Anna Wintour’s Relationship History, Decoded

Anna Wintour might be the queen of fashion week and the front-row whisperer-in-chief, but her personal life? Surprisingly chill. She’s been married, had a long-term partner, and sparked some very interesting dating rumors… all while running “Vogue,” co-chairing the Met Gala each year, and wearing sunglasses indoors like it’s a birthright. Let’s take a look at the handful of people who’ve shared her orbit (and possibly her dinner reservations).

Marriage and Kids

First up, David Shaffer, a child psychiatrist, Columbia professor, and the guy who walked down the aisle with Anna back in 1984. They were married for 15 years and had two kids: Charles in 1985 and Katherine (aka Bee) in 1987.

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The couple kept it classy through their 1999 split, and Bee’s still seen at events with Anna, which tells you everything you need to know about how solid that family unit is. Shaffer later passed in 2023, and his memory lives on through his children and work.

Relationship 2.0

Not long after the divorce, Anna started seeing tech investor Shelby Bryan; and the two were together for nearly two decades. That’s longer than most fashion trends survive.

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They were spotted at plenty of high-profile events but stayed mostly out of the gossip headlines (respect). By 2020, it seems like they quietly parted ways, and neither made a fuss. Classic Wintour: elegance, even in the breakup.

The Rumor Mill

Now for the most British twist in this story: Bill Nighy. Yep, that Bill Nighy… from “Love Actually,” the “Harry Potter” film series, and basically every charming indie movie ever. The two have been seen out and about together, sparking years of “are-they-or-aren’t-they” speculation.

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“They are not in a relationship,” the actor’s representative told People back in 2023, but fans still speculate that there’s something there. Whether it’s romance or just two icons enjoying each other’s company as friends, we’re rooting for whatever makes them happy.

The Bottom Line

While her professional life has been front-page news for decades, Wintour’s approach to romance has stayed refreshingly grounded. No messy news stories, no tell-all interviews: just long-term connections, mutual respect, and the occasional headline that sends the internet into a spiral. For someone constantly surrounded by flashbulbs and fashion drama, she’s kept her private life remarkably private. And, honestly, that might be the most stylish thing about her.