Fashion Talks

Anna Wintour, the legendary editor-in-chief of Vogue and chief content officer of Condé Nast, is more than just a fashion executive—she’s a cultural symbol. From her signature bob haircut and dark sunglasses to her icy composure and undeniable authority, Wintour has become an icon far beyond the front rows of Fashion Week. Over the years, her influence has reached the silver screen, appearing in movies and documentaries that either capture her real-life leadership or interpret her through fictional lenses. These must-see movies dive into her world, offering rare access and fascinating portrayals of fashion’s most powerful woman.

The September Issue (2009)

The definitive Anna Wintour documentary, The September Issue is a behind-the-scenes chronicle of the making of Vogue‘s most important issue of the year—the 2007 fall fashion edition. Directed by R.J. Cutler, the film provides unprecedented access to Wintour’s editorial process, her working relationship with longtime creative director Grace Coddington, and her leadership style. Viewers witness her critical eye, quiet authority, and remarkable ability to steer the fashion industry from her Manhattan office. Rather than painting her as a distant dictator, the documentary humanizes Wintour, revealing both her perfectionism and her deeply held standards for excellence. If there’s one film that captures her power and personality in equal measure, this is it.

The Devil Wears Prada (2006)

While Anna Wintour does not appear in this fictional film, she is unquestionably its spiritual center. Meryl Streep’s portrayal of Miranda Priestly—the icy, commanding editor-in-chief of Runway magazine—is widely known to be inspired by Wintour. Based on Lauren Weisberger’s novel (Weisberger was a former assistant at Vogue), the movie combines satire, glamour, and realism in its depiction of fashion media’s inner workings. Priestly’s withering glances and impossible-to-please standards are exaggerated, but rooted in the real-life image of Wintour that has been cemented in fashion lore. This movie, more than any other, shaped the public’s perception of what it means to be a powerful woman in fashion—and it all points back to Wintour.

The First Monday in May (2016)

This documentary follows the planning and execution of the Metropolitan Museum of Art’s annual Costume Institute Gala—the biggest event on the fashion calendar. Directed by Andrew Rossi, the film focuses on the 2015 “China: Through the Looking Glass” exhibition, curated by Andrew Bolton. Yet, it’s Anna Wintour who stands at the center of it all. As chair of the gala, she oversees everything from guest lists to seating arrangements and celebrity appearances. Her presence is commanding, her decisions final. The First Monday in May not only offers insight into her event-planning brilliance but also reveals the high stakes of merging fashion, art, and commerce on a global stage.

In Vogue: The Editor’s Eye (2012)

Produced for HBO, this documentary celebrates Vogue‘s 120th anniversary by highlighting the visionary editors behind its pages. Anna Wintour plays a prominent role among them, offering reflections on the creative direction and cultural impact of the magazine. Her commentary provides insight into what drives editorial decisions and how fashion photography has evolved under her guidance. While the film covers a broader range of editors, Wintour’s voice stands out as the most authoritative and enduring, reinforcing her position at the top of the fashion editorial hierarchy.

In Vogue: The 90s (2024)

A more recent addition to the list, In Vogue: The 90s examines one of fashion’s most transformative decades—a period when Anna Wintour’s leadership reshaped everything from aesthetics to industry norms. As the editor steering the magazine during this explosive era, Wintour is featured extensively throughout the documentary. She offers not just historical commentary but a personal perspective on the rise of supermodels, the grunge revolution, and the globalization of fashion. This film feels particularly timely, reminding audiences of Wintour’s lasting impact on the cultural and commercial shifts that defined the ’90s.

For anyone fascinated by fashion, media power, or iconic leadership, these films are essential viewing. Anna Wintour may be famously private, but through cinema, the curtain is lifted—if only slightly—on fashion’s most enduring force.