Heads Will Turn! Key West Headdress Ball Takes Fantasy Fest to New Heights

FLORIDA KEYS VIDEO ADVISORY                   October 23, 2026 

Contacts: Chad Newman, Chad@fla-keys.com (310) 283-8441 or Mary B. Haban, Mary@fla-keys.com (305) 394-3142 

Story: Heads Will Turn! Key West Headdress Ball Takes Fantasy Fest to New Heights 

Locator: Key West, Fla. 

Usage: HANDOUT / RIGHTS CLEARED (Unlimited Broadcast & Digital) 

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Photo Captions Below 

Video: B-roll of contestants unveiling towering headdress creations inspired by the "Musical Icons and Iconic Musicals" theme at the 43rd Annual Headdress Ball at the Coffee Butler Amphitheater in Key West, Fla. Footage includes close-ups of headdress details, on-stage performances and Head Above the Rest winner Virginia Wark in her "Saturday Night Fever at Studio 54" headdress. Natural sound of music and cheers. 

Technical Data: 

     TRT: 1:45 

     Filename: KeyWestHeaddress.mp4 

     Audio: Nat. Sound - Stereo Mix 

     B-Roll: Nat. Sound 

Credit: Florida Keys News Bureau (Screen credit appreciated, not mandatory) 

Heads Will Turn! Key West Headdress Ball Takes Fantasy Fest  to New Heights 

KEY WEST, Fla. (October 23, 2026) — Some people let things go to their heads. In Key West, they make a competition out of it! Literally. 

Towering headpieces. Over-the-top costumes. And enough glitz to make even a disco ball jealous. 

Welcome to the 43rd annual Headdress Ball. Where the only thing crazier than the costumes is trying to figure out how to fit them through a doorway. At this party, it's not so much the outfit as it is the head game.And trust us, there's a LOT going on up there. 

More than 500 people packed the sold-out show at the Coffee Butler Amphitheater in Key West, where contestants battled it out for a share of $6,000 in prizes. 

This year's Fantasy Fest theme? "Musical Icons and Iconic Musicals." And these folks didn't miss a beat. One contestant showed up with Elton John's piano on their head. Another gave "Moulin Rouge!" a punk-rock makeover. Foam. Wire. And a little 3-D wizardry. And then there's "Music in Motion." It’s a top hat that its creator says you can actually wear on a bicycle. Because apparently, a regular bike helmet just won't cut it in Key West. 

Longtime host Randy Roberts kept the show rolling as contestants strutted their stuff. Even the award categories like "Glow Getter," "Pretenders in Paradise," and "Size Doesn't Matter" had some serious attitude. 

"Slash-Zilla," a tribute to Guns N' Roses guitarist Slash, won second place. And wait until you hear what went into this winning creation. Netting. Hot glue. A laundry basket. And what its creator calls "the entire dollar store." All thrown together in her Key West kitchen in less than a week. 

The night's big winner? "Head Above the Rest." And this one brought some serious Saturday night fever. 

Key West's Virginia Wark may have finished second last year. But this year, she went for gold, and it paid off with a $2,500 top prize. Her "Saturday Night Fever at Studio 54" headdress shimmered in liquid gold, topped with silver disco balls and tiny clubgoers dancing across her crown. 

The annual Headdress Ball is produced by the Key West Business Guild, with proceeds supporting its year-round efforts to promote Key West as a welcoming destination. 

And the party's not slowing down just yet. Friday night brings Captain Morgan's Masquerade March. On Saturday night, things really get going when the Deep Eddy Vodka Fantasy Fest Parade takes over Duval Street, with tens of thousands expected to pack the streets.  

Fantasy Fest wraps up this Sunday, October 25. For a full schedule of events, visit fantasyfest.com. 

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NOTE TO EDITORS/PRODUCERS: Below is the lineup of Florida Keys News Bureau video coverage for the rest of this week, with corresponding feed dates and delivery times. Separate advisories will be distributed before each feed. 

Saturday, Oct. 24, by 11 a.m.: Captain Morgan's Masquerade March from Friday evening, Oct. 23. This exuberant walking parade through Key West's historic Old Town draws several thousand merrymakers wearing glittering masks, body paint and costumes inspired by the "Musical Icons and Iconic Musicals" theme. Revelers stop along the route at guest houses for music, photos and refreshments. 

Sunday, Oct. 25, by 11 a.m.: Deep Eddy Vodka Fantasy Fest Parade from Saturday night, Oct. 24. The festival's grand finale features dazzling floats, marching groups and costumed participants bringing the "Musical Icons and Iconic Musicals" theme to life before tens of thousands of spectators along Duval Street.