Kelsea Ballerini's Stunning Wardrobe Choices Over The Years

Award-winning country musician Kelsea Ballerini may be known for her chart-topping hits "Peter Pan," "Love Me Like You Mean It," "Yeah Boy," and more, but she's also making quite a name for herself as a fashion icon in the celebrity sphere. The singer began walking red carpets after her career took off in the mid-2010s, and her stunning style evolution has been exciting to watch. 

Florals, sparkles, and feminine silhouettes have been staple features of her closet over the years, but as she's gotten older, Ballerini has also experimented with sexy cutouts, daring skirt slits, and plunging necklines. While she has a special place in her heart for her Nashville roots, the musician has also been candid about embracing less traditional looks for country music stars like Shania Twain and other iconic musicians who came before her. The singer told People in 2023, "I just love playing with fashion. For me, especially as a country artist, I think there's this stigma where it's big hair and big sequins — and obviously that's a part of it. But, I love being able to push those boundaries and expand people's minds on what country music can look like," Ballerini explained.

From esteemed awards shows to exclusive fashion week events, the rising country star has become a regular fixture with a serious eye for style — and her increasingly bold ensembles have had us calling "Dibs" on her as a source of fashion inspiration.

Kelsea Ballerini embodied the whimsical vibes of her hit song "Peter Pan" at the 2017 Grammys. The country singer donned a stunning Ines de Santo gown to the esteemed event: The floor-length number featured nude tulle fabric in gossamer layers throughout the dress, and it was adorned with baby blue daisies, metallic appliqués, and delicate floral embroidery. The romantic gown had a trumpet skirt with a fishtail train, as well as a corset bodice and a high neckline. Sheer half-sleeves with a drop-shoulder silhouette enveloped Ballerini's arms, and the see-through fabric was decorated with the various floral embellishments seen across the feminine gown.

The "Yeah Boy" crooner accessorized with a few dainty rings and a pair of statement stud earrings. Ballerini wore her blond tresses in loose waves around her shoulders, and her makeup included a gilded smokey eye, soft pink blush, and a petal pink lip to match.

Ahead of the 2017 Grammys, Kelsea Ballerini attended the Pre-Grammy Gala and Salute to Industry Icons event. The "Love Me Like You Mean It" singer looked radiant in a shimmering pale gold wrap dress by Berta. The long-sleeve garment featured a plunging V-neckline, an inverted V cutout at the front of the skirt, and a modest train adorned with a sea of sequins. Ballerini's gorgeous gown was cinched at the waist with a metallic belt that included rope and tassel detailing. Additionally, her white platform L.K. Bennett heels matched the glamorous sparkling aesthetic of the dress thanks to the shining adornments on the uppers of the peep-toe pumps.

Ballerini paired gold drop earrings with the evening look, and she channeled her inner Tinker Bell with a slicked-back golden topknot. The country musician's makeup included a generous amount of bronzer, a deep gold smokey eye, and glossy nude lips.

Kelsea Ballerini rocked another jaw-dropping floral gown at the 2017 CMA Awards. At the event — where she was nominated for Female Vocalist of the Year — the "Dibs" singer dressed in a white long-sleeve gown designed by Michael Kors. The floor-length dress featured a fitted sheath silhouette with a tiny train, a V-neckline, a triangular cutout across the stomach, and an open back with strappy detailing. The romantic gown was adorned with gilded floral appliqués throughout the cream-colored fabric, which Ballerini emphasized with golden floral hair clips and a reflective gold clutch.

Among the musician's accessories were a few sparkling rings and gold crawler-style earrings. Ballerini's luminous locks were coaxed into Old Hollywood-style curls, and her glowing makeup included a yellow-gold smokey eye, champagne highlighter, sunkissed bronzer, and glossy pink lips. We're sure she called "Dibs" on the dress at first sight — we certainly would have snagged the mesmerizing ethereal number!

In 2019, Kelsea Ballerini attended the annual New York City amfAR Gala looking sultry and seductive in a stunning black Galia Lahav gown. The strapless garment featured a sweetheart neckline, a corset bodice, and a fitted skirt that flared into a mermaid silhouette and fishtail train at the knees. Semi-sheer lace with floral embroidery decorated the lingerie-style bodice, and the skirt was crafted from luxurious velvet that billowed in lush pleats behind Ballerini.

The "Hole in a Bottle" singer paired a variety of eye-catching diamond accessories with her dark glamour ensemble. On one wrist, Ballerini wore an intricate bracelet sculpted in an ornate vintage pattern, and a square-shaped diamond chain necklace hung across her collarbones to drape across her back. The country crooner wore matching drop-style earrings encrusted with sparkling gems, and her hair was gelled back to show off her glittering jewels. Ballerini's makeup included a silvery smokey eye, bronzer, and a beige-toned nude lip. Additionally, she opted for a bright red manicure for a subtle pop of color.

