When Wiz Khalifa catapulted himself into the hearts of music lovers in 2010 with the infectious single “Black and Yellow,” fans quickly grew attached to the wiry Pittsburgh rapper. Of course his poignant sing-songy records were appealing to the younger demographic, but his fashion sense was what really lured the masses. His swagger emanated from simplicity, and rather than draw attention with gaudy jewelry, Wiz’s bravado came with a fresh pair of shades and his trusty Levi’s®.

Before Wiz, rappers often drowned themselves in the baggiest pair of jeans they could find. Rather than following suit, Khalifa opted to be a trendsetter in not only music, but more importantly, fashion.

Image via Christian Weber

“Baggy jeans are done!” Wiz exclaimed in a 2011 interview with AskMen. “My­ style inspirations are to just be myself; I like to just feel comfortable, but also to be looking crazy, too. I mix a lot of colors and different things together, but the main thing is to just feel comfortable and to be me. I definitely like a lot of Japanese fashion, European fashion, of course, and skateboard fashion and stuff like that. I mix all of that together.”

When Wiz spoke to Complex this week, he revealed that his love for Levi’s originated from seeing one of his idols sport them with grace.

“For me, when I was younger, a stylist told me it was all that Snoop [Dogg] wore,” says Khalifa. “So I immediately fell in love with them.”

From then on—Wiz was 19 at the time—he wore them everywhere he went. From performances at the Bamboozle Festival and his Rolling Papers summer tour in 2011, to appearances on MTV’s RapFix Live and BET’s 106 & Park, Wiz’s loyalty has always remained with the San Francisco-based brand.

today i put on a pair of 501 jeans and felt perfect

— We Dem Boyz (@wizkhalifa) June 10, 2010

It’s not just out and about—it’s even in his music. On numerous songs, Wiz has paid homage to his favorite jeans. On the record “Getting Up,” Wiz rapped, “Excuse me, my jeans Levi,” while on his platinum single “Young, Wild & Free,” Wiz spit, “And look clean don’t it/Washed it the other day, watch how you lean on it/Give me some 501 jeans on it.” There are other Levi’s mentions on the title track for his mixtape Cabin Fever, and the song “Superstar” on his first album, Deal or No Deal.

Last year, to commemorate the 140th anniversary of the 501®, Levi’s released a limited edition book, 501 Interpretations, in which fans, designers, and musicians—including Wiz, of course—modeled the jeans in ways that reflected their personal style. To this day, the 27-year-older rapper finds it incredible that people consider him to be a paid spokesperson for Levi’s, when in reality he was always just trying to be himself.

“I think it’s awesome!” he says with pride in his voice. “It’s really an honor people even consider me one of the first to do so. That’s tight.”

When asked if he has intentions of having his son Sebastian carry the torch and represent Levi’s like himself one day, Wiz gleefully responded, “Definitely, man. Definitely.”