Mady Dewey 2023: Puerto Rico

SI Swimsuit | May 14, 2023

Mady Dewey was photographed by Ben Watts in Puerto Rico alongside Jasmine Sanders, Georgina Burke, Marquita Pring and Lorena Durán.

The Southern California native is the 2022 Swim Search winner and returns for her first full-fledged destination feature in ’23. Dewey is a passionate advocate for female founders breaking into male-dominated VC and tech industries. She is the founder and CEO of a metrics-free social media app, Herd, catered to women and nonbinary people. The app, which boasts more than 85,000 users, is meant to be a safe space for people who want to share without comparing or being compared.

Rich in culture and history, Puerto Rico offers both thrilling adventure and ultimate relaxation. It’s a hot spot for authentic cuisine, exotic wildlife, breathtaking scenery and more. The archipelago located in the Caribbean Sea consists of one main island and four smaller islands, as well as numerous islets, all of which offer secluded sandy spots and immaculate views. It provided an unforgettable setting for the 2023 SI Swimsuit Issue.

To learn more about Puerto Rico, including where to stay, what to eat and can’t-miss beaches and activities, click here.

The styling for Dewey’s photo shoot in Puerto Rico, a top surfing destination in the Caribbean, was inspired by 1970s surf culture—pops of color, laid-back “surf’s up” aesthetic and vintage prints. The SI Swimsuit team carefully chose pieces that could tell a story of a playful, chill and unfussy time.

Hair: Anthony Cristiano for Anthony Cristiano Salon Chicago using Phyto Paris USA Haircare
Makeup: Bryan Zaragoza at See Management using Tom Ford Beauty. 
Photographer: Ben Watts

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 Monica Hansen Beachwear. Earrings by Zealmer. Bracelets by Brinker + Eliza.

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 AANOUKIS Swimwear. Hat 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 Gonza. Shorts by Aviator Nation.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Monica Hansen Beachwear. Earrings by EF Collection.

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

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

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Heavy Manners. Necklaces by Electric Picks.

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 BECCA by Rebecca Virtue. Scarf by Dandy Del Mar.

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 Monica Hansen Beachwear. Necklaces by SOKO and Electric Picks. Bracelets by Nancy Newburg.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by RUTT Australia. Shirt by Juan de Dios. Necklaces by ByRoxStudio.

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 Monica Hansen Beachwear. Earrings by Zealmer.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by AANOUKIS Swimwear. Hat by Aviator Nation.

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

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Monica Hansen Beachwear. Earrings by EF Collection.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Monica Hansen Beachwear. Bracelets by Nancy Newburg Jewelry.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by AANOUKIS Swimwear. Hat by Aviator Nation.

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.

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.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Luna Cara Swim. Necklace by Electric Picks.

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 EF Collection.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by Monica Hansen Beachwear. Necklaces by SOKO and Electric Picks. Bracelets by Nancy Newburg Jewelry.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by RUTT Australia. Shirt by Juan de Dios. Necklaces by ByRoxStudio.

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.

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 Monica Hansen Beachwear. Necklaces by SOKO and Electric Picks. Bracelets by Nancy Newburg.

Mady Dewey was photographed by Ben Watts in Puerto Rico. Swimsuit by RUTT Australia. Shirt by Juan de Dios.

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.