The Stunning Transformation Of Jelly Roll's Daughter, Bailee Ann

As the child of famous country artist Jelly Roll and the stepchild of podcaster Bunnie Xo, Bailee Ann is no stranger to life in the limelight. However, the singer has earned her celebrity title through her exceptional fashion sense and artistic talent. The up-and-coming country star has performed with her father on stage for several years in preparation for a solo career launch in the future, and she has introduced a fresh wave of style to the younger generation of country fans in the process.

Although Jelly Roll and Bunnie Xo's relationship is not without a few red flags, these two have raised a stunning young woman. Bailee Ann takes after both of her parents and continues to develop her talent for singing and trend-setting in equal measure. She has demonstrated a taste for versatile outfits which began early in her formative years and carries on today. Her style transformation has been exciting to witness thus far, and we can't wait to see her shine as a fashionista and artist.

In 2019, Bailee Ann was just 11 years old, but even back then, the young singer was a fashionista in the making. Most can agree that your preteen years are a time for discovering your unique sense of style, and Bailee Ann did just that. Her adorable outfit decisions range from feminine country couture to '90s-inspired grunge fashion.

Jelly Roll shared a photo of Bailee Ann and Bunnie Xo on Facebook on May 22, 2019, to commemorate her 11th birthday. He captioned the photo, "BIG BIRTHDAY BABY! Our Daughter turns 11 today. Not only does she turn 11 today she graduated from elementary school last night, she is officially a middle schooler. Man she is growing up so fast, I'm a proud pappy ..." In the family throwback photo, Bailee Ann wears a fun helicopter ponytail, a floral off-the-shoulder dress, and tan suede boots. The entire ensemble is country-Western chic at its finest.

Several months later, Bailee Ann shared a photo on Instagram with the caption, "First day of middle school and I'm the best dressed! Y'all still in school? How was your first day? Love y'all and thank you for the follows!!" In the photo, she showed off her newly dyed red hair, Nirvana band T-shirt, yellow plaid miniskirt, and black boots. Here, Bailee Ann nailed the nostalgic '90s-era grunge look, which is an impressive feat for an 11-year-old.

The years 2020 and 2021 marked the beginning of Bailee Ann showcasing her unique style. Before this point, she followed standard outfit formulas and played it relatively safe. Between the ages of 12 and 13, the outgoing celeb decided to embark on her own fashion journey and develop her individual style. During this period, she combined her cowboy copper hair with experimental outfit combinations and simple makeup looks.

For instance, in February 2020, Bailee Ann posed outdoors in a winter ensemble, including a denim miniskirt, tan fringe boots, a butter-yellow cowgirl jacket — which, incidentally, was a popular color for spring 2024 trends — and pink tights. "You probably thought I was done changing my hair, right? Wrong," she added as a cheeky caption. Here, she blended the country-girl aesthetic with slightly edgy components.

Bailee Ann continued to experiment with edgy streetwear looks into 2021 with bright colors and prints. For example, in another Instagram photo, she complemented her fiery tresses with dark denim and bright-red kicks. She also sported a trendy animal print shirt with winged eyeliner in a photo posted not long after.

In 2022, the then 14-year-old swapped her lively red hair for a softer blond, and the switch to a lighter shade also manifested in her outfits. She took a slight detour away from dark, edgy colors and, in their place, reached for pinks and pastels. For instance, the teenage celeb showed fans her trend-setting fashion in a beach photo posted to Instagram on December 18, 2022. In the photo, Bailee Ann donned an '80s-inspired Barbie doll outfit with pink knee-high boots, a lilac miniskirt, and a printed abstract blouse, complete with a high ponytail and face-framing pieces. This outfit showcased her love for fashion and playful looks.

Her clothing preferences evolved in 2022 by taking on a more mature feel. She learned to balance darker colors with trendier garments, such as tailored vests and wide-leg jeans. Additionally, the artist proved that her love for the country-girl aesthetic lives, as she posed in a pear-green dress and glitzy ankle boots at the Nashville Grand Ole Opry country music event in another Instagram photo. In this case, you can see that she enjoys getting dolled up for events and having fun with style as much as any other teen her age. 

At 15 years old, budding artist Bailee Ann truly cemented herself as a fashionista. In 2023, her looks ranged from vampy rockstar to country glam, allowing her to come into her own as a style influencer. Her go-to color combination included deep hues, such as red and black, which created a lovely contrast with her mushroom brown or "bronde" hair color. The look she wore to the "Jelly Roll: Save Me" documentary premiere was bold, edgy, and uniquely Bailee Ann. She donned a striking red blazer with a black crop top, tailored trousers, and sparkly silver booties. The rising star also sported blond money pieces and a soft-glam makeup look.

What's more, the black-and-white cowgirl outfit worn during a Las Vegas trip was a fan favorite. Several commenters fawned over the cow-print jacket. One user commented, "Okay but where can I get this jacket it's soo cute." Another user said, "Ummm I need to borrow your jacket. That's adorable." This goes to show how the artist is making her mark in the beauty and fashion world — on top of being a talented country singer.

For many, it's difficult not to cringe when you think about the fashion choices you made at 16 years old. Fortunately for Bailee Ann, she won't have the same experience. The teenager continues to flourish and develop her sense of style as she grows older, and her outfits are only getting trendier. During the annual country music Stagecoach festival in Indio, California, Bailee Ann stepped on stage with father Jelly Roll while wearing a Woodstock-esque ensemble. The country-boho outfit featured a chocolate-brown skirt, denim-vest crop top, a chunky cross belt, and equally chunky jewelry. We're not quite sure what fashion genre this look falls under, but it highlighted her unique sense of style.

The celeb returned to her edgy rockstar tendencies on the 2024 Grammy Awards' red carpet in Los Angeles on February 4. At the event, Bailee Ann wore a black-and-silver ensemble with a leather corset top, a miniskirt with fringe embellishments, and a matching blazer. The country singer also swapped her usual blond highlights for an expensive brunette makeover. Her unique rockstar look stands out from the other members of her family and emphasizes her spotlight-worthy personality.