As stylish as they may be, many of today’s best-dressed athletes did not earn that designation on their own. Those incredible tunnel fits? The street style looks that inspire our online shopping sprees? The breathtaking, bespoke looks worn by a select few as they ascend the Met Gala steps on the first Monday in May? A cadre of stylists who specialize in dressing athletes is often responsible for making that magic happen.
With more and more athletes weaving fashion into their personal brands—and labels clamoring to dress them—these stylists’ work is becoming increasingly visible. What’s less visible, however, are the journeys they took to build their careers, the art and fashion that inspires them, and their own approaches to personal style. In their own words, Sydney Bordonaro, Brittany Hampton, Courtney Mays, Kesha McLeod, and Dex Robinson tell us just that.
Sydney Bordonaro
Hometown: Pittsburgh, Pennsylvania
The roster of athletes I’ve styled—past and present—includes: Tarik Black, Cameron Brink, Rae Burrell, Kahleah Copper, Chelsea Gray, Isabelle Harrison, Tobin Heath, Tyler Herro, Natisha Hiedeman, Hannah Hidalgo, Deja Kelly, Jewell Loyd, Marina Mabrey, Skyy Moore, Kelsey Plum, Christen Press, Didi Richards, Trinity Rodman, Jaedyn Shaw, Jaxon Smith-Njigba, Hailey Van Lith, Courtney Williams, Grant Williams, and many, many others. I’d say close to 100 over the last five years.
My first job in fashion was: In August 2021, when Jewell Loyd asked me to style her for her pregame tunnel walks. This was before WNBA fits started to really pop off. I played Division I basketball at Pepperdine and Long Beach State University and got my master’s in sports management because I wanted to be a sports agent. Covid derailed my first job as an agent assistant in May 2020. After moving back to LA, Jewell randomly hit me up, and I fell into styling athletes. It’s been the most unexpected blessing.
I got my big break: In May 2023, doing a global Google Pixel campaign with Napheesa Collier, Kahleah Copper, Dearica Hamby, Isabelle Harrison, Arike Ogunbowale, Kelsey Plum, and Didi Richards. Not only was it my first major commercial, but it was my first actual production. Prior to that, I had only styled pregame tunnel walks. I learned more on set over those three weeks than I did in the previous year and a half of styling. I’m eternally grateful for that opportunity—it changed my life.
I learned style from: My nana, my mom, and Allen Iverson.
The first artist who resonated with me was: Allen Iverson—an artist with a basketball.
My style GOAT is: Teyana Taylor—forever and always!
Two incredibly dressed athletes (who I don’t work with): Jordan Clarkson and Olivia Miles.
My take on the best tunnel fits: Angel Reese has been eating since her rookie season. Every single fit is a hitter. A lot of respect to her and her team. If we’re talking all-time, you have to mention Russell Westbrook’s name also. I think he’s one of the first guys to really get it poppin’ in the mid-2010s and to bring that style back from the Iverson days.
You’ll catch me cheering for: Pittsburgh Steelers or any team LeBron or my clients are on.
When I win the lotto, I’m buying: A home in the Hollywood Hills.
Courtney Mays
Hometown: Cleveland, Ohio
The roster of athletes I’ve styled—past and present—includes: Mookie Betts, Sue Bird, Tina Charles, Steph Curry, Brittney Griner, LeBron James, Jonquel Jones, DeAndre Jordan, Kevin Love, Baker Mayfield, Chris Paul, Megan Rapinoe, Breanna Stewart, Diana Taurasi, Karl-Anthony Towns, Russell Westbrook… I could keep going!
My first job in fashion was: At a local boutique in my hometown. A family friend owned an accessories store called Details, where I worked on the sales floor while also assisting with buying trips and with visual merchandising. I was only 15 or 16 years old, but I was completely captivated. It was my first real glimpse into the fashion world that I had always dreamed of, and it confirmed that fashion wasn’t just an interest but an art form and a means of storytelling where I wanted to thrive.
I got my big break: Every project is a big break, as it always gives way to other opportunities and adventures. But I would say that moving to New York was my first big break! New York was a true kaleidoscope of inspiration, and it allowed me to nurture my love of fashion. It was risky and challenging, but it was the engine that got me here.
I learned style from: My parents have always been my greatest style inspirations. My mom embodies effortless elegance—her wardrobe is timeless, thoughtful, and every bit as beautifully curated as the interiors she created in our homes growing up. My dad is the definition of classic sophistication, never without his silk tie, a beautiful watch, and a perfectly tailored double-breasted suit. Together, they taught me that true style is less about following trends and more about expressing yourself with intention, confidence, and attention to detail.
