Serena Williams’ Stylist On Her Iconic Looks At The ESPY Awards | Essence

Amid prepping for the whirlwind that was this year’s Met Gala, Serena Williams got the call: she’d be hosting the upcoming ESPY Awards. Produced by ESPN since 1993, the Excellence in Sports Performance Yearly Awards, known by many as the ESPYS, celebrates landmark athletic and philanthropic achievements throughout the calendar year.

Now, Williams’ longtime stylist, Kesha McLeod, would be tasked with dressing the iconic athlete for one of the biggest nights in sports—and arguably, her evolving career. To date, Williams is only the fourth woman and the first Black woman to host the awards show, which the 12-time ESPYS winner called “a dream come true.”

“Working with Serena over maybe the past 12 years,” said McLeod, “We see Serena on red carpets, we see her on the court, and I don’t think people can see who she is. This is who she is, so every look is like a reflection of that.”

Since April, McLeod has been immersed in copious amounts of planning. For the New Jersey-based stylist, her days have consisted of waking up in the wee hours of the morning and getting on calls with designers in Milan, Paris, and Germany to coordinate a cohesive vision. “We built all of these concept mood boards of Serena throughout the years. That alone took a whole week.” Replete with eight outfit changes, the intentionality in McLeod’s styling was evident, from Williams’ red carpet Giorgio Armani gown to Ferragamo, Versace, David Koma, Galia Lahav, and more.

McLeod said, “[There is] history with a lot of these designers. Galia Lahav did her wedding. It was honing into a lot of people that have supported her through the years. Donatella [Versace] did the reception dress for her wedding and has been a huge supporter of Serena all these years. David Koma dressed Serena and Olympia for the ‘King Richard’ premiere, and that was the first time Olympia hit a red carpet.”

Be it FaceTime fittings or WhatsApp calls, open communication is paramount to McLeod’s styling relationship with Williams. Whether it’s the shimmery glamour of the custom fishscale-like Ferragamo gown or the feather-trimmed Galia Lahav minidress, Williams’ humor, charisma, and confidence exuded through her clothing.

From the opening monologue to honoring the Billie Jean King award recipient, every outfit change corresponded with the tone required at each part of the show. Williams wore a playful and somewhat sexy Dolce & Gabbana corset for the Maria Sharapova serenade, which McLeod refers to as “Tennis Ball Two,” a nod to Jamie Foxx serenading Williams at the 2003 ESPYS with “Can I Be Your Tennis Ball?”

McLeod expanded on how she landed on the exquisite numbers from yesterday evening. “We did dress rehearsals listening to the script and looking at that vision. When it came to the corset one, I [wondered] what outfit she could move really well in as she’s standing and doing dances—and I also wanted that back shot. So, having those little key moments is how I looked at the looks.”

While there is familiarity and kinship with those designers, said McLeod, audiences can see the evolution of Williams’ style over time, a testament to the trust she has in herself and her yearslong relationship with McLeod. Dating as far back as 2011, McLeod styled Williams for the ESPYS in a bombshell fuschia Rachel Roy dress. 

The infamous dress, which McLeod previously thought she would get fired for, made the rounds on X (formerly Twitter) during the live show. At the time, McLeod had to speak to multiple members of Williams’ team before finally connecting with her. However, the 23-time Grand Slam women’s singles champion is keenly aware that styling is an interactive team sport. It’s the same glam team, said McLeod, but without the middlemen.

“She wants nobody else to talk for her. She knew exactly what it needed to look like, and she trusted me and held my hand throughout the whole process,” said McLeod. “When she was walking out on stage, I got emotional. For me, it’s watching someone now be affirmed in who they are.”

Building a core team that can meet the moment, one that was equipped to work with greatness was imperative, said McLeod. But most importantly, McLeod said that preparation and creative control contribute to what onlookers see as a “perfectly executed vision.” As the multihyphenate Williams continues to evolve off the tennis court, McLeod hopes to be alongside her on the journey.

“It’s just full circle that I can do what I do, professionally styling the best of the best for 18 years. For her and the clients I have, everybody’s a champion. But to have somebody who is one of one and nobody above her is still such a surreal moment for me,” McLeod added.