07-07-2025
Finding Hope at Drag University
HOUSTON – The email said they'd spend the weekend in drag, so Chloe Montgomery packed the only dress she owned. It was white with a flower print, feminine in a way she found fresh. The first time Montgomery saw the dress, she'd felt the thrill of becoming herself. But eight months had gone by, and she hadn't worked up the courage to wear it. Maybe this weekend, she told herself.
Montgomery had spent six weeks attending classes at Drag University, a free program that taught Black and Latino Texans not only how to lip sync and put together an outfit, but how to navigate life in a state that has long led the way in curtailing LGBTQ+ rights.
There was so much Montgomery was afraid of. She didn't know how to dance or apply makeup. She worried she'd look bad in the dress. She hadn't told most of her friends or colleagues she was transgender, and increasingly, both her state and the country were targeting people like her. In March, one Texas state lawmaker had introduced a bill to make transitioning a felony. It stalled. And President Donald Trump signed a slew of executive orders that targeted trans people, including one that deemed it the official policy of the United States that sex is not mutable – a stance shared by two-thirds of Americans.
The growing anti-trans sentiments terrified Montgomery, but this was Drag University's final weekend and she knew she couldn't waste it on her fears. The organizers had rented a bright and airy house with a pool and sprawling trees. Montgomery looked out across the expansive yard and told herself that this weekend, she would do the things that scared her. Soon, she and the others would graduate, and she would no longer have Drag U to buoy her each week. She would have to lift her own self up.
Still, she wasn't quite ready to try on the dress, so Saturday morning, Montgomery slipped on a crop top and a flannel button-down she'd found at a thrift store. She pulled on a borrowed blond wig, and she took a spot on a big leather couch. The seven other students were, like her, working-class queer people in their 20s and 30s who were trying to find meaning and power through drag.
They had learned the fundamentals, and this retreat was supposed to be both a reward and a culmination. It was the last time they'd meet before they graduated and performed for an audience in May. Over the next two days, they would try out their acts in front of professionals, and they'd talk about all the things that led them to drag.
The group spent the first day of the getaway talking to a Harris County family court judge who presides over name changes. Though Texas has tried to outlaw many aspects of transitioning, for now, adults can still decide what to call themselves.
Your name, Judge Lillian Alexander told the group, is 'what you want it to be. And I honor that. So I'd like each of you to tell me your name.'
Montgomery knew her classmates by their drag monikers. She called them Kaycee and Mahalo and Selina Vile, but as they went around, they introduced themselves to the judge by their legal names. Kevin. Angel. Kimmet.
Montgomery wasn't sure how to answer. For some people, drag is a persona, a costume they put on for special moments. All year, Montgomery had treated her feminine self as something she put on and took off, too. Online and at work, everybody knew her by the name her parents had chosen. It was still her legal name, but it wasn't the one she called herself anymore.
The judge caught Montgomery's eye. All of a sudden, Montgomery felt ready.
'Chloe,' she said, and it felt like a declaration, like the first of many steps she'd need to take to embody herself. 'My name is Chloe.'
Though most of the people in Drag University have lived their whole lives in Texas, Montgomery is a transplant. She moved to Houston from Providence, Rhode Island, last year because it was the cheapest city she could find with a sizable population of Black queer people. She arrived hoping to puzzle herself out.
She'd left Howard University a decade earlier without finishing her journalism degree, and she'd felt mostly lost in the years since. She'd long thought privately that she wanted to be a woman, but she'd never hated what she thought of as her 'boy body.' She just felt disconnected from it.
She realized she was trans in her 30s, but even then, she wrestled with the idea. Her life would be easier, she thought, if she continued living as a guy. She wouldn't lose friends. She wouldn't have to endure whatever comments people made. But once she understood that sense of disconnection was gender dysphoria, she found the truth impossible to ignore.
Almost as soon as she started estrogen last summer, Montgomery's mind and body began to align. The medication enabled her to do more than just exist. With it, she could be silly for the first time in years. She cracked jokes and daydreamed about creating a meaningful life for herself, one with close friends and a job she liked.
Montgomery earned $16.50 an hour doing quality control at a car dealership. The salary barely covered her groceries and rent, but she longed for a single piece of feminine clothing, so one night, she went online and picked out a $25 dress she suspected she'd look good in. The top was fitted, narrow at the hips, and the flower-printed skirt widened into a flowy hem.
