SI LifeStyle

Inside Maddy Westbeld’s Signature Style: Confident, Comfortable and Unapologetic

The Chicago Sky rookie and her stylist weigh in on what has made creating tunnel looks this season so special.

Ananya Panchal

Maddy Westbeld
Maddy Westbeld / Erica Denhoff/Getty Images

In just her first WNBA season, Chicago Sky forward Maddy Westbeld has made one thing clear: she’s here to show up, both on the court and in the tunnel.

The 23-year-old rookie has quickly emerged as a fashion standout, pairing crisp tailoring with curve-hugging knits, body chains and statement accessories that are turning heads across the league.

Maddy Westbeld
Maddy Westbeld / Gary Dineen/Getty Images

Her looks feel confident and curated, often rooted in a refined, minimalist palette with playful, eye-catching twists. And that intentionality is no accident.

“Right now, my personal style is definitely classy and chic with a little high fashion sprinkled in,” Westbeld tells SI Swimsuit. “I don’t have a dress code anymore, so I can be a little more edgy with my style while still keeping it classy.”

How it started: Westbeld’s fashion journey

Maddy Westbeld
Maddy Westbeld / Courtesy of Chicago Sky

Westbeld’s style evolution began long before her WNBA debut. After undergoing surgery at the end of her Notre Dame career, fashion became more than just self-expression—it was a tool for healing.

“It definitely helped me stay confident through my injury and allowed me to find a passion that was outside of basketball, especially to keep me occupied throughout my rehab,” she explains.

It wasn’t long before game day outfits turned into a creative outlet and a confidence boost. She developed a sharp eye for proportion, gravitating toward wide-leg trousers, cropped silhouettes, sleek belts and pointed-toe heels. Her signature curls and radiant glam always complete the look.

Maddy Westbeld
Maddy Westbeld / Jeff Haynes/Getty Images

That foundation continues to shape her WNBA tunnel moments, where every outfit blends power, polish and personality.

Tunnel game: a collaborative process

Westbeld doesn’t go it alone. She partners with stylist and brand consultant Desiree Olavarrieta to plan and refine her looks. Each time they meet in person, the duo builds out multiple outfits for upcoming games.

“It gives us the opportunity to pick the outfits out beforehand, depending on how I’m feeling on that particular game day,” Westbeld says. “If I happen to go shopping on my own, I’ll FaceTime her and always get her feedback on things that I put together myself.”

For Olavarrieta, their work is about more than clothes—it’s about authenticity and storytelling: “Tunnel fits are where we get to play. We use that space to really push the envelope.”

But even with that creative freedom, she says, “Maddy has such a grounded presence, so it’s important that whatever she wears doesn’t feel like a costume—it has to reflect her energy. Confidence is key, but comfort is non-negotiable. If she’s not feeling it, it’s not happening.”

The two first connected at Notre Dame, and now, watching Westbeld grow into herself as a rookie has felt “full circle.”

Maddy Westbeld
Maddy Westbeld / Gary Dineen/Getty Images

“Honestly, the best part is how much Maddy cares,” she shares. “She’s passionate about fashion in a way that makes my job easy—we’re constantly sending each other inspo, bouncing ideas, and nine times out of ten, we’re already thinking the same thing. We just get each other. It’s not forced, it’s fun. There’s something really rewarding about building from the ground up with someone you believe in, both on and off the court.”

Finding inspo

Westbeld doesn’t necessarily chase trends, but she draws inspiration from Instagram, Pinterest and online fashion sites, screenshotting looks with her stylist that align with her staples and silhouette.

That intentionality shows in everything from her go-to brands—Revolve, Aritzia, Ryoko Rain—to her thoughtful accessorizing. She leans into comfort and consistency on travel days (Alo, Essentials), but isn’t afraid to take a risk when the moment calls for it.

Westbeld is also influenced by some of the WNBA’s most stylish players. “Skylar [Diggins-Smith] has always been an inspiration of mine because of how powerful and unapologetic she is in every facet,” she says. “Fashion [has] little to do with the clothes and fabric on your back, but it mostly has to do with the aura you bring to the table. Tiffany Hayes, Rickea Jackson and, of course, my teammate Angel [Reese] are just a few [who] are the epitome of aura.”

Maddy Westbeld
Maddy Westbeld / David Sherman/Getty Images

That energy resonates across the league. “We are able to see the benefits of our athletes who have refused to be limited by just their sport, especially in fashion and beauty,” Westbeld notes. “So many W players are into these spaces naturally. You can say we are walking billboard[s], and many powerful women are the hot commodity right now. The W is the perfect hub.”

Olavarrieta agrees the rise of WNBA fashion is long overdue—and says watching it unfold in real time has been both exciting and meaningful. “It’s been amazing to watch—and even more powerful to be part of,” she shares.

While players have always had style, she explains, they’re finally being seen for it. The tunnel is somewhat of a runway, but it has also become a platform for self-expression and brand building.

This shift, she notes, is reshaping more than just sports fashion. “It’s not about fitting into a mold—it’s about breaking them,” Olavarrieta adds.

With each pregame look, athletes are challenging expectations and redefining how female athletes are perceived—“not just as competitors,” she says, “but as cultural leaders.”

More Maddy Westbeld:

manual

Published
Home/Fashion & Beauty