Fantasy Fest kicks off In less than a month with one of the island’s splashiest, most glitter-fueled evenings. Every night in Key West is a celebration of the eccentric, but for one wildly impressive night each October, the island pushes the boundaries of its imagination even further. The Headdress Ball takes center stage Thursday, Oct. 22, at the Coffee Butler Amphitheater in Truman Waterfront Park. Hosted by The Key West Business Guild, the event, now in its 43rd iteration, continues to raise the stakes of pageantry and spectacle.
Headdress Ball, the premier LGBTQ+ event of Fantasy Fest, has always featured creations judged “from the shoulders up.” But not this year.
The program has officially absorbed “Pretenders in Paradise,” the much-loved, stand-alone costume competition that has taken place in conjunction with the start of the festival for decades. The integration of a new award celebrates the synthesis and expands the creative canvas of the event by honoring the contestant whose (assuredly) over-the-top costume and soaring headdress will blend together into one seamless, cohesive work of art. The addition of Pretenders in Paradise solidifies the Headdress Ball as the ultimate showcase for costuming and wearable art in Key West.
In addition, organizers are introducing six new awards categories, totaling $6,000 in prizes. The “Head Above the Rest” Grand Prize ($2,500) recognizes the entry that demonstrates the most exceptional artistic vision, originality, craftsmanship, creativity, presentation and overall impact. Other honors include the Spirit of Fantasy Fest Award ($1,000) for the best interpretation of the annual theme; the Glow Getter ($500), which recognizes the headdress with the most creative illumination. The Size Doesn’t Matter Award ($500), honors the costume that proves compact designs can carry massive conceptual weight. The Dream Team Award ($500) rewards pairs and groups of artists, and the Pretenders in Paradise Award ($1,000) serves as a tribute to the beloved former costume competition, recognizing the contestant whose costume and headdress come together as one cohesive work of art.
Entrants should be aware, the competition is steep. Last year, Guy Hermelin took home first-place and a $5,000 grand prize for his masterpiece, “Astraea the Magnificent Dream Dragon.” The massive and intricate dragon design elevated the competition and raised the bar for this year.
The Headdress Ball has become synonymous with many facets of Fantasy Fest as a high-stakes, multi-sensory explosion of queer culture, local artistry and fierce competition. Up to 15 contestants are expected to walk the amphitheater stage on Oct. 22, each presenting months of meticulous craftsmanship.
Key West’s own legendary female impersonator and Broadway-caliber entertainer Randy Roberts is the host for the evening, which also features live musical and dance performances while WEOW’s RudeGirl mixes high-octane music.
Gates at the amphitheater open at 6:30 p.m., allowing guests to mingle, purchase cocktails and find their spots before the main curtain rises at 8 p.m.. Tickets range from $30 for general admission lawn seating — where attendees bring blankets and lawn chairs — to $40 per reserved chair and $290-$400 VIP and premium tables, where guests can pre-order food.
The 2026 Headdress Ball stands as a testament to Key West’s enduring spirit of inclusivity and creative freedom, honoring the past by keeping the Pretenders in Paradise alive, while stepping boldly into the future of immersive costume art.