She felt hopeful when it arrived, but she couldn't bring herself to let the world see her the way she saw herself. She stashed the dress in her closet without trying it on, and she showed up to work each week still dressed in men's clothes.
All fall, she felt broke and alone. Then, a few weeks after the presidential election, she saw an Instagram ad that the Black LGBTQ+ nonprofit Normal Anomaly Initiative had posted for Drag University.
'This cohort will learn skills to enrich their drag careers, including makeup application, hair styling, beginner garment tailoring, and stage presence,' the announcement said.
Montgomery was intrigued. Politicians have tried to criminalize drag since at least the 1800s, and Montgomery had read that performers and trans people were among the first to fight for civil rights, though they rarely went at it alone.
It would be easier to transition, she thought, if she had a community alongside her.
They met Tuesday nights all winter at an LGBTQ+ drop-in center south of downtown.
Each participant gravitated toward a different kind of drag. Syca'Ru was an androgynous person who called themself 'a drag thing.' Berry Kay was a cisgender woman who channeled 'the divine feminine.' Beau Vine performed as a bull. They spent hours learning how to breathe and pose and talk to powerful people. They wrote speeches. They chose names. Montgomery had called herself 'Chloe' for months, but in class, she adopted a new last name, one cribbed from her favorite Cape Verdean song – 'Yamore.'
Between lessons, the group talked about everything that was happening in Texas and in their own lives. State leaders had once again tried to restrict drag performances – a move they say is needed to protect children – and they'd banned trans people from changing their sex on official documents. The Drag U participants told each other they felt afraid in ways they once hadn't.
Most weeks, Montgomery left Drag U lessons and cried the whole way home. Her classmates saw her as a woman. But a few hours a week no longer felt like enough.
The Monday before the final class, Montgomery shared her first Instagram picture of Chloe. She'd driven to the grocery store, and she snapped a selfie in the parking lot. She was sweating under her bobbed wig, and she wasn't wearing anything particularly special, but she felt like she'd captured something real. She paired it with a quote from the movie 'Twisters': 'If you feel it, chase it.'
For Montgomery, transitioning was a series of highs and lows. Nearly 100 people liked her Instagram post, but she was still too broke to buy makeup or her own wigs. Plus, every day, the government seemed to find a new way to target queer people.
By the time Montgomery arrived for the final retreat, Drag U organizers and participants felt beaten down. Texas had introduced 88 anti-LGBTQ+ bills since classes started, and Trump had criticized the Kennedy Center for the Performing Arts because the venue featured drag shows.
'THIS WILL STOP,' the president wrote on Truth Social after he appointed himself the center's chairman.
Drag U's organizers weren't sure how they'd endure. Executive Director Ian L. Haddock told the group he worried Trump's promise to slash funding for anything related to diversity, equity and inclusion issues would affect LGBTQ+ initiatives. The administration had also ordered massive cuts to the Centers for Disease Control and Prevention, a reliable source of funding for the nonprofit.
'In this sociopolitical climate, everything has been obliterated,' Haddock said. 'Many organizations like ours will not make it through.'
For now, Haddock said, he wanted the weekend to be a respite. His staff spent hours cooking seafood, tacos and other big meals. They brought out video cameras and lush backdrops to make the participants feel like stars, then they introduced an actual star – A'Keria Chanel Davenport from 'RuPaul's Drag Race.'
Davenport arrived midday in a shimmering blue suit dress she'd customized with pink ostrich feathers. She told the group she had transitioned and detransitioned, and these days she was 'totally a dude' at home, even as she presented a glamorous femininity onstage. She'd been around a while, she explained, and she'd learned that the only way to survive a tough political climate was to pursue a life you love.
'This art form saved me,' Davenport said. 'I have no control over who's president. But what I can control is how I find my safe space, and drag is my safe space. So you have to keep going because if you find your community, and you celebrate yourself as well as each other, trust me, it's very rewarding.'
The next morning, Haddock told the performers they'd each get $250 to spend on a graduation outfit. Beau Vine buried his face in his hands.
'I can finally afford JoAnn Fabrics,' he said.
Montgomery wasn't sure yet what she'd wear to graduation. She hadn't worked up the nerve to put on the dress, even during the retreat. She left it folded the first day, and on the second, she chose a black catsuit and pink-accented Nike high-tops instead.
She was quiet as she took her spot on the couch. She knew both drag and transitioning required so much more than an outfit, but she'd come here to feel liberated, and that meant she'd need to wear the dress in front of people.
