The Anna Wintour Effect: How To Build An Iconic Brand Legacy In 2025

Forbes

19 hours ago

Anna Wintour at The 78th Annual Tony Awards held at Radio City Music Hall on June 08, 2025 in New ... More York, New York. (Photo by John Nacion/Variety via Getty Images)
Before social media gave leaders an opportunity to brand themselves, I've long said Anna Wintour was leading the conversation.
As the legendary Editor-in-Chief of Vogue and global chief content officer of Condé Nast, Wintour spent decades building her brand and shaping the public conversation through sheer taste, quiet control, and unapologetic decision-making. From helping launch Christian Lacroix to championing Michael Kors and Giorgio Armani, her editorial decisions didn't just define fashion—they solidified her status as one of business's most powerful personal brands and one of fashion's most iconic and influential leaders.
LONDON, ENGLAND - FEBRUARY 20: Queen Elizabeth II and Anna Wintour attend the Richard Quinn show ... More during London Fashion Week February 2018 on February 20, 2018 in London, England. (Photo by Tristan Fewings/BFC/Getty Images)
And she did it all without ever pandering to public opinion. Anna Wintour masterfully built a personal brand unlike anyone else in fashion. In doing so she has become a living, breathing embodiment of the rules of The Kim Kardashian Principle.
While other editors navigated the daily grind in a visible state of exhaustion, Wintour, with her signature bob, dark sunglasses, and famously enigmatic composure, cultivated an air of mystery and authority that few could emulate. Her unwavering control and sharp decisiveness weren't just traits; they were brand pillars that made her instantly recognizable and endlessly fascinating. And when others in the industry relied on warmth and social charm, Wintour's cool, almost regal distance became her superpower — a living embodiment of exclusivity and taste — and a clear message to all that she wasn't in the business of being liked and had no fear in being different. Wintour stood apart as a true icon — the ultimate curator not only of style, but of her own myth.
So what can we learn from one of the most iconic, enduring and inspiring business brands of our time?
Here's what I believe made Anna Wintour iconic—and that every business leader would benefit from taking seriously.
Be Consistent — Even When It's Unpopular
Vogue's April 2014 cover, photographed by Annie Leibovitz.
Whether she was putting Cindy Crawford and the supermodels of the eighties on her covers, turning fashion's biggest night, the Met Gala into a cultural juggernaut alongside the Costume Institute, or insisting on couture in an era of fast fashion, Wintour never wavered.
Take 2014. Anna Wintour broke the internet (and the hearts of many die-hard core Vogue fans) when she placed Kim Kardashian on the cover of American Vogue—alongside Kanye West. Critics slammed it and the Fashion Wire Press called it 'a cultural misstep.' But Wintour didn't flinch where other leaders would have easily crumbled. Because she saw what only a few others did at that stage: Kim Kardashian wasn't just a reality star—she was a new reality standard. A self-made brand, a pioneer with unmatched digital influence.
In a leadership landscape obsessed with flexibility, Anna Wintour's leadership style wasn't that of chasing approval but leading the culture. She showed us the value of a steadfast vision. And I'd say, her sunglasses were far more than just a signature—they were a symbol of her inner strength as a leader and her unshaken clarity.
And research would agree. Maintaining consistent branding fosters trust and recognition—cornerstones of loyalty and long-term engagement. A Lucidpress case study found that brands with consistent presentation across channels see up to 23% higher revenue. Additionally, Forbes emphasizes that consistency enhances credibility, supports recognition, and boosts customer loyalty.
Define Your Narrative—Or Someone Else Will
WASHINGTON, DC - JANUARY 4: Anna Wintour, Editor-in-Chief of Vogue, receives the Presidential Medal ... More of Freedom by U.S. President Joe Biden in the East Room of the White House on January 4, 2025 in Washington, DC. President Biden is awarding 19 recipients with the nation's highest civilian honor. President Biden is awarding 19 recipients with the nation's highest civilian honor. (Photo by)
Wintour's precision bob, Chanel suits, and icy restraint created a powerful persona but her level of transparency made her the editor of all fashion editors and a living logo. Where other editors would remain strategically coy. Anna Wintour didn't shy away from her political biases. As many of you know, I've spoken at length about the power of polarizing brands before. She put Michelle Obama on the cover twice (2009 and 2013) which was risky for a fashion magazine but in the process solidified Wintour as a political influencer as much as a fashion one. She also fundraised for Democratic candidates, blurring lines between editorial independence and political power.
In the Hollywood blockbuster, The Devil Wears Prada, Meryl Streep's Miranda Priestly—allegedly modeled on Wintour—became a cinematic shorthand for power, polish, and control. She entered the cultural vernacular through building her brand in a mythological and culturally relevant way. And while Wintour never confirmed the connection. She didn't need to.
And it was this exact brand that took her through the high and lows of Vogue's sales and CondeNast's profitability calls. Where other lesser known executives were axed by the waist side, Wintour's power brand made her unshakeable and unbreakable, and in the cut throat world of editing—unthrowoutable.
The lesson? Mystery creates magnetism. In an age of under or overexposure, curation is always currency.