The first artists who resonated with me were: The members of the funk band Cameo. When I was 8 years old, my dad took me to our local record store for an album signing. As an adult, my longtime client Kevin Love introduced me to Rashid Johnson—an artist I had admired for so long. Then my friend and colleague Lindsay Kagawa Colas connected me with Mickalene Thomas. These are the people I am most excited about. Artists are my version of celebrity.
My style GOATS are: A splash of Jenna Lyons and Tracee Ellis Ross mixed with Willy Chavarria, Solange, and Jeff Goldblum.
Three incredibly dressed athletes (who I don’t work with): Tyrod Taylor, Dwight Powell, and Ashlyn Harris.
The best tunnel fits: Are authentic and fit well. I’m impressed by athletes who embrace their authentic sense of style and have a true understanding of their size and proportions rather than trying to create viral moments. Honestly, my favorite tunnel look photos are captured as teams are heading onto or off of team buses or exiting hotel lobbies. Something about the light and street style element always feels elevated. And any photo by Jim Poorten!
Always on my playlist: Miles Davis.
I could win a gold medal in: Taboo or Heads Up, as long as my partner, Candice, is on my team. And I’m the vibesetter: the playlist, the lighting, the charcuterie board—I got you!
You’ll catch me cheering for: In the words of the oracle Ms. Issa Rae,“I’m rooting for everybody Black.” Black women doing anything, actually, but especially all of us in the sports community. There is such a vast community of women who truly move the needle in the business on and off the court. They are the inspiration and the voice of many leagues.
Brittany Hampton
Hometown: San Francisco, California
The roster of athletes I’ve styled—past and present—includes: Cameron Brink, Paige Bueckers, Sabrina Ionescu, Cee Dee Lamb, Evan Mobley, Nika Mühl, Koa Peat, Kelsey Plum, Sloane Stephens, Nigel Sylvester, and Russell Westbrook.
My first job in fashion was: I had my first two jobs in fashion at the same time. I was a junior agent at Ford Models while simultaneously becoming the in-house stylist at Nickelodeon.
I got my big break: Winning House of DVF. It opened doors, but the career I’ve built since has come from years of consistency, meaningful relationships, and always showing up.
I learned style from: The women in my family. My grandmother was a fashion designer, so I’ve always paid attention to how people tell stories through what they wear—building a brand without saying a word.
The first artist who resonated with me was: Diane von Furstenberg. I did my college entry project on her and later had the opportunity to work for her. I’ve always admired her work ethic and the way she embraces every type of woman through her brand.
The best tunnel fits: Tell a story that reflects a player’s true personality. We see athletes in uniform most of the time, so the tunnel is a chance for them to express who they are beyond the game. It gives fans a glimpse into their individuality before they ever step onto the court.
Right now I’m wearing: A cropped tee, a full-zip hoodie, tailored trousers, a Goyard shawl, Nike Moon sneakers, and rings stacked on both hands. I’m en route to Ibiza and I like to travel comfortably, with plenty of layers.
I could win a gold medal in: The details. It’s always about the details.
You’ll catch me cheering for: The Golden State Valkyries and the Golden State Warriors.
When I win the lotto, I’m buying: A work of art by Kara Walker and a home in Sausalito, California.
Kesha McLeod
Hometown: Queens, New York
The roster of athletes I’ve styled—past and present—includes: Jonquel Jones, Deebo Samuel, P.J. Tucker, Serena Williams, Venus Williams, and elite talent across sports and entertainment.
My first job in fashion was: Working at Mony’s and Pulse in Green Acres Mall. It taught me that fashion is just as much about people as it is about clothes.
I got my big break: My career has been built through a series of opportunities, but one of the first pivotal moments was working with stylist Rachel Johnson on projects for her client LeBron James. It gave me a firsthand look at the level of excellence, precision, and professionalism the industry requires.
I learned style from: My cousins. They introduced me to brands like Iceberg, Girbaud, and whatever was next before I even knew what fashion was. Watching them taught me that style wasn’t about labels. It was about confidence, individuality, and wearing the clothes instead of letting the clothes wear you.
The first artist who resonated with me was: Pharrell Williams. I met him at The Neptunes Present… Clones album release at Tower Records, and from that moment, I was hooked on the intersection of music, style, and culture!
