Naomi Osaka doesn’t just know how to deliver a tennis masterclass; she also knows how to tell a story through her clothes. Whether she’s stepping onto the court or turning heads with a signature look off it, the Japanese star has never shied away from making a statement with her fashion choices. And when it comes to dealing with criticism, Osaka has already made her stance clear.

At this year’s US Open, she admitted that she doesn’t mind “being the first to do something and getting trashed for it.” So, when the four-time Grand Slam champion arrived at Vogue World: Milano in a black, sheer Chantilly blouse and matching skirt, she once again made a bold yet elegant fashion statement. But the opinions didn’t stop at the runway.

This time, Boris Becker had something to say, taking a subtle dig at Osaka before weighing in on her striking look.

“That’s the right environment to wear beautiful dresses ….looking good Naomi!” he wrote on X, all while suggesting that the runway is the ideal place to don the outfits instead of tennis courts.

While Becker’s comment may appear complimentary at first glance, the sarcasm behind it doesn’t take long to surface. His remarks suggest that he isn’t particularly fond of Osaka’s penchant for making bold fashion statements at tennis tournaments and Grand Slams.

Earlier this month at Flushing Meadows, Naomi Osaka once again grabbed attention with a series of striking outfits created in collaboration with American stylist Law Roach. For her opening US Open match, Roach commissioned a custom look from Who Decides War, featuring a dramatic white tulle skirt paired with an asymmetrical grey hooded top covered in newspaper clippings chronicling moments from Osaka’s career.

Founded in New York by Everard Best and Téla D’Amore, Who Decides War is known for its detailed denim work, hand-distressed finishes, and its blend of high-fashion craftsmanship with streetwear, often incorporating elements of Black American culture, faith, and history.

Osaka completed the ensemble with cornrows, a red-and-black headband, and matching Nike arm sleeves, intentionally paying homage to Allen Iverson. The biggest reveal, however, came underneath the elaborate outer layers, where Osaka was wearing her actual Nike match kit, a black tank top with a metallic silver skirt. The outfit effectively set the tone for Osaka’s US Open wardrobe, with Roach and the Japanese star building an entire fashion narrative around the tournament.

The statement became even more apparent during her second-round clash against Katerina Siniakova. This time, Roach dressed Osaka in a custom Thom Browne ensemble inspired by tennis, complete with miniature racquet details and a long, flowing silhouette. The outfit may have looked familiar, and that was intentional. It echoed the Thom Browne creation Roach previously designed for Zendaya during the Challengers press tour.

For Osaka’s third appearance, Roach brought together MONSE’s deconstructed gabardine tailoring with Nike’s grey Studio Fleece. The combination created a striking mix of formal suiting and athletic wear, while a hand-embroidered Swoosh on the back completed the outfit. It was business attire, reimagined in Osaka’s own style.

For her fourth-round walk-out against Elena Rybakina at the 2026 US Open, Osaka continued the fashion theme with a custom patchwork coat created by Brooklyn-based brand KidSuper.

Notably, all of Osaka’s Grand Slam outfits have drawn the attention of fans. But while her fits have been praised, she hasn’t been able to back that up with success on the court. Currently ranked No. 17, she is yet to win a title this season. Though a win-loss record of 28-11 isn’t anything bad, her performances in the later stages have simply not been up to par.

This is one of the reasons why Osaka faces criticism whenever she arrives wearing a fancy outfit on court. A similar story followed after her appearance at the Vogue event. While some claimed that modeling has become Osaka’s primary interest, others felt that her outfit wasn’t anything great.

However, upon receiving criticism over her outfits, Osaka called out the haters and stated, “You know…I don’t give a f**k if you don’t like me. I don’t mind being the first to do something and getting trashed for it. This happened when I talked about mental health and for some reason it’s happening with my clothes lol. I’m literally Haitian. It’s in my blood to be this way; as long as the people after me have an easier path it’s worth it.”

Nevertheless, at the Vogue World, while some claimed that modeling has become Osaka’s primary interest, others felt that her outfit wasn’t anything great.