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Anna Wintour has been a staple of the annual Met Gala. As Vogue‘s Global Editorial Director, the fashion icon is serving as co-chair once again for the Metropolitan Museum of Art’s Costume Institute fundraiser, and her dating history is a fixture of intrigue among fans.
In 2023, Anna went to the Met Gala with actor Bill Nighy, but her rep later denied the Anna was dating the Oscar nominee. The rep said that Anna and Bill were just “great friends.”
Anna is legendary for her career as editor-in-chief at Vogue and her enormous influence on the fashion industry, and for being the alleged inspiration for Lauren Weisberger’s larger-than-life character, Miranda Priestley of the bestselling book The Devil Wears Prada. She served as the EIC at Vogue from 1988 to 2025. She’s also widely known for her amazing style sense, made instantly recognizable with her unmistakable pageboy haircut, bangs, and large sunglasses.
Anna is a mother to two children, Charles Shaffer born in 1985, and Katherine Shaffer, born in 1987, with her first husband, David Shaffer. After divorcing David, Anna married Shelby Bryan, and it’s obvious that each relationship profoundly affected the influential editor‘s personal life. Here’s everything you should know about Anna’s two marriages and relationships.
David Shaffer
David Shaffer is a well-known and respected child psychiatrist in New York, and Anna and David were married in 1984. David already had two sons by his first wife, caterer Serena Bass, but that didn’t stop Anna and David from having two more — son Charles “Charlie” born 1985, and daughter Katherine “Bee” in 1987. While both excelled in their respective professions, with Anna rising the ranks at Vogue and becoming a famous pop culture icon and David doing groundbreaking work in the field of adolescent suicide prevention, their marriage only lasted 15 years and they divorced in 1999.
Still, the marriage was successful in that it produced two equally successful children. Bee graduated from Columbia University in 2009 and married director Francesco Carrozzini, (who happens to be the son of Vogue Italia editor-in-chief Franca Sozzani) in July of 2018. Physician Son Charlie 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 baby boy in 2021, which makes Anna a grandmother three times over!
Shelby Bryan
Anna started dating business executive, entrepreneur, and venture capitalist Shelby Bryan in 1999, with some reports saying that their relationship ended her marriage to David and that Shelby was married to Katherine Bryan at the time. Shelby and Katherine divorced in 2001, two years after Anna and David divorced, and Anna and Shelby got married in 2004. From that point, Shelby became a fixture by Anna’s side, all the way through 2020. The renowned investor, who holds an MBA from Harvard Business School, and Anna finally split in October of that year, with a source telling Page Six that they’d actually been apart for a while. “It’s been quite a while since they’ve been seen together,” the source said.
Bill Nighy
Anna was first romantically linked to Oscar nominee Bill Nighy in August 2021, when they were seen on a romantic dinner date in Italy. The pair continued to fuel dating rumors the following year when Anna hosted a screening of Bill’s moving Living in New York City in December 2022. They walked the 2023 Met Gala red carpet together, which fans thought was confirmation that the two are dating. But Anna’s rep later clarified to People that Anna and Bill “are not in a relationship.” The rep also said that the two stars “have simply been great 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 is also an actress and filmmaker.
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