Haddock loaded a few of his favorite drag performances onto a big TV. As Montgomery and the others watched an artist named Jazell Barbie Royale lip sync in a revealing gold leotard, Royale appeared in real life.
'What y'all watching?' she asked with a coy smile.
The group screamed and doubled over. Montgomery jumped up. Royale has won nearly every pageant imaginable, and she had flown to Houston just to talk to them.
Montgomery watched Royale, and she longed to be as poised as she was. Royale wasn't just a drag queen. She was a trans woman who'd come out two decades ago.
'Back then,' Royale said. 'People had to be as stealth as possible for their safety. We didn't have any rights. We didn't have mentors or gender-affirming care or doctors to prescribe hormones.'
Montgomery knew she was lucky in ways many trans people were not. She had insurance and a doctor she liked. Her estrogen prescription was good for several months.
'All right,' Royale said. 'I want to see y'all perform. Pick a song. You have 30 seconds.'
Montgomery's heart sped up. In a few minutes, everyone would see what an awkward dancer she was. She wiped her hands on her catsuit, told the DJ her song choice, then tried to snap along as the first few people went. Royale told Syca'Ru they had the talent to be a professional, and after Beau Vine finished a high-energy, Bruno Mars-esque performance, Royale said the drag king knew exactly who he was. Montgomery pulled a pair of sunglasses over her eyes.
Royale had a small number of critiques for the other performers – slow down, vary your moves – but when Montgomery took the stage to Janelle Monáe's 'I Like That,' Royale stopped her after 45 seconds.
'I want you to go back and pick a song you actually feel,' Royale said.
Syca'Ru jumped up to brush Montgomery's hair, and a few of the performers checked to make sure Montgomery was okay. But she didn't feel shaken. Hadn't this been what she wanted? A community? Mentorship? Joy?
Montgomery told the DJ to play Adele's 'Someone Like You.' She'd been listening to it on repeat after an old relationship she'd hoped to rekindle hadn't rekindled after all. She pulled an enormous pink boa around her shoulders. She tossed her sunglasses aside, and the song began. Montgomery didn't dance with the kind of liquid ease Syca'Ru did. She kept her shoulders tight, and she moved in the smallest of squares. But when Montgomery finished, Royale told her she'd done much better.
'When you're onstage, you have to leave behind all insecurities,' Royale said.
By that evening, the only thing left to do was record their final projects, a video diary where each person explained why drag is important to them.
Most chose a special outfit to wear. Beau paired a cowbell necklace with a leather, floor-length vest he'd sewn himself. Hermes wore the Autism Self Advocacy Network T-shirt that most spoke to their neurodivergence. Montgomery knew she only had one option. The dress.
She carried it to the bathroom. She slipped it over her head. She knew she needed something to cinch the waist, but she only had a men's belt, so she tightened the brown strap around her middle, then twisted it so the buckle was in the back. It wasn't perfect, but it was right. When Montgomery looked in the mirror, she felt a euphoria she'd never experienced. The person in the reflection was her.
'Chloe,' Haddock shouted. 'You're next.'
Montgomery walked into the living room to wait her turn. She put in her AirPods and queued up Beyoncé's 'Dance for You.'
The song is Beyoncé's ode to a man, but Montgomery heard the lyrics as a promise to herself.
Wanna show you how much I appreciate you, yes.
Wanna show you how much I'm dedicated to you, yes.
Montgomery twirled and moved her arms the way she imagined a ballerina would. The flowery hem of her dress swished, and she allowed herself to take up the entire room. She was dancing for herself as herself, and she'd never felt anything better.
When it was time to record, Montgomery swooped her hands around and attempted to explain all that the last two months had meant to her.
'I am trying to find who I am,' she said. 'And in finding myself, I am able to become the most powerful version of myself, a version who is free, who is unapologetic. And that makes me feel great because the little version of myself was too afraid to be seen.'
Her eyes glistened, then spilled over. Even now, she couldn't really dance or put on makeup. But that didn't bother her anymore.
'Chloe Yamore means 'Chloe, I love you,'' she said. 'I love you enough to go for it even though I'm afraid.'
Soon, she knew, she'd tell her boss she was a woman. She'd change her name on Instagram, and she'd allow her friends and family members to know her as Chloe. But first she'd do the thing she'd been putting off all year. She would leave this house and go out into the world. This time, she would not let her fears get the best of her. This time, she would wear the dress.
