The 19-year-old is a new brand of mega-watt stardom with his unbridled energy and colorful personality.
Charles has swept up hoards of Gen Z makeup enthusiasts with his online YouTube tutorials.
The celebrated social media star got his start at just 16 years old on Instagram, where he offered basic makeup tips and created elaborate eye shadow designs.
Within just a few months, followers flocked to his handle and subscribed to his channel; now, just over two years later, Charles has a reach of 15 million on both YouTube and Instagram.
"I was working really, really hard," he said, thinking back to when he first started on YouTube. "I think people just like being around me and watching my content because it's relatable but still really fun and inspires people. That's like the goal the end of the day. And I think that that's what draws people in."
Charles calls his fans "sisters" who are part of a new generation where it seems like anything goes.
Teen Vogue executive editor Samhita Mukhopadhyay told ABC News that Charles' platform embraces who he is -- and his fans reinforce that.
"He’s saying, 'Yeah I’m a boy, and I’m a boy that wears makeup, and I’m a boy that wears heels, and that’s OK,'" she explained. "He also has the reinforcement of 15 million fans who are saying, 'It's OK for you to be the way that you are; we accept you.'”
At just 17, Charles was named the first-ever male face of CoverGirl in 2016.
"I was shook," he said of being announced the face of the makeup brand's campaign. "I had just started working with the a manager at the time, and she was like, 'Hey, we got an email from CoverGirl' -- and she was like, ‘Yeah, you’re going to be the face of CoverGirl."
He said when everyone started congratulating him, he realized, "Oh, this is, I think, a little bit of a bigger deal than we would've anticipated."
Mukhopadhyay said it was a smart move for the legacy cosmetics brand.
"You have this kid who's garnering millions of people’s attention, so if you’re a legacy cosmetics brand, why wouldn’t you pay attention to the next hot thing in makeup?" she explained.
Charles launched his own line of "sisters" apparel and an eye shadow palette in November 2018. Both sold out in minutes -- and the coveted colorful palette has been restocked and sold out on four different occasions.
"You can literally create any look imaginable, whether it be a super simple light airy makeup look or a night on the town day night makeup book or literally a crazy rainbow drag makeup looks," he said of the endless options with his makeup kit.
Influencers like Charles have created a seismic shift in the beauty industry, and Mukhopadhyay said it’s in part due to "diversity and inclusion."
"There’s a shift in the industry to diversity and inclusion in a way that’s not happening in other industries because of influencers -- and audiences that can speak directly to these influencers," she explained.
Vice president of marketing at Carbon, Brittany Hennessy, who has written about the power of social media influencers, said the change in makeup consumption created an appetite for new content from creators like Charles.
"Makeup used to be something that you put on for special occasions. Then it evolved into something you wear every day," she said. "Now, with YouTube and Instagram and beauty boys and tutorials, makeup is something that people do a whole face and then they just take it off. It’s like playing dress up."
Mukhopadhyay added that "how influencers are disrupting the market" has become a large part of the conversation.
But for an influencer like Charles who appears emotionally transparent despite a full face of makeup, there are still misconceptions about who he really is.
"I think the biggest one is that I'm transgender -- it goes without saying, I’m not," he said. "I'm confident in myself and my gender identity -- [I’m] happy being a boy. But at the same time, I love makeup I have a full set of nails on all the time."
Charles said he has also "done drag looks, worn full wigs, butt pads, the full shebang. Been a woman [for a] few minutes. And I love it."
Social media can be a double-edged sword. Hennessy said that social media can be a "dangerous place" especially for young teenagers, "because it’s a place where they can go and feel really ugly if a photo doesn’t get enough likes."
Conversely, she said they also have access to “find things that make them really happy and learn different ways to express themselves."
Charles said his hope is that in the near future, there won’t be "a conversation anymore" about males in the beauty world, "that people just accept it."
"I want to be a role model for everybody no matter what age, size, where they come from, color. And so like, if that means talking about it to get the word out there and to tell people that it's OK to express yourself, I'm down. I'll talk about it all day long,” he said.
Hennessy said Charles is a great example of non-conformity to help others express themselves.
"The popularity of non-traditional social media stars like James Charles is great because it really gives their audience a chance to just feel like they can express themselves and they don’t have to conform to a specific box," she said. "And you know if James Charles can do it, they can do it."
His unique and beloved personality has also made him a target of hate, which has at times been difficult for his parents, Christine and Skip Dickinson.
"It was really, really hard for us as a family to go through. But I understood it the whole time and I knew what they were doing,” he explained of his parents, who tried to keep him safe from ridicule. "It took a lot of trust for them to understand where I was coming from and once we finally met in the middle it was -- perfect."
Charles' dad addressed protecting his son in a YouTube video after hateful comments appeared on Instagram when the young beauty influencer was named the face of CoverGirl.
"When I first started it was really hard to not look back,” Charles admitted. “I would've gotten into a lot of fights and a lot of drama early on.”
As he grew, Charles said he “got a little better at it and learned to hold myself back and got involved a little bit less.” Now, he "barely" reads comments at all.
Charles, his parents and 15 of his starstruck “sisters” gathered for a meet and greet in New York City at the Sugar Factory and the beauty boy opened up about bullies.
"I did get bullied a lot in high school and personally, I just ignored it," he told the young girls.
"I would try really hard to not pay attention and sometimes too, it is important to stand up for yourself. And sometimes I would clap back and they weren't expecting that," he added.
He also revealed a secret to his "sisters" -- that he’s interested in other ventures beyond makeup.
"I never rest I always like to be going," he said. "I want to work on music, I'm working on sister's apparel a whole lot -- you never know what products will come out."
The ambitious teenager said that once he accomplishes one thing, he’s "on to the next."