Winnie Harlow 2024: 60th Anniversary Legends

SI Swimsuit | May 14, 2024

Winnie Harlow was photographed by Yu Tsai in Hollywood, Fla., for the 2024 SI Swimsuit Issue, along with fellow brand legends Chrissy Teigen, Kate Love, Brenna Huckaby, Christie Brinkley, Halima Aden, Kate Upton, Leyna Bloom, Martha Stewart, Megan Rapinoe, Molly Sims, Paige Spiranac, Sue Bird, Tyra Banks, Gayle King, Brooks Nader, Maye Musk, Camille Kostek, Danielle Herrington, Nina Agdal, Jasmine Sanders, Lily Aldridge, Hailey Clauson, Hunter McGrady, Paulina Porizkova, Brooklyn Decker and Roshumba Williams.

Harlow made her SI Swimsuit debut with a trip to Great Exuma in 2019. There, she continued her mission to showcase the diversity of beauty—a cause inspired by her experience of childhood bullying. Her modeling career has brought her to the covers of international editions of Vogue, Harper’s BAZAAR and ELLE among others. She has walked the runway for various designer brands and starred in several brand campaigns. In 2022, Harlow announced the launch of her own skincare brand, Cay Skin, which is dedicated to look good, feel good formulas and inclusivity. 

The model returns to SI Swimsuit for the 60th anniversary issue this year. For her second brand feature, she traveled to Hollywood, Fla., to pose alongside other brand regulars. With the help of stylist Molly Dickinson, the legend stepped out for the photo shoot in a Gaurav Gupta dress, Alevì shoes and Charlie Lapson jewelry.

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Hair: Ashley Akemi
Makeup: Adam Burrell
Styling: Molly Dickson
Styling Team: Sophie Faith, Abigail Hall, Clarke Johnson, Brianna Millstein, Dijana Nedelcovych and Halle Smith
Nails: Julie Kandalec and Christina Aude at Start Touch Agency using Gold Bond and PLA Nails
Skin Prep and Facial Massage: Maria Cristina Bruno using iS Clinical and The FIX
Photographer: Yu Tsai

Winnie Harlow was photographed by Yu Tsai in Hollywood, Fla. Dress by Gaurav Gupta. Shoes by Alevì. Jewelry by Charlie Lapson. / Yu Tsai/Sports Illustrated

Winnie Harlow was photographed by Yu Tsai in Hollywood, Fla. Dress by Gaurav Gupta. Shoes by Alevì. Jewelry by Charlie Lapson. / Yu Tsai/Sports Illustrated

Winnie Harlow was photographed by Yu Tsai in Hollywood, Fla. Dress by Gaurav Gupta. Shoes by Alevì. Jewelry by Charlie Lapson. / Yu Tsai/Sports Illustrated

Winnie Harlow was photographed by Yu Tsai in Hollywood, Fla.Dress by Gaurav Gupta. Shoes by Alevì. Jewelry by Charlie Lapson. / Yu Tsai/Sports Illustrated

Hunter McGrady, Tyra Banks, Lily Aldridge, Kate Upton, Danielle Herrington, Molly Sims, Roshumba Williams, Hailey Clauson, Paige Spiranac, Kate Love, Brooks Nader, Winnie Harlow, Camille Kostek, Brenna Huckaby, Halima Aden, Martha Stewart, Christie Brinkley, Gayle King, Nina Agdal, Sue Bird, Maye Musk, Leyna Bloom, Chrissy Teigen, Brooklyn Decker, Megan Rapinoe, Paulina Porizkova and Jasmine Sanders. / Yu Tsai/Sports Illustrated