Wintour didn't just make herself an icon she made icons of fashion photographers like Peter Lindbergh and Richard Avedon. Who can forget the Wintour-commissioned now legendary Lindbergh shoot in January 1990 for the cover of British Vogue featuring Linda Evangelista, Naomi Campbell, Cindy Crawford, Tatjana Patitz, and Christy Turlington. The image is often credited with launching the "supermodel" era and remains one of the most iconic fashion images ever created. And in addition to making Wintour allegedly broke careers too—most famously of Vogue editors Grace Mirabella and André Leon Talley—according to their interviews and memoirs anyways. Whatever the truth, Wintour understood the power of shaping narrative in a direct and transparent manner. And while inside Condé Nast, she earned nicknames like 'Nuclear Wintour' because of her reputation for firing people abruptly there is no doubt that from launching designers through the Fashion Fund to championing emerging talent, she was in charge of directing her story, not just starring in it—and by discovering and elevating people, not tearing them down.
Naomi Campbell, Linda Evangelista, Tatjana Patitz, Christy Turlington and Cindy Crawford.
What do I make of all this mystique? There is enormous power in overexposure as there is in mystique. As long as it's done authentically. You don't need to show everything but you do need to take risks and shape what matters when it comes to your personal brand.
Numerous research into brand mystique shows that being authentically elusive can drive engagement and demand. One LinkedIn analysis highlights that mystery—as seen in 'anti‑advertising' strategies—creates intrigue and emotional pull, prompting audiences to seek deeper connections.
Turn Gatekeeping Into Gravitas
NEW YORK, NEW YORK - MAY 05: (L-R) Anna Wintour, Met Gala Chair, and Colman Domingo and Lewis ... More Hamilton, Met Gala Co-Chairs, attend the 2025 Met Gala Celebrating "Superfine: Tailoring Black Style" at Metropolitan Museum of Art on May 05, 2025 in New York City. (Photo by)
Gatekeeping has become a dirty word but Anna Wintour made it a power strategy with her power brand.
From Milan Fashion Week to Paris couture, she reigned with restraint. If you were seated at her Met Gala, you weren't just seen—you were sanctified. Guests like Oprah Winfrey, Gigi Hadid, and Kanye West didn't just attend—they abided by her codes—and felt privileged for the blessing.
That exclusivity? It wasn't arrogance. It was personal branding at its finest baaed on one of Wintour's key branding pillars. And that setting of a vision and aligning people towards that vision—especially those who typically march to their own drum beat—is the textbook Harvard Business School definition of effective leadership.
The September Issue—Vogue's blockbuster annual release—often ran over 800 pages and became fashion's holy text. And the 2009 documentary of the same name proved what insiders already knew: Wintour didn't just reflect trends. She ordained them.
And as leaders back then scrambled to pretend to 'make everyone feel included,' Wintour had no shame in reminding us that selectivity can also create significance. When everyone's invited, no one feels special—and she was willing to take the brunt of this stance for decades.
Scarcity isn't just psychological—it's commercial. A paper in Psychology & Marketing concluded that limited-edition scarcity (time-bound or quantity-based) significantly enhances perceived value and purchase intent among consumers. Meanwhile, luxury brand playbooks affirm that exclusivity and scarcity heighten prestige, deepen emotional bonds, and support sustainable growth.
NEW YORK - JUNE 19: (L-R) Actors Stanley Tucci, Meryl Streep, Adrian Grenier, Anne Hathaway, Emily ... More Blunt and Daniel Sunjata attend the 20th Century Fox premiere of The Devil Wears Prada at the Loews Lincoln Center Theatre on June 19, 2006 in New York City. (Photo by)
The Enduring Blueprint For Personal Brand Power
As Anna Wintour prepares to step away from her daily oversight of American Vogue into a new role at Condé Nast after more than three decades at the helm of Vogue, the legendary editorial director leaves behind more than a fashion legacy that other fashion editors would die for—she leaves a proven case study in personal branding. In a world obsessed with relatability, Anna Wintour doubled down on refinement.
When Wintour declared chic dead, she wasn't mourning a loss — she was proving that her own brand was bigger than any trend. She didn't chase trends. She created them. She didn't speak often. But when she did, the world listened. She didn't try to be one of the crowd, she was the ultimate outsider. And she was far from a people pleaser. Her collaborations with Christian Dior, Kering Gucci, and Helmut Newton weren't just fashion moments—they were brand moves. And her influence didn't fade with time. It continued to reinforce her iconic status.
From left, Italian fashion designer Gianni Versace (1946 - 1997), British-American fashion editor & ... More journalist Anna Wintour, German fashion designer Karl Lagerfeld (1933 - 2019), and French fashion designer Christian Lacroix attend a party for the 'Gang of Three' during Fall Fashion Week at the Paramount Hotel, New York, New York, September 7, 1990. (Photo by)
Because real branding isn't about turning heads at the Met Gala or chasing clicks or shouting the loudest in the room. It's about delivering undeniable value.
And most importantly? Above all the headlines and building the blueprint for fashion as entertainment. Above elevating fashion's global influence and transforming fashion from an elite, insider world into a global cultural force. Above being immortalized in The Devil Wears Prada… want to know what I believe Anna Wintour shows every business leader alive? The sheer power of building your personal brand.
Still haven't got one? Do yourself a favor. Go get you sum.
Named Esquire's Influencer of the Year, Jeetendr Sehdev is a media personality and leading voice in fashion, entertainment, and influence, and author of the New York Times bestselling phenomenon The Kim Kardashian Principle: Why Shameless Sells (and How to Do It Right).