Behind the bob and the blackout sunglasses is the woman who doesn’t just cover fashion – she decides it. 

You don’t need to read Vogue to know Anna Wintour – or at the very least, the chokehold her influence has on the world. The front row she made sacred. The frost she made fashionable. The infamous Monday in May the world begs to be invited to.

In the religion of fashion, there’s before Anna, and there’s after Anna. Before, editors stayed backstage. Covers were models, not celebrities. Fashion was glossy, but not yet gospel.

Then came 1988. Home & Away debuts. Nike says Just Do It. CDs outsell vinyl for the first time. Vogue’s about to be torn up and rebuilt in the Wintour image.

This is the rise of Anna Wintour: media monarch, cultural architect, and the woman who turned fashion into scripture.

Born to Rule

Anna Wintour didn’t stumble into fashion – she was raised for it. Born to Charles Wintour, editor of London’s Evening Standard, and Eleanor Baker, a Harvard-educated American with her own media pedigree, Anna grew up in a house where influence was inherited and opinions weren’t optional.

It was her dad who set the tone early. When a teenage Anna asked what to put down for “career ambitions,” he told her: “Editor of Vogue, of course.”

At 15, she ditched school uniforms for hemlines, bobbed her hair (permanently), and started interning at Harper’s & Queen. By 20, she was working in fashion retail and clubbing with the Rolling Stones. But London was just for play.

By the 70’s she moved to New York and quickly made herself known. First came a short-lived stint at Harper’s Bazaar, where she was fired after nine months for being “too European.” Then came Viva, Savvy, New York Magazine.

By 1983, Condé Nast came calling. Wintour joined Vogue as its first-ever creative director. When then-editor Grace Mirabella asked what role Anna wanted at Vogue, Anna told her: “Yours.”

British Vogue, circa 1985

When Beatrix Miller retired in 1985 after two decades at the helm of British Vogue, Condé Nast handed the reins to a then-35-year-old Anna Wintour. They didn’t get an editor. They got a regime change.

Entire departments were replaced. Columns were cut. Shoots were scrapped. If you were loyal to the old way of doing things, you were shown the door. The nickname “Nuclear Wintour” came quickly and hasn’t gone away since. 

Years later, Anna addressed the nickname head on: “If I’m such a bitch then they must really be a glutton for punishment, because they’re still here”.

Anna’s Vogue was colder, cleaner, sharper. She pushed for younger models, shorter hemlines, and more street. She wanted clothes that looked like they might actually be worn – and covers that didn’t play safe.

At the same time, in New York, Wintour was already building alliances. She formed a close working relationship with Alexander Liberman, Condé Nast’s longtime editorial director and the man who controlled the crown jewels. Alongside fashion editor Polly Mellen and creative lead Jade Hobson, Wintour operated almost autonomously – inside the system, but firmly outside the hierarchy.

Her boss, Vogue US editor-in-chief Grace Mirabella, described Wintour’s tenure under her as “a very bizarre three years during which Anna created a kind of office within the office, working with Liberman, Mellen, and Jade Hobson, and against me”. She wasn’t wrong. Anna wasn’t subtle. She was staging a takeover. 

The Coup

In 1987, Anna was handed House & Garden – not quite her dream job, more like a stylish decoy. Officially, she was there to revamp the flailing interiors title. Unofficially, everyone knew it was the waiting room for her throne.

She took the job. She took a red pen. And she took no prisoners.

Within a week, $2 million worth of shoots were scrapped. Entire issues axed. The name was cut to HG. Out went the garden spreads. In came Versace bedding and fashion editorials styled in front of marble fireplaces.

Subscriptions plummeted. Advertisers panicked. But Condé Nast? They saw exactly what they needed to see. She could burn it down. She could rebuild it. She could hold her nerve.

Meanwhile, Vogue US was flatlining. Grace Mirabella was still at the top, but the writing was on the impossible-to-penetrate walls. Her version of Vogue was practical, polite, and above all else – it was being outpaced.

Elle came to the US with the subtlety of a thunderstorm . French by origin, Elle was everything Vogue wasn’t: fresh, youthful, unafraid of denim. By the late ’80s, it was siphoning readers and advertisers at speed; making Vogue look like a museum catalogue.

Condé Nast had a problem and Anna Wintour was the solution. And then: the fax.

