Jelly Roll’s Stylist Weaves Fan Letters Into His Grammys Look – A Tribute to His Supporters

Jelly Roll’s Stylist Weaves Fan Letters Into His Grammys Look – A Tribute to His Supporters

The singer-songwriter is known for his blend of different genres. Jelly Roll, who was born Jason DeFord, is one of the brightest music stars. Jelly Roll scored the first top-ranked No.

one album on the Billboard 200 chart with Beautifully Broken in October 2024. He also announced 2025 as the year of his Big Ass Stadium Tour alongside Post Malone in November 2024.

He was nominated for Two Grammy Awards — Best Country Song and Best Country Solo Performance -before the February. 2 ceremony.
So, what do you think the country rap star is thinking about his biggest show?
When it comes time to get outfitted for the 67th Annual Grammy Awards, Jelly Roll’s stylist, Krista Roser, wants to be aware of the fires ravaging areas in Los Angeles County.

The Grammys, which are being broadcast live to CBS at the Crypto.com Arena, are the first award show to be held in the city since the Golden Globes.
“With the fires going on right now in L.A., I just felt like we needed to be very respectful,” Roser told Yahoo Entertainment about working with the “I Am Not Okay” singer.

“I do not believe it’s the moment to show off. I don’t think this is an appropriate moment to be a fashionista. I believe it’s the moment to think and note the world’s current situation. If you decide to make a statement, it should be positive in your view of what’s happening worldwide.”

Jelly Roll has taken the world of music with a vengeance in recent years. However, his path to fame wasn’t without a lot of hardship. Jelly Roll has spoken openly about his time both in and out of prison institutions between his teens and early 20s, as well as his time as a dealer in drugs. But the singer from Nashville, Tenn., was released from prison for the final time at age 24 and has found it to the top of the charts for music and as an arena headliner on sold-out concerts.

Roser was first introduced to contact by Jelly Roll three years earlier when a mutual acquaintance introduced them.
“Our industry is very word-of-mouth based, and I worked with a football player that [Jelly Roll] was friends with at the time,” she said. “I think they were hanging out, and he recommended me to him, so [Jelly Roll came to me himself, and we talked. After a phone call, he declares, ‘You’re my girlfriend. I’ve been friends with him since then.”
The 39-year-old’s hit single, “I Am Not Okay,” received nominations for Best Country Song and Best Country Solo Performance at the 2025 Grammys.

The track from 2024, which candidly reveals his battle with mental health, is often played in Roser’s mind when she thinks about what outfit to dress him in.

Jelly Roll’s Stylist Weaves Fan Letters Into His Grammys Look – A Tribute to His Supporters

“His music is so much more than just music,” she added. “He is so much to so many people when it comes to people going through their journeys: people in prison, basically anyone going through a tough time.”

For the 2025 Grammys style, Roser is drawing upon concerns about the current situation within the U.S., from the devastating hurricanes that struck parts of North Carolina in 2024 and the wildfires that erupted in Los Angeles to the “excited or nervous” reactions to President Trump’s return to the presidency for the second time.

“I am making use of a lot of the letters, comments, and messages that Jelly Roll received from people going through a particular phase of life, as well as how his music or message has assisted in this manner. I’m integrating people to join the band in a cool way,” she said.

A musician’s style, Roser explained, requires more significant focus on the details than the way something appears. Also, it’s about how clothes move and how the musician moves in the outfit.
“When somebody’s singing, it’s all about what they’re comfortable in, stagewise,” she explained. “So we use many stretch fabrics and comfortable fabrics. We also love to practice moving our clothes to ensure that if Jelly Roll puts his arms up or moves about, it appears great from any angle and in all situations.”

At the 2024 Grammys, when Jelly Roll received nominations for his first two Grammys of his career, the singer was wearing a Louis Vuitton suit created by the producer-singer Pharrell Williams. The latter is the men’s creative director at Louis Vuitton, a luxury label.
“We did a whole custom Louis Vuitton [look], and that was such an honour to be a part of,” Roser stated about the look she wore last year.

Though she usually prefers dressing singers like the “Need a Favor” singer with clothing specifically for his appearance, Roser wanted to take the opposite approach to dressing the singer at the upcoming Grammy Awards. She wore clothes designed by Los Angeles-based designers to show her gratitude for the California fires, which started to burn on January 7.

“We tend to do mostly custom … because it’s not very easy to see people-of-size inclusivity in fashion,” she explained. “But this year, I wanted to utilize our L.A.-based designers and keep it close to home.”

She’s also stealing cues from the star himself. Jelly Roll recently revealed to Roser that he’s currently at the end of the “Johnny Cash Farmer Era,” which appears to mix Americana and traditional influences. His wife, social media icon Bunnie Xo. is also known by the name of Bunnie DeFord, was a part of her celebration of his “farmer era” in December 2024 after she posted an image on TikTok of him wearing dark overalls made of denim.

“[His fashion has] changed slightly over the past few years. We’ve altered each album a little bit depending on the overall feel,” said Roser. “[It’s about] utilizing that statement and making it reflect the different events and things we’re doing.”

Roser considers clothing an avenue to express herself. She’s focused on ensuring her clients’ clothes feel real. It’s an intricate balance between taking the reigns as stylist and respecting a client’s individuality. Roser and Jelly Roll manage to nail the task each time.

“I style based on who my artist is and what they want their message to be,” she stated. “I think of clothing like a language, and I want their clothing to reflect their music and their statement [of] who they are.”