One of Orlando’s most iconic charity events, The Headdress Ball is back after almost a decade

Every element of Headdress is designed to surprise, delight, and create a night guests never forget.

The Headdress Ball has been an iconic Central Florida charity event known for bold expression, electric energy, and unforgettable nights. It created iconic moments people still remember nearly a decade after it ended.

This amazing black-tie charity event has raised more than $7 million for HIV and STI prevention services across Central Florida, AND now, the icon is back!

Headdress Gala is returning to Orlando on September 19, 2026 at the Hilton Orlando for a night of immersive performances, community, and celebration in support of Hope & Help.

The Headdress Gala will feature singers.dancers. drag performers. aerialists. acrobats. and more! Ples, this isn’t just about what’s on stage...

Everyone is encouraged to wear fascinators, headdresses, and statement jewelry. Bold, creative black tie that turns heads. There will be a red carpet. There will be photographers. Show up ready to be seen.

Every ticket supports Hope & Help. HIV/STI prevention. Testing. Treatment. Healthcare for thousands across seven counties.

Before it was a gala, before the runway and the spectacle, it was two people who cared deeply about their friend and their community.

Hattie Wolfe and Sam Ewing helped create what would become the Headdress Ball in the late 1980s as a small fundraiser to support someone they loved who was battling AIDS. None of it was about attention. It was about showing up when it mattered most.

That single act of compassion grew into one of Central Florida’s most important fundraising traditions, generating millions of dollars for Hope & Help and helping expand lifesaving HIV prevention, education, and care throughout our region.

Every ticket. Every sponsorship. Every dollar raised. It supports Hope & Help Center of Central Florida. For over 30 years, Hope & Help has provided HIV/STI prevention, testing, and treatment across seven Central Florida counties.Thousands of patients served. Barriers to healthcare removed. Lives saved.

The Headdress Gala fuels that mission and pushes it forward. Expanded services. New care models. Mental health support. A future where access to quality healthcare is never out of reach.

Tickets and tables are now available.

headdressgala.com

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