strategist investigates
By Chloe Anello
Photo-Illustration: The Strategist; Photos: Retailers, Getty
If you actually play tennis, it can be disorienting to see (and see and see and see) the dresses you wear on court worn by so many fashion people. Brother Vellies’s Aurora James called herself a “tennis girly” in a July 2023 interview with Vogue. Photographer and Gallery Girls alum Angela Pham posts herself in weekly tennis outfits, like a white scalloped dress from high-end label Marysia, which has increasingly adapted its signature swimsuit styles for racquet sports. Many megainfluencers, like Aimee Song and Tasha Franken, can be seen lightheartedly practicing their forehands on social media. And, of course, numerous models (and brands) have taken tennis courts by storm for photo shoots. In the words of East Hampton–based tennis coach Justine Rusk: “You never know who’s a tennis player now.”
Given the resurgence of preppy Y2K-era clothes à la Gossip Girl, as well as the nonstop rise of more contemporary athleisure styles like the ubiquitous Outdoor Voices Exercise Dress, people everywhere are dressing themselves like they’re ready to hit the court. But tenniscore has not been wasted on actual tennis players. “I do find myself walking around, running errands, and having brunch in my tennis clothes,” says Lisa Bonder Kerkorian, a former professional tennis player with a career-high ranking of nine when she was on tour in the ’80s. Susan Bloch, a former runway model in the ’70s and ’80s and lifelong devotee of the sport, agrees: “Put on a pair of sandals, and you look perfectly fine to go out to lunch.”
It wasn’t always this way. Although the tennis dresses of the moment may look and feel nice, they’re a relatively new phenomenon. Back in Chris Evert’s day, when she was competing in expertly tailored and fancifully detailed looks like the lace dress she wore to her 1971 U.S. Open match against Billie Jean King, high style came with the price of torturous fabrics. Designer Ted Tinling, who helped Evert achieve her icon status, favored ultrafeminine dresses that often relied on “polyester and sequins and just really heavy material,” says former professional player and current ESPN pundit Alexandra Stevenson. Kerkorian recalls those dresses being “soaking wet and stretched out down to the knees because of the weight of the sweat holding them down.”
Materials got more innovative over the subsequent decades — even the classic Lacoste polo dress became more breathable — but tennis fashion didn’t really feel exciting again until Serena Williams took over the scene in statement pieces like the sheer black Nike dress she paired with high black Nike Shox boots for the 2004 U.S. Open. And even then, Williams “pushed the envelope and went outside the norm” with her tennis attire, says Traci Green, head coach for Harvard’s women’s tennis, making Williams the exception rather than the rule. Players on and off the pro circuit were usually limited to uniform scoop-neck designs by the major sport brands like Nike and Adidas. So yes, by the early aughts, these dresses were refreshingly lightweight and moisture-wicking but also not anything one would think to wear beyond the baseline.
Then came the pandemic. The United States Tennis Association estimated in January of this year that tennis — a sport that inherently requires more than six feet of social distancing between opponents — has grown by 33 percent since 2020, and by over 1 million players from 2022. (See also: pickleball.) Seizing the opportunity, workout and athleisure brands big and small are now giving us the latest iteration of the tennis dress — a best-of-both-worlds version, marrying the Evert-Tinling level of style with Nike-caliber comfort and technology.
One such brand is Outdoor Voices: In addition to the cult-y exercise dress it first launched in 2018 (one that Strategist editor Maxine Builder admits to wearing as much in everyday life as she does to workouts, including tennis), it has started featuring more and more tennis-specific pieces — including the Warmup Dress and Doubles Dress. Ditto Vuori, Lululemon, and Alo Yoga, which Rusk thinks are “almost, almost to the same level as Nike or Adidas” in terms of functionality when you’re diving for that drop shot.
Girlfriend Collective, the body-positive, size-inclusive counterpart to OV, has debuted a one-shoulder tennis dress that Strategist contributing editor Jessica Silvester, who’s also a competitive USTA player, has worn for both matches and for dinner at Tavern on the Green. Free People, after signing professional player Sloane Stephens to its Movement line, launched tennis dresses that fit in with the brand’s breezy daytime pieces. Non-athletic, prep-inspired brand Recreational Habits has launched its own sleek one-shoulder tennis dress, which is reminiscent of its non-sport styles (but now made for an actual sport). Z Supply, another label formerly known for its ready-to-wear rather than activewear, is offering an overhead-ready pleated dress these days as well. (Key to many of these styles’ success, it should be said, are the supportive shelf bras and built-in shorts that securely hold tennis balls.)
