A cover that nobody saw coming
At first, it seemed like an impossible thought. In a taxi, on the way to Rue des Capucines in Paris to view the vatwalk pieces from Balenciaga, sat the newly appointed editor-in-chief of Vogue, Chloe Malle, next to Anna Wintour. She knew that The Devil Wears Prada 2 was in the works. The idea bubbled up, perhaps too big, perhaps too bold, but she decided to say it anyway.
How would Anna Wintour feel about being on the cover of Vogue together with Meryl Streep, the actress who portrayed her distinctive and slightly caricatured likeness in the film?
A silence followed. Only a small smile appeared around Anna's mouth. No answer, no rejection, no confirmation. And Chloe didn’t dare to ask further.
Only days later did Anna Wintour come back to it. It was, she said, “a very nice idea,” but not quite her style.
What transpired in the meantime remains a mystery. Perhaps it was the phone call Anna had with Meryl Streep, in which she inquired about the tone of The Devil Wears Prada 2 and how her character would be portrayed. Perhaps time played a role, the fact that Anna is now somewhat retired, a grandmother of four grandchildren and four step-grandchildren, and that life, inevitably, softens.
Whatever the reason: this month it is happening.
Twenty years after the release of the first film, The Devil Wears Prada 2 is coming out. And at the same time, Anna Wintour and Meryl Streep are together on the cover of Vogue.
The word “iconic” is on my forbidden words list (too clichéd and hollow), but this cover will certainly be historic.
Not only because Anna Wintour appears on the cover of the magazine where she has been the face and direction for decades. But especially because she does so alongside Meryl Streep, the woman who once, with an icy gaze and perfectly timed silences, portrayed a character that was undeniably inspired by her.
Additionally, the cover was shot by Annie Leibovitz, 76 years old, a photographer who is inextricably linked to the visual DNA of Vogue. The styling was in the hands of Grace Coddington, for years Anna Wintour's creative right hand and still one of the most influential figures in the fashion world.
A gathering of women, careers, and eras, in short, and perhaps that is why it is so special: because it is not just a cover, but a moment.
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More than fashion: a conversation that goes deeper
After the shoot, the women took ample time to engage in conversation. About the film, about life, about being a woman, about building a career, and of course about fashion. Both Anna and Meryl have a particular fondness for coats. For the deep-thinking Meryl because the coat is a garment that covers everything and for Anna, practically, because they are so easy to try on. But what stands out is that the conversation quickly goes beyond just clothing. It becomes a reflection on power, positioning, and the role of women in the public domain.
Remarkably, Meryl Streep seems to have an even sharper, more substantive view on fashion in that conversation than Anna Wintour.
Anna emphasizes how she admires women like Michelle Obama, who according to her wears different designers and still remains herself. An interesting observation, although one might wonder to what extent that is always the case. Sometimes she too, like many in the public spotlight, seems a bit of a plaything of the stylist who doesn't really seem to follow a line.
Anna also speaks out about Melania Trump, who she believes generally looks good. To which Meryl Streep immediately adds nuance. She states that you can dress however you want, but you can never escape the cultural and historical context in which you operate. She implicitly refers to that one moment when Melania Trump wore a coat with the text “I really don’t care, do you?” during a visit to vulnerable children. For Meryl, that is inextricably linked to how clothing is read and interpreted.
It is a sharp distinction: fashion as aesthetics versus fashion as a bearer of meaning.
Vulnerability as uniform
It becomes even more interesting when Meryl Streep broadens the conversation to how women dress in relation to power.
She observes that men in professional contexts almost always uniform themselves: suits, ties, covered arms. Women, on the other hand, often show more skin, bare arms, heels, as if an implicit message is being sent: we are here, we are participating, but we are not threatening.
As if vulnerability has become part of the uniform.
It is a provocative thought. That the way women present themselves, still, consciously or unconsciously, sends a reassuring signal to a world that has historically been dominated by men.
Taking space without threat
Meryl sees that same dynamic reflected in her career as an actress. She notes that she could flourish precisely in outspoken, larger roles because women in film are rarely seen as a threat to men. After all, they would not quickly “take away” a male role.
That space, paradoxically arising from underestimation, gave her the freedom to shine, to be present, to push boundaries.
Chronically unemployed, even at the top
Another insight that lingers is her remark about the profession itself. That acting, even at the highest level, is essentially a form of chronic unemployment.
You are dependent. On a director. On a choice that falls on you. You are not the one who has the process fully in hand, like a writer or composer does.
Building a body of work like hers, impressive, layered, long-lasting, is therefore not just a matter of talent, but especially of patience and perseverance.
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Self-deprecation at the top
Perhaps the most surprising moment in the conversation comes when both women are asked if they could switch jobs.
Anna Wintour's answer is as dry as it is disarming: impossible. She can do nothing, she says. Not dance, not sing, not make clothes, not cook, not sew.
For a woman who has long been seen as the most powerful figure in the fashion industry, that is a striking statement. But therein lies something reassuring as well. No one can do everything. And even someone like Anna Wintour knows her limitations.
Although one thing is clear: a sharp eye, vision, and leadership are indeed part of her arsenal.
And, perhaps even more importantly, a subtle sense of humor.
A moment to look forward to
The timing of this cover is no coincidence. With the release of The Devil Wears Prada 2, twenty years after the first part, it feels like a circle that has come full circle.
The film premieres on April 29, and now I am squeezing my fists so hard that my knuckles turn white because I get to be there.
And even better: tickets are being given away. So keep an eye on us and follow us on Instagram @amayzine to see how you can get those tickets.
Who knows, you might find yourself in the audience.
Source/Credit: Annie Leibovitz. Vogue, May 2026.
