That mindset makes Diggins-Smith a perfect creative partner for a stylist like Jay. “She understands how fashion can elevate you into a lot of other spaces,” he says of his client. Both are competitive in their fields, always wanting to raise the bar with no concept of a ceiling. “I’m not competing necessarily with others, but I’m always competing with myself,” he says. “We both have this competitive nature of, How do we perform to the best of our ability? And, How do we outdo our last performance?” As a result of their partnership, Diggins-Smith’s tunnel ‘fits have never been more impressive, specifically in the debut season of Unrivaled—a new three-on-three league based in Miami founded by her teammate Napheesa Collier and the New York Liberty and Mist basketball club’s Breanna Stewart.

Playing in a brand-new league offered the duo a chance to experiment with fashion and flex their creativity ahead of the 2025 WNBA season, which is expected to be one of the W’s biggest and most high-profile in its 28-year lifetime. Together, they decided to utilize a styling technique Jay learned from Law Roach known as method styling to play with Diggins-Smith’s Unrivaled team name and incorporate it into her tunnel ‘fits throughout its inaugural season. “When you’re given something like a mascot or a movie premiere, and you get a theme, it’s fun to dress within that world,” Jay says. “I wanted to take that into the tunnel with Skylar.”

Her first look in Unrivaled was by AnOnlyChild: a brown, tailored suit with bold shoulders reminiscent of an owl’s wings. “We’ve been trying to incorporate looks that feel and look like nature,” Jay says, alluding to colors like green and brown. “The Lapointe look—the green one with fur on the sleeves—that was also very owl-esque [with] wings,” he continues. “The details are subtle,” adds Diggins-Smith, “but intentional, like owl-shaped jewelry or patterns that hint at feathers.” For her, creating this character and building meaning into her looks for Unrivaled connected her to her team and created a better on-court product. “The owl theme is all about wisdom, intuition, and vision—three things that resonate deeply with me both on and off the court,” she says. “It was our way of adding depth that goes beyond aesthetics. It’s about foresight and staying ahead of the game.”

Throughout this season, Diggins-Smith has also showcased a number of rare designer handbags by the likes of Chanel and Louis Vuitton. “We were blessed to work with What Goes Around Comes Around for [Skylar’s] bags going down the tunnel, and I know the relationship is going to continue,” Jay says. When he told a former co-worker at Patricia Field named Barbie Beach—now a marketing, events, and public relations manager at WGACA—that he was working with Diggins-Smith and was interested in collaborating with the luxury consignment retailer, she immediately said yes. “I’m happy that we get to work with historic bags—bags that have a story,” Jay says. “They just add more to Skylar’s fashion story.”

Soon, Unrivaled—and its Sephora-branded tunnel—will be in its players’ rearview mirrors. No matter who takes home its first-ever championship trophy, the league’s debut season will come to a close tonight. Fortunately, fans of professional women’s basketball don’t have long to wait for what many consider the main event to begin, with the 2025 WNBA Draft taking place on April 14, followed by training camp and WNBA Tip-Off 2025 on May 16 and 17. This season is set to break records in every possible way, and with so much media coverage to come, it makes sense that Diggins-Smith and Jay would want to continue elevating their partnership and the tunnel ‘fits that come from it.

Though he’s proud of the looks they put together for Unrivaled, styling for the novel league wasn’t without its challenges. “There were some moments we couldn’t necessarily make happen yet,” Jay says, alluding to Unrivaled’s newness causing some unwillingness from brands to send looks. It’s a whole new ball game in the W. “You can expect for her to be in a lot of editorial looks,” says Jay of Diggins-Smith’s early WNBA tunnel ‘fits next season. “With the W, more brands will be receptive to wanting to loan to her because of the notoriety [it] has. We will be able to showcase more different designers on Skylar—more custom looks.” There’s even a bespoke Off-White ensemble in the works, though the date and occasion for its big entrance remains to be seen.

“We’ve already started brainstorming,” Diggins-Smith says. “It’s about keeping things fresh, staying unpredictable, and continuing to layer meaning into every look.” Fashion is an extension of Diggins-Smith’s identity and a way for her to communicate with her fans without words. “[They] get to see who we are beyond the jersey—beyond the game,” she says. “It’s a glimpse into our personality. We’re multidimensional, not just athletes.” She knows that her looks can make an impact—from introducing the game to new audiences to showing young, up-and-coming female athletes that there’s nothing wrong with expressing themselves in personal and authentic ways—especially when she and Jay are intentional about them. “Stay tuned,” Diggins-Smith tells me. “It’s going to be something special.”

The best stylist-client relationships are built on the understanding that fashion isn’t the trivial concept society likes to make it out to be. There is much more to a good outfit than one piece paired with another, whether the resulting ensemble will be seen by millions on Instagram or just a few close friends or family members. Jay knows that all too well. “Immediately after I graduated [high school], when I was 19 years old, I was diagnosed with leukemia,” he tells me. “I did chemotherapy and went into remission and was in remission for 10 years.” It was during that decade that Jay began styling. “Styling was one of the tools that kept me alive because I always hung on to the thought of the future and what I wanted to be and what I wanted to do,” he says. “Fashion has been a big part of how I was able to survive.”

Soon, Jay will be in charge of styling one of the WNBA’s most elite dressers, thus shining a much-deserved spotlight on the impressive résumé he’s been building for more than 20 years. And this is only the beginning. In 2025, the WNBA is expanding from 12 to 13 teams and adding an additional four games to its regular season. Twenty twenty-six will introduce the league’s monumental new $2.2 billion media-rights deal, two more franchises, and an entirely renegotiated collective bargaining agreement that’s expected to significantly increase player salaries and benefits. Everything about the league is growing, and together, Jay and Diggins-Smith possess every necessary trait to match that growth with their future looks. “We are trying to go to the next level each time we show up,” Jay says of his partnership with Diggins-Smith. “I’ve said ‘elevate’ so many times, but that really is the vibe.”