Jannik Sinner bonds with $50M-worth fashion icon Anna Wintour and Chinese singer Xiao Zhan at Gucci show in Milan

Jannik Sinner attended the Milan Fashion Week, where Gucci showed off its classic and minimalist designs. The World No. 1 rubbed shoulders with Vogue's editor-in-chief Anna Wintour and Chinese actor and singer Xiao Zhan at the event.

Sinner, who won this year's Australian Open, accepted a three-month suspension from WADA earlier this month. The Italian will be out of action until May 9. Considering his long layoff, it made sense for the 23-year-old to let his hair down and make his presence known at the Gucci Fall/Winter 2025 show in Milan on Tuesday, February 25.

Jannik Sinner was joined by $50 million-worth fashion legend Anna Wintour (via Celebrity Net Worth). The top-ranked ATP player, who donned a simple yet elegant black jacket and jade blue t-shirt combo, sat with Wintour at one point of the show, going by the pictures doing the rounds of X.

The duo was also joined by Xiao Zhan, a Mandopop artist who has established a global presence with his work in music and acting. Xiao was in a much more flamboyant outfit as he stunned in a well-fitted brown leather jacket.

Sinner and Gucci go way back. In 2022, the 23-year-old Italian became the fashion brand's global ambassador and sported their duffel bag (in collaboration with his other sponsor, HEAD) on multiple occasions.

The Italian turned heads with his pastel grey-patterned bag at last year's Wimbledon, a tournament known for its all-white ethic.

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Jannik Sinner to miss title defense at Miami Masters 2025

Jannik Sinner won the 2024 title in Miami | Image Source - Getty

Jannik Sinner will be forced to skip the Indian Wells Masters, the Miami Masters, the Monte-Carlo Masters, and the Madrid Masters due to his three-month ban. This means that the World No. 1 will not be able to defend his 2024 Miami crown, leading to a 1,000-point drop-off in the ATP rankings.

All in all, Sinner will drop 1,600 points from his absences in Indian Wells, Miami, Monte Carlo, and Madrid (he had already surrendered his 400 points from Indian Wells last year after his provisional suspension). The Italian will likely be back in time for the Italian Open, a tune-up event to the French Open.

The second part of the 2025 ATP Tour season will see the 23-year-old in a precarious position in terms of rankings. He has 6,930 points on the line on account of his titles in New York, Turin, Shanghai, Cincinnati, and Halle, and deep showings in SW19, Montreal, and Beijing from last year.