Combining captivating entertainment and creative competition, the Key West Headdress Ball has been the premier LGBTQ+ event of the subtropical island’s 10-day Fantasy Fest costuming and masking celebration for the last 40 years!  The ball typically features up to 25 contestants showcasing their unique headdresses, some that tower high above their designers.

The Headdress Ball has been produced since its inception by the Key West Business Guild, one of the oldest LGBTQ+ business organizations in the U.S.  The event serves as a major annual fundraiser for the organization.

This year, the Key West Art & Historical Society is partnering with the Headdress Ball to showcase the works of art that will be worn in the 2023 competition, held on October 26.

This exhibit is sponsored in part by the Department of State, Division of Arts and Culture, the Florida Council on Arts and Culture and the State of Florida, with additional support provided by The Helmerich Trust and Key West Business Guild.