Why Jelly Roll Says This Significant Tattoo Represents ‘Redemption’ and ‘Second Chances’ (Exclusive)

Wherever Jelly Roll is headed, it’s in style.

The 40-year-old musician has just released his second collaboration with HEYDUDE and says that no matter the occasion, you can always catch him wearing the brand. “My team can tell you this firsthand: We are from the hotel to the plane to the show to the event to rehearsal, which is something to be grateful for, but you are even more grateful when you are able to be comfortable as much as possible,” Jelly Roll tells PEOPLE. 

The artist, who mentions he’s worn HEYDUDES “on the red carpet, performing, rehearsals for SNL, all over,” admits that this opportunity makes him feel incredibly lucky. “From who I represent and the people I represent in America, also even in country music, to being one of the first country artists with my own shoe… I don’t know man, it’s just cool and it could have happened with anybody,” he shares. 

Jelly Roll adds, “I’m a dude anyways, and it worked out perfectly… They’re affordable, but they’re fly. I come from a middle-class, lower-class family and you can wear these with pride.”

It’s not just his shoes that represent Jelly Roll. The “Lonely Road” singer is also well-known for his tattoos, which tell a story. “My broken chains — want to hear the story about these? This is fun,” he says. “The broken chains are on my arm. One, it is just about breaking chains in life — anything that is bounding us, any bondage that we have, any addiction, anything we think God can’t get us through. We can break those chains.”

The idea for the chains came to Jelly Roll through music. “It started because me and Taylor Phillips and Jackson Dean wrote a song on the bus called ‘I Can’t Break These Chains,’” he shares. “We loved the song so much we got the tattoo of the breaking chains that day. And we still never put that song out! We should put that song out.”

It only made sense to incorporate those chains into the shoe design. “I love that this symbol is on the shoes. It’s Jelly Roll all over the shoes — redemption, second chances, self-belief, faith, family. I stand on everything I stand for when I wear these shoes.”

Jelly Roll is known for embracing second chances, often reflecting on his past as a convicted drug dealer and addict. “I think second chances are earned,” he says. “I think sometimes you can earn them in opportunity — there are opportunities to earn — but I believe that second chances are earned.”

With his second chance, Jelly Roll has created new opportunities, sparked change and can hardly believe how his life has shifted. “There are so many experiences that in real time you can’t quite even believe they are happening because how can you believe that you’re at this show or talking to this person,” he tells PEOPLE. 

He adds, “But if you’re asking me what I am most proud of, it’s going back to see the kids at the juvenile and being able to visit with different facilities across the country and now internationally when I am touring and hearing the stories of those that feel like they may not feel represented all the time. Being able to speak on a real level with someone about how they are one good decision from changing their life and being on track is something that I don’t take for granted that I get the opportunity to do.”

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Jelly Roll is dedicated to using his journey to inspire and uplift others, never taking any moment for granted. “Showcasing that second chances are possible? There is nothing I am prouder of,” he says. “And I want to continue to be an example of that.”