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Naomi Osaka walks onto court during the U.S. Open on Aug. 31, in New York City.Patrick Smith/Getty Images

Naomi Osaka has never shied away from the spotlight, especially when it comes to showing off her style.

Her on-court looks – often self-funded and co-designed – have long been conversation starters. Her U.S. Open Allen Iverson-inspired ensemble – a nod to Nike’s basketball theme at the tournament – was no different, as the Who Decides War custom look paid homage to the NBA legend with an oversized hooded vest, tulle skirt and Nike arm sleeves.

She isn’t the only player turning heads in New York. Combining a love of fashion, wearability and comfort is a priority for Romanian pro Sorana Cirstea. Her collaboration with New Balance, her longtime sponsor, has evolved with her personal style. For the U.S. Open, Cirstea wore a pale yellow dress with a mesh inlay and socks with lace details, a nod to the style she describes as “minimalist with a twist.” In Paris earlier this summer, she opted for a bubblegum-pink look that she said is a far cry from her usual style.

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Sorana Cirstea celebrates a point during the U.S. Open.Caleb Bowlin/Getty Images

“I never really wear pink off the court – I actually don’t think I own any pink items – but this year, for the French Open, I had an unbelievable pink outfit,” she said. “With New Balance, it’s a lot about the details and also about quality. They take so much feedback with every little detail, from the socks to the shoes to the accessories, everything that comes into an outfit.”

A teenage Serena Williams blazed the sponsorship trail in the late nineties when she signed a deal with Puma reportedly worth $12- to $13-million USD. Williams brought her own outfit ideas to the brand, but it was designer Amy Denet Deal who was responsible for the iconic butter-yellow dress Williams wore to defeat world No. 1 Martina Hingis at the 1999 U.S. Open to claim the championship. With that win, Puma awarded her a US$500,000 bonus, and she officially became the brand’s muse. In 2003, the tennis pro partnered with Nike – a relationship that is ongoing today – for a groundbreaking deal worth up to US$55-million.

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Players today have various levels of involvement in their on-court looks. Some work with brands to personalize their outfits, while others simply wear what they’re given. But sponsorship deals on and off the court come with million-dollar price tags. Coco Gauff has a long-term, multi-million-dollar deal with New Balance. Naomi Osaka inked a contract with Nike worth US$10-million annually. Canadian star Leylah Fernandez, who signed with Lululemon in 2022, makes an estimated US$5-million in sponsorship deals per year.

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Leylah Fernandez plays during the U.S. Open.Sarah Stier/Getty Images

Hungarian competitor Fanny Stollár, who is in the middle of a two-year sponsorship deal with Japanese brand Mizuno, puts her stamp on its brightly coloured looks with accessories such as her silver, radiant-cut engagement ring and long nails. She said her nails, which are often painted Ferrari red, make her stand out.

“I like Mizuno because it’s different,” she said. “You don’t see a lot of players wear it.” She also likes what Wilson is doing on the court. “I love the dresses that Marta Kostyuk is wearing,” she said, referencing her navy blue kit with a double-layered tennis skirt at last year’s U.S. Open and her white lace dress at Wimbledon.

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Marta Kostyuk celebrates winning match point at Wimbledon in London, in July.James Fearn/Getty Images

Italian pro Jasmine Paolini, who is sponsored by Asics, had two looks planned for this year’s U.S. Open: an ombre purple pleated kit for the day sessions and an ensemble from the brand’s The Night Energy Collection for night sessions (Paolini was knocked out of the tournament before she had a chance to wear the latter). She is highly involved in choosing her on-court outfits.

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“We were trying to find something that is comfortable that I like that fits my personality,” she said. “I like a short skirt because I’m short, so we had to adjust [the hem] a little bit. And I like when the neck has a more feminine cut.” But the most important piece for Paolini are the shoes. “I think they are so comfortable,” she said.

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Jasmine Paolini celebrates winning match point during the U.S. Open.Sarah Stier/Getty Images

Cirstea, who spends her downtime when travelling for international competitions shopping at high-end boutiques such as Khaite, The Row, Toteme and Jacquemus, thinks that the trend of showcasing fashion on the court is growing. She cited luxury fashion collaborations such as New Balance’s partnership with Miu Miu as one reason for this.

“I love the jackets from the collaboration,” she said, referring to the trendy, oversized technical pieces. “You can wear it on and off the court, with something very elegant but also with something very sporty at the gym. It’s so versatile.”

Cirstea said the best thing about U.S. Open fashion is how varied it is and how many players embrace it.

“I know Aryna Sabalenka is wearing Gucci at the moment, and I think they’re doing a very good job,” she said. “Belinda Bencic is one of my good friends, and she’s so stylish, too.”

She added that it’s nice to be surrounded by so many stylish female players, women who have “different senses of style, but good style.”

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