Anna Wintour Hilariously Shades Anne Hathaway with 4 Simple Words During Surprise Oscars Appearance

Awards shows are known for delivering a surprise or two, and the 2026 Oscars were no exception. The 98th Academy Awards brought Hollywood’s biggest names to the Dolby Theatre to celebrate the best films of 2025 and along with the trophies came plenty of memorable onstage moments. One of the most talked-about came courtesy of Anne Hathaway and Anna Wintour.

The Devil Wears Prada actress and the longtime Vogue editor took the stage together to present the awards for Best Costume Design and Best Makeup and Hairstyling. But before getting to the nominees, the pair shared a brief (and very cheeky) exchange.

"You 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 when, say, the most important people in costuming will be judging how one looks?" Hathaway said before turning to Wintour. "Anna, just curious, what do you think of my dress tonight?"

Wintour’s response was perfectly timed. After putting on a pair of sunglasses, she skipped the question entirely and jumped straight to business: "And the nominees are…"

And that wasn't the end of it. While presenting the second category, Hatahway asked Wintour if she’d like to read the nominees.

"Thank you, Emily," Wintour replied, referencing the name Meryl Streep’s character repeatedly used to belittle Hathaway’s character (whose real name was Andy) in The Devil Wears Prada.

The playful exchange felt especially fitting given the timing. The bit arrives just weeks before The Devil Wears Prada 2 is set to hit theaters.

The original 2006 film followed Andy Sachs (Anne Hathaway), an aspiring journalist who lands a job working under the formidable Miranda Priestly (Meryl Streep) at Runway magazine.

The sequel, out May 1, follows Miranda Priestly navigating the decline of print media while facing off against her former assistant, Emily Charlton, now a powerful luxury executive. Andy Sachs has also climbed the ranks and returns as a digital media executive, setting the stage for a fresh round of high-stakes workplace drama.

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