Anna Wintour's love life: The untold story of her romantic life

Anna Wintour may be the queen of cold stares and front-row fashion diplomacy, but her love life? Surprisingly human—and more layered than her signature Chanel skirts. While the Vogue editor-in-chief has spent decades curating the world’s most powerful fashion images, she’s kept her personal affairs tightly zipped.

Still, over the years, enough details have trickled out to piece together a quietly fascinating romantic story.Let’s start with the man who was by her side for over 15 years: Shelby Bryan, a Texas-born telecom tycoon with the kind of all-American charisma that seemed almost too casual for Wintour’s razor-sharp aura. They began dating in 1999, and their relationship was instantly tabloid gold. Not only because of who Anna is, but because Shelby was still married when their romance began.

This sparked whispers that Wintour was stepping into homewrecker territory—a plot twist more fitting for a soap opera than fashion week.Still, Shelby and Anna stuck together for years. He moved into her Manhattan townhouse, attended galas, and even occasionally smiled in public (a big deal in Wintour World). For a woman famously icy and guarded, Shelby brought out a softer side. Friends said she’d giggle around him.

But by 2020, things had changed. Whispers of a split began circulating—he was reportedly back in Texas, and Anna had stopped wearing the couple's signature social uniform: her polite, practiced smile when Shelby was around. Romance aside, Anna Wintour’s relationships have always been deeply intertwined with her work. Her first marriage, to child psychiatrist David Shaffer, was her most private chapter. They were together for over 15 years, had two children, and parted ways quietly in the late '90s.

There was no Vogue cover announcing the divorce. Just the slow, silent unraveling of two busy people going in different directions.In the end, Anna’s love life mirrors her wardrobe: minimal but deliberate, curated yet never obvious. She's never spilled to tabloids or used relationships for PR. There are no teary interviews, no tell-all memoirs. So yes, behind those ever-present sunglasses is a woman who’s not just a fashion icon, but someone who’s loved deeply, quietly, and on her own terms. And honestly, that’s the most stylish thing of all.