Hint: It’s not the tennis dress. But as she is inducted into the International Tennis Hall of Fame, the former star athlete is ready to use it.
On Monday, the first day of the US Open women’s singles draw, two days after her induction into the International Tennis Hall of Fame and five years after she officially left the game, Maria Sharapova once again stood centre court in Flushing Meadow, Queens, to receive an official US Open ring. As usual, she was wearing a tennis dress designed to make history.
Specifically, a new version of the tennis dress she wore when she won the US Open in 2006.
That one, inspired by Audrey Hepburn’s little black Givenchy dress in Breakfast at Tiffany’s and bedecked with Swarovski crystals at the neckline, was the first “evening” dress worn by a female competitor. It was also the first time a player had worn a different look for a night game than a day game, and overnight it made Sharapova one of the first tennis dress influencers. This dress is similar, though rather than stopping at her upper thigh, it is midcalf length with a long pleated underskirt.
“It’s a version of the dress for someone that’s grown up,” said Sharapova, 38, a few days before the ceremony. And it is a sign that she is getting ready to compete again – though this time in a new arena.
Sharapova’s legacy as a player is complicated. She was never a beloved tennis figure. Often referred to as the “ice queen” during her time on the women’s tour, when she won five Grand Slam tournaments, she famously saw her peers not as comrades in arms but obstacles to be eliminated. Injuries and a 15-month doping ban further complicated her story, and she retired in 2020.
But she was also among the first athletes to think of themselves as a brand, a strategic approach that made her the highest-paid female athlete in any sport for 11 consecutive years, from 2005 to 2015 – this despite being ranked No 1 for only 21 nonconsecutive weeks. She was the face of TAG Heuer, Tiffany, Porsche and Motorola and one of the first tennis players to demand a seat at the Nike design table. She was a front-row presence before athletes on the front row were a regular thing.
She paved the way for what has become “this merger of sport and fashion,” said Martin Lotti, the chief design officer of Nike, who was a member of the team that worked with Sharapova on the 2006 little black dress. “She helped create that, not just in tennis but for other sports as well.” She was friends with Anna Wintour, attended the Met Gala more than once and announced her retirement in Vogue.
Yet at a time when many other athletes are following a playbook she wrote, looking to fashion as a way to kick-start the second phase of their careers, Sharapova is changing her game.
She is not a face of Moncler; she is a member of the board. Her reality TV role was as a guest judge on Shark Tank. In January, rather than going to the Australian Open, she went to the World Economic Forum in Davos, Switzerland. She has been sharing her opinions about women and leadership. And this fall she will enter the podcast fray with Pretty Tough, a new show from Vox Media in which she will interview female power players of all kinds about their experiences – and how being perceived as aggressive, spiky and blunt, all words often used to criticise women, can actually be an asset.
“I consistently think about women that have become leaders, but for some reason, they soften their edge,” Sharapova said. “They have made important decisions, have put in so much work, and yet they have to apologise for that leadership. I come from a very different perspective.” For her, fashion was never an end; it was a means.
Performance pressure
When Sharapova retired, it would have been easy for her to fall back on the tennis dress. After all, pretty much every time Grand Slam season rolls around, a new Maria Sharapova fan account pops up recapping all the tennis looks she wore while playing. There was the white tie-and-shorts combo she wore for Wimbledon in 2008; the lemon-yellow sundress style at the French Open in 2011; the crimson frock with the New York skyline picked out in crystal at the US Open in 2007.
In part the attention on her clothes had to do with the style of the dresses, which skewed more teatime than tennis, and in part it was because she was among the first Nike athletes to get her own looks. It’s hard to imagine now, when custom dress reveals are an essential part of tournament strategy, but once upon a time, that was unheard of.
“Nike had so many athletes, there were many times where you end up wearing the same dress or the same skirt and top as your opponent,” Sharapova said.
That happened to her at Wimbledon in 2006. “There was like, a conscious part of me that said, ‘Oh, if I do well and become a champion, I would love for that to never happen again,’” she said. The difference is that she didn’t say it to herself; she said it to Nike.
