Key West Announces the New “Queen of New Year’s Eve” for the 29th Annual High Heel Shoe Drop

The 2nd annual “If the Shoe Fits” national talent competition and pageant to find the new Queen of New Year’s Eve has announced the winner of the six-city 2026 tour as Jada Pinkett Fox of Dallas, Texas.  

Presented by Bourbon Street Pub, New Orleans House and the Monroe County Tourist Development Council, the National Finals took place for a delighted crowd of several hundred audience members Saturday, October 10th on Duval Street, closed to traffic and presented on the same stage used for the annual New Year’s Eve Extravaganza.  Onstage to open the show and perform her farewell number before helping to hand off the title was last year’s winner Mulan Alexander, also of Dallas.

Judges included Joey Schroeder (founder of the High Heel Shoe Drop and owner of Bourbon Street Pub), Bria Ansara (New Year’s Eve Show Director), Jeffrey Smead (General Manager of Island House Key West, supporting partner of “If the Shoe Fits”), Mark Gardner (General Manager of the soon to re-open Aqua Key West) and the original star of the High Heel Shoe Drop for 25 years, Sushi.   The high-energy and masterfully produced event was emceed by Patrik Gallineaux, “If the Shoe Fits” Director of Production and co-host of the annual Shoe Drop.  Local guest performers included Beatrix Dixie, Holly Dae, Jessica Devereaux and Stevie B. Lords.

Rounding out the six National Finalists were TP Lords representing South Florida (1st-runner up), Fifi Dubois representing New York City (2nd runner-up), Calypso Jete representing Los Angeles/West Hollywood, Brandii Benet representing Minneapolis and Arsyn Ick representing North Florida. All contestants competed in 3 categories including “Introductions and First Impressions”, Talent, and the Key West-style combination Evening Gown and Interview round 3, in which the audience was given noisemakers and confetti cannons with each contestant introduced to grand fanfare as the New Queen, sitting in the actual shoe chair while being “interviewed by CNN” on New Year’s Eve.  

This year’s competition was a fierce showdown of dancing, special effects, original songwriting, and in the case of the eventual winner Jada Pinkett Fox show-stopping live vocals. Jada has won a 6-day return stay at New Orleans House for New Year’s Eve plus a $2,000 appearance fee courtesy of Bourbon Street Pub and the TDC plus round-trip airfare courtesy of Island House with all flights arranged by HE Travel.   In what is now a much-anticipated annual tradition, Jada will receive a custom couture costume designed by Sushi, to be debuted on December 31st.

“We are so thrilled to showcase Key West and our new Queen of New Year’s Eve to the world this December 31st with our 29th annual High Heel Shoe Drop Extravaganza,” said ‘If the Shoe Fits’ Production Director and host Patrik Gallineaux.  “Jada Pinkett Fox will truly ‘WOW’ the thousands joining us live on Duval Street and the millions watching via CNN“.

In fact, CNN is confirmed to again go live this New Year’s Eve from the Shoe Drop with correspondent Randi Kayefacilitating coverage with Anderson Cooper and Andy Cohen in Times Square leading up to the “Queen of New Year’s Eve” descending during the countdown to 2027 at midnight.

“All of Key West looks forward to welcoming Jada Pinkett Fox back to Key West at the end of December,” said Shoe Drop Executive Producer Joey Schroeder. “She is such a professional, full of positive energy; a true beam of light—the PERFECT New Year’s Eve Queen to welcome 2027.”

A 3rd annual “If the Shoe Fits” competition is tentatively planned for summer 2027 with the National Finals again in October.

Updates can be found at https://bourbonstpub.com/iftheshoefits/  and www.facebook.com/iftheshoefitskw. 

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