Anna Wintour knows how to make an entrance, even when the runway happens to lead into a tennis stadium.
The fashion icon arrived at the US Open alongside her daughter Bee Shaffer and daughter-in-law Elizabeth Cordry, turning a simple walk into Arthur Ashe Stadium into an unmistakably stylish family moment.
The three women leaned into polished, coordinated looks without dressing identically. Wintour, instantly recognizable behind her signature sunglasses, walked between Bee and Elizabeth as cameras captured the trio arriving together for one of the biggest nights of US Open Fan Week.
Anna Wintour makes the US Open a family affair
Bee, 39, is Wintour’s daughter with her late former husband David Shaffer and has built much of her career away from her mother’s fashion empire, working in television and theater production. Elizabeth is married to Wintour’s son Charles Shaffer, making their appearance together a rare glimpse of the family surrounding one of fashion’s most recognizable figures.
The three have shared the spotlight before. Wintour, Bee and Elizabeth were also photographed together earlier this year at the New York premiere of The Devil Wears Prada 2, where Wintour’s unmistakable influence on the world of fashion made their family appearance particularly fitting.
This time, however, tennis provided the backdrop. Wintour was at Arthur Ashe Stadium for Roger Federer: An Icon Returns to New York, a special exhibition featuring the 20-time Grand Slam champion alongside fellow tennis legends Andre Agassi, Andy Roddick and John McEnroe.
The night ultimately belonged to Federer. Back on Arthur Ashe for the first time since his final US Open appearance in 2019, the 45-year-old showed flashes of the brilliance that once made him nearly unbeatable in New York, defeating longtime rival and friend Roddick 6-3 in a one-set exhibition before teaming up with McEnroe for doubles against Roddick and Agassi.
Afterward, Federer addressed the packed stadium during an emotional return to the court where he won five consecutive US Open titles. “It’s great to be back in New York,” he told the crowd as he reflected on his memories at the tournament and in the city.
The moment carried even greater meaning because Federer never had a proper US Open farewell after his final appearance in 2019, making this return an opportunity to finally thank New York and say goodbye on his own terms.
For Wintour, a longtime tennis fan and close friend of Federer, being at Arthur Ashe was hardly surprising. What made the entrance stand out was having Bee and Elizabeth at her side.
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