Key West Business Guild Reinvents the Iconic Headdress Ball with Exciting New Award Categories

October 22, 2026 – (KEY WEST, FL). The Key West Business Guild is introducing an exciting new chapter in one of Fantasy Fest's most celebrated traditions.  The 43rd Annual Headdress Ball, taking place Thursday, October 22, 2026, at the Coffee Butler Amphitheater, will feature an expanded awards program designed to recognize more artists, celebrate a wider range of creative expression, and encourage even greater participation in the iconic competition.

For more than four decades, the Headdress Ball has showcased the imagination and artistry that have become synonymous with Fantasy Fest.  While contestants will continue competing for the coveted grand prize, this year's competition introduces several new specialty awards that honor creativity in unique ways, from innovative lighting effects and collaborative designs to cohesive costume presentations and creations inspired by the official Fantasy Fest theme.

“The Headdress Ball has always been about celebrating artistic expression and pushing creative boundaries,” said Fritzie Estimond, Executive Director of the Key West Business Guild.  “We wanted to create more opportunities to recognize the incredible talent that takes the stage each year.  These new awards celebrate different styles of creativity while encouraging both returning artists and first-time contestants to be part of one of Fantasy Fest's most iconic events.”

New award categories include:

• Glow Getter Award – Recognizing the headdress that makes the biggest impact through creative illumination featuring LEDs, neon, or other lighting effects.
• Size Doesn't Matter Award – Honoring the artist who proves that spectacular creativity isn't measured in size by making a bold impression with a more compact design.
• Pretenders in Paradise Award – A tribute to the beloved former Fantasy Fest costume competition, recognizing the contestant whose costume and headdress come together as one cohesive work of art.
• Dream Team Award – Celebrating two or more artists who combine their talents to create a unified and visually stunning presentation.
• Spirit of Fantasy Fest Award – Presented to the creation that best captures the official Fantasy Fest theme.
• Head Above the Rest Award – The competition's highest honor, recognizing the contestant whose creation best combines artistic vision, originality, craftsmanship, creativity, presentation, and overall impact.

Head Above the Rest$2,500
Spirit of Fantasy Fest$1,000
Pretenders in Paradise$750
Glow Getter$500
Dream Team$500
Size Doesn’t Matter$500
Total Prize Purse: $6,000

Hosted once again by legendary Key West entertainer Randy Roberts, with music by WEOW's RudeGirl, the 43rd Annual Headdress Ball promises another unforgettable evening of creativity, glamour, and entertainment. Contestants will unveil their spectacular headdress creations as they compete before a live audience for the evening's top honors.  The event will also feature performances by some of Key West's most celebrated local entertainers, along with full bar service, specialty wines, and the convenience of pre-ordered food delivered directly to guests' tables. Doors open at 6:30 p.m., and the show begins at 8:00 p.m.

For tickets, contestant registration, and additional information, visit gaykeywestfl.com/headdress-ball or call 305-294-4603.  This event is sold out every year.  Advance ticket purchases are strongly recommended.