Anna Wintour’s name resonates with many – especially those familiar with her impact on the $2.3 trillion global fashion industry.

“I’ve worked with Nuclear Wintour many times – each time more frigid than the next,” a publicist responded when I requested commentary on Anna Wintour from the high-powered publicists and journalists within the PR industry’s most exclusive inner sanctum: the invitation-only private Facebook group, PR, Marketing and Media Czars. The group’s collective clandestine acumen could end celebrity careers, devastate industries, and—among those who practice PR’s darker arts—even topple governments.

“Demeaning demands and toxicity are her weapons of choice to achieve her goals,” the publicist continued. “And much of those demands were not necessarily professional, but for personal reasons, often to the detriment of an underling or brand publicist’s work. And despite her ‘departure,’ Anna will still have her claws into Conde Nast and Vogue as the global chief content officer...in that context, tread lightly.”

Wintour – “Nuclear Wintour” to those who’ve been within her blast radius – and fashion’s last reigning empress, has relinquished her editor-in-chief crown at American Vogue after 37 years.

She’s keeping her roles as global editorial director of Vogue and chief content officer of Condé Nast. The editor-in-chief title is simply vanishing, replaced by a “head of editorial content,” who will report directly to her. And true to her carefully choreographed universe, even her departure can be seen as performance art, designed to maintain maximum control while feigning a changing of the guard.

“Wintour has undeniably progressed the fashion industry as a publisher, alongside birthing numerous influential design and editorial careers,” writer and creative director Darren Griffin told me in an email, as did most sources quoted in this article. “But it’s fair to wonder if her near 40-year post as fashion president and chief has become a moving goalpost for new voices and emerging storytellers within the cultural zeitgeist. At what point does her tenure begin to work at cross purposes with what’s relevant aesthetically and culturally?”

For nearly four decades, Wintour operated as “the algorithm before algorithms,” as Trevor Perkins of PERK PR + Creative described her. Understanding the impressionable consumers’ passionate pursuit of luxury, she set the stylistic pulse long before TikTok trends existed, choosing which designers to elevate, what celebrities merited covers, and how fashion movements could define entire decades. So powerful was her gravitational force, Vanessa Friedman once noted in The New York Times, “she does not put a finger in the wind to judge trends: she is the wind.”

Wintour is rumored to have inspired the main character of Meryl Streep and Anne Hathaway’s hit movie. While her devil persona may have worn Prada, so did Pope Benedict XVI, which speaks to the good she’s done with her influence. She transformed the Met Gala from a modest fundraiser into what became “an A.T.M. for the Met,” raising a record-breaking $31 million this year alone.

Through the CFDA/Vogue Fashion Fund, which she co-founded in 2003 as fashion’s ultimate venture capital firm, she’s overseen disbursements of over $8 million to emerging designers. Her philanthropic reach extends beyond fashion, with CFDA/Vogue initiatives raising well over $20 million for AIDS research as she championed causes like Born Free Africa in the fight against mother-to-child HIV transmission.

“She was the first to consistently put celebrities on the cover of Vogue,” said Sally-Anne Stevens, founder of ‘b. the agency,’ who has partnered with Vogue for over two decades. “That move alone shifted fashion into the mainstream and brought music, film and fashion into the same cultural space. She understood the power of celebrity long before it became the engine behind modern influence.”

As a result, luxury brands poured hundreds of thousands into Vogue just to appear in the legendary September issue.

No one can deny Wintour’s eye for talent. She backed Marc Jacobs, Alexander McQueen, and John Galliano early in their trajectories, initiating the rise of the superstar fashion creative designer, however much this trend has fallen out of fashion. But in the case of Galliano, she engineered a professional comeback many thought unlikely, displaying a necromancy for resurrecting dead careers while also giving opportunity to budding ones.

“American Vogue with Anna at the helm most certainly played a role in my career,” shared Shannon Rusbuldt Amar, former Vogue model and cast member in the Vogue-produced documentary, The Models. “When fashion clients know that you have shot for the publication, they automatically take you more seriously, which obviously leads to bigger and better jobs.”

