Virginia Wark, one of Key West’s most creative minds, takes first place in the 2018 Headdress Ball. PETE ARNOW/Contributed

The Key West Headdress Ball, Mardi Gras edition, is happening — finally — after three postponements due to COVID-19. 

The colorful and creative event is the Key West Business Guild’s major fundraiser and all net proceeds go to promoting Key West worldwide as a premier LGBT+ destination. 

The Headdress Ball is typically part of the annual Fantasy Fest celebration, but this will be the first time it’s a standalone event. (The ball will return to the Fantasy Fest lineup next fall.) The event takes place outside at the Coffee Butler Amphitheater with distanced seating at the tables.

The program consists of the judging of Headdress Ball creations and performances by some of Key West’s best talent. The panel of judges includes JT Thompson, founder of Key West’s One Human Family initiative; Key West Police Chief Sean  Brandenburg; and Key West City Manager Patti McLauchlin. First place wins $3,000 (judged from the shoulders up); second place wins $1,000 and third place wins $500.

Mayor Teri Johnston will open this year’s program, which features performances by Christopher Peterson, The Aquanettes, Aqua’s Diva Inga, the Nick Mazza Dancers, Bourbon Street Pub performer Bria Ansara and Luke Fox. The crew from Waterfront Playhouse will present a sneak preview of their 83rd season next fall. WEOW/92.7’s Rudegirl provides the music. The emcee is comedienne and WGAY radio personality Laurie Thibaud of Aqua Idol fame.  

The Key West Mad Hatter will be selling their hats. Bar and table service is provided by Aquaplex while Clemente’s and Dirty South will handle the food. 

Gates open at 6:30 p.m. and the show starts at 8 pm. Following the ball, the Aquaplex Sidebar, 504 Angela St., presents a free dance party with happy hour drink prices and classic disco music. Tickets for the Headdress Ball include four-top table seating, chair and grass seating and are available at For contestant preregistration, call the Business Guild office at 305-294-4603. 

The event producers offer special thanks to the major sponsors, Centennial Bank and Destination Florida Keys magazine and to everyone who has held onto their tickets for the past two and a quarter years, and to the entertainers who volunteer their time and donate their talent for the event.

Key West Business Guild’s Headdress Ball 
Saturday, Feb. 26
Coffee Butler Amphitheater 
Gates open at 6:30 p.m., show starts at 8 p.m.
Limited tickets are still available at

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