Anna Wintour’s Vogue And The Reckoning Of Fashion’s Last Empress

It’s the Vogue job a million girls would kill for, yet who would want to step into the Pradas of the Last Fashion Empress Anna Wintour?

Well, allegedly, Lauren Sanchez Bezos!

Fresh from losing the auction for the original Hermès Birkin bag once owned by the handbag’s namesake Jane Birkin, the newly minted second richest wife in the world after Mrs. Zuckerberg is rumored to be applying her under $10.1M losing bid value towards her husband’s acquisition of Vogue’s parent company, Condé Nast.

“Anna Wintour announced she was stepping down one day before Sanchez was on the digital cover,” speculated one power publicist in PR, Marketing and Media Czars, the exclusive, high-powered Facebook Group of journalists and public relations professionals. “One would assume she wasn’t in favor of the placement –understandably so!”

A magazine founder smirked, “I knew it. He probably did something to make Anna leave. And then he would give the magazine to his wife. So petty. If this happens, it will be the end of Vogue.”

When another editor pointed out Anna hadn’t officially left the building, the founder continued, “She left the spot that Bezos’s wife will have after Anna criticized her taste in fashion.”

“Bezos’s wife will never be ‘head of editorial content’ under Anna. Please,” sniffed the editor in chief of a fashion industry publication.

As the debate raged, only one publicist defended Sanchez Bezos as “extremely bright and talented” who would “bring integrity back to the once-great magazine.” This response was met with a sea of laughing emojis and another publicist’s retort, “not sure her taste is the same as the typical Vogue demographic.”

“Vogue doesn’t know their demographic,” the Sanchez Bezos backer replied. “The readership has been in deep decline year after year.”

All industry insider gossip aside, the question remains, who will be Wintour’s successor? And what exactly will they inherit?

Where Vogue Stands

“Considering what’s going on at Condé Nast and has been a normal course of business for them in the last 15 years operating at losses and selling assets to cover, that might not be the stupidest thing they could do,” Sean-Patrick Hillman, editor in chief and co-publisher of New York Lifestyles Magazine said in response to a possible Bezos acquisition.

Once the crown jewel of legacy publishing, Condé Nast spent much of the last decade and a half playing high-gloss triage while chasing digital relevance and brand extensions to counter a collapsing print advertising market. From 2008 through 2021, the publishing giant operated in chronic deficit, posting losses exceeding $120 million in 2017 alone while hemorrhaging staff through repeated layoffs and magazine closures and divesting assets by selling titles like Brides, Golf Digest, and W to shore up finances.

2021’s $2 billion revenue marked Condé’s first profitable year in nearly a decade, but like much of the fashion industry, this celebrated “return to profitability” was only a passing fad. Pre-tax profits plummeted from roughly $29.1 million USD in 2022 to $10.4 million in 2023. The company’s January 2024 $87.5 million sale of Vogue House, Conde Nast’s UK headquarters for over 60 years, generated a significant one-time profit, suggesting asset sales are no longer a relic of past desperation and are now key to Condé’s financial stability.

Against this corporate financial quagmire, Wintour hasn’t made a complete mess of Vogue from a purely performance metric. Circulation declined just 3.1% from its 2022 peak to 1.23 million—modest compared to the industry’s 8% annual freefall—while maintaining 12 million print readers and reaching 117 million across all platforms. Digital revenues now exceed print, with the magazine commanding $1 million for Met Gala livestream ad slots. Revenue diversification has proven crucial, with nearly 40% of income flowing from consumer subscriptions and e-commerce partnerships generating 39% growth. Events like the Gala contribute 19% of revenue, with the annual event alone exceeding the Super Bowl’s cultural footprint by generating $543 million in media impact value.

While Wintour’s successor won’t inherit a money-losing periodical, they will inherit a complicated but functional machine operating within a financially precarious parent company. So perhaps Hillman has a point – selling Condé to Bezos for Vogue to become a billionaire’s wife’s plaything might just deliver much needed shareholder value.

Vogue And The Impossible Job Description

For all of Vogue’s financial resilience, Wintour’s descendant must still confront a brand facing an identity crisis. Influence has migrated to social media, where trends are born and die within days. While Vogue clings to a monthly publishing cycle and a digital brochure format, TikTok creators speak for a youth culture craving instant gratification and interactive community while proving more willing to give new brands a chance merely for showing up consistently.

“One of our recent Bryant University grads, Mikayla Nogueira, built a global audience from her bedroom by sharing makeup tutorials and launched her own brand, POV Beauty,” shared Stefanie Boyer, professor of marketing at Bryant University and co-author of The Little Black Book of Social Media: Strategies to Ignite Your Influencer, Professional or Business Brand. “Today, influence is built through connection and authenticity.”

