Contestants in the 2022 Headdress Ball line the stage awaiting the judges’ decisions for the $3,000 first-prize winner. FLORIDA KEYS NEWS BUREAU/Contributed

The year was 1983. Disco balls still glittered in Key West, where a still-new fall festival, called Fantasy Fest, was in its fourth year and drawing new events annually. That year spawned the Headdress Ball, now in its fourth decade of design and creative costuming.

This year’s 40th annual Headdress Ball, an over-the-top showcase for mask-makers and costumers, takes place Thursday, Oct. 26, at Key West’s Coffee Butler Amphitheater in Truman Waterfront Park. Doors open at 6:30 p.m. and the show starts at 8 p.m.

The Headdress Ball is the festival’s premier LGBTQ event. Plans call for it to feature 12 to 15 contestants, all wowing the audience with unique headdresses — even some featuring moving parts or towering high above their wearers.

Although most participants are costumed from head to toe, entrants will be judged only from the shoulders up as they vie for the first-place prize of $3,000. 

The event includes live entertainment by female impersonator Randy Roberts, Key West’s Laurie Thibaud as emcee and music overseen by DJ Rude Girl. The event always starts with an introduction of the newly crowned king and queen of Fantasy Fest. 

Ticketholders are welcome at the amphitheater at 6:30 p.m., providing ample time for them to mingle and take photos with entrants before the show begins at 8 p.m. 

Spectators also can enjoy bar and wine service and have preordered food delivered to their table during the event.

The Headdress Ball has been produced for the past 40 years by the Key West Business Guild, one of the oldest LGBTQ business organizations in the United States. Proceeds from the event help the guild support Key West’s gay and gay-friendly enterprises, community and the island’s position as a leading LGBTQ vacation spot. 

Tickets are $320 for a premium table for four people, $270 for a VIP table for four, $35 per person for chair seating and $30 per person for general admission with lawn seating. To purchase tickets and preorder food, visit

Headdress history

Longtime Key Wester Pete Arnow, who has organized the Headdress Ball for the  past 30 years, recalled the start of one of Key West’s most dazzling events, writing, “The Headdress Ball  was one of the first events of the newly organized Fantasy Fest celebration in the early 1980s. The first ball was held at the old Monster Bar (now the Hog’s Breath) on Front Street. 

As it grew, the Headdress Ball moved to the Copa Dance Club (now Wyland Gallery) in 1985. Bleachers were installed on Duval Street so people could watch the elaborate headdress entries arrive. This was the disco era, so the Headdress Ball consisted of an elaborate disco dance with Miami’s top DJs.

“When the Copa burned down, the ball moved to the Bourbon Street Pub, then to the Eaton Street Theater (today’s Key West Theater) and then was produced under a tent at the Atlantic Shores Resort. Table seating was added. When the Shores closed, the Southernmost Hotel hosted the event. The Headdress Ball outgrew that location and was moved to a bigger tent at the Truman Waterfront Park. In 2017 Key West Mayor Craig Cates and the City of Key West afforded the Headdress Ball the honor of first to perform at the new Coffee Butler Amphitheater right after Hurricane Irma. COVID canceled the 2020 and 2021 Headdress Ball.