Meryl Streep and Anna Wintour Makes the Perfect Pair on Vogue’s Latest Cover

Meryl Streep and Anna Wintour appear together on the Vogue May 2026 cover, photographed by Annie Leibovitz and styled by Grace Coddington.

Streep, known for her portrayal of Miranda Priestly in The Devil Wears Prada, is joined by Wintour, Vogue’s editor-in-chief and the inspiration for the character. Both wear coordinated yellow scarves with epaulets, projecting confidence and camaraderie. Wintour is dressed in a red Prada maxi dress with Manolo Blahnik shoes, while Streep wears a black Prada suit and her signature wig from the film.

This cover marks a significant cultural moment, coinciding with the upcoming release of The Devil Wears Prada 2 on May 1, 2026. The interview, moderated by Greta Gerwig, offers an engaging discussion on fashion’s evolution, leadership, aging, grandparenting, and Streep’s return as Miranda Priestly in a transformed media landscape. The feature highlights legacy, resilience, and the intersection of fiction and reality in a celebrated film.

Photographed at the Crosby Street Hotel in New York, the images convey confidence and camaraderie. Streep wears a Dolce & Gabbana coat, Loro Piana pants, and Prada accessories, while Wintour chooses Chanel and Manolo Blahnik shoes. Both wear Prada sunglasses, referencing the film’s fashion legacy. The styling reflects their influence: Wintour as Vogue’s long-standing editor and Streep as the acclaimed actress behind Miranda Priestly.

Wintour, making her first appearance on a Vogue cover in this role, described the experience as an “honor,” particularly being portrayed by Streep.

Meryl Streep noted that her inspiration for Miranda came from Wintour’s curiosity and responsibility, as well as from directors like Mike Nichols and Clint Eastwood, resulting in a character who is unapologetically strong.

The interview, presented as a lightly edited transcript, addresses current topics. Streep shares that she was interested in the sequel’s focus on the business challenges of sustaining a publication. She observes that the new script captures the realities of the industry, with Miranda portrayed as more authentic and unconcerned with others’ opinions, reflected in her simplified style.

Wintour played a key role behind the scenes, contacting Streep directly when she heard about the sequel. After reviewing the script, Streep reassured her: “Anna, I think it’s going to be all right.” Wintour expressed trust in Streep’s judgment and praised the costumes, especially a red Jezebel dress by Pierpaolo Piccioli.

The Devil Wears Prada 2, directed by David Frankel and written by Aline Brosh McKenna, features Anne Hathaway as Andy Sachs, now a Features Editor at Runway, Emily Blunt as Emily Charlton, a luxury group executive, and Stanley Tucci as Nigel. New cast members include Kenneth Branagh as Miranda’s husband and reportedly Justin Theroux.

The story follows Miranda as she navigates the decline of print media and shifting power dynamics, with Andy returning to assist. The film promises humor, fashion, and a meaningful conclusion.

Streep and Wintour discuss changes in the fashion industry. Wintour observes that fashion is now more democratic, with companies hiring innovative fashion designers and platforms broadening access. She prefers to describe fashion media as “evolving” rather than “disintegrating.” Both agree that authentic self-expression defines modern power dressing.

At 76, both women offer candid reflections on later life. Streep, grandmother to six young grandchildren, describes the experience as “divine” but brief, emphasizing the importance of time spent together. Wintour, with four grandchildren and four step-grandchildren, values family traditions and highlights the essential support family provides.

Wintour describes feeling “as alive, excited, and aware as ever,” seeing experience as a source of balance. Streep agrees, emphasizing the need to keep innovating to remain creative. They discuss legacy, noting the lasting influence of figures like Karl Lagerfeld and the importance of balancing history with progress.

The conversation addresses career uncertainties, including Streep’s experiences with gaps between roles and the unpredictability of acting, as well as Wintour’s management of significant changes at Vogue, especially during the COVID era. Their mutual respect is evident, with Wintour praising Streep’s talent and Streep acknowledging Wintour’s curiosity and sense of responsibility.

Twenty years after the original film’s success, The Devil Wears Prada 2 arrives at a critical moment. Print media faces ongoing challenges, digital platforms lead, and fashion is more inclusive yet competitive. The Vogue cover bridges art and reality, encouraging audiences to revisit Miranda Priestly and gain new perspective from her real-life inspiration.

The cover provides authentic styling inspiration for fashion enthusiasts and builds anticipation for the sequel among film fans. Greta Gerwig’s moderation and Annie Leibovitz’s photography elevate the feature, making it a memorable cultural moment.

As theaters prepare for May 1, 2026, this joint appearance highlights why The Devil Wears Prada remains relevant: it explores ambition, growth, relationships, and the impact of women in culture, both on screen and behind the scenes.

The May 2026 issue of Vogue will be available soon, featuring the complete interview. Online reactions are already enthusiastic, with widespread anticipation for one of the year’s most notable cinematic events.

Whether you are a dedicated Prada fan, a Streep admirer, or interested in the intersection of Hollywood and fashion, this cover and the upcoming sequel promise to engage.

Mark your calendars: Miranda Priestly returns with her signature wit, wisdom, and style.

Photo Courtesy: Vogue