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Congratulations to the 37th Annual Headdress Ball Winners!


Saturday, February 26th, 2022

38th Annual Headdress Ball

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

Saturday, February 26th, 2022


The Key West Business Guild’s Fundraising 38th Annual  Headdress Ball, after a  two year’s absence due to the pandemic, returns as a special Mardi Gras Edition on Saturday evening, February 26, 2022, 8 PM at the Coffee Butler amphitheater. Seating for the tables and General Admission has been distance spread out this year.  First Place prize is $3,000; Second Place is $1000, and Third Place is $ 500 for the best Headdresses, judged from the shoulders up. Eight great talent acts by Key West performers will also be featured. Laurie Thibaud of Aqua Idol fame, will be the emcee. Christopher Peterson opens the show and there will be a special act by the Aquanettes. Bar service during the performance.  Proceeds from the Headdress Ball go to promote LBGTQ+ Tourism to Key West.
Following the show there will be a special Happy Hour Disco Dance at the Aqua Sidebar.

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 January 28th, 2022 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. Headdresses can be supported on the shoulders, but must remain on the head. 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!


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