Play Henry is making sports stylish

When they first met, UVA grads Ellie Jamison and Grace Collins had plenty to bond over: They’d both played lacrosse in college, each of them missed the role competitive sports played in their lives, and they picked up pickleball to fill the void—oh, and they both had brothers named Henry. We’ll get back to the Henry thing later, but Jamison says that, as the women started playing more pickleball together, they noticed a gap in the paddle market.

“Most high-performance paddles felt overly masculine, while the more ‘aesthetic’ options were hyper-feminine and low quality,” Jamison says. “We were shocked that we couldn’t find gear that combined performance with our sense of style.” 

In 2023, they partnered with a professional pickleball player to develop a prototype—a sleek, stylish paddle with practical features for serious players (carbon fiber faces, 16mm honeycomb cores, and elongated handles) in chic colors like Espresso brown (a bestseller and Collins’ go-to) and Butter yellow (Jamison’s pick). The first presale sold out.

The company, which the women named Play Henry after their brothers (“We like to joke that it’s a tribute to our very first ‘competitors,’” Jamison says), launched a custom collaboration paddle with Free People Movement, the national retailer’s activewear arm, in the spring, and its padel racquet collection in July, specifically designed in weight and style for women—one of the only women-focused padel brands available.

In summer of 2025, Play Henry relocated its headquarters to New York City, where Jamison says there’s more opportunity for growth. But with such strong ties to Charlottesville (Jamison is a double Hoo, with degrees from the university’s Frank Batten School of Leadership and Public Policy and Darden School of Business, and Collins graduated from Darden in 2024), Play Henry will always have a home in Virginia. 

“We’re excited to come back for tournaments and continue supporting the amazing local partners who believed in us early on—special shout-out to C’Ville Tennis Pro Shop, Boar’s Head Resort, and Quattro Tizi,” Jamison says. And what about the support of the Henrys? “They absolutely love it. They’re some of our most loyal customers (we’d be worried if they weren’t!).”