On October 10, the streets of Duval Street in Key West transformed into a glittering stage for the second national finale of If the Shoe Fits. Six performers journeyed from far-flung corners of the United States to compete for the coveted title of Queen of New Year’s Eve. The Dallas-based drag sensation Jada Pinkett Fox emerged victorious, earning the right to slide down the island’s famous giant red high heel as the clock strikes midnight on December 31, 2027.
The competition was structured around three distinct rounds: a brief introduction that set the first impression, a talent showcase, and an evening-gown plus interview segment. Judges – including the founder of the shoe drop, the original 25-year star Sushi, and local hospitality leaders – evaluated each act on charisma, stage presence, and originality. The field featured TP Lords of South Florida, Fifi Dubois of New York, Calypso Jete from Los Angeles/West Hollywood, Brandii Benet of Minneapolis, and Arsyn Ick of North Florida.
The national finals on Duval Street
Performers dazzled the crowd with a blend of dancing, special-effects choreography, and original songwriting. Jada Pinkett Fox capped her set with a powerful live vocal number that drew a roar from the hundreds of on-lookers. The judge’s panel praised her ability to command the stage, noting that her performance “truly wowed the thousands.” Production director Patrik Gallineaux later echoed this sentiment, saying, “We are so thrilled to showcase Key West and our new Queen of New Year’s Eve to the world this December 31 with our 29th annual High Heel Shoe Drop Extravaganza.”
What the crown brings and the 2027 shoe drop
Beyond the title, the winner receives a six-day stay at the historic New Orleans House, a $2,000 appearance fee, and round-trip airfare arranged through Island House. The prize also includes a custom couture costume handcrafted by legendary drag icon Sushi, who will debut the garment during the midnight descent. The winning queen will join a live audience on a traffic-free segment of Duval Street, where the iconic giant red high heel serves as both a stage prop and the ultimate photo backdrop.
The iconic giant red high heel
Since its debut, the towering shoe has become synonymous with Key West’s New Year’s Eve celebration. At midnight, the newly crowned queen slides inside the heel, a ritual streamed to a global audience. CNN will broadcast the event live, with correspondent Randi Kaye on the ground and longtime hosts Anderson Cooper and Andy Cohen anchoring the network’s Times Square coverage. The combination of local festivity and worldwide media ensures that “millions watching via CNN” will share in the spectacle.
As the 29th annual High Heel Shoe Drop approaches, anticipation builds across the island. Local businesses, including Bourbon Street Pub and the Monroe County Tourist Development Council, have rallied behind the celebration, promising a three-hour show that blends music, dance, and the tradition of the red-shoe descent. With Jada Pinkett Fox at the helm, organizers expect a night that “truly wow[s] the thousands” gathered on Duval Street and the countless viewers tuning in from home.
