Anna Wintour Odds: Will Former Vogue Editor-In-Chief Feature In Devil Wears Prada 2?

Q: Has Anna Wintour ever publicly acknowledged "The Devil Wears Prada" film?

While Anna Wintour has famously remained tight-lipped about the direct inspiration for Miranda Priestly, she has made subtle, often humorous, acknowledgments over the years. Famously, she wore Prada to the film's premiere, a quiet wink to the speculation. Her silence has only fueled the mystique, and a direct cameo would be a significant departure from her long-standing public approach.

Q: What impact could a hypothetical Anna Wintour cameo have on "The Devil Wears Prada 2"?

A cameo, however brief, would undoubtedly send shockwaves through both the fashion and film worlds. It would be a monumental pop culture moment, bringing immense publicity and fan engagement to the sequel. It would also further blur the lines between the fictional world of Runway and the real world of Vogue , delighting those who have long speculated about the film's inspirations.

By Steve Bittenbender Jul 9th, 2025 11:16 AM EDT

Odds are, if you’re a regular to this site, then you are not familiar with Anna Wintour, and if you are familiar, there’s probably one reason why.

Wintour has served as the editor-in-chief of Vogue since 1988, and late last week, she announced she would be leaving the top editorial post at the haute fashion publication. During her time there, Wintour developed a reputation for being a demanding boss.

She was the inspiration for the book “The Devil Wears Prada,” written by a former assistant of hers. That 2003 book would become a hit movie in the summer of 2006, starring Meryl Streep as a Wintour-like editor of an influential fashion magazine and Anne Hathaway as the assistant always under her heel.

There had long been rumors about a possible sequel to the movie, and on Monday, mere days after Wintour’s shocking announcement, 20th Century Studios announced via Instagram that “The Devil Wears Prada 2” is in production and set for release next year.

With that in mind and with the football season still 10 weeks away, Bookies.com has created odds on whether Wintour will be making an appearance in the upcoming film. These odds are for entertainment purposes only, as you won’t find them at a licensed U.S. betting sites. However, it wouldn’t surprise us if Kalshi creates a market for it.

Anna Wintour Odds

Outcome	Odds	Percent Chance
Not appear	-450	81.8%
Have a cameo appearance	+600	14.3%
The Field (i.e., have a larger/speaking role, listed in credits, etc.)	+2450	3.9%

Odds are projected and do not reflect any odds that may be available at legal betting sites or betting apps.

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As of now, both Streep and Hathaway are set to return as their characters, as are Emily Blunt and Stanley Tucci. Deadline has reported that actor Kenneth Branagh has been brought on to play Priestly’s husband.

Q&A

**Is Anna Wintour stepping down from Vogue a sign she might be open to a "Devil Wears Prada 2" cameo?**

Anna Wintour recently announced she is stepping down as Editor-in-Chief of American Vogue after 37 years. While she will remain Condé Nast's Global Chief Content Officer and Global Editorial Director of Vogue, this shift in her day-to-day responsibilities at the iconic American magazine could potentially free up her schedule or alter her public persona in a way that makes a cameo more plausible. Historically, Wintour has maintained a dignified distance from directly acknowledging the film's inspiration. However, a less direct role at Vogue might open new avenues for engaging with pop culture.

Has Anna Wintour ever publicly acknowledged "The Devil Wears Prada" film?

What are the odds of Anna Wintour appearing in "The Devil Wears Prada 2" now?

While the idea is tantalizing for fans, the odds of a direct cameo remain relatively low. Anna Wintour's professional identity is deeply intertwined with her serious role in the fashion industry. A playful appearance in "The Devil Wears Prada 2" might be seen as undermining the very gravitas she has cultivated. However, with her shifting focus to more global leadership roles within Condé Nast and Vogue, it's not entirely out of the realm of possibility that she might consider a fleeting, perhaps even humorous, self-aware moment. We'll have to wait and see if the filmmakers decide to directly invite her.

Anna Wintour Odds: Will Former Vogue Editor-In-Chief Feature In Devil Wears Prada 2?

Anna Wintour Odds

Q&A

Is Anna Wintour stepping down from Vogue a sign she might be open to a "Devil Wears Prada 2" cameo?

Has Anna Wintour ever publicly acknowledged "The Devil Wears Prada" film?

What are the odds of Anna Wintour appearing in "The Devil Wears Prada 2" now?

What impact could a hypothetical Anna Wintour cameo have on "The Devil Wears Prada 2"?

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**Is Anna Wintour stepping down from Vogue a sign she might be open to a "Devil Wears Prada 2" cameo?**