(Photo via Headdress Gala’s Facebook)
ORLANDO | Orlando’s iconic black-tie charity event, Headdress Gala, will return after nearly a decade Sept. 19 with its bold and theatrical energy.
Originally known as Headdress Ball, the event began as a grassroots effort by friends caring for a loved one dying of AIDS-related complications. For decades, Headdress has stood apart in Central Florida, known for theatrical staging, bold performances and a room charged with energy.
The Gala benefits Hope & Help of Central Florida, supporting its work in HIV and STI prevention, testing, treatment and education.
Thresa Giles, CEO of Hope & Help, talked with the board about priorities for the year and they wanted to bring back the original Headdress Ball. Giles found the creators — Hattie Wolf and Sam Ewing, who also detail their efforts in “Greetings From Queertown: Orlando,” now streaming on YouTube — to speak about their vision. They will be honored the night of.
Giles wants the Gala to be a purposeful and enjoyable time that she thinks everyone deserves. She wants the community to come back together.
“We were sort of torn apart when overnight they tried to erase the Pulse crosswalk, but you saw people come together because it’s important,” Giles shares. “We are here, we are just as important and we’re going to be here.”
Across 29 historic events, the Gala has raised more than $7 million in support of HIV and STI prevention and care services, shaping its legacy as both a cultural event and a serious force for impact.
This year’s theme, “Metamorphosis: The Power of Expression,” leans into what Headdress has always done best: spotlighting individuality, amplifying creativity and turning a black-tie fundraiser into something unforgettable.
“The reason we chose metamorphosis is because there has been a lot of change,” Giles says. “The name has evolved into gala and that metamorphosis is bringing that change no matter what’s going on, no matter what’s happening in the world and how scary some of that world could be. We can take an evening and meta-morph to that world of make-believe in entertainment and innovation.”
Giles says the Gala honors the legacy of Hope & Help while positioning the organization for meaningful growth in the years ahead.
Every ticket funds HIV/STI prevention, testing and treatment for thousands of patients across Central Florida at Hope & Help. For over 30 years, Hope & Help has been on the front lines of HIV/STI prevention, testing, and treatment across seven Central Florida counties: Orange, Osceola, Lake, Seminole, Brevard, Hillsborough and Pinellas.
Although Giles couldn’t share all the details on the entertainment and performances, she says it will be over the top. The headliners will be announced sometime in April and will be shared on social media.
“At first I was overwhelmed because it is so much bigger than anyone thinks it is, it’s not just a regular event,” Giles explains. “But then I came back into the excitement of doing the run of show … It’s almost like a Broadway production.”
The Headdress Gala will be on Sept. 19 at Hilton Orlando, 6001 Destination Pkwy, Orlando. Tickets can be purchased at HeaddressGala.com.
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