Lil Nas X Says Wearing a Skirt on Tour Helped Him 'Set My Younger Self Free'

Lil Nas X is breaking down stereotypes, one bedazzled outfit at a time.

Since he first shot to fame with his hit "Old Town Road" in 2019, the Atlanta-bred singer has slayed everywhere from the runway at New York Fashion Week to the red carpet at the Grammys, with his style noticeably taking an even more bold and unabashed turn after he publicly came out as gay in the months following his debut.

"Style is a form of self-expression," Lil Nas X tells PEOPLE in this week's issue. "It's a way to show people who you are, or at least how you want them to perceive you. I feel like to get further in life, you have to shed skins and do things that you normally wouldn't."

Despite his confidence, Lil Nas X, 23, admits he felt a twinge of insecurity before his recent tour stop in his hometown.

"I was really nervous about going out on stage in front of my family and everybody in my cute, little Coach skirt," he says. "But as soon as I walked out, I felt like I was setting my younger self free. Afterwards, my family — a lot of whom used to believe in everything opposite to what's up on that stage — told me they were really proud. I feel like I'm changing some minds."

RELATED: Lil Nas X Offered Pizza to Anti-LGBTQ Protestors Outside His Concert: 'This Is Really Good Promo!'

lil nas X Detroit concert
lil nas X Detroit concert

Lil Nas X

Though Lil Nas X says his personality has remained "the same" since his pre-fame days — "I was always the goofy class clown," he cracks — he now feels a "lot more ambitious and unafraid to go after my dreams."

"I'm less afraid to step out of my comfort zone," he says. "Lil Nas X is helping Montero become more himself. Music has made me much more confident."

So much so that not even a group of anti-LGBTQ protestors could rain on Lil Nas X's parade when they appeared outside his concert in Boston on Sept. 18.

"I sent them pizza!" he says. "One of the protestors was actually really cute, and I called him out on Twitter, but I haven't heard from him. He's either laughing or having a really hard time in the group chat right now!"

The rapper remains very open to meeting someone, telling PEOPLE he did go out "on a date last week."

RELATED VIDEO: Lil Nas X Reveals He's Pregnant — with His Album — in Over-the-Top Announcement Photos

Lil Nas X's journey to self-actualization is personified in Coach's new "Courage to Be Real" campaign video. Directed by Petra Collins, the short film follows the musician as he moves from different rooms that represent key moments in his personal journey — from his early days in the Atlanta suburbs, to achieving fame through music, to reaching new creative heights in digital worlds and becoming the multi-hyphenate superstar he is today.

RELATED: Lil Nas X Shuts Down the 2022 VMAs Black Carpet in a 'Heavy' Feathered Headpiece: 'I Feel Amazing'

"I really wanted to make sure they were going to show me breaking down doors — so, in the video, I literally go through them," he says. "I'm really happy with how it came out."

Lil Nas X in Coach's "Courage to Be Real" Campaign

The campaign is Lil Nas X's first for Coach as its newest global ambassador. Last month, he also made his NYFW runway debut during the fashion house's Spring 2023 show.

"That was really cool," he says. "I felt a little out of place with all these models, but I was like, 'Oh nah, I got this. I'm meant to be here.' I looked a little angry in the face, but I was actually really happy!"

Lil Nas X walks the runway during the Coach September 2022 New York Fashion Week: The Shows
Lil Nas X walks the runway during the Coach September 2022 New York Fashion Week: The Shows

Randy Brooke/WireImage Lil Nas X

Getting to sit next to Anna Wintour during Vogue World's fashion show was also a surreal moment for him.

"She was really nice and congratulated me on everything," he says. "I'm just happy Anna even knows of my work. I didn't know I'd be sitting next to her."

With Wintour's seal of approval, Lil Nas X says he's ready for whatever his next chapter brings. "It's the end of the beginning," he says.