Thelma Houston to perform at Headdress Gala
Thelma Houston Credit: Courtesy

Dress to impress, and then take it a step further all for a good cause. Saturday’s Headdress Gala is a night celebrating fashion, creativity, performance and community solidarity. With the last Headdress Gala (formerly the Headdress Ball) having taken place nearly a decade ago in 2017, this returning tradition is set to leave Central Florida shook. The party supports HIV/STI prevention through Hope & Help, a Florida-based nonprofit providing preventative care, treatment and even holistic primary medical care across Florida.

This year’s fête, themed “Metamorphosis,” includes a star turn from Motown titan Thelma Houston as the headliner, best known for Grammy-winning disco smash “Don’t Leave Me This Way.” Get ready for an assuredly unique blend of drag, acrobatics, production and high-fashion headwear. 

We talked with with Thresa Giles, CEO of the nonprofit Hope & Help and also the event presenter, to find out more about the returning Headdress Gala, happening Saturday at the Hilton Orlando.

Tell us about bringing back the Headdress Gala.

Thresa Giles: So it’s been probably closer to nine years, maybe seven or eight years since they’ve had it. When I came on board a little over a year or so ago, I found out about the Headdress, originally called Headdress Ball. So I actually found out who the creators were, went and talked with them to find out why was it important, why did it [become] such an icon, and also why did it stop. I’ve taken everything that they intended it to be, and now also brought it forward to where we are in 2026.

So it is definitely the iconic event that it was when it was first created (by Sam Ewing and Hattie Wolfe), but it’s also like a twist, like a metamorphosis, which is our thing, to what we are today. … What Headdress is and what we believe the Gala is, is that we’re all, in Central Florida, we’re all in this together. We’re supporting each other and it’s the night, no matter what is happening out in that world, you have one night of just being able to be who you are, express yourself and have an enjoyable time.

How were you able to get Thelma Houston to join in as a headlining performer?

A lot of times people resonate with your theme, resonate with what’s happening. And of course, we told our story when we reached out to say who we were, why we existed, and what we’re doing for our community. And she was like, “Absolutely. That’s exactly where I want to be.” And so we were very honored when she said yes.

How did you go about curating the eclectic lineup of performers?

The first thing I did was partner with two great people that have ran Headdress before. They understood it back in 2014. And so being able to go to the production company and getting the event planner all in one has just been phenomenal. So they started using their resources and contacting some of the original people that were back with Headdress from 2002. I will say three of the original headdresses that made their debut between 2001 and 2005 will be showcased at this Headdress.

He still had it and he made it. So when we open up the ballroom, one of the headdresses will be on the stage. It’s going to evolve throughout. It’s going to metamorph throughout the night, and it will change. And then the other two will make their debut again, but these are three of the original, and that’s what I really wanted, that feel. Original from back in the early 2000s that still exists today.

This is a charity event, but also very performance-oriented. How do you blend these two missions for attendees?

It’s well-planned, meaning making sure that we tie everything back to the purpose, the reason that they’re there. And at every interval. throughout the night, you’re always going to be reminded of why we exist, whether it be from people that are attending that actually have used our services, hearing from the community throughout the night, in-between every act, there’s always going to be a reminder of why we’re here, whether it’s through a video, through words, through expression.

So every part of the night, when it starts with at 6 p.m. to 10.30 p.m., even after the gala has ended, we go right into a party with a purpose. And the reason we called it that is because the purpose is the hope and the help, transforming people’s lives, their mindset to think about themselves, think about their health, think about their mental health. So every part of the Gala will always be the remembrance of it. There’s always that reminder.

6 p.m. Saturday, Sept. 19; Hilton Orlando, 6001 Destination Parkway; headdressgala.com, $350-$5,000.

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This article appears in Sept. 16-22, 2026.