Once considered fashion’s north star, Vogue’s editorial voice is now competing with algorithms, influencers, and fast-moving microtrends. Its digital footprint is eclipsed by People Style, which commands the #1 position of most relevant US fashion publications with 195,887,577 site visits according to a Muck Rack ranking, compared to Vogue’s anemic by comparison #6 spot with 18,599,319 site visits.

“Vogue has been on shaky ground with Wintour as of late,” beauty historian and author Rachel Weingarten told me in email, as did many quoted in this article. “While she once was the embodiment of everything stylish and trendy, that’s not entirely the case anymore. It could be Gen Z nipping at her heels, reader dissatisfaction with the obsessive celebritization of print, or the death knell of legacy magazines in general.”

Vogue’s aspirational editorial is perceived as aloof to younger readers navigating economic uncertainty. Gen Z isn’t buying $670 trench coats as steals or seeing themselves reflected in Vogue’s casting choices.

“While there have been efforts to diversify, on the covers, on the runway, it often feels performative,” said Sharmon Lebby, founder and CEO of Blessed Designs Consulting. “The deeper shift hasn’t happened. What’s needed now is real space for fresh perspectives, especially from communities that have long been on the margins.”

In short, Wintour’s beneficiary will need to rebuild trust with a generation that doesn’t see the glossy as theirs. How that happens is anyone’s guess, given Wintour’s newly created “head of editorial content” title is a thinly veiled declaration no one gets to call themselves the editor in chief of American Vogue but her, even though this is technically no longer her title. Her heir-apparent will have diminished authority, impossible expectations, and the unenviable task of modernizing an institution whose departing leader refuses to depart.

“A brand like Vogue now has to decide whether it leads the next cultural movement or holds onto the last one,” said marketing strategist Leah Miller of Versys Media. “That decision will determine its relevance in the next 10 years.”

This decision also carries psychological consequences extending beyond fashion preferences, argued Briana Sefcik, director of trauma and family wellness at The Last Resort Recovery. She framed Vogue’s representation problem as a mental health crisis. “When young women see only one version of beauty reflected back at them, they learn to devalue their own identities. But when they see themselves, their bodies, cultures, and stories, represented with dignity, it creates psychological permission to exist fully and confidently.”

Sefcik’s assessment that “the media has the power to either re-traumatize or help heal” crystallizes why Vogue’s performative diversity efforts have failed to connect with younger audiences. She added, “Trauma-informed storytelling means moving beyond surface-level inclusion and asking: how do our narratives make people feel about themselves? With Anna Wintour’s departure, there’s an opportunity to redefine influence, not through fear or exclusivity, but through emotional intelligence, vulnerability, and true representation.”

Contenders For Vogue’s Head of Editorial Content

Industry speculation centers on several candidates representing different modernization approaches. Chioma Nnadi emerges as the obvious choice, currently serving as head of editorial content at British Vogue. She has the institutional knowledge Condé Nast typically favors.

“Many see her as Anna’s only credible successor,” noted Effie Kanyua, former director of PR & communications for Hearst UK & Europe who has guided succession planning for luxury publications. “She has the experience and credentials to take US Vogue forward.”

Nnadi’s tenure at British Vogue has balanced heritage with innovation, maintaining cachet while expanding cultural relevance. She’s someone capable of evolution without revolution—something Condé Nast’s board likely seeks.

“British Vogue’s Chioma Nnadi and Harper’s Bazaar editor Samara Nasr certainly fit the bill, but would they leave their prestigious posts?” wondered Jenny Davis, professor of fashion media at Southern Methodist University. “My pick for the position is Lindsay Peoples. She’s a shining star who still has room to rise. She’s young, smart, stylish, insanely talented and even better, she’s a Condé alum — she’s the former editor of Teen Vogue and was Condé’s youngest-ever magazine editor-in-chief.”

Peoples’ successes as EIC of New York Magazine’s digital property, The Cut, led to a standalone print version when legacy magazines have mostly given up on producing physical copies. With her co-founding the Black in Fashion Council, which brings underrepresented voices into fashion discourse, her appointment would signal Vogue’s genuine commitment towards charting a high fashion and inclusive path.

Chloe Malle, editor of Vogue.com, is New York Times’ chief fashion critic Vanessa Friedman’s favored candidate. “The big money is on Chloe Malle,” Friedman noted in her email newsletter. “She’s very chic, young, knows Anna and how she works, and has been happy toiling away in the semi-background like the other regional H.O.E.C.s.”

