As excited as I am about Anna Leigh Waters’ Nike apparel deal, I can’t shake the feeling that it marks the end of an era.

Waters signed with FILA early in her career, and the partnership delivered some truly iconic fashion moments on the court.

While there were a few misses along the way, the hits far outweighed them, so let’s revisit some of Waters’ best FILA fits through the years.

The electric color pallet

Waters’ early days with FILA were bold and vibrant. This was the period when she proved she wasn’t just a lucky winner, but a consistent, steady force poised to dominate the sport. Neon pinks, electric blues, striped accents, and even tie-dye defined the era—fitting for a young teenager whose style reflected a sense of youthful playfulness.

Baby polos

When I think of Leigh and Anna Leigh playing pickleball together, these are the outfits that come to mind. The white, red, and pink matching sets were undeniably fun. I’m still not entirely sure why they were wearing what looked like only the top half of a polo shirt. It was certainly experimental, but somehow it worked. They looked like retro pickleball-playing Barbie dolls, in the best possible way.

The brighter, the better

The next era felt like a return to Waters’ roots. With bright neon pink and vibrant blue dominating the color palette, these looks were impossible to miss. It also turned into one of her longest fashion runs. While rich purple shades appeared toward the end, pink remains my personal favorite.

Whataburger 

This was one of my favorite moments in pro pickleball fashion, but not because of the outfit itself. Honestly, the pattern on the shorts was pretty atrocious. But after @memesofpickleball compared the look to Whataburger, Waters didn’t take offense. Instead, she leaned into it and did a photoshoot at a Whataburger. Iconic.

Magnifying mesh

This mesh skirt moment was everything. The black biker shorts paired with a mesh skirt overlay offered an edgier take on Waters’ previously playful styles, while still feeling age-appropriate. Styled with tie-dye, it was a fun yet fashion-forward look for the World No. 1.

Peachy keen

This look is famously remembered on pickleball meme pages as the “SpongeBob and Patrick” outfit, but honestly, I don’t hate it. The pastels were a refreshing change after so many bold pinks and purples.

Gray, gray, go away

I’ll admit it, I’m biased, but the gray looks just weren’t my favorite. I’ve never been a fan of gray, and the swirling line down the torso felt neither pretty nor sophisticated. The muted palette did nothing for me, and I was more than happy to see this look retired. 

Retro racket sports

I think my favorite FILA fits were this 2024 lineup, which came in navy, cream, and pink. There’s something irresistibly charming about the subtle collar detail on the top, paired with the matching two-tiered pleated skirt. I wanted this in my own pickleball wardrobe so badly.

Beautiful burgundy and orange

I absolutely loved the burgundy and orange kit she wore at a few tournaments in 2025. It quickly became one of my favorites. The colors were stunning, and the fit was incredibly flattering on her.

An unlikely pair: Purple and yellow

For her final FILA look, Waters sported a lavender-based kit, alternating with white and yellow. I found the purple and yellow pairing to be a fun, unexpected combination—probably wouldn’t work off the court, but on the court, it was genuinely charming. To me, the colors felt like a nod to Waters’ early bold and playful looks, but with a more sophisticated twist thanks to the softer tones.

Of course, all good things must come to an end, and personally, I’m beyond excited to see what Waters’ Nike era will bring.

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