as a potential successor — and even for a time sported an Anna-type bob – and her selection would prove loyalty wins out. While she isn’t particularly known as a digital whiz in the style of Eva Chen (see below), Astley would be a safe choice.

ODDS: 20 to 1

Sally Singer

Another Anna loyalist and longtime favorite, Singer, Vogue’s digital creative director, already has that magical word “digital” in her title. And that is a bigger deal than ever — just ask Glamour’s new editor in chief Samantha Barry. Might Singer be able to add print to her purview? Does print even matter anymore? (Well, yes, but for how long?)

ODDS: 25 to 1

Lucy Yeomans

This could work: A steady pair of editorial hands, Yeomans was formerly editor of British Harper’s Bazaar and now has the top job at Porter magazine, which is published by Net-a-porter Group. She’s also in charge of Porter’s digital offshoots and is known for championing smart, artistic and accomplished women from a variety of industries. With her thick blonde mane, high heels — and passion for luxury — she’d certainly slot easily into the role, although it won’t be easy to woo her away from YNAP commercial powerhouse.

ODDS: 30 to 1

Stella Bugbee

The first lady of New York magazine took a section on shopping and ramped it up to a stand-alone web site that covers everything from fashion to feminism, while making the signature NYMag sensibility its own. With a background in fashion and design, it’s no wonder Bugbee’s name pops up on seemingly every list of magazine job prospects. Her mix of style and digital definitely makes her a contender for Vogue. But so far she hasn’t taken any of the others — could she resist the Vogue temptation?

ODDS: 40 to 1

Kristina O’Neill

She has helmed WSJ for the past five years, bringing fashion to financiers — and in the battle of the newspaper supplements, making hers more focused, better looking and insider-y interesting than rival T: The New York Times Magazine. The Harper’s Bazaar veteran is clearly adept at merging style and substance, a skill that puts her in the running for any fashion magazine top job — including rumors, late last year, that she might be headed back to Harper’s. Still, running a supplement with a guaranteed readership base is light years away from overseeing Vogue — although the perks and budgets would be substantially greater.

ODDS: 50 to 1

Elaine Welteroth

The former Teen Vogue editor in chief — another one — was reportedly in the running for the Glamour job but when that went to Samantha Barry, she left Condé, but not before she’d already lined up CAA representation. Although Welteroth was a celebrity editor while helming Teen Vogue, the halo around her has dimmed since her departure as that of her putative successor, chief content officer Phillip Picardi (see below), has risen.

ODDS: 75 to 1

Eva Chen

It would be hard to pull Chen away from documenting Ren and Tao’s lunches and posting photos of her #EvaChenPose in the backs of Ubers. But she does have that follower count, knows Condé from her days at Teen Vogue and the ill-fated Lucky and great insights about how to monetize content. Still, she’s already jumped from “old” media so jumping back in might be seen as a step backward.

ODDS: 100 to 1

Phillip Picardi

Phill-with-two-Ls, the chief content officer of Teen Vogue and Condé’s digital LGBTQ venture Them, was recently described by The New York Times in terms best reserved for the second coming. Could the 26-year-old ascend to Anna’s throne? She certainly hints at the possibility, as least in the fawning Times profile. “For Phill, anything is possible,” Wintour told the newspaper. “It’s his road to take.” But while digital and youth are intertwined like peanut butter and jelly, in Picardi’s case, his relative inexperience could work against him.

ODDS: 300 to 1

Natalie Massenet

Massenet has it all. She’s even already a Dame. A close pal of Anna’s and long-rumored to be her successor — she’s denied this more than once — Massenet would be the Newhouse family’s dream come true what with her commercial and fashion connections, entrepreneurial grit and talent for twisting arms, all with a big American smile. Then again, with her mucho millions in the bank, role as non-executive co-chair of Farfetch, a new career as an investor with her venture capital firm Imaginary Ventures and a baby at home, who needs the aggravation?

ODDS: 1,000 to 1

Emily Weiss

The Millennial anti-makeup makeup queen who managed to not only convince VC investors and a whole generation that the best way to achieve shiny, sweaty, natural faces is by buying her minimally packaged products but also to convince well-established names in fashion to open up their medicine cabinets for all to see. If anyone has a shot at keeping print alive while focusing on digital, betting on someone who went from “The Hills” and an assistant gig at Vogue to starting her own multimillion dollar business — all before 30 — isn’t the worst idea. If she wanted to sell out completely and go on to a new chapter, this might be it.

ODDS: 5,000 to 1

Hope Hicks

She may not have any magazine experience but, then, she didn’t have any political experience either until 2016. And she is currently available. After wrangling the greatest American ego that is President Trump and his Twitter habit and dealing with the hornet’s nest that is the current West Wing — all while maintaining a perfect blowout and an air of mystery — the Newhouse family and egotistical fashion designers would be a breeze.

ODDS: 500,000 to 1


Sure, it’s very unlikely. Then again, she is Oprah. If running for president didn’t interest her, maybe running Vogue would — with a little help from Gayle King, that is.

ODDS: 10 million to 1

Meghan Markle

Well, if Oprah is a long shot, the future princess and likely Duchess of Sussex is even a greater one. Still, according to the new Andrew Morton biography, Markle wants to walk in the designer shoes of the late Princess Diana and take up her mantle of charity work. After years of suffering under the bland and conventional Duchess of Cambridge, wouldn’t it be wonderful to have a young royal who not only wore great clothes, but also had the power to mix them up on the pages of a fashion magazine? While she’s at it, she can give all the young royals a fashion makeover, too.

ODDS: 65 million (the U.K. population) to 1

Joanna Lumley as Patsy Stone in “Absolutely Fabulous”

Lumley already has on-screen experience in the magazine business as the Bollinger-guzzling, chain-smoking fashion director who rarely turns up for work. But that could be a problem at Condé Nast, what with its new code of conduct and all. But Pats certainly has the svelte figure and the cutting comments that go with the job, and — who knows? — she might well just pull it off.

ODDS: “I already did that job in the Sixties, sweetie, but I don’t remember much.”

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