(Photos via Hope & Help, Design by Dylan Todd)
The iconic Headdress Gala returns to Central Florida Sept. 19 after nearly a decade.
The black-tie fundraiser supports Hope & Help Center’s vital work across seven Central Florida counties, supporting HIV/STI prevention, testing and care. Since 1989 more than $7 million has been raised for HIV and STI prevention services.
Originally known as Headdress Ball, the event began as a grassroots effort by friends caring for a loved one dying of AIDS-related complications. In 1987, Orlando interior designers Sam Ewing and Hattie Wolfe lost someone they loved. Patrick Bryan, a fourth-grade teacher known for his gentle manner and warmth, died at 26 years old.
Ewing says he wanted to do something to honor his friend. He and Wolfe got on the phone and raised $6,000 from friends. When they delivered the funds to Hope & Help, the organization asked them to take charge of fundraising.
He says they agreed to do anything to help but needed to find better ways to raise money. A florist on Hope & Help’s board mentioned attending a floral headdress fundraiser in Los Angeles.
In 1989, Ewing and Wolfe spray-painted the Beacham Theatre clean, sold $15 tickets and held the first event — originally called “Night Blooming.” It didn’t become Headdress Ball until 1992. The night included drag queens and headdresses that were created that same day.
Since the first event, Headdress Ball was known as a night filled with bold theatrical performances, fearless self-expression and a room full of people who showed up ready. Headdress Ball didn’t just raise funds, it built Hope & Help into what it is today.
Each year would improve from the previous and Ewing says Hardrive Productions, Inc. really made the night stand out. Ewing and Wolfe were involved with the ball for 25 years.
Ewing says he noticed a response in those that attended Headdress as the community would become more involved to help raise awareness for HIV.
“The stories were so heart wrenching, I’m almost choked up now talking about it,” Ewing shares. “We brought two communities together for one cause and it turned out to be brilliant.”
Headdress Ball went on an extended hiatus after its 29th annual event in 2017 due to a shifting operational landscape and organizational restructuring for its beneficiary, Hope & Help. This year, Ewing is attending as a guest.
“It’s one of the things I’m proudest of in my life, and I just hope that it can live up to what we created, and I wish them all the best of luck this year,” Ewing says.
Thresa Giles, CEO of Hope & Help, talked with the board about priorities for the year. They wanted to bring back the original Headdress Ball.
She spoke with Ewing and Wolfe about their vision and they will be honored the night of at Hilton Orlando.
“The first thing that I wanted to do is really find and talk with Sam Ewing and Hattie Wolfe,” Giles shares. “I was fortunate to able to talk with them on the phone just to hear their input, about why it was even formed, how it got to where it is.”
She says this year will be more than an experience; it will immerse guests the minute they walk into the gala. She says that there will be lights, lasers, aerial dancers and original headdresses. The stage will be unlike any other stage they’ve done before.
“We will have three original Headdresses that they had back since 2002 that were actually saved, and they will make their premiere,” Giles says. “We found the original owner who actually designed it, and he is allowing us to use them. One of those Headdresses will start out one way, but by the end of the night it will be something totally different.”
Grammy Award-winning Motown legend Thelma Houston will headline the gala, something Giles says is most exciting.
Houston is an American singer and actress best known for her powerful 1976 cover of “Don’t Leave Me This Way,” which reached number one on the charts and won her a Grammy Award.
Houston is a celebrated LGBTQ+ ally and icon. Her 1976 disco anthem “Don’t Leave Me This Way” became an enduring dance-floor classic and later a powerful fixture during the HIV/AIDS crisis, cementing her lifelong bond with the community.
She has actively worked with organizations like AIDS Project Los Angeles, Project Angel Food and the Minority AIDS Project.
“I’m extremely pleased to headline the Headdress Gala benefit for Hope & Help this year,” Houston says. “Their mission is one close to my heart, and the work they’ve done for their community is just remarkable. This night is bound to be an incredible one!”
Other entertainment will include over 70 artists like Darcel Stevens, TP Lords, Mala Mia, Amber Mills, Rosie Webber, Bridgette Galore and Gidget Galore.
Alexis Mateo from “RuPaul’s Drag Race” and its “All Stars” spin-off will also be a special guest. The hosts of the night are Johnny Magic, Sondra Rae, Julie Broughton, Chad Pitt and Stevens.
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.
“Taking everything I learned from Hattie and Sam, putting that into where we are today, and honoring what they put together, that’s what the power of expression is about,” Giles shares. “That’s what Metamorphosis is about.
Even though you might change it, you change for what we are today, that power of expression, you never, ever forget where we came from.”
For the dress code, guests are encouraged to be bold, creative and expressive. Fascinators, headdresses and statement pieces are encouraged and celebrated. There will be a red carpet with photographers ready to capture the night.
The festivities will begin at 6 p.m. with general admission check-in and VIP check-in. Red carpet photos will continue until the main ballroom opens at 7:30 p.m. At 10 p.m. the after party will begin and go strong until 1 a.m.
Tanya Hollins, Chief Strategy Officer of Hope & Help, says the money raised from the night will benefit Hope & Help in many ways. She says it is about more than raising money for Hope & Help, it’s about raising money to support the programs that support the community.
“We are able to provide transportation services for our clients who need it, food for those who are impacted by food insecurities,” Hollins says. “We are able to help support our clinic, which also then provides those much-needed medical services for all in our community. We are able to help support groups that we have that then impact all the community.”
Ryan Seunarine, Chief Program Officer of Hope & Help, thinks the gala is not only good for the community, but good for raising funds that go directly back to supporting the community.
“It’s a very inclusive event where we can all get together under one roof, a shared common safe space, to be ourselves and celebrate,” Seunarine shares. “Celebrate the legacy that came before us while we’re looking forward to our future.”
He says the gala protects and honors the legacy of those that came before them. It will educate attendees about Project Stop the Stigma.
Florida ranks among the highest states in the U.S. for HIV rates, with over 132,000 people living with the virus and recording more than 4,300 new diagnoses annually. The state’s overall prevalence rate sits at roughly 574 cases per 100,000 residents, driven heavily by urban centers in South and Central Florida, according to America’s HIV Epidemic Analysis Dashboard.
In Florida the total number of people living with HIV is 135,000 individuals. New annual diagnoses are between 4,300 and 4,600 cases per year. The death rate is 2.8 per 100,000 people, placing it high among U.S. states.
Giles says the highest rate comes from heterosexual African American women at about 20%, and that right after that are heterosexual Latin women.
“Until we can really express that message or what we call Project Stop the Stigma, we need to really share that this is serious,” Giles shares. “Now, HIV is not a death sentence. But knowledge is power, and if you can prevent, if you can take PrEP or PEP, to make sure that you’re safe, it’s about your health and being healthy.”
Giles wants the community to know that Hope & Help will always help the community. The organization works to ensure every person regardless of background, identity or circumstance has access to the care and support they need to live healthier, fuller lives.
“You’re not alone, and we will walk 100%, with you,” Giles says. “I think it’s very important that people know that we are here. And where a door is closed, there’s always a window. That we’ll find a way to get anything and everything that you need.”
The Headdress Gala will be on Sept. 19 at Hilton Orlando, located at 6001 Destination Pkwy, Orlando.
For more information and to purchase tickets, visit HeaddressGala.com. Learn more about Hope & Help at HopeAndHelp.org.
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