Anna Wintour recently sparked dating rumors with actor Bill Nighy as the pair were photographed on a dinner date in Italy. The duo were spotted enjoying a hearty meal at the Pierluigi restaurant in Rome on Thursday, 26 August 2021.
The Love Actually actor appeared at the venue with a pair of roses and gifted them to the fashion mogul. The pair reportedly enjoyed each other’s company as they chatted away through the night. Speculations about a possible romance between the two have made the rounds since 2015.
In an old interview, Bill Nighy was even asked about his rumored relationship with the Vogue editor-in-chief. At the time, he mentioned:
“Obviously I have nothing to say about that. There are a lot of rumors about me and probably about Anna Wintour.”
The latest rumors come nearly a year after Anna Wintour’s split from her ex-husband Shelby Bryan. Anna and Shelby repeatedly made the news throughout their decade-long romance.
However, multiple media reports suggest that the relationship fizzled out around 2013, long before their official separation. The 71-year-old was previously married to Dr. David Shaffer, a child psychiatrist from South Africa.
Meanwhile, the fashion journalist has also shared a close friendship with Bill Nighy since 2010. Over the years, the duo have been consistently spotted together at several events, dinners, fashion shows and movie theaters.
Who is Shelby Bryan? A look into Anna Wintour's past relationships
Anna Wintour is undoubtedly one of the most prominent figures in the fashion industry. She is often regarded as the most powerful woman in fashion media. She has served as the editor-in-chief of Vogue since 1988.
She is also the global editorial director of the outlet. She was appointed global chief content officer and artistic director of Conde Nast in 2020. Anna has also served as the inspiration behind the bestselling novel The Devil Wears Prada and its film adaptation.
Anna Wintour married Shelby Bryan in 2004. The duo reportedly met at a Benefit Ball for the New York Ballet in 1999. The same year, she parted ways with her first husband, David Shaffer. Rumors were rife that an alleged affair between Anna and Shelby led to the former’s first divorce.
Shelby Bryan is a pioneer in the American telecommunications industry. He is a successful entrepreneur, business executive, venture capitalist and futurist. He has been a staunch supporter of the Democratic Party.
He served as the National Finance Chair of the Democratic Senatorial campaign Committee in the late 1980s. He was also part of the President’s Foreign Intelligence Advisory Board from 1999 until 2001.
Meanwhile, Anna Wintour has also been an active supporter of the Democratic Party since Hillary Clinton’s senate run in 2000. She also contributed to Barack Obama’s presidential runs in 2008 and 2012. She also supported Hillary Clinton’s 2016 presidential campaign.
Anna and Shelby’s marriage garnered massive attention as it brought together the world of fashion, business and politics. Following nearly 10 years of highly publicized romance, their relationship reportedly hit a rough patch in 2013 after Shelby’s legal tax issues came to light.
It was revealed that the businessman owed $1.2 million in taxes to the IRS. According to The Telegraph, he also owed $20,000 in Harris County property taxes. Anna and Shelby’s public appearances turned seemingly rare after 2013.
The former pair were last seen together at the 2018 U.S. Open Tennis. In 2015, Shelby was linked to ex-wife Katherine after the latter’s second husband passed away. However, sources close to the entrepreneur denied the reconciliation rumors.
Anna Wintour officially called it quits with Shelby Bryan in October 2020 after 16 years of marriage. While the fashion icon shares two children, Charles and Katherine, with her first husband, she does not have any children with Shelby.
In addition to her marriages, Anna Wintour has also been linked to other men in the past, including British novelist Piers Paul Read and gossip columnist Nigel Dempster. The editor is yet to confirm or deny the latest dating rumors with Bill Nighy.