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Anna Wintour has long been a prominent figure at the yearly Met Gala. As Vogue’s Global Editorial Director, the fashion superstar is reprising her role as co-chair for the Metropolitan Museum of Art’s Costume Institute benefit, and her romantic past has always captivated admirers.
In 2023, Anna attended the Met Gala alongside actor Bill Nighy, though her representative later refuted the notion that Anna was seeing the Oscar-nominated star. The representative clarified that Anna and Bill were simply “great friends.”
Anna is celebrated for her tenure as editor-in-chief at Vogue and her profound impact on the fashion world, in addition to allegedly serving as the model for Lauren Weisberger’s unforgettable character, Miranda Priestley from the famous novel The Devil Wears Prada. She held the EIC position at Vogue from 1988 to 2025. She is also widely recognized for her exceptional style, instantly identified by her iconic pageboy haircut, bangs, and oversized sunglasses.
Anna is a parent to two kids, Charles Shaffer born in 1985, and Katherine Shaffer, born in 1987, with her first spouse, David Shaffer. Following her split from David, Anna wed Shelby Bryan, and it’s clear that both relationships had a strong effect on the influential editor’s private life. Here’s everything you should understand about Anna’s two marriages and connections.
David Shaffer
Anna Wintour arrives with David Shaffer at the 1999 CFDA Awards in New York City on June 2, 1999. (Matt Baron/BEI/Shutterstock)
David Shaffer, a respected and established child psychiatrist in New York, married Anna in 1984. He already had two sons with his prior spouse, caterer Serena Bass. That didn’t prevent Anna and David from having two more children — a son named Charles “Charlie,” born in 1985, and a daughter named Katherine “Bee,” born in 1987. While they both achieved great heights in their fields, with Anna becoming an icon in pop culture while climbing the ranks at Vogue and David pioneering adolescent suicide prevention, their marriage only lasted 15 years, ending in a 1999 divorce.
Nevertheless, their marriage was triumphant in that it yielded two similarly accomplished children. Bee obtained a degree from Columbia University in 2009 and wed director Francesco Carrozzini, (who is incidentally the son of Vogue Italia editor-in-chief Franca Sozzani) in July 2018. Son Charlie, a physician, graduated from the University of Oxford and Columbia College of Physicians and Surgeons and has since welcomed two daughters with wife Elizabeth Shaffer. Bee had a son in 2021, making Anna a grandmother to three!
Shelby Bryan
Anna Wintour appears with Shelby Bryan at the Frick Museum in New York City on February 6, 2003. (Matt Baron/BEI/Shutterstock)
Anna began a relationship with business leader, entrepreneur, and venture capitalist Shelby Bryan in 1999, and some accounts claim that their romance led to her split from David and that Shelby was then married to Katherine Bryan. Shelby and Katherine finalized their divorce in 2001, two years after Anna and David separated. Anna and Shelby were then married in 2004. Then, Shelby became a constant presence alongside Anna, up until 2020. The well-known investor, who holds an MBA from Harvard Business School, and Anna eventually parted ways in October of that year. A source informed Page Six that they’d been separated for a while. “It’s been quite a while since they’ve been seen together,” stated the source.
Bill Nighy
Anna Wintour and Bill Nighy at the 2023 Met Gala (Photo: David Fisher/Shutterstock)
Anna was first linked romantically to Oscar-nominated actor Bill Nighy in August 2021, after they were spotted on a romantic dinner in Italy. The two kept fueling romance speculation the following year when Anna hosted a viewing of Bill’s poignant film Living in New York City in December 2022. They appeared together on the 2023 Met Gala red carpet, leading fans to believe it was confirmation of their romance. But Anna’s representative then clarified to People that Anna and Bill “are not an item.” The representative also stated that the two stars “have simply been close friends for two decades.” Bill was previously in a relationship with British actress Diana Quick from 1982 to 2008. They have a daughter, Mary Nighy, who also works as an actress and filmmaker.