Maddy Westbeld Brings Fall ’Fit With ’90s Twist to WNBA Playoffs

The Chicago Sky player traveled to Phoenix to support her sister, Kathryn, who is headed to the finals with the Mercury.

Maddy Westbeld / David Berding/Getty Images

Chicago Sky rookie Maddy Westbeld may be making waves with her game-day tunnel looks, but even when she’s not suiting up, the 23-year-old knows how to serve. Over the weekend, she stepped out in Phoenix to support her sister, Mercury forward Kathryn Westbeld, during a nail-biting semifinal game—and brought a whole autumn vibe to the arena.

From the courtside seats to her confident fit, the fashion-forward rookie reminded fans that style and sisterhood go hand in hand.

Styling

Maddy Westbeld / Christian Petersen/Getty Images

Westbeld’s outfit was a masterclass in laid-back luxury with a fun, flirty ’90s twist. She wore a fitted sleeveless, cropped turtleneck with a dramatic upside-down V hemline that showed off her sculpted abs—simple, but statement-making. On the bottom, she opted for ultra-trendy gray-tan barrel jeans, paired with dark brown flip-flop kitten heels that added just the right amount of edge.

Her natural curls were styled in a playful half-pony with face-framing pieces loose in the front, creating a look that felt effortlessly nostalgic. The Notre Dame alum kept her accessories minimal but effective: a delicate necklace, silver rings and bracelets elevated the vibe without overpowering it.

Sister goals

Of course, the best accessory of the night was her courtside energy. Westbeld flashed her signature dimpled smile as she cheered on her older sister, who helped lead the Mercury to a clutch 86–81 victory over the Lynx and into the 2025 WNBA Finals.

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“My sister is my best friend; her story is really inspiring and I have a front row seat. I’ve watched it closely and have observed her character throughout her journey.” the Ohio native told SI Swimsuit earlier this summer. “The respect level of our relationship has only grown, especially since both of us are playing in the W now. We’re six years apart, she is and always will be my greatest role model. I’m just her biggest fan in everything that she does.”

Maddy has often spoken about the respect and admiration she holds for Kathryn. The two have made headlines this season not just for sharing a last name, but for showing the power of sisterhood in sports.

Maddy Westbeld / Gary Dineen/Getty Images

More than a fan

By showing up for her sister and celebrating the league beyond her own team’s season, Westbeld continues to affirm what makes this new generation of WNBA stars so exciting: they’re not just athletes—they’re cultural drivers, connectors and brand-builders.

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“I think that the W is getting the moment it has deserved because those people are investing into it and the right eyes are buying in,” she said. “The product has ALWAYS been there, but it hasn’t caught the correct audience, until now. 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. So many W players are into these spaces naturally, you can say we are walking billboard and many powerful women are the hot commodity right now. The W is the perfect hub.”

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