Q&A With SI Swimsuit Legend Winnie Harlow

The Cay Skin founder returns to SI Swimsuit for the 60th anniversary magazine.

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

Turning 60 has never looked so good. To celebrate the big milestone in style, Sports Illustrated Swimsuit called upon 27 “Legends”—women of all ages, sizes, tribes and backgrounds—who epitomize trailblazing influence and game-changing impact. 

From supermodel OGs who made their first splash on the magazine’s glossy pages in the 1970s and ’80s to stars newer to the SI Swimsuit sisterhood—the Legends symbolize diversity, inclusivity, empowerment and self-love.  

“The Legends hold the power to represent the collective us,” SI Swimsuit editor in chief MJ Day says. “Each one has played a significant role in the brand’s last 10 years, holding important conversations that have helped shift societal perceptions and led to incredible change for women.” 

The Legends had plenty to say in their one-on-one interviews, held during a three-day SI Swimsuit event at the Seminole Hard Rock Hotel & Casino in Hollywood, Fla., where photo shoots for the 60th anniversary issue were underway amidst a flurry of glam teams, wardrobe stylists and veteran fashion lensmen. The Legends were unfiltered, funny, wise, compassionate, profound, and at times, searingly honest—proving that a woman’s inner beauty is her most important superpower of all.   

See more from the Legends photo shoot here.

Winnie Harlow is a model, beauty diversity advocate and the founder of skincare company Cay Skin. She made her SI Swimsuit debut back in 2019, traveling to Great Exuma for her first brand feature. The 2024 issue brings her back into the fold as a part of the 60th anniversary Legends photo shoot.

What does being an SI Swimsuit Legend mean to you?

“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.”

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

View Winnie Harlow’s 2024 Legends photo gallery here.

Describe yourself in three words.

“Caring, discerning, lion-hearted.”

What do you love most about being yourself?

“Being unapologetically myself at all times. My friends and family tell me I am genuine, fiercely loyal, kind-hearted, compassionate and extremely hardworking. I hope to continue to exude those traits everywhere I go.”

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

What can women do to better empower each other?

“Sharing our stories and, in turn, putting ourselves in someone else’s shoes. Our stories and experiences are so helpful when shared.”

What excites you most about your life right now?

“Right now, I am most excited about continuing to grow and develop Cay Skin. 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.”