43rd Annual Headdress Ball
About the event
Your Key West Mayor OR your 2026 Headdress Ball judge?
How about BOTH? 💅
This name needs no introduction, and we're thrilled to have him at this year's Headdress Ball!
Sam Kaufman is the Mayor of Key West and a local attorney who has proudly served the community in elected office since 2015.
A longtime advocate for equality, inclusion, and individual freedom, Sam believes Key West is special because we welcome people for who they are and celebrate what makes each of us unique.
He is proud to represent a community where creativity, diversity, and self-expression are part of our identity.
Sam is thrilled to serve as a judge for the 43rd Annual Headdress Ball and looks forward to celebrating the incredible talent, imagination, and spirit that make this event a true Key West tradition.
Can you guess the final guest at this year's judge table? 💭 Find out tomorrow morning!
📸 nickdollphotography
kaufmanforkeywest
Nearby Hotels
via Stay22Key West, United States Open in Maps →
Our three picks · Key West
via Stay22Men-only gay guesthouse above the Bourbon St. Pub on Duval Street, Key West, with a pool and clothing-optional sundeck.
Men-only, clothing-optional gay resort on Fleming Street, a block off Duval, with pool, hot tub, sauna, gym and café.
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Last verified: 21 Oct 2026 Source: instagram.com Report an issue