Dame Anna Wintour has spent decades commanding the fashion world with an iron will and a pair of sunglasses. From the moment she took over Vogue in 1988, she didn’t just edit a magazine—she redefined what fashion media could be. Her bold editorial choices, unmistakable bob, and commanding presence made her both feared and admired in equal measure.
And now, after nearly 40 years at the helm, Wintour has stepped down as editor-in-chief of American Vogue, signaling the end of an era—but not the end of her reign. She’s still holding the reins as Condé Nast’s global chief content officer and global editorial director of Vogue, quietly steering the future of fashion from behind the curtain.
Over the years, Wintour’s influence has extended far beyond glossy pages and runway shows, but behind all that, her personal life has had its own story arc. She’s been married twice before, each relationship unfolding during different chapters of her meteoric rise.
Now, as she steps into a more scaled-back role at Condé Nast, one question lingers among curious followers: Who is she dating today? In the sections ahead, we’ll take a closer look at the men who’ve shared her life, past and possibly present.
Her First Husband Was a Brilliant Psychiatrist
Wintour’s first marriage began in 1984, when she tied the knot with Dr. David Shaffer, a South African-born child and adolescent psychiatrist whose work would go on to transform the study of youth suicide.
At the time, he was already a respected figure at Columbia University, and their union represented a pairing of intellect and ambition: he, a leader in mental health research; she, a rising star at Condé Nast on her way to becoming fashion’s most influential voice.
The couple’s life together spanned 15 years and included two children. While Wintour’s editorial empire expanded, Dr. Shaffer was conducting groundbreaking research into suicide prevention, ultimately leading to the development of screening tools and protocols now used in schools and hospitals.
His impact reached far beyond academia—thanks in part to Wintour’s support, he co-founded what is now known as the Center for Youth Mental Health at NewYork-Presbyterian.
Their marriage ended in 1999 amid rumors of Wintour’s budding relationship with telecom mogul Shelby Bryan. Despite the split, the two remained close. In fact, as Dr. Shaffer faced his final years battling Alzheimer’s disease, Wintour welcomed him into her Long Island estate, where he lived with the family until his passing in October 2023.
“It was just the only way forward,” she later said, describing the arrangement. Their daughter Bee put it more simply: “We have a family that should be so dysfunctional, but it’s oddly so functional.”
Anna Wintour’s Two Children Have Thrived in Their Own Fields
Anna shares two children with her first husband, Dr. David Shaffer: Charles “Charlie” Shaffer, born in 1985, and Katherine “Bee” Shaffer Carrozzini, born in 1987.
Charlie became a psychiatrist like his father, graduating from Oxford and then Columbia’s College of Physicians and Surgeons. He married Elizabeth Cordry in 2014 at Anna’s Mastic Beach home, with high-profile guests like Oscar de la Renta in attendance.
The couple now has two daughters—Caroline (born 2017) and Ella Rose (born 2019). During the COVID-19 pandemic, Anna publicly praised her son for returning to the ICU after recovering from illness himself, calling him a source of pride and strength.
Bee pursued a career in entertainment, steering clear of the fashion world despite her Vogue lineage. After graduating from Columbia University, she worked as a segment producer at Late Night with Seth Meyers and later became a Broadway producer, with credits including Parade, The Wiz, and The Last Five Years.
In 2018, she married director Francesco Carrozzini—son of the late Vogue Italia editor Franca Sozzani—at her mother’s estate in a private ceremony with a strict no-phone policy. The couple welcomed their first child, a son named Oliver Sozzani, in October 2021.
Today, Wintour is a grandmother of three, affectionately called “Anna” by her grandkids, not “grandma”—a fitting detail for someone who’s always done things her own way.
Her Second Marriage Ended Quietly After Years in the Spotlight
Shortly after her divorce from David Shaffer, Anna began dating venture capitalist Shelby Bryan in 1999. Their relationship quickly became the subject of Manhattan gossip, with reports suggesting both had left their respective spouses to be together.
Bryan finalized his divorce from his wife, Katherine, in 2001—two years after Anna’s split—and by 2004, he and Wintour were officially married.
For the next 16 years, Shelby was a familiar presence at Wintour’s side, appearing with her at red carpet events, the Met Gala, and countless tennis matches.
A Harvard MBA and prominent business executive, Bryan was well-known in elite circles, but by 2013, financial troubles began to surface. Reports revealed he owed over $1.2 million in back taxes, casting a shadow over their otherwise polished public image.
By October 2020, their relationship had come to an end. Though news of the breakup broke that fall, sources claimed the couple had quietly separated well before then. True to form, Wintour never addressed the split publicly.
Is Anna Wintour Dating Bill Nighy?
Wintour has been repeatedly linked to British actor Bill Nighy in recent years. The two were first seen together in August 2021 during a dinner in Italy, and since then, they’ve been spotted at several public events, including a New York screening of Living in December 2022.
In May 2023, they walked the Met Gala red carpet together, which led many to assume they were officially a couple.
However, a representative for Wintour later clarified that they are not in a relationship and have simply been close friends for over 20 years. Despite the denial, the pair has continued to appear together at events, fueling ongoing speculation about their status. For now, both maintain that their bond is purely platonic.
