While her sense of humour is perhaps not the first thing that comes to mind when most of us think of Anna Wintour, she certainly managed to raise a smile while presenting at the 2026 Oscars.

Early on in Sunday night’s ceremony, the long-time Vogue editor came on stage to present two awards with Anne Hathaway.

Anne, of course, is the star of The Devil Wears Prada and its upcoming sequel, both of which feature the character Miranda Priestly, heavily rumoured to have been inspired by Anna.

Introducing the Best Costume Design prize, the Oscar winner told the audience: “A character’s costume is key to telling a story.

“One could argue that one’s wardrobe in real life is also key. Does it make one appear elegant and attractive on, say, the most important night in Hollywood, and say when the most important people in fashion will be judging how one looks?”

Turning to her co-host, she continued: “Anna, just curious, what do you think of my dress tonight?”

By way of response, Anna simply donned her sunglasses and declared: “And the nominees are…”

Following this, the duo then announced the winners for Best Makeup And Hairstyling, with Anna intentionally misnaming her co-presenter “Emily” in an even more explicit nod to The Devil Wears Prada.

In the original Devil Wears Prada film and the new follow-up, Meryl Streep plays Miranda Priestly, the editor of the fictitious Runway magazine, whose look and mannerisms have sparked comparisons with Anna Wintour for two decades now.

Last year, the award-winning journalist and Met Gala organised claimed: “I went to the [Devil Wears Prada] premiere wearing Prada, completely having no idea what the film was going to be about.

“I think that the fashion industry was very sweetly concerned for me about the film that it was gonna paint me in some kind of difficult light.”

Praising Meryl’s “fantastic” work in the movie, she then insisted: “I found [the film] highly enjoyable and very funny. It had a lot of humour to it, it had a lot of wit.

“I mean, [the actors are] all amazing. And in the end, I thought it was a fair shot.”

Take a look at the full list of winners from the 2026 Oscars here.