headdress ball logo

Congratulations to the 37th Annual Headdress Ball Winners!

October 28, 2021

38th Annual Headdress Ball

Gates Open 6:30 pm. Show begins 8 pm Coffee Butler Amphitheater

TICKETS ON SALE NOW  @ Keystix.com


The Key West Business Guild presents the 38th Annual Headdress Ball on Thursday, October 28, 2021 at 8 pm. This is the premier LGBTQ+ event of the Fantasy Fest celebration and the event proudly returns to the Coffee Butler Amphitheater at the Truman Waterfront Park.  Tom Luna returns as the outrageous emcee with Rude Girl from WEOW 92.7 radio rocking out our sound. The Aquanettes will open the show and are joined by some of the best local talent including Christopher Peterson and the cast of the Waterfront Playhouse’s Rocky Horror Picture Show! Over fifteen contestants will parade their Headdress creations on the amphitheater stage to vie for the $3,000 first prize.

Interested in competing?

This unique competition allows contestants to go “head to head” to impress the audience with what they’ve got from the shoulders up!

Prizes for Best Headdress: $3,000, $1,000 second, $500 third.

This is a Headdress competition and as such costumes are not considered in the awarding of points. Though the audience enjoys fully costumed entries, please note that the Judging will be done from the shoulders up! Contestants preregistered for the competition by September 15, 2021 will be listed in the Headdress Ball program. Note to contestants – please be advised that the Headdresses must be worn on the head during the competition. Contestants may have an assistant on stage if needed.

Entries can include costumed “spotters” however the physical presence of the spotters cannot be required for the support of the headdress.

There is no admission fee for those entering the Headdress Ball competition.

Register here!


Key West
Partly Cloudy
6:57am8:09pm EDT
Feels like: 95°F
Wind: 12mph SSE
Humidity: 75%
Pressure: 29.97"Hg
UV index: 0