In July 1988, Mirabella was fired without warning. She found out the same day as the press. Anna’s first cover arrived in November. Model Michaela Bercu, smiling in the sun, wearing jeans (gasp) and a Christian Lacroix jacket that wouldn’t zip up. It was effortless. Unstyled. Too human for Vogue. The printers thought it was a mistake. “I had just looked at that picture and sensed the winds of change,” Wintour said.

And just like that, Vogue got its edge back and Anna Wintour got her throne.

The Art of Knowing Early 

Anna’s most enduring legacy might not be a magazine at all, but a particular kind of foresight. The ability to sense what (and who) was about to matter, just before the world did. She swapped supermodels for celebrities at a time when fame still felt faintly unserious, and red carpets weren’t yet content pipelines.

Anna understood that relevance would become fashion’s most valuable currency. That we weren’t just buying clothes, we were buying stories. Public lives. Women we recognised or were about to. 

She didn’t just reflect culture. She created it. It’s hard to know whether fashion folded into celebrity because it was always going to – or because she gave it the runway.

That’s the funny thing with timing. By the time everyone sees something clearly, the moment’s already passed. 

Anna didn’t predict the zeitgeist – she printed it.

The First Monday in May

Technically, the Met Gala wasn’t hers to begin with.

Let’s throw it back to its inception – 1948. A quiet fundraiser for the Costume Institute. Society wives. Society rules. A seated dinner. But like most things that pre-date Anna Wintour, it didn’t really matter until she got involved.

By the mid-90s, she’d quietly turned it into fashion’s most powerful guest list. She picked the theme. She approved the outfits. She decided who sat where, who arrived when, who made it up the steps at all.

Designers didn’t just dress their muses. They paid tens of thousands of dollars for the privilege – knowing the entire world was watching.

It became a spectacle wrapped in tulle. A single night that could shift public opinion, revive a career, or cement a designer’s place in fashion history.

Think:

Rihanna in Guo Pei, 2015 – a towering yellow cape with a 16-foot train, hand-embroidered over two years. It made Rihanna the queen of the Met. It made Guo Pei an international name overnight.

Kim Kardashian in Givenchy, 2013 – heavily pregnant and heavily criticised, her first appearance drew brutal comparisons to a couch. But it also marked the beginning of her Wintour-approved transformation from reality TV punchline to high fashion power player.

Billie Eilish in Oscar de la Renta, 2021 – Old Hollywood silhouette, new-gen politics. She agreed to wear the dress only if the brand stopped using fur. So they did. 

Lady Gaga in Brandon Maxwell, 2019 – four outfit reveals in one performance-art entrance. High camp meets brand theatre. Everyone else on the carpet looked like they’d forgotten the assignment.

Keira Knightley in Erdem, 2007 – moody florals, undone elegance, and the moment Erdem went from London insider to global name. U.S. retailers picked up the phone. Stockists followed. The Met made it exportable.

And behind it all, Anna. No press tours. No commentary. Just presence. The night belongs to the celebrities. The photos belong to the brands. But the Met? The Met will always belong to her. 

 

The Exit

On June 26, 2025, the fashion world clutched its pearls: Anna Wintour would step down as editor-in-chief of Vogue US after 37 years at the top.

She’ll stay on as Condé Nast’s Chief Content Officer and Global Editorial Director for Vogue, but the title that mattered most – the one that shaped not just a magazine, but an entire industry, is no longer hers.

The timing is almost poetic. High fashion is in the middle of an identity crisis – or maybe just finally admitting to one.

Creative directors are playing musical chairs: names shuffled, houses reset. Jonathan Anderson has just been appointed to Dior, overseeing men’s, women’s and couture for the first time since Christian Dior himself. Pharrell’s appointment at Louis Vuitton has blurred the line between celebrity and creative leadership entirely.

Meanwhile, Chanel – fashion’s most storied house – remains leaderless months after Virginie Viard’s exit. The seat is still empty. The message is clear: even fashion’s biggest names don’t know what comes next.

For the first time in decades, there is real space in fashion. Vacant roles. Fewer sure bets. A hunger for newness – not just in silhouette but perspective. The discourse around fashion has shifted. The sameness that once passed as house codes now reads as creative fatigue. To find something genuinely original, you look to the edges – to the mid-tier brands with smaller budgets and louder ideas.

Anna Wintour’s exit doesn’t just close a chapter. It signals the start of something else: The era of the untouchable tastemaker is ending. Fashion is ready for a takeover. And what comes next won’t look like before.