As for the latest looks that more directly reference the Lacoste aesthetic —or those that at least include a collar —Italian label Donna Sport offers a collared dress that it has marketed both for the court and co*cktails. New York City–based brand Michi, which was founded in 2010 to “solve the problem of unflattering and uncomfortable sportswear,” has taken a modern high-neck approach. And in the V-neck department, Jupp Sport, created by tennis coach and former junior-tour player Maddie Jupp, released a vintage-inspired tennis dress that is straight out of the ’70s. Finally, in yet another show of the tennis dress marrying old with new, at this year’s U.S. Open, Jessica Pegula debuted an Adidas dress in “Billie Jean blue,” inspired by Billie Jean King. Of course, it’s also available in a version you can buy online — just like the other dresses below that are equipped for baselining and brunching alike.
Some Tennis Dresses to Buy
Lululemon came up the most — specifically this dress, which is now pretty much sold out, speaking to just how popular it is. Recommended by Virginia Thornton, founder of Black Girls Tennis Club, the dress features an asymmetrical hem, similar to Pegula’s Adidas dress, that seemed to be favored among the women consulted because it has a bit more visual interest to it than a straight skirt. And the fabric is dreamy to play in.“Technology is so much more superior now. You pick up a dress and it weighs nothing,” says Stevenson of some Lululemon garments, adding that she wears Lululemon nearly every day when coaching.
The skirt also features built-in shorts, which actually caused some controversy among the experts. On one hand, the shorts make getting dressed even easier, and they’re always the proper length. However, going to the bathroom can be trickier, and the shorts underneath might not fit properly — they can be far too tight or include elements like elastic on the shorts band, which Stevenson particularly hates. (She says she rolls up the shorts underneath to avoid the sticky feeling of the elastic on her legs.)
Because it is almost sold out, these two are similar options, just with a few different details, like a split neckline, sheer bodice, and open back.
$128
The most modern iteration of the classic Lacoste polo, this Lululemon dress looks overtly preppy yet it has the updated materials players today crave.
$118
Or, if you prefer to look a little more 21st century while still giving a nod to the designs of the past.
$100
Both Rusk and Green say neon colors are popular — which Green thinks could be thanks to the lasting influence of Rafael Nadal — have been huge on the court. Neither of them recommended this specific dress, but it still emulates that trend and features similar elements other experts love: a fun back, flouncy skirt, and built-in shorts with a pocket.
“I see some of the teenagers coming on with, like, the tiniest thing you’ve ever seen. I don’t know; I feel like that’s a generational thing,” says Rusk. While she can’t say for sure it’s always this dress the teens wear, for anyone who does want a particularly skimpy tennis dress, look no further. It has built-in shorts with a pocket, plus it comes in five bright colors, which, again, is something Green says she’s seen a lot of recently with younger players.
$148
“Free People has a great selection of tennis dresses that appear pretty minimal from the front but have cute and surprising cutouts in the back — you know, business in the front, party in the back,” says Thornton, who predicts we’ll hear more about this brand within tennis circles, especially now with Stephens on board. This also comes with built-in shorts and a flouncy skirt that moves well with the body.
$139
Bloch heads to Athleta for longer skirts. As a six-foot-tall woman, she prefers something with a little more coverage than, say, the Alo Yoga dresses mentioned earlier. The dresses sometimes come in tall — although there are none available at the time of publication — which sets them apart. This one is relatively traditional-looking yet it features pockets and adequate ventilation, thanks to mesh inserts, making it merciful for hot weather.
$125
As a more simplistic dress that won’t cling too tightly to your body, sustainable tennis brand J Game — also an up-and-comer in the tenniswear world, founded by an NYC-based USTA player just a couple of years ago — created this timeless piece that comes in navy, black, and a blue crocodile print. It has nothing built in, so you can pair it with your own sports bra and shorts if you please.
$449
The aforementioned Marysia dress seen on Pham (and other influencers, for what it’s worth). The scalloped hem on the neckline and skirt look exceptionally delicate and reminiscent of something Evert might’ve worn back in the day — only with updated fabrics, of course. Marysia also makes a high-neck, V-neck, and boatneck version of the same dress.
$259
For those craving the vintage-aesthetic, Jupp Sport gives us the full pleated skirt that few brands do today. It could be mistaken as Tory Sport, which Rusk says she has yet to see worn in action on the court. But in this case, it was created by an actual tennis player with the sport in mind.
$230
And finally, if you really just want Lacoste, we like this updated stretch-twill take on the dress in collaboration with Sporty & Rich, a lifestyle brand headed by Emily Oberg. It’s significantly pricier than Alo or Lululemon, but you get the brand name and iconic association.
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