Winnie Harlow Is Using Her Platform to Inspire Future Generations of Female Entrepreneurs

The SI Swimsuit legend and Cay Skin founder was photographed for the 2019 and 2024 issues.

Winnie Harlow was photographed by Laretta Houston in Great Exuma, Bahamas. / Laretta Houston/Sports Illustrated

SI Swimsuit legend Winnie Harlow had already made a name for herself before she graced the pages of the magazine in 2019. The Jamaican supermodel and Canada native, who is best known from her 2014 run on America’s Next Top Model, traveled to Great Exuma, Bahamas with photographer Laretta Houston for her feature, and it truly was epic.

Five years later, she returned to the fold for the 2024 issue, which also marked the publication’s 60th anniversary year. The 30-year-old, who was diagnosed with the skin condition vitiligo at the age of 4, posed alongside 26 fellow franchise legends in Hollywood, Fla., and celebrated the legacy of the brand.

“It feels empowering as a woman to be recognized alongside so many legendary women who are revered for their talent, intellect, business acumen, philanthropic contributions, and for breaking down boundaries for women in their respective fields. When we were on set the day of the shoot, I was in awe of all the generations of accomplished women who were around me; it filled me with a sense of pride to be working alongside them, but also a sense of motivation to continue to empower the next generation of strong women,” Harlow gushed. “[Women can empower each other by] sharing our stories and, in turn, putting ourselves in someone else’s shoes. Our stories and experiences are so helpful when shared.”

Today, the industry stalwart is a fashion icon and former Making the Cut reality competition series judge. Harlow, who was the recipient of the 2023 Global Citizen Award from the United Nations Association in Canada, uses her platform to challenge beauty standards and advocate for the vitiligo community, as well as champion diversity in the modeling world. The former Victoria‘s Secret model founded her award-winning skincare and sunscreen brand Cay Skin in 2022, and is dedicated to creating products for all skin types and complexions. Moving forward, Harlow hopes to inspire young Black women to chase their dreams.

“I am most excited about continuing to grow and develop Cay Skin,” she shared while on set. “Stepping into my new role as a business owner has challenged and excited me in ways I hadn’t previously experienced as a model and I love encouraging the next generation of young Black female entrepreneurs to follow their business instincts too.”

Below are some of our favorite photos from her 2019 SI Swimsuit photo shoot in the Bahamas.

Laretta Houston/Sports Illustrated

Laretta Houston/Sports Illustrated

Laretta Houston/Sports Illustrated

Laretta Houston/Sports Illustrated

Laretta Houston/Sports Illustrated