There’s something inherently good-natured about pickleball. And when comedians get on the court—like longtime friends and pickleball-fashion fans Matt Walsh, Jessica St. Clair, and June Diane Raphael—things get really playful. In their case, stylish too. Walsh cofounded New York’s famed Upright Citizens Brigade, where St. Clair and Raphael met and honed their improv skills. Their careers have crisscrossed since then, but a shared love of the sport has helped them forge a new connection. Here, the women, who cohost the beloved podcast the Deep Dive, bring their game faces to Walsh’s home court, where the trio don summer’s biggest hits in pickleball wear for next-level looks.

ON JESSICA (LEFT):

Alo shirt, $98; aloyoga.com. Splits59 skirt, $124; splits59.com. Nike sneakers, $75; nike.com. Luxe paddle, $75; luxepickleball.com

ON MATT (CENTER):

ProKennex hat, $25; pickleballsavings.com. Flint Park shirt, $58, and shorts, $68; flint-park.com. New Balance shoes, $120; newbalance.com. ProKennex paddle, $170; prokennex-pickleball.com 

ON JUNE (RIGHT):

Alo jacket, $128; aloyoga.com. P.E Nation dress, $110; us.pe-nation.com. Birdies shoes, $145; birdies.com. Luxe paddle, $78; luxepickleball.com

The cute gear was what really got Jessica St. Clair into the game. “I’m like, If we can get outfits… And some of our friends said they actually drink martinis while playing. This sounds like a sport tailor-made for June and me,” says the actress, who’s in Avenue 5 this fall. The two don’t partner, though: “Our trash talking is so intense you don’t want it coming from the same side.” Not even Walsh is safe. “He did found the theater that gave us our careers,” says St. Clair. “But when it comes to who is going to take pickleball to the Olympics, I’d say June and I have a better shot.”  

ON JUNE:

J.Crew shirt, $55, and bandanna (worn on wrist), $40; jcrew.com. Sunday Best skirt, $88; aritzia.com. Curated Adornments jewelry (stylist’s own)

ON MATT:

ProKennex hat, $25; pickleballsavings.com. Vuori shirt, $69; vuoriclothing.com. Alo shorts, $98; aloyoga.com. APL socks, $60 for three-pack; athleticpropulsionlabs.com. Reebok shoes, $69; reebok.com. Recess paddle (on ground), $86; recesspickleball.com

ON JESSICA:

Outdoor Voices dress, $108; outdoorvoices.com. Birdies shoes, $145; birdies.com. Luxe paddle, $78; luxepickleball.com

For June Diane Raphael, who recently starred in the Netflix series Grace and Frankie, the draw of pickleball was, “first and foremost, the name,” she says. “It just sounds like a good time.” But it was a group text that convinced her and St. Clair to try it. “So many of our friends were becoming obsessed, we felt like we didn’t really have a choice,” she says. Raphael believes it’s the perfect activity for the times we’re in: “We need to get out energy that has truly nowhere to go right now. That’s why I love playing.”

Matt Walsh taped his home court early in the pandemic, but he’s been playing pickleball for several years, since the actor’s Veep co-star, Julia Louis-Dreyfus, introduced him to it (he played Mike McLintock on the show). “That’s the moment I remember, like, Oh, this is so fun,” he says. Walsh’s wife, Morgan, and their three kids play too. “I have yet to be beaten,” says Walsh, whose next role is in Apple TV+’s dramatic series Manhunt. “I’m still the family champ.” 

ON MATT:

Puma hat, $30; puma.com. All in Motion sunglasses, $20; target.com. Swet Tailor shirt, $79; swettailor.com. Outdoor Voices shorts, $68; outdoorvoices.com. Reebok shoes, $69; reebok.com. ProKennex paddle, $170; prokennex-pickleball.com 

ON JUNE:

Stuart Weitzman heels; stuartweitzman.com 

ON JESSICA:

Lacoste sweater, $198; bandier.com. Flint Park shirt, $58; flint-park.com. Stuart Weitzman heels; stuartweitzman.com

STYLING BY ABBY ARAD AND VANESSA POWELL. HAIR BY ADDIE MARKOWITZ FOR EXCLUSIVE ARTISTS MANAGEMENT. MAKEUP BY KATHLEEN KARRIDENE