The 42nd Annual Headdress Ball Returns to Key West Bigger, Bolder, and More Bedazzled Than Ever!

Get ready for a night of outrageous creativity and show-stopping spectacle as the 42nd Annual Headdress Ball takes the stage at Key West’s stunning Coffee Butler Amphitheater. A dazzling highlight of Fantasy Fest 2025, this signature event is produced by the Key West Business Guild/Gay Key West and proudly reigns as Fantasy Fest’s premier LGBTQ+ celebration.

This year’s theme, “Bedtime Stories and Magical Monsters,” invites a dreamlike world of fairy tale fantasy and mythical mayhem—and at the center of it all, we welcome back the internationally acclaimed performer and Key West icon, Randy Roberts, as your glamorous hostess for the evening.

Expect more than 15 dazzling contestants to strut their stuff in awe-inspiring, shoulder-up showpieces, all competing for the coveted $5,000 grand prize. While many come dressed head to toe, judges will be focused solely on the creativity above the shoulders—where fantasy takes flight.

Keeping the party going will be crowd-favorite DJ Rude Girl, spinning the soundtrack to an unforgettable night, along with special guest performers throughout the competition.

Highlights Include:

·        Spectacular headdresses judged from the shoulders up

·        Hostess Randy Roberts and DJ Rude Girl

·        Live performances and surprise entertainment

·        Food and drink available — preorder online with your tickets!

Now in its 42nd year, the Headdress Ball is a fundraiser for the Key West Business Guild, one of the oldest LGBTQ+ business organizations in the country. Proceeds directly support the Guild’s year-round efforts to promote gay and gay-friendly businesses, advocate for LGBTQ+ rights, and strengthen Key West’s place as a top LGBTQ+ destination.

TICKETS:

·        $320 – Premium Table (seats 4)

·        $270 – VIP Table (seats 4)

·        $35 – Reserved Chair Seating

·        $30 – General Admission Lawn Seating

Order tickets and preorder food at keystix.com
Interested in competing? Apply at gaykeywestfl.com/headdress-ball