Like all Webby Award winners, Jools Lebron was required to limit her acceptance speech to five words.
“Very demure. Very successful. Period.”
It was a fitting choice for the beauty influencer, who received the honor in 2025. The previous year, she went viral after popularizing the “very demure, very mindful” catchphrase on TikTok. In a matter of weeks, she booked campaigns with major brands such as Lyft and Verizon, appeared on “Jimmy Kimmel Live,” and gained celebrity fans including JLo and Kim Kardashian. By the end of 2024, Dictionary.com had selected “demure” as the word of the year.
But Lebron’s speech only told half the story.
Privately, the Chicagoan was battling a cocaine addiction fueled by her sudden fame and fortune.
“I felt hopeless,” said Lebron, 33, of Austin, who finally shared her struggle with her family — and on TikTok — earlier this year.
“I had to say, ‘I’m not at home working for five days straight. I’ve been doing drugs for five days straight and I can’t stop anymore.’ I had to say something to someone, because to everyone, everything was going so good.”
Today, Lebron is sober and working to rebuild not only her life, but her career and finances, which were impacted by her substance abuse issues. Concerned that she has been “dissolved down to a meme,” she is determined to become a force in the beauty industry. But more than that, she wants to inspire others who look up to her as a curvy Black and Puerto Rican trans woman.
“That’s what I want to be known for,” she said. “Divas who might be the bigger girl in the friend group, who might be the trans girl in the friend group, who might be the one who feels like the odd one out, can feel beautiful. They can say, ‘There’s someone that looks like me who is doing it,’ and that’s going to give them every bit of power that they need to continue on.”
A ‘very bold’ personality captures the internet
In conversation, Lebron is boisterous, funny and friendly, and laughs often. She is regularly seen with winged black eyeliner and hip-length hair. Given her flashy nature, she was being ironic when she provided her famous “demure” makeup tips on TikTok. Filmed on a break during her shift at the Mariano’s in Western Springs, the video now has 57.5 million views.
“I’m clearly giving Bratz doll,” she said. “So the whole thing was me playing on the fact that I’m not demure. I’m very ostentatious, I’m very bold, I’m very crazy. I was making fun of myself.”
Lebron’s tongue-in-cheek approach and memorable delivery captured the public’s attention, said Christina Steed, a marketing consultant and professor in DePaul University’s College of Communication, who studies and works on social media campaigns.
“Her use of an old-fashioned word became this cultural phenomenon that played on social expectations and humor to give people who resonated with it an everyday language,” Steed said.
“It could be used for going to work, ordering coffee, posting selfies. [‘Very demure’] had infinite adaptability. You could insert it in almost any aspect of your life, and it connected you to other people who were doing the same thing.”
Lebron’s knack for entertaining goes back to her childhood in Humboldt Park and Stickney. With dreams of being a pop star, she was always performing, dancing and cracking jokes.
“Who she is now is who she’s been since she was little,” said her mother, Esther Fregoso, 58, who said she regrets not doing more to encourage Lebron’s gender expression.
“Jools didn’t have options to get big hair when she was little, but that’s definitely something that she wanted,” Fregoso said. “Looking back, I feel a little bit guilty, because times are different now and parents accommodate a lot of stuff. We were not running around saying, ‘Let’s get her a wig.’ Looking back on that, I wish I had.”
Instead, Lebron said she compensated by wearing hair extensions, tight clothes and makeup under the guise of being a “scene kid” who embraced 2000s-era emo, metalcore and pop punk music.
“I always tried to look for a loophole,” she said.
For Lebron, coming out as gay in high school did not bring the relief she craved, and she struggled with her identity as she entered adulthood.
“I felt like I was still trapped, like there was still something that was weighing on me,” she said. “It sent me into such a depression that I unfortunately made an attempt at my life.”
After receiving therapy, Lebron came out as trans at 21.
“It was the first time I felt like there wasn’t a war internally,” she said.
A ‘perfect storm’ of fame, trauma and money
But life was not easy for Lebron as she navigated the ups and downs of a career as an influencer. She got her start on YouTube in the 2010s reviewing Bratz and Monster High dolls, and providing makeup tutorials. Failing to gain momentum, she worked a series of restaurant jobs and took cosmetology classes at the Paul Mitchell school in Chicago.
Later, a pivot to TikTok brought Lebron a wave of success; she gained nearly 1 million followers in three years and partnered on brand campaigns. But after she made comments about helping Palestinians amid the war in Gaza, Lebron said her management dropped her. TikTok users reported her videos, her account was demonetized and brands stopped reaching out.
Forced to move back home, she battled depression and had her first bout with drug addiction.
“I was crashing out because I just felt so heartbroken,” she said.
Following that low point, the success of the “demure” video seemed like a godsend. Suddenly, she was getting recognized in public and making more money than she’d ever seen; from the end of 2024 to mid-2025, she estimates earning $500,000.
But she also had ample access to drugs.
“When you’re in these influencer spaces, it is more common to be offered cocaine than to be offered a cigarette,” she said. “It was so normalized.”
Lebron said the drugs not only contributed to her reckless spending, but intensified her feeling that she was losing touch with reality. And based on her past life experiences, she feared something bad would eventually happen to curtail her happiness.
“I just couldn’t accept that good things were truly happening to me,” she said.
Lebron said she used her money to woo a series of men, some of whom were abusive. She said she was trying to meet a desire for power and control, while also putting herself in harm’s way because, deep down, she didn’t expect to have a good life as a trans woman of color.
Lebron’s close friend, Sage Bash, said she could see those dynamics at play.
“She’s a trans woman who has had to fight for survival in various stages of her life,” said Bash, 34, of the Lower West Side, who is also a trans woman. “It doesn’t matter if she has a rock star personality if someone just hates trans people.”
Bash said Lebron faced a “perfect storm” of fame, trauma and money without enough resources to navigate through it all.
“She felt like [drugs] were her only escape,” Bash said.
Lebron said she has stayed sober by going to therapy and being accountable to her family and followers. And others have said her story has helped them.
“I just feel so bad for that version of myself,” she said. “I deserve so much more, and I don’t want to go through that again.”
Her mother praised her progress and dedication to supporting others.
“She is on a journey and it is a struggle every single day,” Fregoso said. “She’s trying her best to be an advocate for herself and for underdogs.”
Lebron has started to pick up more brand campaigns. Her latest Illinois-based partnerships include a Peach Crème Lon Lon Milk lip gloss with SushyGlow, and a limited-edition Divalicious shake at Protein Bar and Kitchen, which benefited the LGBTQ+ nonprofit Center on Halsted during Pride month.
But she is also focusing on embracing the “little things,” from taking walks outside to spending time with her family members, who live with her in a two-unit building.
“I’m counting my blessings because I didn’t think I would leave the ‘very demure’ era alive,” she said. “I’m still kicking, I’m in good health and I have the job of my dreams.”