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In a captivating exchange orchestrated by Vogue, cinematic legend Meryl Streep and fashion titan Anna Wintour convened with acclaimed director Greta Gerwig. This gathering, months in the making, provided a unique platform to discuss the highly anticipated sequel to The Devil Wears Prada, the dynamic shifts within the fashion industry, and the profound lessons gleaned from decades of experience. Their discussion traversed topics from the symbolic power of clothing to the enduring legacy of mentors, culminating in a shared reflection on the joys of grand-parenting and the importance of commitment in both personal and professional spheres.

A Candid Exchange: The "Mirandas" Reunited

In a grand suite at the elegant Crosby Street Hotel, Meryl Streep and Anna Wintour, both adorned in striking yellow scarves, met for an extraordinary discussion moderated by filmmaker Greta Gerwig. The occasion was the imminent release of DWP2, the sequel to The Devil Wears Prada. Their conversation, meticulously planned and orchestrated by a powerhouse team including photographer Annie Leibovitz and stylist Grace Coddington, began playfully with a shared appreciation for coats—a subtle nod to the original film's iconic fashion moments. Streep quipped that coats cleverly conceal "the sins of whatever else is underneath," a sentiment echoed by Wintour for their ease of trying on. The dialogue swiftly transitioned into deeper reflections on the nuanced role of clothing in expressing power, particularly for women. Wintour emphasized the importance of authenticity in dressing, citing figures like Michelle Obama who consistently maintain their unique style. Streep, however, raised concerns about the implicit pressures on women in power to appear less threatening, recalling the controversial "I Really Don't Care, Do U?" jacket worn by a former first lady. She noted the stark contrast between the sartorial expectations for men and women in public life, highlighting a perceived need for women to project "smallness" to counteract societal anxieties about their advancement. The conversation then shifted to the character of Miranda Priestly, with Gerwig pondering Streep's decision to reprise the role after two decades. Streep revealed her fascination with the "business part" of the character, exploring the immense responsibility of leading a major organization and navigating a world where institutions are constantly challenged. Wintour, in turn, expressed her admiration for the first film's portrayal of fashion as a global economic force, asserting that while much has changed, the industry continues to evolve and reach new audiences. She recounted a personal anecdote of calling Streep to ascertain the quality of the sequel's script, demonstrating their deep mutual trust. The discussion then broadened to the democratization of fashion, with Wintour highlighting how once-exclusive haute couture has become more accessible and culturally pervasive, pointing to collaborations between high fashion designers and mainstream brands. As the conversation drew to a close, Gerwig prompted Streep and Wintour to reflect on being 76. Wintour, noting that even their photographer, Annie Leibovitz, shares their age, embraced aging as an advantage, bringing balance and perspective. Streep emphasized the importance of lifelong curiosity and "breaking new water" to stay vibrant. They both shared heartwarming insights into their roles as grandmothers, balancing family commitments with demanding careers. Wintour stressed the importance of making time for family, while Streep relished every fleeting moment with her six grandchildren. They spoke of commitment as the foundation of life and work, with Streep referencing playwright Tom Stoppard's notion of constantly shifting one's weight in an uncertain world. Wintour reflected on the leadership challenges during the COVID-19 pandemic, underscoring the resilience required to navigate unforeseen crises. Finally, the group playfully imagined swapping roles. Wintour humbly claimed a lack of traditional artistic talents, while Streep humorously expressed dread over Wintour's daily shoe choices but enthusiasm for the creative energy of working with young people and fostering beauty. The discussion concluded with fond memories of the original film's costumes and the collaborative spirit of filmmaking, with Streep revealing her dedication to remaining in character by knitting alone in her trailer during the first film's production. Both expressed hope for a "triumphant" ending to the forthcoming sequel, leaving audiences eagerly anticipating its release.

This candid dialogue between Meryl Streep and Anna Wintour offers a compelling lens through which to view not only the evolving landscape of fashion and film but also the broader challenges and triumphs of women in leadership. Their reflections underscore the importance of authenticity, resilience, and a deep-seated commitment to both professional endeavors and personal connections. It's a powerful reminder that true influence stems not just from power, but from an unwavering sense of self, a willingness to adapt, and the wisdom to cherish life's most precious moments.

This article explores the lasting cultural influence of "The Devil Wears Prada" and the behind-the-scenes story of Vogue's May cover, which brings together Meryl Streep and Anna Wintour. It highlights the widespread recognition of the film and its central characters, even among those outside the fashion world. The piece also details the collaborative efforts to secure both iconic figures for the cover, celebrating the upcoming sequel and the ongoing relevance of the original story.

The writer recounts attending the premiere of the original "Devil Wears Prada" with their mother, noting their prom dress choice and the subsequent encounter with Anna Wintour and her daughter, Bee. Years later, when the idea of a sequel arose, the Vogue team decided to capitalize on its release, which coincided with the Met Gala. The initial thought was to feature Meryl Streep, but the bold idea of including both "Mirandas" - Anna Wintour and Meryl Streep - for the May cover of 2026 quickly gained traction. This ambitious plan was set in motion to commemorate the film's impact and its connection to the fashion magazine.

The author shares a personal anecdote from a Parisian towncar ride with Anna Wintour in early October. During a discussion about upcoming cover stories, the writer cautiously proposed the idea of Anna appearing on the cover with Meryl Streep. Anna, though amused, initially declined, stating it wasn't her usual style. However, Meryl Streep later convinced her to participate, much to the writer's gratitude. This collaboration was seen as a perfect way to immortalize a significant cultural moment, bridging the world of cinema and high fashion.

Since beginning their tenure at Vogue after the film's 2006 debut, the author frequently encountered questions comparing their workplace experiences to those depicted in "The Devil Wears Prada." Friends' parents, suburban business professionals, and even doormen would inquire about the similarities to the fictional "Miranda Priestly" and the realities of working at Vogue. This phenomenon underscored how universally recognizable Anna Wintour and, by extension, Vogue had become, especially among individuals outside the fashion sphere. Interestingly, Meryl Streep's portrayal of Miranda is reportedly the role men most frequently ask her about.

The interview between Meryl Streep and Anna Wintour, conducted by Greta Gerwig, provided many unexpected revelations. They discussed the motivation behind the sequel, Anna's reaction to its development (she called Meryl), and playful banter about each other's demanding roles. Meryl confessed she wouldn't want Anna's job, citing the daunting footwear, while Anna couldn't fathom taking on Meryl's profession. The conversation also touched upon the longevity of designers, professional attire, and the expressive power of clothing, recalling Miranda's memorable cerulean sweater monologue.

In addition to the cover story, the May issue of Vogue featured "Costume Art," an exhibition at The Metropolitan Museum, showcasing the intersection of fashion and fine art. Ethan James Green photographed various pieces within The Met's new Condé M. Nast Galleries, while Annie Leibovitz captured portraits of the Gala host committee. Five visual artists offered diverse perspectives on body types within the exhibition, and a pajama party at The Mark Hotel paid homage to the tradition of witnessing the sunrise after a glamorous, late-night ball gown event.

During these preparations, the idea emerged to select "The Devil Wears Prada" as Vogue's second Book Club pick. The author admitted to never having read Lauren Weisberger's 2003 novel, describing it as a thrilling narrative filled with details like five-inch stilettos, endless corporate car accounts, and the seemingly exorbitant cost of New York coffee. The book club plans to host an early screening of the film for its members and friends of Vogue, with a special mission to invite as many former assistants to Anna Wintour as possible.