A Dallas drag performer is headed to the bottom of the Florida Keys to make a very dramatic entrance. Jada Pinkett Fox, who represents Round-Up Saloon in Dallas, Texas, has won the national If the Shoe Fits pageant and will become Key West's new Queen of New Year's Eve, descending inside the city's iconic eight-foot red high heel as the clock strikes midnight on Dec. 31 to ring in 2027.
Fox was chosen on Oct. 10 from a field of six finalists during the National Finals held on Duval Street, according to Dallas Voice. The other finalists brought to Key West for the final round included TP Lords of South Florida, who took first runner-up, and Fifi Dubois of New York City, who placed second runner-up, alongside Calypso Jete of Los Angeles and West Hollywood, Brandii Benet of Minneapolis, and Arsyn Ick of North Florida. Organizers say Fox was selected as the contestant who best embodied the glamour, professionalism and spirit established by prior Queens of New Year's Eve, as Keys Weekly reported.
A Second Season for a New Key West Tradition
If the Shoe Fits launched in 2025 and gives professional entertainers and drag performers across the country a shot at headlining Key West's New Year's Eve celebration, according to the competition's official page at Bourbon St. Pub. The tour's reach has expanded since its debut: Dallas Voice described the 2026 edition as a six-city tour, while the Bourbon St. Pub page states the 2026 tour visited seven U.S. cities between late August and October, adding Minneapolis and Jacksonville as new stops. Organizers say the competition sought performers with exceptional stage presence, charisma and the ability to command crowds of thousands.
The pageant is presented by Bourbon Street Pub, New Orleans House and the Monroe County Tourist Development Council, with support from Island House Key West. This year's edition crowns a queen for the 29th annual High Heel Shoe Drop, a milestone that places Fox in a lineage of performers including Sushi, who reigned for 25 years, along with Christopher Peterson, Randy Roberts and reigning national champion Mulan Alexander — also a Dallas native, per the same Bourbon St. Pub page.
Couture Costume and a Three-Hour Stage Show
As part of her reign, Fox will debut a custom couture costume designed by Sushi on Dec. 31, the same night she stars in a three-hour New Year's Eve stage show on Duval Street before her midnight descent in the red shoe. The prize package also includes a $2,000 appearance fee and an additional stay at New Orleans House for New Year's Eve — described by Dallas Voice as six days, while the competition's own page lists it as five days and four nights.
CNN has confirmed it will again broadcast live from the Shoe Drop this New Year's Eve, continuing international coverage of a celebration that has drawn cameras to Duval Street for years. The red shoe itself hangs about 15 feet above the street during the drop, according to Florida Keys & Key West tourism officials, and the event has long been billed as one of several warm-weather Keys takeoffs on New York City's Times Square ball drop, as NBC Miami has noted.
From a Local Drag Legend to a National Contest
Key West's drag queen drop started in 1996 with Gary Marion, better known as Sushi, in the shoe, according to CNN. Marion climbed into the giant red heel for 25 consecutive years before retiring, as reported by WLRN. Christopher Peterson succeeded Sushi as the drop's featured passenger for 2024, with thousands of people gathering outside the Bourbon St. Pub complex on Duval Street to watch, per CBS News Miami.
It wasn't until last year that a national contest decided who would wear the crown. Mulan Alexander, also of Dallas, won that spot through the If the Shoe Fits contest to ring in 2026, marking the first time in the Red Shoe Drop's 28-year history that a competition — rather than direct selection — determined the star, Keys Weekly reported at the time. The event's crowd has shifted over the decades too, evolving from one rooted primarily in Key West's gay community into what CNN describes as a mixture of tourists and locals from every walk of life.
