We’re in Love With These 6 Groovy Photos of Mady Dewey in Puerto Rico

The Swim Search winner returned to the SI Swimsuit Issue this year as a rookie.

Ananya Panchal | Dec 3, 2023

Mady Dewey was photographed by Ben Watts in Puerto Rico.

Ben Watts/Sports Illustrated

Swim Searcher Mady Dewey made a splash with her SI Swimsuit photoshoot in the Dominican Republic last year. The tech entrepreneur and former Herd Social cofounder was then named winner of the open casting call, securing her rookie spot in the 2023 issue.

The 27-year-old, who recently got engaged to longtime boyfriend Jack Hillman, returned to the fold and was captured by Ben Watts in Puerto Rico earlier this year. She donned a series of colorful and fun 1970s surf culture-inspired swimwear looks for the feature.

“I can’t even describe how it feels to be a Sports Illustrated Swimsuit rookie. Like I say it out loud, and I still don’t fully recognize that that’s what’s happening right now. It’s an honor,” Dewey gushed. “I cannot even begin to explain how grateful I am for the chance to even do this once, let alone now to get to come back and be a rookie and just to have the opportunity to try something new, try something outside of what I do day in and day out has been such a joy.”

Today, the Southern California native lives in San Francisco with her fiancé and a works as the head of product marketing at Try Your Best. The Socially Well podcast cohost hopes her SI Swimsuit features serve as inspiration to fellow women in the tech industry to chase all of their dreams—regardless of how big or unorthodox they may seem.

Below are six of our favorite photos from Dewey’s rookie photoshoot in Puerto Rico.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Gonza. Shorts by Aviator Nation.

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

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

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.

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

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Monica Hansen Beachwear. Earrings by Zealmer. Bracelets by Brinker + Eliza.

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Published Dec 3, 2023

ANANYA PANCHAL

Ananya Panchal is a writer on the Lifestyle and Trending News team for SI Swimsuit. Before joining SI Swimsuit in 2022, she worked at Bustle, the San Francisco Chronicle and the TODAY Show. When she is not writing or doom-scrolling on social media, Panchal can be found playing sudoku, rewatching One Tree Hill or trying new restaurants. She's also a coffee and chocolate (separately) enthusiast. Panchal has a bachelor’s in communications and journalism from Boston University.