The 7 Most Iconic Anna Wintour Images Of 2025: A Post-Vogue EIC Style Retrospective

Dame Anna Wintour remains the undisputed global arbiter of style, and the images captured of her in 2025 tell the story of a monumental year, marking a seismic shift in the fashion world. After nearly four decades, the legendary editor-in-chief of American Vogue stepped down from her most famous role in June 2025, transitioning her focus entirely to her position as Chief Content Officer and Global Editorial Director for Condé Nast. The photographs from this period—especially from the Met Gala and her first post-EIC public appearances—are not just fashion moments; they are historical documents of a new era for the "Queen of Fashion" herself.

This retrospective looks at the most significant and talked-about images of Anna Wintour from the current date, December 18, 2025, focusing on the visual evidence of her continued influence, her signature style, and the major professional change that dominated her year. Her iconic bob haircut and ever-present sunglasses were front-row fixtures at every major Fashion Week, but it was her appearances around the Met Gala and her new chapter that cemented her visual legacy for the year.

Anna Wintour: Complete Biography & Professional Profile

The individual behind the iconic images is a powerful figure who has shaped global culture for decades. Here is a brief but complete profile of the fashion icon:

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• Full Name: Dame Anna Wintour DBE
• Born: November 3, 1949, in London, England.
• Nationality: British and American.
• Father: Charles Wintour (Editor of the Evening Standard).
• Key Role (1988–2025): Editor-in-Chief of American Vogue (Stepped down in June 2025).
• Current Key Roles: Global Chief Content Officer for Condé Nast and Global Editorial Director of Vogue.
• Major Initiatives: Co-chair of the Met Gala (formally the Costume Institute Gala), Founder of the CFDA/Vogue Fashion Fund (2003).
• Spouses: Dr. David Shaffer (m. 1984; div. 1999), Shelby Bryan (m. 2004; div. 2020).
• Children: Charles Shaffer and Katherine "Bee" Shaffer.
• Notable Awards & Honors: Dame Commander of the Order of the British Empire (DBE) (2017), Presidential Medal of Freedom (2025).

The 2025 Met Gala: A Tailored Louis Vuitton Statement

The annual Met Gala is Anna Wintour’s most visible and important event, and the images from the 2025 edition were among the most highly anticipated of the year. As the co-chair, her outfit is always a crucial moment, setting the tone for the entire evening.

1. The Custom Louis Vuitton Ensemble

For the May 5, 2025, Met Gala, Anna Wintour wore a custom Louis Vuitton creation designed by Pharrell Williams. The theme was "Superfine: Tailoring Black Style," with a dress code of "tailored for you." Wintour's look was a masterful interpretation of the theme, featuring a stunning blue coat and a silver embroidered dress.

The ensemble was reportedly an homage to the late Virgil Abloh, a key figure in modern fashion and a close collaborator with Louis Vuitton. This choice was a powerful visual statement, blending high fashion with a nod to a modern legacy. The images showcased her signature silhouette—a structured coat over a floor-length dress—but with a fresh, contemporary color palette of aquamarine blue and silver.

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2. The Viral Lipstick Stain Image

Perhaps the most unexpected and humanizing image of the night was one that quickly went viral: a photograph showing a small, bright red lipstick stain on the bottom of her custom Louis Vuitton dress. This seemingly minor detail offered a rare glimpse behind the curtain of the famously immaculate fashion figure. The resulting images resonated with the public, proving that even the most meticulously prepared style icon can have a small, relatable wardrobe malfunction. It was a moment of levity captured by the cameras, contrasting sharply with her usual composed public image.

3. The Co-Chair Power Shot

The official co-chair photographs from the 2025 Met Gala are significant images of power and influence. Anna Wintour was photographed alongside her co-chairs: Pharrell Williams, A$AP Rocky, and Lewis Hamilton. These images visually articulate her role as the connector between the worlds of high fashion, music, and sports. Her presence in the center of this group of cultural titans underscores her unparalleled influence not just at the Metropolitan Museum of Art’s Costume Institute, but across the entire global entertainment landscape.

The New Era: Post-Vogue EIC Appearances

The news of Anna Wintour stepping down as Editor-in-Chief of American Vogue in June 2025 sent shockwaves through the industry. The subsequent images of her public appearances were scrutinized for any sign of change, but her enduring style remained a constant. Her successor, Chloe Malle, was appointed to lead the US flagship, allowing Wintour to focus on her global editorial duties at Condé Nast.

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4. The Marc Jacobs Comeback Look

Her first public appearance following the announcement was highly anticipated. On June 30, 2025, Wintour attended the Marc Jacobs' Fall 2025 runway show, held at the New York Public Library. The images captured her sitting front-row, looking completely composed and in control. This appearance visually confirmed that while her title at American Vogue had changed, her status as a front-row fixture and a major force in New York fashion had not diminished. The photographs were a powerful symbol of her transition, not retirement.

5. The New York Fashion Week (NYFW) 2025 Front Row

Images from New York Fashion Week 2025 showed Anna Wintour maintaining her relentless schedule, attending shows by major American designers. These photographs are crucial for understanding her ongoing role. They demonstrate her commitment to championing American talent—a legacy she established through initiatives like the CFDA/Vogue Fashion Fund. Her presence at NYFW continues to be a visual endorsement that can launch a designer's career, cementing her role as a global tastemaker.

6. The Dior Paris Fashion Week Image

In October 2025, images surfaced of Anna Wintour attending the Dior fashion show in Paris during Fashion Week. This overseas appearance highlighted her expanded global focus as the Chief Content Officer for Condé Nast. The photographs often showed her interacting with European fashion house executives and designers, illustrating the scope of her editorial oversight across all international *Vogue* editions. Her continued championing of designers like Christian Lacroix and Giorgio Armani, who she supported early in her career, is reflected in her global fashion week attendance.

7. The Presidential Medal of Freedom Ceremony

While not a fashion image in the traditional sense, the photographs from the ceremony where President Joe Biden awarded her the Presidential Medal of Freedom in 2025 are arguably the most significant of the year. These images capture the moment her cultural influence was formally recognized by the highest civilian honor in the United States. Clad in one of her signature colorful, tweed ensembles—often a Chanel piece—the pictures are a testament to her impact beyond the pages of a magazine, solidifying her status as a cultural and media executive, not just a fashion editor.

The Enduring Legacy of Anna Wintour’s Visual Brand

The collection of images of Anna Wintour from 2025 confirms that her influence is undiminished, even after stepping away from the daily demands of American *Vogue*. Her iconic look—the perfectly tailored dress, the statement jewelry, and the impenetrable shield of her dark sunglasses—has become a potent symbol of power and consistency in a constantly changing industry. Whether she is co-chairing the Met Gala with A$AP Rocky or sitting front-row at a Marc Jacobs show, every photograph is a calculated part of her visual brand.

Her work in elevating celebrity covers, championing young designers, and transforming the Met Gala into a global cultural phenomenon is all documented through the lens of the world's photographers. The photographs from this transitional year serve as a powerful reminder of her enduring legacy, proving that Anna Wintour remains the ultimate visual authority in the world of fashion and media. The shift in her career simply means her iconic images will now reflect a global, rather than purely American, focus.