Draped in matching yellow scarves, Meryl Streep and Anna Wintour make their entrance like two commanding forces fashion’s own generals, shoulder to shoulder. The setting is a sprawling suite inside the Crosby Street Hotel, where the mood is equal parts polished and playful as one intriguing question lingers in the air: what happens when two Mirandas share the same room?
Adding to the moment, both women graceful, powerful, and in their seventies embody a legacy of influence that feels both timeless and electric. Joining them is filmmaker Greta Gerwig, who previously directed Streep in the 2019 adaptation of Little Women. A devoted admirer of The Devil Wears Prada universe, Gerwig steps in as moderator, guiding the conversation with effortless charm as anticipation builds for DWP2 the sequel set to captivate audiences when it arrives in theaters on May 1.See more inside…
Streep in a Dolce & Gabbana coat, Loro Piana pants, and Prada shoes and sunglasses. Wintour in a Chanel coat, brooch, sunglasses, and dress, and Manolo Blahnik boots.
Greta Gerwig: The question of how you present yourself is so much what The Devil Wears Pradais about. For men, there’s a clear code: You dress for the job you want. But for women, dressing has always been more nebulous. Anna, how much do you think about that? Do you think about how women are meant to dress to communicate power?
Anna Wintour: I don’t think wearing a power suit to the office is in any way necessary. Think about the women that one admires: Mrs. Obama comes to mind. Whether she’s wearing J.Crew or Duro Olowu or Matthieu Blazy’s Chanel, she always looks like herself. I’m full of admiration for New York City’s new first lady because she looks so cool and wears a lot of vintage—young and modern and also entirely herself. To be fair, Melania Trump also always looks like herself when she dresses.
Meryl Streep: I have so many thoughts about this. I think the most…powerful message that our current first lady sent was in the coat that said “I Really Don’t Care, Do U?” when she was going to see migrant children who were incarcerated. All dress is about expressing yourself, but we’re also subject to larger historical and political sweeps of expectation. I’m stunned at how women in power have to have bare arms on television while men are covered in shirts and ties or a suit. There’s an apology built into women. They have to show their smallness. It’s compensatory: The advancements of women in the second half of the 20th century and the beginning of this one have been destabilizing. It’s as if women have to say, “I’m little. I can’t walk in these shoes. I can’t run. I’m bare, not threatening.”
Gerwig: How does being a grandmother balance with work?
Streep: It’s just grabbing seconds, just grabbing everything you can of them, with the knowledge of how completely fleeting it all is and how rapidly time goes. This is what my mother said to me, and I said, “Yeah, yeah.” It’s the longest, shortest time. And you can’t get anything back. So take as much as you can…. I find it divine. I have six grandchildren, six under six. They’re six, five, four, three, two, and one. I hope we’re not done, but we’ll see. I can’t even talk about how much it means to me that my kids give me as much time as they do with their kids. The only thing is that they’re on two coasts, so I’m in the airplane a lot.
Gerwig: And you, Anna, also have grandchildren.
Wintour: I don’t have as many as Meryl. I only have four, and I have four step-grandchildren that grew up all around us. Being a mother when you have the jobs that we have—you have to make the time. I was relentless about going to the games and turning up at the parent-teacher meetings, being there when it was important. I felt like Vogue could always wait and that it’s okay to be a busy mother. You make it work. We have a family compound on Long Island, and I try to make it a center for all of us, who are spread all over the world. We love to celebrate birthdays and weddings; traditions are important—we’re English, so we constantly play games and stage countless tennis tournaments—and we try to take care of each other through thick and thin. I try to instill in my children and my grandchildren that it’s family that counts and family who will give you love and support. If you have that, everything else will be fine.
Read more at Vogue
Anna Wintour and Meryl Streep in Prada. Wintour wears Manolo Blahnik shoes, S.J. Phillips necklaces, and Chanel sunglasses. Streep wears Prada sunglasses and a Cartier watch. For Wintour: hair, Bobby Michael; makeup, Melissa Silver. For Streep: hair and makeup, Donald S Mcinnes.
Photographed by Annie Leibovitz. Vogue, May 2026