Malle’s digital expertise in online engagement and content strategy could lure back younger audiences. Yet her relationship with Wintour might be a limitation that makes her hesitant to step on the toes of a mentor who could learn quite a bit from her mentee.

Edward Enninful continues generating speculation despite launching his own global media and entertainment company, EE72, in February. As former EIC of British Vogue, he proved traditional fashion publications can embrace inclusivity without sacrificing luxury appeal. Multiple sources mentioned Enninful as their dream candidate, though it appears his attention is focused on 72 Magazine, his digital platform and quarterly print publication debuting later this year.

Other speculation includes Amy Astley, global editorial director at Architectural Digest; Kate Betts, a Condé Nast veteran now creating content for luxury brands with her own consultancy; and Eva Chen, Instagram’s director of fashion partnerships, a role that would translate well in fixing Vogue’s flailing social media dynamics.

The Future of Vogue For The CMO Perspective

With the consumer’s passionate pursuit of luxury no longer being steered by luxury’s once formidable power broker, fashion and luxury industry CMOs should be considering their next play. And according to several sources, marketing directors at unknown brands Vogue never invited to the party may now have their chance.

“Anna taking a step back at Vogue may provide more opportunity to innovators and smaller fashion/lifestyle brands at the iconic magazine,” Hillman offered. “It’s the perfect time to start strategizing your approach to the publishing team in how you want to position yourself, brand or company.”

“When established gatekeepers leave, it’s like when the ‘good ol’ boys network’ I faced in advertising started changing—suddenly there’s space for new voices and perspectives that were previously shut out,” added Nicole Farber, CEO of ENX2 Marketing. “For marketers, this means fashion brands need to diversify their media relationships NOW.”

According to Karen Cleaver, chief operating officer at Underground Marketing, fashion agencies are reshuffling entire operational systems to function without Wintour’s centralized authorization. “What’s really happening behind the scenes is a workflow revolution. Fashion PR teams are restructuring their entire approval processes—instead of one final decision-maker, they’re implementing committee-based systems. We’re processing 40% more content requests from agencies serving fashion brands compared to last quarter. Wintour’s departure means those carefully calibrated tones that relied on her aesthetic approval suddenly need recalibration. Our content teams are already fielding requests to help fashion brands develop more autonomous brand voices that don’t depend on single gatekeepers.”

Other fashion insiders are also adapting their creative strategies for a post-Wintour landscape. “As a stylist, I’m already prepping celebrity looks with subtle nods to a Vogue-less future,” celebrity stylist Pilar Scratch noted. “More inclusive sizing, bold color play, gender fluid styling; the kind of wardrobe headlines that shout ‘We’re ready for Her Vogue, however it shows up.’ It’s time to pitch narrative shifts: diversity, tech, sustainability, while Vogue undergoes its own rebranding. That alignment can be transformative if you’re first out of the gate, not 50th. It’s an opportunity to drive fresh visuals, fresh voices, and fresh energy into narratives once tethered to Anna’s legacy.”

And what would a modernized version of Vogue look like? “We might see Vogue become more personality-led through its content creators or contributors rather than a single figurehead,” suggested Kintija Sluka, head of PR & Performance at One March PR. “Think more behind-the-scenes access, more real-time editorial voices, maybe even a bigger push into video and creator collabs.’’

Scratch added, “I expect upcoming editors to pull Vogue deeper into digital. TikTok styling tutorials, AI-curated capsule wardrobe drops, metaverse fashion previews. But don’t sleep on IRL. Expect Vogue to double down on live pop-up events, styling clinics, and experiential retail. Because in a world gone virtual, people still crave to feel velvet under their fingers.”

Ultimately, luxury brand marketers and CMOs must accept Wintour’s way won’t deliver their next generation of customers. “There’s a bigger shift playing out – aspiration isn’t being defined by the media anymore, it’s being shaped by communities,” declared Albert Varkki, fashion expert and co-founder of Von Baer. “These days, fashion authority could just as easily be a 22-year-old stylist in Lagos with 40,000 followers, or someone writing longform critiques on Substack through a climate lens. Cultural relevance now comes from being part of the conversation, not floating above it.”

Whether the pending head of editorial content reports to Anna Wintour, Lauren Sanchez Bezos, or some yet-unknown successor, Vogue’s uphill battle requires earning influence with audiences no longer trusting it to define trends. And while Wintour’s once-envied crown may remain on the masthead, its authority to command the culture has faded. Should Vogue evolve into a more dynamic, inclusive brand or fade into curated irrelevance depends on if its next leader is willing to reflect the world in the magazine’s pages and digital presence as it is and not as fashion’s last empress once imagined it to be.