Meryl streep and anna wintour: a rare glimpse inside a powerhouse conversation
The Crosby Street Hotel suite felt unexpectedly cozy, a refuge from record-breaking winter temperatures, as two titans of American culture—Meryl Streep and Anna Wintour—engaged in a conversation orchestrated by filmmaker Greta Gerwig. It wasn't just a chat between friends; it was a meticulously planned event, paired with a striking Annie Leibovitz photoshoot, capturing a moment decades in the making.
The enduring question: how do women communicate power through dress?
The discussion, moderated by Gerwig, delved into the complexities of female presentation and the unspoken codes of power dressing. While men navigate a relatively straightforward sartorial landscape – dress for the job you want – women face a far more nuanced challenge. Wintour, ever the astute observer, dismissed the notion of a power suit as a necessity, citing Mrs. Obama as a prime example of effortless authority. “Whether she’s wearing J.Crew or Duro Olowu… she always looks like herself,” Wintour stated, a sentiment that underscores the importance of authenticity over adherence to rigid conventions.
Streep, with her trademark thoughtfulness, introduced a crucial layer of complexity. “All dress is about expressing yourself, but we’re also subject to larger historical and political sweeps of expectation,” she observed, highlighting the lingering double standards that demand women simultaneously project strength and avoid appearing “threatening.” The conversation touched upon the historical context that allowed for bolder female roles in film, noting, as Streep pointed out in reference to Rosalind Russell and Spencer Tracy, that women weren't perceived as a direct threat to male dominance, fostering a space for playful, even outrageous, characters.

The return of miranda priestly: a reflection of a changing business landscape
The conversation naturally progressed to The Devil Wears Prada, the film that cemented Wintour's influence in popular culture. Gerwig posited a question that’s been on many minds: What does Miranda Priestly represent now, two decades later? Streep responded, “I was interested in the business part of it… running a big organization, keeping it going somehow.” She saw an opportunity to explore the resilience of institutions facing disruption, remarking, “I wondered what they were going to do now that everything’s disintegrating.”
Wintour countered with a note of optimism. “I like to think we’re evolving rather than disintegrating,” she declared, emphasizing the industry’s adaptation to new platforms and wider reach. The conversation underscored the fashion industry’s evolution, moving beyond the exclusivity of haute couture to a more democratic landscape, influencing broader culture and sparking interest in everything from Wuthering Heights costumes to the wardrobes of Euphoria characters. Zara’s partnership with John Galliano, and Coach's hiring of Stuart Vevers were cited as examples of this dynamic shift.

Age, influence, and the enduring power of connection
The exchange shifted to a more personal note, with Gerwig prompting both women to reflect on aging and its impact on their lives and careers. Wintour embraced her age, asserting, “I feel as alive, excited, and aware as ever,” while Streep spoke of carrying the memories of loved ones, “They are in here, you’re going to use them, and they’re going to live.” The conversation concluded with a poignant reflection on the importance of family and the passing of knowledge, with Wintour stating, “Family counts and family who will give you love and support. If you have that, everything else will be fine.”
As Streep eloquently summarized, “Always breaking new water. Always breaking the waves. And we’re not done yet.” The room, and indeed, the conversation, left a lingering sense that these two women, despite their decades of experience, remain as dynamic and influential as ever, shaping not only the world of fashion and film, but the very definition of power and grace.