My style GOAT is: I honestly can’t pick just one. My clients become my muses, and some of them are the actual GOATs in their sports. Being able to study how they move through the world continues to shape how I think about style.
My personal wardrobe MVPs are: A double-breasted blazer, a pair of Nike Vomeros, and a great pair of black trousers. I feel like I can conquer the world, be comfortable, and still mean business.
The best tunnel fits: Are authentic. You can always tell when someone is wearing the clothes versus when the clothes are wearing them.
Two incredibly dressed athletes (who I don’t work with): Stefon Diggs and Shai Gilgeous-Alexander.
Right now I’m wearing: A Velour Garments sweatsuit and a sports bra. That’s my off-duty uniform. If I’m not running around for work, you’ll probably find me in the winter or summer version of this every day.
I could win a gold medal in: Persistence. I’ll figure it out, one way or another.
You’ll catch me cheering for: New York Knicks. Hometown heroes.
Always on my playlist: N.E.R.D. Whether I need energy or I’m winding down, they’re always in rotation.
Courtside or box seats?: Courtside if I’m client-facing. Box seats if I’m actually trying to get work done.
Bed at 9 p.m. or dinner at 9 p.m.?: Bed at 9 p.m. My phone goes on Do Not Disturb at 8:45 p.m., and everybody who knows me knows not to expect a reply after that.
When I win the lotto, I’m buying: A commissioned coffee table by Rashid Johnson for my open-to-nature home in upstate New York or Connecticut.
Dex Robinson
Hometown: Richmond, Virginia. Richmond taught me how to make a way out of no way—and how to find beauty where other people might miss it. It’s where I learned that style isn’t about labels; it’s about identity, confidence, and community. Richmond gave me my eye long before fashion did.
The roster of athletes I’ve styled—past and present—includes: Mikal Bridges, Jaylen Brown, Justin Fields, Tim Hardaway Jr., Jalen Hurts, Khalil Mack, DK Metcalf, Nigel Sylvester, Tyrod Taylor, PJ Washington, and many others across the NFL, NBA, and beyond.
My first job in fashion was: A designer menswear sales intern at Nordstrom. I learned merchandising, fittings, and, most importantly, how clothes move on real people.
I got my big break: By earning people’s trust. Every opportunity—from athletes to Nike and Jordan Brand—came because someone believed I could tell their story with intention.
I learned style from: My family first. I grew up around people who understood that how you presented yourself mattered, even if you didn’t have much. My grandmother especially taught me the basics: leave the house clean, neat, and matching, and learn how to make something out of whatever you have. From there, I kept learning by watching Black people get dressed—at church, family functions, barbershops, and on my HBCU campus. The culture has always been my greatest fashion school.
The first artist who resonated with me was: Lenny Kravitz. He made rock-star ease feel elegant, masculine, and completely his own.
My style GOAT is: Pharrell Williams. He’s never just worn clothes—he builds worlds. Seeing that kind of creative range from another Virginia kid made it feel possible for me, too.
My personal wardrobe MVPs are: Boots, a great bag, and a great pair of denim.
Two incredibly dressed athletes (who I don’t work with): Nickeil Alexander-Walker and Tyrese Haliburton.
The best tunnel fits: Feel timeless but still show range. They don’t feel like costumes—they feel like an extension of the person wearing them.
Right now I’m wearing: Diallo, of course—pieces that feel intentional, lived-in, and quietly confident.
I could win a gold medal in: Layering. Two tops, maybe three—and somehow it still looks effortless.
You’ll catch me cheering for : Is this a real question? Knicks in five.
Courtside or box seats?: Courtside. The energy is better—and if the fit can’t be seen, what are we doing?
Bed at 9 p.m. or dinner at 9 p.m.?: Dinner at 9 p.m. Always.
When I win the lotto, I’m buying: A work by Barkley L. Hendricks and a home in London. No hesitations.
More of our favorite stories from CULTURED
The Author of One of Mark Zuckerberg’s First Profiles Critiques ‘The Social Reckoning’
It’s Hard to Get People to Look at Art. Will They Listen to It Instead?
WNBA Star Paige Bueckers and Artist Sadie Barnette on Why So Many Artists Love Basketball
One Prominent Writer Tells Us How She Really Affords the Freelance Grind
All of New York’s Best Wellness Treatments (and Their At-Home Dupes)
Sign up for our newsletter here to get these stories direct to your inbox.
in your life?