As publicist Jane Owen put it simply, “To be featured in Vogue meant you were part of the story of fashion itself.”

Wintour created magnificent beauty for the beautiful people while masking what many describe as a toxic empire built on fear and favoritism. With the same scepter she used to anoint designers, she thought nothing of doing the opposite to bury the living.

“What must the late André Leon Talley be thinking behind that velvet rope in the sky?” posed Sharon Geltner, award-winning arts and culture writer.

Perhaps most controversial was her treatment of André Leon Talley, Vogue’s groundbreaking and flamboyant creative director who, at Wintour’s side, helped shape the magazine’s relevance for decades. After leaving the magazine, Talley publicly described feeling discarded by Wintour despite years of loyalty, highlighting what Sharmon Lebby, founder of Blessed Designs Consulting, considered the performative nature of Vogue’s diversity, equity and inclusion efforts.

“It was people like Bethann Hardison who actually advanced DEI. Not Anna. Not Vogue,” Lebby told me. “André Leon Talley didn’t benefit from inclusivity, he bulldozed his way into fashion on his own terms. Vogue and Anna were just along for the ride.”

Former employees describe a workplace culture where terror trumped creativity; where Wintour’s personal whims superseded professional judgment. As one source recounted, a client spent three months perfecting a pitch to Wintour’s liking just to receive a dismissive response that “Anna had moved on.”

Her autocratic methods extended far beyond The Devil Wears Prada lore. One publicist pointedly referenced the infamous 2011 Vogue profile of Asma al-Assad, Syria’s first lady, titled “A Rose in the Desert,” which praised the dictator’s wife as “the freshest and most magnetic of first ladies” – just months before Syria descended into civil war. The article remains one of journalism’s most embarrassing misjudgments.

“She should have been fired for the article on Assad’s wife,” the publicist fumed. “[The article] praised Assad, calling him ‘democratic.’”

Wintour’s semi-departure comes amid a fundamental transformation in fashion. The imperial editor model she perfected has become outdated and counterproductive.

“Her vision is still a dream world that people want to belong to, and that’s not what fashion is about today,” Quynh Mai, founder of Qulture agency, pointed out. “Fashion is about self-expression, loving yourself, and being yourself. She’s a part of the old guard where fashion is about aspiration, inspiration, and admiration. This no longer speaks to today’s youthful or modern customer.”

The numbers match this cultural shift. Fashion advertising fell 50% during the pandemic as luxury brands slashed budgets remain slashed. Meanwhile, TikTok creators began moving fashion trends faster than Vogue’s lengthy editorial process. Wintour’s gatekeeping model became a liability when audiences chose democratized influence over dictated taste.

Monia Benchoufi Moulin, CEO of MADAME WILLIAM M., offered the harshest assessment. “Her autocratic reign forced designers to bow before her for pre-runway approval. Under her rule, shows grew darker, colder, and joyless — all smiles erased, all freshness extinguished. The altar of elegance became a temple of trend fatigue.”

But this critique isn’t entirely unfair, given a growing sentiment: as Wintour’s power calcified, her personal aesthetic began to eclipse her original purpose as steward of a business empire built on luring advertisers who want to reach a tapped-in audience.

Moulin continued, “Vogue under Wintour ceased to be a discovery platform; it became an echo chamber for advertiser dollars and editorial nepotism. A new era could revive authentic storytelling, celebrate nuanced creativity, and return to fashion’s core: to inspire, not impose. Her obsession with self-relevance drowned Vogue in noise, stripping fashion of its mystique. Her departure ends a long chapter of dictatorship in fashion. Let this be a turning point — one that restores freedom, and meaning. Fashion deserves to dream again.”

Jasmine Charbonier, owner of Charbonier Consulting and a fashion industry veteran, recounted having to navigate 15 different channels to get a maybe on having a client’s collection featured in Vogue.

“The era of the all-powerful fashion editor is ending,” she said. “And honestly — as someone who’s spent years navigating those waters — it’s probably about time.”

