PHOTOS: Headdress Gala makes triumphant return in Orlando

(Photo by Bellanee Plaza)

ORLANDO | Attendees entered the Hilton Orlando on Sept. 19 to see stilt walkers and elaborate headpieces for the Headdress Gala in support of Hope & Help.

Founded in 1988, Hope & Help is a nonprofit health organization that provides “compassionate, comprehensive care and education to eliminate the spread of HIV and reduce related health disparities in Central Florida,” according to its website.

This year’s event centered on the theme “Metamorphosis: The Power of Expression,” giving attendees an opportunity to express themselves through colors, imagination and elaborate headpieces. The theme also added a visual element to an evening focused on raising funds and awareness for the organization’s work in Central Florida.

“The Headdress Gala is more than a fundraiser; it is a declaration that beauty, creativity, and compassion can coexist with purpose,” stated Theresa Giles, CEO of Hope & Help, in the 2026 Headdress Gala program.

Throughout the evening, attendees had the opportunity to participate in live auctions featuring items such as a Virgin Voyages cruise and an autographed “Jolene” music sheet from the late Dolly Parton.

Local entertainers and community figures also took the stage to discuss the importance of the gala’s return after a nearly decade-long hiatus.

As previously reported by Watermark Out News, the Headdress Ball went on an extended hiatus following its 29th annual event in 2017 due to a shifting operational landscape and organizational restructuring for its beneficiary, Hope & Help.

The return of the event brought together community members, entertainers and supporters for an evening that combined fundraising with performances and recognition of individuals involved in HIV/AIDS awareness and community initiatives.

Among those recognized during the evening was Orlando Mayor Buddy Dyer, who received the Chuck Hummer Visionary Award in recognition of his support for HIV/AIDS awareness and initiatives supporting housing and community-centered care throughout Central Florida.

Entertainment throughout the night included singers and drag performers who brought music, dance and performances to the stage.

Mala Mia, a “rising star” of Orlando’s drag scene, according to the event program, performed to “Alien Superstar” by Beyoncé, leading the audience in singing along to the song.

Another performer was Alexis Mateo, who also began her career in Florida. The “RuPaul’s Drag Race” Season 3 finalist brought Latin flair to the Headdress Gala stage, adding another style of performance to the night’s lineup.

The evening’s music was led by Grammy Award-winning singer Thelma Houston, an advocate in the fight against HIV and AIDS. Houston brought the disco era to Orlando with a performance that had attendees on their feet and dancing throughout the night.

The return of the Headdress Gala also marked the continuation of an event that has a history of bringing attention to HIV/AIDS awareness and supporting the work of Hope & Help in Central Florida.

For more information about the services provided by Hope & Help, visit HopeAndHelp.org.

Watermark Out News attended the Headdress Gala. View our photos below.

Photos below by Bellanee Plaza.