Sharapova thinks of that incident as her first boardroom experience. She used to sit in on her contract negotiations because, she said, her father told her that “although you might not be familiar with all the terms, this will set up your financial trajectory for the next 10 years”.
As she talked, Sharapova was sitting in the office of her Los Angeles house, which she shares with her fiancé, Alexander Gilkes, one of the founders of Paddle8, the online auction house, and their son, Theodore, who is 3. Their home is under renovation because they are selling it, the better to split their time between California and Europe to be closer to their families. (Gilkes is English.)
“You do not want to see the boxes,” she said.
Architecture is one of Sharapova’s hobbies. (Before she wanted to be a tennis player, she wanted to be an architect.) She helped design her house. The transition from being very good at one thing to risking being not so good at another is complicated, she said.
“The one thing that you build as an athlete is a lot of confidence, and with confidence, it very easily can turn into ego,” Sharapova said. “Then it becomes really difficult to ask questions and acknowledge that you are not an expert. But you can never lose sight of the fact that something that you are so deeply great at will come to an end, and sometimes that means failing in other things to figure out what else you are passionate about.”
A brief flirtation with designing a collection for Cole Haan in 2009 taught her this. When she told Wintour about it, she said, Wintour raised an eyebrow and told her she’d better be sure about it because “you only get one chance”.
“People questioned whether I had the authority to lean into design in that way,” Sharapova said. “I had the one platform, which was tennis, and it wasn’t clear people thought I could do anything else. But a little competitive voice in me said, ‘Well, let me show you.’ I like leaning into the pressure. If you don’t feel that there’s something on the line, then what are you working toward?”
The scariest choice
When Sharapova was a Tiffany ambassador, she got to meet Frank Gehry, who taught her something about perspective. She recalled that they were talking about a jewellery collaboration he did with the company. “He’s like: ‘You know that Tiffany collection I did? They say they are hearts, but I look at them, and I’m thinking they might be butts.’”
She had started a candy brand, Sugarpova, in 2012, but closed it in 2021. Since then, she has largely focused on being an investor and strategic adviser to companies that sell consumer products, especially in the wellness space. She has a portfolio of 11, including Cofertility, an egg-sharing fertility company; Therabody, the company that makes Theragun massage tools; and Supergoop, the skin-care line.
Of all her post-tennis pursuits, the one that scared her most was joining the Moncler board. “I was really hesitant to take that role,” she said – and not because Moncler is a winter sports brand. “It was very intimidating,” she said. “You’re sitting in a room, navigating a billion-dollar public company in real time. During meetings, there are proper microphones with an interpreter, and in order to speak, you have to press a button. It’s not like: ‘Oh, hey, here’s my thought. I have an opinion.’”
Still, Remo Ruffini, the CEO of Moncler, wanted her for the board precisely because, he said, “the world of luxury has been quite insular for many years”. He thought she could bring the perspective of someone who understands sports culture in general and was not afraid to speak her mind.
It’s the speaking part that may now prove most relevant. It’s what brought her to Davos, where she talked about women’s leadership for CNBC and IBM. “It was like speed dating for business with suits and ties,” she said. (For her that meant a tan Burberry pantsuit, a Tod’s leather trench coat and Tibi trousers, all documented on Instagram, where she has 4.7 million followers.)
It’s also what inspired the dress she asked her friend Gabriela Hearst to design for the Tennis Hall of Fame formal ceremony, which is a white silk gown with a matching cape, like a superhero’s. The dress, Hearst said, reflected the point Sharapova wanted to make in her speech, which she had said was about the superpower of being heard.
She firmly believes that it’s about time everyone recognised that the qualities required to become a Hall of Fame female athlete are pretty much the same qualities required to become a successful chief executive.
“There are a lot of parallels between sport and business,” Sharapova said. “Everything from the competitive nature of an industry to the need to invest your time and, quite honestly, a lot of money in a project you believe in and not see a return for a long time. The effort it takes for any female athlete to get to a professional level and compete for millions of dollars in front of millions of eyeballs is huge, and not enough is said about it.”
She’s going to start talking.
This article originally appeared in The New York Times.
Written by: Vanessa Friedman
Photographs by: Sam Ramirez, Chang W. Lee
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