Fashion media has already moved beyond the top-down model of editorial monarchy. As Friedman noted in her New York Times article, publications worldwide have abolished editor-in-chief titles in favor of “heads of editorial content.” The new generation of fashion leaders — Lindsay Peoples Wagner at The Cut, Edward Enninful formerly at British Vogue, Samira Nasr at Harper’s Bazaar — operate with collaborative spirits and inclusive missions foreign to Wintour’s modus operandi.

“American Vogue is overdue for a refresh,” Jenny Davis, Professor of Fashion Media at Southern Methodist University, told me. “Anna may be an icon, but it’s been a long time since she’s been plugged into the generational zeitgeist. In today’s challenging print media environment, it’s imperative that a magazine editorial director stays abreast of what’s happening in fashion, music, streetwear, youth culture and anything and everything that’s new and next.”

And yet, Wintour’s strategic maneuvering ensures her influence persists.

By holding global oversight while shedding daily American operations, she retains her position as fashion’s haute puppet master – carefully staged and still all-controlling. The “head of editorial content” – who will most likely never hold the editor-in-chief title as long as Wintour draws breath – will wield significantly less power than traditional editors-in-chief, functioning more like a regional manager.

“This announcement doesn’t change much,” Lebby sighed. “From a branding perspective, that’s about consistency. From a marketing and cultural perspective, it reads as control. It signals that Vogue isn’t truly ready to evolve.”

Richard Dukas of Dukas Linden Public Relations noted, “Few people have a name so iconic and intrinsic in their industry as Anna Wintour.”

Yet iconic sans evolution becomes irrelevance. The most successful leaders know when their methods no longer serve their missions.

“Like Joe Biden, it’s time for her to know when it’s time to step down,” Mai added. “Time to leave while the party is good. Time to leave while her legacy and iconic status is still intact.”

Dukas continued, “Whenever an iconic founder or prominent executive departs a well-known brand, it presents both challenges and opportunities. While a leader’s job is to build a company that will survive and thrive long after they are gone (think Henry Ford), good PR messaging often paints them as indispensable. They have truly done their job if they have crafted a succession plan far in advance that can be quickly executed.”

In examining Wintour’s legacy, four insights emerge for C-suite leaders navigating their own institutional power structures and future planning:

Wintour’s gradual power consolidation over four decades is how personal brands become inseparable from institutional ones. This “retirement” allows her to maintain her influence in a selfish strategy that doesn’t quite bode well for Vogue when she leaves this mortal coil.

The younger generation’s rejection of Wintour’s imperial style reflects a new preference for authenticity over authoritative. Brands relying on a single, all-powerful figure risk obsolescence when cultural winds shift, as Vogue continues to experience under an empress who seemingly only takes advice from a mirror.

Fear-driven workplace cultures, once tolerated as creative necessities, have become liabilities for an organization’s future as social awareness evolves. Gen Z and Gen Alpha are now questioning the value of working in toxic environments. They’re choosing entrepreneurial routes over enduring a well-heeled boss from hell.

Wintour’s disconnect from digital-native audiences shows legacy alone can’t protect relevance, particularly when she’s cultivated an environment where challenging the empress’s nudity becomes career suicide. The C-suite must be ruthless in evaluating whether their strategies reflect today’s consumer values.

Wintour’s 37-year reign at American Vogue isn’t quite over as she stubbornly holds court in an industry rejecting the monarchy she built. And yet, her legacy will be for being the oldest person at a party filled with young, fresh creatives plugged into the contemporary current.

I received over 100 emails from industry insiders wanting to be included in this article. Eighty percent of the comments were clearly AI generated, as almost everyone described “the end of an era” and “decentralizing fashion” and “gatekeeping” in proof ChatGPT has been busy. As I lamented my frustration to the Facebook Czars group, one former People Magazine editor offered another take:

“Ok, but hear me out,” she said. “The fact that your call for sources on a piece about Anna Wintour ended in a slew of AI responses says a lot about how people think and feel about her.”