Kelsey Anderson All Smiles After Her Runway Debut for Cupshe’s 10-Year Anniversary Show Photo Credit: Mark Gunter
Fashion and Style

Celebrity Sightings at Miami Swim Week 2025: Who Walked, Watched, and Partied

From Reality Stars to Rap Royalty, the Biggest Names Turned Up for This Year’s Runway Shows and Celebrations

Caroline Dalal

Miami Swim Week 2025 brought out a star-studded crowd, both on and off the runway. From Lexi Wood and Kelsey Anderson making waves at Cupshe’s 10-year anniversary show to Megan Thee Stallion being honored at the debut Swimwear Icons Hall of Fame, the week was packed with headline-worthy moments.

WHO WALKED…

Lexi Wood

Summer House star Lexi Wood takes the cat-walk by storm as she strutted down Cusphe’s 10 year anniversary runway show.

Kelsey Anderson

We absolutely do accept your rose, Kelsey Anderson! This Bachelor contestant turned ‘IT girl’ made her runway-debut in her very own Cupshe x Kelsey Anderson: Summer Postcards collection. 

Jessica Vestal

Love Is Blind’s Jessica Vestal makes her runway debut at Cupshe’s 10-year anniversary show in a black one piece.

Riley Milford

One for the books, Riley Milford makes her global debut on the Oh Polly platform representing transgender models around the world.

WHO WATCHED…

Celebrity Support on the Cupshe Runway

Love Island USA stars Kendall Washington, JaNa Craig and Olivia Walker support Jessica Vestal make her debut on the Cupshe runway.

Kaylor Martin

Love Island USA's Kaylor Martin joined fans, media, and friends of the brand for Cupshe’s 10-year anniversary runway show celebration.

Larsa Pippin & Kiki Barth

Real Housewives of Miami’s Larsa Pippin & Kiki Barth sat front row for the Leslie Amon show.

Rick Ross

Rapper Rick Ross sat front row to watch the Oh Polly catwalk.

WHO PARTIED…

Kelsey Anderson with Aurora and Sophia Culpo

Kelsey Anderson and sister-duo Aurora Culpo and Sophia Culpo are all smiles post Cupshe show! 

Nicole Williams, Ellie Thumann, MJ Day, and Katie Austin

Nicole Williams, Ellie Thumann, Sports Illustrated Editor, MJ Day and Katie Austin celebrate the debut of the Swimwear Icons Hall of Fame Honors Night at the iconic Bass Museum.

Megan Thee Stallion

Megan Thee Stallion was honored at the Swimwear Icons Hall of Fame Honors Night for her impact across music and fashion and her ability to inspire a new generation to embrace bold, self-expression.

Isabela Grutman, Karen Lima and Thais Martins

Isabela Grutman, Karen Lima and Thais Martins celebrate the debut of the Swimwear Icons Hall of Fame Honors Night at the iconic Bass Museum.

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