Anna Wintour Leaves Vogue: A Look Back at Her Reign

By: Sahra Mohamed

Dame Anna Wintour, British-American fashion journalist and editor, circa 1995. (Photo by Eamonn McCabe/Popperfoto via Getty Images)

Anna Wintour, the Editor-in-Chief of American Vogue since 1988, announced on June 26, 2025, that she is stepping down from that role after 37 years. She’ll continue as Condé Nast’s Global Chief Content Officer and as Global Editorial Director of all Vogue editions, overseeing titles like British Vogue, Vanity Fair, and GQ. Wintour’s appointment followed her tenure at British Vogue from 1985–1987. She took over the U.S. edition and introduced changes, beginning with her 1988 debut cover featuring model Michaela Bercu in $50 Guess jeans and a $10,000 Christian Lacroix sweater, considered one of the most influential magazine covers of all time. Under her leadership, Vogue introduced celebrity covers as the new norm. It became as much about cultural influence and power as it was about fashion. Under her leadership, the magazine featured covers with First Lady Michelle Obama, Beyoncé, and Serena Williams. Vogue launched its iconic September issues under her watch, and she turned the Met Gala into one of the world’s most exclusive and closely watched events. As co-chair since the 1990s, Wintour curated a tightly controlled guest list featuring politicians, supermodels, designers, and celebrities, ensuring the A-list attendance remained elite. Among the regular co-chairs is Rihanna, who arrived with her third pregnancy announcement at the 2025 gala themed “Superfine: Tailoring Black Style.” Wintour has publicly praised Rihanna and her beau A$AP Rocky as the most stylish and influential celebrity couple in fashion, a sign of her close ties with global superstars.

Alongside her editorial leadership, Wintour oversaw some of the most memorable Vogue covers and Met Gala themes in fashion history. Her tenure included iconic covers such as Madonna’s 1989 appearance, Naomi Campbell’s September 1989 cover, Michelle Obama’s 2009 issue, Beyoncé’s historic 2018 September cover shot by the first Black photographer Tyler Mitchell, and Harry Styles becoming the first solo male cover star in 2020. At the Met Gala, Wintour helped developed themes that blended fashion and culture, including 2011’s “Alexander McQueen: Savage Beauty,” 2015’s “China: Through the Looking Glass,” 2018’s “Heavenly Bodies: Fashion and the Catholic Imagination,” and 2025’s “Superfine: Tailoring Black Style,” which featured multiple co-chairs, including Louis Vuitton Men’s Creative Director Pharrell Williams. Another notable aspect of her leadership was mentoring young editorial talent. In 2016, she appointed Elaine Welteroth as the first African‑American Editor‑in‑Chief of Teen Vogue at age 29, a move credited with changing the magazine’s coverage to include politics and youth social justice. Wintour has also played a major role in international talent development. She appointed Chioma Nnadi, as Head of Editorial Content at British Vogue in 2023. Nnadi became the first Black woman to hold that position, and Wintour praised her editorial vision. However, one of the most scrutinized relationships from her era is with the late André Leon Talley, Vogue’s former Creative Director and Editor-at-Large. Talley credited Wintour for opening doors, he was the highest-ranking Black man in fashion journalism but their relationship had tension. He described being sidelined at events like the Met Gala, and their bond was affected by silence and power shifts. His memoir, The Chiffon Trenches, he framed their connection as a complicated mix of affection and estrangement.

Wintour’s influence was felt outside her office. She formed bonds with many legendary icons including Andy Warhol and Jean-Michel Basquiat. She is also credited with mentoring British Vogue’s Edward Enninful, whose work opened an era of inclusivity. Throughout her career, Anna Wintour cultivated close relationships with some of the most influential designers in fashion. She was an early supporter of John Galliano, famously helping fund his 1984 graduation collection and later backing his rise to Dior. She also played a pivotal role in the careers of Marc Jacobs and Tom Ford, featuring their work in Vogue early on and giving them editorial support. Her influence extended to Alexander McQueen, whose captivating designs received consistent coverage in the magazine before his appointment at Givenchy. As Wintour steps back, it’s worth revisiting some of the most iconic moments and images that defined her Vogue era, from carefully curated covers to Met Gala themes that captured the world’s imagination.

Iconic Vogue Covers Under Wintour

November 1988 – Michaela Bercu – Photographed by Peter Lindbergh