Swim Search Winner Mady Dewey’s 6 Best Photos in the Dominican Republic

The tech entrepreneur returned to the fold as a rookie in this year’s magazine.

Cara O’Bleness | Sep 1, 2023

Mady Dewey was photographed by Yu Tsai in the Dominican Republic.

Yu Tsai/Sports Illustrated

While this year’s Swim Search voting recently drew to a close, last year’s open casting call winner Mady Dewey continues to thrive. The model earned her moniker after posing for the publication in the Dominican Republic, where she worked with photographer Yu Tsai. The tech entrepreneur returned to the fold for her rookie feature this year, and traveled to Puerto Rico, where she posed for Derek Kettela.

SI Swimsuit was Dewey’s first-ever modeling gig, as the California native is a tech entrepreneur by day. She currently works as head of product marketing at Try Your Best, and is a former product marketing manager for creators at Discord.

“One of the biggest reasons why I did this was because I felt like [as] someone who works in a tech environment, I didn’t see people that were going after their creative dreams or their dreams outside of just their career, it felt like you had to be placed into this box, like you could only be someone who was smart or career motivated,” Dewey explained of participating in the Swim Search. “And I did this because I want women to see that they can do everything that they want. They can break the stereotype of what a person in their industry looks like, and I just hope that I can be that person for other girls.”

In honor of Dewey’s incredible rookie year, we’re throwing it back to her first-ever photoshoot with SI Swimsuit. Below are a few of our favorite captures from the Dominican Republic.

MTg5NDU2NTQ2NTkyOTI0OTM0 — Yu Tsai/Sports Illustrated

MTg5NDU2NTQ2NTkyMjA0Mzg1 — Yu Tsai/Sports Illustrated

MTg5NDU2NTQ2NTkyMzM1NDU3 — Yu Tsai/Sports Illustrated

MTg5NDU2NTQ2NTkyODU5Mzk4 — Yu Tsai/Sports Illustrated

MTg5NDU2NTQ2NTkyNDY2NTI5 — Yu Tsai/Sports Illustrated

MTg5NDU2NTQ2NTkyMjY5OTIx — Yu Tsai/Sports Illustrated

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Published Sep 1, 2023

CARA O’BLENESS

Cara O’Bleness is a writer and editor on the Lifestyle and Trending News team for SI Swimsuit. Prior to joining SI Swimsuit in 2022, she worked as a writer and editor across a number of content verticals, including food, lifestyle, health and wellness, and small business and entrepreneurship. In her free time, O’Bleness loves reading, spending time with her family and making her way through Michigan’s many microbreweries. She is a graduate of Michigan State University’s School of Journalism.