Business Guild Presents 34th annual Headdress Ball, The Premier Gay and Lesbian Event of Fantasy Fest.

Revelers hoping to make “headlines” in Key West can take center stage Thursday, Oct. 27, at the 34th annual Headdress Ball.

The glamorous gala is to be held under a gigantic tent at Key West’s Truman Waterfront, located at the end of Southard Street beyond Truman Annex.

Entrants wearing elaborate masks, cowls, bonnets and other headgear — many decorated with feathers, sequins and unexpected or bizarre accessories — are to vie for cash prizes at the head-turning event. Some headdresses in past years have featured moving parts, while others tower far taller than their wearers.

The first-place winner takes home $3,000. Second prize is $1,000 and the third-place finisher is to receive $500.

Scheduled in conjunction with the annual Fantasy Fest masking and costuming celebration, the ball is billed as the festival’s premier gay and lesbian event. Popular Key West entertainer Tom Luna returns as emcee, with music by WEOW 92.7’s Rudegirl. The show will be opened by La Te Da’s
Christopher Peterson, and there will be a special appearance by Broadway Star Terri White as well as the Aquanettes.

Spectators at the “heady” competition can expect to see Keys celebrity judges, dazzling entertainment and a liberal dose of the outrageous. Between headdress presentations, organizers plan a talent revue featuring the renowned female impersonator Christopher Peterson and other top local performers.

Doors open at 6:30 p.m. and the show, emceed by noted Florida Keys actor Tom Luna, begins at 8 p.m.

The Headdress Ball is presented by the Key West Business Guild and raises funds for the organization’s programs.

Tickets are $30 per person for general admission. Pricing for reserved tables for four people begins at $250. To purchase tickets, visit

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