Creativity Takes Flight at Key West’s 42nd Annual Headdress Ball

Key West, Fla. (October 7, 2025) — Feathers, sequins, lights, and sheer imagination will take center stage at the 42nd Annual Headdress Ball, set for Thursday, Oct. 23, 2025, at the Coffee Butler Amphitheater in Truman Waterfront Park. A crown jewel of Fantasy Fest’s 10-day celebration, the event invites creators to push the limits of artistry with spectacular, larger-than-life headdresses modeled under the stars. 

This year’s Headdress Ball embraces the Fantasy Fest theme “Bedtime Stories and Magical Monsters”, promising an evening where dreams and nightmares collide in dazzling pageantry. More than 15 contestants are expected to compete, each unveiling headpieces adorned with feathers, beads, sequins, exotic adornments, and even moving parts. While many contestants will be costumed head to toe, judging focuses squarely on the headdress, with designers vying for top honors and a grand prize of $3,000. 

Known as Fantasy Fest’s premier LGBTQ event, the Headdress Ball offers a showcase of both design and performance. Beloved Key West entertainer Randy Roberts returns as master of ceremonies, keeping the evening witty and lively, while DJ Rude Girl spins the soundtrack. Between runway presentations, the audience will be treated to entertainment from some of the island’s most celebrated performers, ensuring the energy never dips. 

“The Headdress Ball is where artistry, camp, and creativity come together in true Key West style,” said Rob Dougherty, executive director of the Key West Business Guild, which produces the event. “Guests can expect a night filled with over-the-top design, amazing talent, and plenty of surprises.” 

Gates open at 6:30 p.m., offering attendees time to enjoy food and drink service before the show begins at 8 p.m. Tickets start at $30 for general admission, with reserved VIP tables for four beginning at $270, including tableside food and beverage options. Tickets are available now at keystix.com. 

The Headdress Ball is also a fundraiser for the Key West Business Guild, a not-for-profit organization founded in 1978 that supports the island’s LGBTQ businesses, community, and international reputation as a welcoming destination. 

The event unfolds as part of Fantasy Fest 2025 (Oct. 17–26), a costuming and masking extravaganza featuring parades, masquerades, galas, and street fairs. Complete information is available at fantasyfest.com and gaykeywestfl.com/headdress-ball. 

High-resolution images, photo credits, and captions are available at this link.   

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