Mady Dewey Served Ultimate Summer Surfer Girl Vibes in Puerto Rico

The Swim Search winner posed for Ben Watts for the 2023 SI Swimsuit Issue.

Mady Dewey was photographed by Ben Watts in Puerto Rico. / Ben Watts/Sports Illustrated

Two-time SI Swimsuit model Mady Dewey is all about defying stereotypes. The Southern California native applied to the Swim Search in 2022 with no expectations—but she ended up winning the open casting call, following her photo shoot with Yu Tsai in the Dominican Republic. The title secured her rookie spot in the 2023 issue, for which she traveled to Puerto Rico with visual artist Ben Watts.

“I’ve been a long-time lover of Sports Illustrated, but Camille Kostek really inspired me to apply for Swim Search. For so long, I thought being a model couldn’t happen given my career in tech and naturally curvy body,” she shared. “Seeing Camille on the cover [in 2019] changed that for me. I ultimately decided to try out for Swim Search to show women that your dreams don’t have to be linear to be worth pursuing, and to hopefully break down the boxes women in tech and business are so often placed in.”

Kostek, who is now an SI Swimsuit legend and seven-time brand model, was the first casting call alumna to land on the cover of the magazine.

Dewey uses her platform to inspire women to step out of the box and chase their wildest dreams. The ferocious advocate for women in tech is a former Discord employee and is also the former cofounder of metrics-free social media app Herd. Today, Dewey is the head of product marketing at Try Your Best, a startup that aims to create a community rewards system connecting brand and fans.

Below are six phenomenal photos from her 2023 SI Swimsuit photo shoot in Puerto Rico.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by isabella rose. / Ben Watts/Sports Illustrated

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by RUTT Australia. Necklaces by ByRoxStudio. / Ben Watts/Sports Illustrated

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Ezili Swim. / Ben Watts/Sports Illustrated

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Monica Hansen Beachwear. Earrings by Zealmer. / Ben Watts/Sports Illustrated

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by BECCA by Rebecca Virtue. Scarf by Dandy Del Mar. Necklaces by Brinker + Eliza. / Ben Watts/Sports Illustrated

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Andi Bagus. Sunglasses by Otra Eyewear. Necklace by ByRoxStudio. / Ben Watts/Sports Illustrated