Anna Wintour is fashion's most powerful woman. She is famously secretive about her love life.

She's the iconic bob-wielding fashion matriarch who's struck fear in the hearts of assistants for decades, but Anna Wintour's private romantic history is every bit as fascinating as her professional reign in the fashion world.

The Vogue editor-in-chief might keep her emotions hidden behind those signature dark sunglasses, but her relationship history reveals a woman who's weathered multiple marriages, high-profile splits, and even a rumoured fling with Bob Marley (yes, really).

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Her romantic life has been riveting. For example, in his memoir, André Leon Talley revealed the curious detail that Anna Wintour's intimate 1984 wedding to David Shaffer included all her ex-boyfriends being flown in from England.

Whether an English tradition or the ultimate power move, the image of Wintour's former flames witnessing her midday nuptials speaks volumes about fashion's most enigmatic figure.

Here's everything we know about Anna Wintour's notoriously private dating life.

Dr. David Shaffer.

Image: Getty

Anna's first trip down the aisle came in 1984 when she married child psychiatrist David Shaffer. The power pairing lasted 15 years and produced two children — son Charles, now 40, and daughter Bee, 37.

Their marriage represented a classic New York elite coupling: he, the distinguished Columbia University psychiatrist, and she, the ambitious fashion editor, climbing the ranks at Condé Nast.

The marriage ended in 1999 amid rumours that Wintour had already moved on with telecommunications tycoon Shelby Bryan. While neither has ever publicly discussed their split in detail (would you expect anything less from the notoriously private Wintour?), the divorce marked a turning point in Anna's personal and professional life, as she fully embraced her public persona helming American Vogue.

Bob Marley.

Image: Getty

Perhaps one of the most bizarre yet intriguing relationship rumours in Wintour's dating history.

In Amy Odell's unauthorised biography, Anna: The Biography, we're offered rare glimpses into Wintour's fiercely protected personal world, including curious anecdotes about her attendance at a Bob Marley concert with then-husband David Shaffer.

Following the event, which Wintour reportedly described to staff as a "life-changing experience," whispers circulated about a supposed two-week liaison with the reggae icon — though the origins of this rumour remain decidedly murky.

Shelby Bryan.

Image: Getty.

Following her divorce from Shaffer, Wintour began dating venture capitalist Shelby Bryan. Their relationship raised eyebrows from the start — rumours swirled that Bryan had left his wife Katherine to be with Anna, creating quite the Manhattan scandal.

The couple married in 2004, with Bryan becoming Wintour's red carpet companion and tennis match partner for the next 16 years. But trouble began brewing around 2013, when reports emerged that Bryan owed approximately $1.2 million in taxes to the IRS.

By October 2020, their relationship was officially over. Their split capped off what had already been a difficult year for Wintour, who faced criticism about racial issues at Vogue and a scathing portrayal in her former confidante André Leon Talley's memoir.

At the time, many publications claimed that the couple had been separated for quite some time, prior to the news breaking.

"The couple privately split years ago," a source told People.

In true Wintour fashion, she's never publicly commented on what went wrong in either marriage — maintaining the same steely composure that's made her fashion's most enduring and intimidating icon.

Bill Nighy.

Image: Getty

Fashion's most intriguing non-couple continues to captivate society's imagination, despite their protestations to the contrary. When Bill Nighy and Anna Wintour arrived arm-in-arm at the 2023 Met Gala, the collective gasp from the fashion world was practically audible.

Though Nighy's representatives swiftly issued a statement declaring the pair "simply great friends for two decades," their undeniable chemistry sparked immediate speculation.

The couple have frequently been spotted together since at least 2020, sparking romance speculation despite official denials.

From intimate dinners to a cosy New York film screening in December 2022 and a relaxed Roman holiday in August 2023, the pair's public appearances have only intensified curiosity about their relationship.

Each sighting reveals the usually composed Vogue matriarch noticeably at ease in the British actor's company.

Feature Image: Getty.