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Anna Wintour just made history on the cover of Vogue’s May 2026 issue. She posed alongside Meryl Streep, who plays her iconic character Miranda Priestly. The two 76-year-old powerhouses reveal everything about fashion, power, and looking amazing at their age.
🔥 Quick Facts
- Cover story:Vogue’s May 2026 issue, photographed by legendary Annie Leibovitz
- Devil Wears Prada 2: Opens in theaters on May 1, 2026, starring Anne Hathaway and Meryl Streep
- Both actors: Both 76 years old, both speaking on power, fashion, and staying culturally relevant
- Moderator: Director Greta Gerwig facilitated the historic conversation with both icons
The Cover That Broke Fashion History
Anna Wintour has spent over 30 years leading Vogue as its former editor-in-chief. Now, she appears on her own magazine’s cover for the first time. The iconic fashion leader joins Meryl Streep in a moment that blurs reality and fiction. Annie Leibovitz captured the shoot, styled by legendary Grace Coddington. Both wore Prada, Chanel, and Manolo Blahnik. The cover itself became a cultural moment in hours, gaining 632,000 likes on Instagram alone. Months of planning went into this encounter, as confirmed by search results from April 7, 2026.
The timing is perfect. Devil Wears Prada 2 hits theaters in 3 weeks. Yet this isn’t just movie promotion. This is a celebration of two women who refused to age out of influence, power, or style.
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What Meryl Revealed About Playing Miranda Again
Meryl Streep didn’t simply reprise her role. She reimagined Miranda Priestly for a changing world. According to the interview, Streep focused on the “business part” of Priestly’s character, considering how she leads in turbulent times. “I was interested in the business part of it, that thing of carrying the weight of many, many people’s jobs, running a big organization, keeping it going somehow,” Streep shared with Greta Gerwig. She simplified Miranda’s look this time around, making her less floppy hair and more essential. “We made her simpler and just more essentially her,” Streep explained. The actress who played her icon 20 years ago returns with deeper understanding of power, ambition, and sacrifice.
Streep also revealed something shocking: nobody wanted to dress the original Miranda. “Everybody was afraid of Anna on the first one, so we couldn’t find any clothes. Nobody would give us any clothes.” This time, designer Pierpaolo Piccioli of Valentino created a red dress that even Wintour praised as exceptional.
Icon Comparison Table
| Aspect | Anna Wintour | Meryl Streep |
| Age | 76 years old | 76 years old |
| Children | Multiple with tradition devotion | Six grandchildren, ages 1-6 |
| Role | Former Vogue Editor-in-Chief | Plays Miranda Priestly (inspired by Wintour) |
| Philosophy | “Age is an advantage” | “Always breaking new water” |
Anna’s Honest Take on Power and Fashion
Anna Wintour dropped wisdom that will reshape how women think about success. “I don’t think wearing a power suit to the office is in any way necessary,” she told Greta Gerwig. Instead, she emphasized authenticity and self-expression. Wintour referenced Michelle Obama, calling her a model of dressing with purpose. She even acknowledged Melania Trump’s consistency in personal style. “Age is actually an advantage,” Wintour declared. She spoke about balance, proportion, and leadership that comes with lived experience. “With a life well lived, you can lead more easily.” This isn’t generic advice. This is decades of running a global fashion empire talking.
Wintour also revealed something surprising: “I have no gifts. I have absolutely no gifts at all. I can’t sing, I can’t dance, I can’t act.” Yet somehow she runs a multinational corporation. That’s not a gift, Streep joked. That’s everything.
“I like coats. They cover all the sins of whatever else is underneath. And they’re easy to try on.”
— Exchange between Meryl Streep and Anna Wintour
Will Both Icons Return to Their Roles?
The question everyone’s asking: Is this The Devil Wears Prada’s last hurrah? Streep teased a dramatic ending. “Yes, it’s a happy ending. Or not happy, exactly. But it’s real and it’s triumphant.” When Wintour asked about the plot before this interview dropped, Streep admitted something hilarious. “That’s, like, the last thing I ever remember about a movie. I am the best audience for my own movies because I never remember what happened.” Both iconic women showed genuine excitement about the film during their May 2026 cover shoot. Chemistry between them felt authentic and warm, filmed by Oscar-winning photographer Annie Leibovitz. The real question remains: Will audiences embrace this sequel as much as they loved the original? And will Meryl and Streep return again in 10 years, still looking stunning?
I saw one of these in New Zealand and I bought one.