Iconic Tennis Outfits: Keys, Pegula, Brady, and Krawczyk revisit the fashion moments that stood out

When it comes to tennis, the drama on court is only part of the story. The outfits players wear have become almost as memorable as the matches themselves, sparking debates, admiration, and even controversy. That’s exactly what happened during a recent episode of The Player’s Box, featuring Desirae Krawczyk, Madison Keys, Jessica Pegula, and Jennifer Brady.

From bold fashion statements to subtle touches of elegance, tennis attire has evolved into a cultural talking point. The four players came together on the new podcast to reflect on the recent US Open, and one of the subjects that stood out most was the iconic outfits worn by their colleagues over the years. Each player revealed which looks made the biggest impression on them—and why.

Their recollections stretched from Serena Williams’ denim skirt and boots at the US Open, to Maria Sharapova’s little black dress, and even to the eccentric, experimental looks of Bethanie Mattek-Sands. Some admitted they hardly pay attention to outfits, while others confessed they were so inspired that they tried to recreate the look themselves at their own local tennis clubs.

As the conversation unfolded, it became clear that fashion in tennis is more than just fabric—it’s memory, identity, and sometimes even intimidation. These were the moments that stood out most.

Madison Keys: Serena’s denim US Open look

Madison Keys didn’t hesitate when asked about the outfits that stuck in her mind. “Historically, the US Open—in my opinion, that’s where you get the iconic outfits,” Keys said. “Like the Serena jeans skirt, the zip-up boots with the jacket. I went out and I bought a Nike denim skirt, and I wore it to practice the next week. I absolutely did. I was still living in Illinois, so I was under 10 years old. I needed that to go to my local tennis club as an eight-year-old. I needed the denim skirt.”

Serena Williams’ 2004 US Open denim look, complete with a studded mini-skirt and knee-high boots, is widely considered one of the boldest statements in tennis fashion. For Keys, it was not just a fashion moment—it was formative. “I can look at almost any outfit and remember the year or the match,” she added. “That’s how I can tell you who did what, who won that year. All of it.”

Keys admitted she even tried to convince her mom to buy the matching boots. “It’s not for sale,” she laughed. “But I definitely tried to make her buy the boots.”