Winnie Harlow Inspires on the Cover of the 60th Anniversary SI Swimsuit Issue

This year marks the Canadian model’s second photo shoot with the brand.

Winnie Harlow was photographed by Yu Tsai in Hollywood, Fla. / Yu Tsai/Sports Illustrated

Winnie Harlow is an SI Swimsuit legend. Along with 26 other talented trailblazers and brand regulars, she posed for the 60th anniversary legends photo shoot, cementing her place in brand history.

The Canadian model first joined the franchise in 2019, traveling to Great Exuma, Bahamas, for her debut photo shoot with photographer Laretta Houston. For Harlow, it was another addition to her already impressive resume, which includes the likes of cover features in international editions ofVogue, Harper’s Bazaar and ELLE, among others.

Having experienced childhood bullying due to her vitiligo, the 29-year-old has dedicated her whole career to changing the narrative around stereotypical notions of beauty. Just as she has done at every other step of her career, she used the opportunity with SI Swimsuit to showcase the diversity of beauty.

Now, she returns to the magazine for the second time to make the same case. Her 2024 feature brought her to the Seminole Hard Rock & Casino in Hollywood, Fla., where she was photographed by Yu Tsai. For the occasion, the model wore a silver strapless dress from designer Guarav Gupta, featuring a corseted bodice and a trailing silk skirt. Harlow paired the gown with a pair of silver metallic pointed heels from Alevì and Charlie Lapson diamond jewelry.

In typical fashion, Harlow shone on set in Florida, putting her beauty on full display. The photo shoot brought her first cover feature with the brand in the form of a stunning group photo alongside fellow brand legends.

Below are some of our favorite snapshots from the day.

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