Few names in fashion command as much respect—and intrigue—as Anna Wintour. Born in London in 1949, Wintour’s career has spanned continents and decades, culminating in her legendary tenure as editor-in-chief of Vogue from 1988 to 2025 and her role as global chief content officer of Condé Nast.
With her signature bob and ever-present sunglasses, Wintour is both a tastemaker and a gatekeeper, shaping the industry’s direction and presiding over the Met Gala, fashion’s most exclusive night. While her professional life is public, her personal life has often played out behind a veil of privacy—until recent years, when her relationships became the subject of global fascination.
The Early Years: Marriage to David Shaffer
Anna Wintour’s first marriage was to Dr. David Shaffer, a respected child psychiatrist affiliated with Columbia University and the New York State Psychiatric Institute. The couple wed in 1984 and had two children: Charles (Charlie) Shaffer and Katherine (Bee) Shaffer.
For 15 years, Wintour balanced the demands of a burgeoning media career with family life. However, the marriage ended in 1999. While the precise reasons remain private, reports suggest that Wintour’s relentless work ethic and rising public profile contributed to the strain, as did rumors of her growing closeness to another man, Shelby Bryan.
The Shelby Bryan Era: A High-Profile Romance
Shortly after her divorce, Wintour began a relationship with telecom executive Shelby Bryan. Their romance, which reportedly began while both were still married to others, soon became one of New York’s most talked-about partnerships. In 2004, Wintour and Bryan married in a private ceremony.
Though they shared no children together, their union lasted for over 16 years. The couple was often seen at social events and tennis matches, but in later years, their public appearances together dwindled.
Behind the scenes, the relationship faced mounting pressures. In 2013, Bryan’s financial troubles—including a reported $1.2 million tax debt—cast a shadow over their marriage.
By 2020, the pair had quietly separated, with sources confirming they had “split after more than 20 years together”. Rumors swirled about Bryan rekindling ties with his ex-wife, but insiders insisted they remained only friends.
Is Anna Wintour Dating Bill Nighy?
Following her split from Bryan, Anna Wintour’s close friendship with British actor Bill Nighy became a subject of intense media speculation. The two, both in their seventies and icons in their respective fields, have been friends for decades, frequently spotted together at theaters, restaurants, and even on trips abroad.
In 2021, photos of them enjoying dinner in Rome sparked rumors of romance, which only intensified when they appeared arm-in-arm at the 2023 Met Gala.
Their red carpet debut together seemed to confirm what many had suspected: that their relationship had evolved beyond friendship. Wintour, in Chanel couture, and Nighy, in classic eveningwear, drew global attention as they ascended the Met steps.
Yet, even as the internet buzzed, Nighy’s representatives publicly denied any romantic involvement, insisting the pair were simply long-time friends. Wintour herself has remained characteristically silent, leaving the true nature of their bond open to interpretation.
Family Ties: Anna Wintour’s Children
Amid her high-profile relationships, Wintour’s role as a mother has remained a constant. Her son, Charles Shaffer, has largely stayed out of the public eye, while her daughter, Katherine “Bee” Shaffer, has embraced the spotlight, working as a television producer and often accompanying her mother to major events.
Both children have spoken warmly of their relationship with Wintour, describing her as supportive but demanding—a reflection of the same qualities that have defined her career.
The Private Life of a Public Icon Anna Wintour!
Anna Wintour’s personal life, though often shielded from the public, reveals a woman as complex and compelling as the industry she helped shape. From her marriages to David Shaffer and Shelby Bryan to her enigmatic connection with Bill Nighy, Wintour’s relationships have been marked by both discretion and intrigue.
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Through it all, her devotion to her children and her work has remained unwavering, solidifying her legacy as not just a fashion icon, but a figure of enduring fascination.
