Artistry Rules at Fantasy Fest Headdress Ball

From left, Jill Malcolm, Guy Hermelin, and Virginia Wark, all of Key West, Fla., are met with cheers after being named the top three winners at the 42nd annual Headdress Ball at the Coffee Butler Amphitheater in Key West, Thursday night, Oct. 23, 2025. Hermelin captured First Place with “Astraea the Magnificent Dream Dragon.” Wark earned Second for “Sandworm Escape.” And Malcolm took Third Place for her creation “Bookish Bride.” The event, themed “Bedtime Stories and Magical Monsters,” is part of Fantasy Fest which continues through Sunday. (Mark Hedden/Florida Keys News Bureau)

(Press Release) KEY WEST, Fla. (Oct. 24, 2025) — Outrageous headwear. Towering creations. Magnificent Masks. And larger-than-life personalities rocked center stage in Key West, Florida Thursday night. 

The over-the-top evening was all part of the 42nd Annual Headdress Ball — a signature event during Fantasy Fest that challenges competitors to unleash their creative prowess with show-stopping designs...from the shoulders up! The contestants transformed Key Wests’ Coffee Butler Amphitheater into a dazzling spectacle as they competed for a five-thousand-dollar grand prize — and a coveted title. 

The theme? “Bedtime Stories and Magical Monsters.” And the creations from contestants were nothing short of pure theatrical magic. 

The crowd went wild as contestants brought their high-energy performances to life, with longtime host Randy Roberts at the helm. Their jaw-dropping head-dresses ranged from fantastical dream-world beasts to intricate mechanical designs. But they didn’t stop there...many contestants got decked out in full-body costumes, which added to the evening’s dramatic flair. 

The elaborate event raises funds to support year-round efforts to promote Key West as destination where everyone feels welcome. 

And if you’re having a case of serious FOMO, there’s still time to take in Fantasy Fest which continues through Sunday, Oct. 26, with the Captain Morgan Masquerade March on Friday and Saturday night’s wildly popular grand finale — the Deep Eddy Vodka Fantasy Fest Parade; which packs the streets and rooftops of Key West’s famed Duval Street.  

---