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Anna Wintour, fashion’s biggest name and a self-proclaimed Roger Federer superfan, was thrilled to have Jannik Sinner beside her during their latest Milan Fashion Week outing. The pair sat beside each other as they graced Gucci’s 2025 Fall/Winter show.
Sinner, who's been unwinding with his family in South Tyrol, Italy, amid his three-month suspension, made his first public appearance at Milan Fashion Week on Tuesday, February 25. As the global brand ambassador for Italian luxury fashion house Gucci, the World No. 1 stepped out in style, wearing a black jacket over his blue t-shirt and blue-gray trousers. He paired the Gucci look with his signature white Nike sneakers.
Jannik Sinner was seated in the front row beside Vogue’s Editor-in-Chief, Anna Wintour, and Chinese actor and singer Xiao Zhan. Sinner and Wintour were captured sharing a few laughs as they bonded ahead of the show.
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In one video, Anna Wintour also expressed that she was delighted to be seated beside the World No. 1.
"Anna loves tennis!" the person behind the camera was heard as saying.
"True," Wintour smilingly responded. "Good call."
Wintour has been very vocal about her love for the sport over the years and is frequently spotted attending various tennis events. Her admiration for Roger Federer is no secret, having graced the 20-time Grand Slam champion’s players’ box numerous times during his career.
The fashion icon, who chairs the MET Gala, also makes it a point to have tennis representation at the esteemed event, with the likes of Serena Williams, Naomi Osaka, and Roger Federer appointed as co-chairs in the past.
A look at what Jannik Sinner's been up to amid his on-court absence
Jannik Sinner is serving a three-month suspension, having resolved his doping test case with the WADA in mid-February. The Italian, who tested positive for low traces of the prohibited substance Clostebol last March, was initially handed no suspension by the ITIA after evidence proved that his failed tests were the result of cross-contamination with his physiotherapist.
However, the WADA launched an appeal, claiming that Jannik Sinner should bear some responsibility for his team member’s error. After an exhaustive investigation that established that Sinner’s case was “a million miles away from doping,” the agency ultimately approached the World No. 1 ahead of their CAS trial, asking for a three-month suspension attributed to his team’s negligence.
Ahead of his anticipated return, the three-time Grand Slam champion has been unwinding at his hometown in South Tyrol, indulging in other sports. Last week he was spotted skiing on the slopes of Sexten, which was followed by a golf club excursion.
Sinner’s suspension is set to be lifted on May 4 ahead of the 2025 Italian Open (May 7-18). Meanwhile, he is expected to resume his official training on April 13.