Kelsea Ballerini looked romantic and whimsical as ever at the 2020 CMA Awards. The "I Quit Drinking" singer opted for an elaborate floor-length gown adorned with red rose appliqués and embroidered with rich green leaves across the semi-sheer fabric. The strapless garment featured a fitted bodice and an A-line skirt that was trimmed with oversized full-bloom roses crafted from tulle. In addition to the floral elements, the gown was also affixed with a smattering of sequins and gemstones.

Keeping the full focus on her dress, Ballerini went sans jewelry, save for a few delicate earrings and her engagement ring from her former husband, Morgan Evans. She donned a pair of red Dolce & Gabanna stilettos with faux roses fastened to the back of the heels, which expertly complimented her dramatic gown. The country musician's honey-highlighted hair was styled away from her face in cascading waves, and a bold cherry lip was the star of her soft-glam makeup.

Kelsea Ballerini maintained her reputation as a red carpet stunner the following year as well. For the 2021 CMA Awards — where she won the video of the year and musical event of the year awards for "Half of My Hometown" with Kenny Chesney — Ballerini donned a sexy white gown designed by Valdrin Sahiti. The country music star's long-sleeve ensemble featured a mock neck, a fitted bodice with a white corset sculpting her waist, and a floor-length A-line skirt with a daring hip-high slit. The thick fabric elegantly gathered at one side of Ballerini's hips and billowed into a modest train. 

With the sophisticated and sultry gown, the award-winning singer chose transparent pointed-toe pumps decorated with silver detailing, an assortment of silver rings, and draping chain earrings hanging from her lobes. Ballerini's silvery-blond strands were side-parted and slicked back into a low bun, and her makeup included a bronze smokey eye and soft pink lips. 

In 2021, Kelsea Ballerini not only attended The Hollywood Reporter's Power 100 Women in Entertainment event, but she also presented the Spotify Scholarship award. The country singer sparkled from head to toe in a bossy blush-pink power suit, which included wide-leg trousers and a fitted tuxedo jacket. Both the jacket and pants were adorned with sparkling embellishments throughout the material, save for the luxe silk lapels that were left bare. Ballerini opted to wear the jacket without a visible layer beneath, which amped up the sexy, empowered vibe of the look. 

The "Mountain With a View" singer kept her accessories minimal with a large pair of statement stud earrings, and her makeup was similarly muted, featuring an elevated natural look. Ballerini's usually blond hair was dyed a lustrous "bronde" (a brunette-toned blond), and her mane was styled in side-parted loose waves. She appeared poised and powerful, acing the theme of the celebratory occasion.

Kelsea Ballerini breathed new life into Old Hollywood glamour with her 2022 ACM Awards ensemble. The "Penthouse" singer arrived in a sultry black gown with a halter neckline and an ankle-length hem. The stunning sheath dress featured a plunging neckline that dipped between Ballerini's breasts and stopped just above her belly button, and the base of the cutout was adorned with glittering rhinestones in an intricate pattern. The gown's back was open with a thick band winding around the waist to hold the garment in place, and the musician accentuated the striking number with black opera-style gloves. 

Ballerini also added a sparkling collar necklace to complement the jewel appliqué in the dress, and she wore delicate silver hoops in her ears. Simple, strappy black heels completed the outfit, and the country star's smokey cat eye added even more drama to the gorgeous look. Ballerini kept the rest of her makeup muted and wore her blond tresses in a messy low ponytail with wavy strands hanging loose to frame her face. 

Kelsea Ballerini channeled elegant vintage vibes once more at the 2022 Grammys. The award-winning musician walked the red carpet in a simple yet captivating black gown with an asymmetrical strapless neckline and a floor-length hem. The mesmerizing velvet dress was fitted throughout the bodice and flowed into a looser but still fitted sheath skirt. An audacious slit from the top of Ballerini's hip to the floor revealed her entire left leg, showing off the strappy black heels fastened to her feet. The gown would have been absolutely gorgeous on its own, but an oversized white bow at the waist provided a unique element that made the formal ensemble even more enchanting. The ivory adornment was embellished with rhinestones, adding a little sparkle to Ballerini's classic look.

The "Yeah Boy" singer accessorized with a sparkling pair of diamond drop earrings and a few dainty rings on her fingers. Ballerini's golden mane was parted down the middle and blown out with a slight curl at the ends of her strands, adding even more elegance to the entrancing ensemble.

Though she wasn't able to attend the 2022 CMT Music Awards in person after testing positive for COVID-19, Kelsea Ballerini didn't let the setback stop her from attending virtually. Walking the pink carpet at home in front of her house, the chart-topping singer wore a monochromatic white ensemble with an ample pop of sparkle. Ballerini donned a pair of high-waisted straight-leg trousers, and a matching tuxedo jacket with an oversized fit was draped across her shoulders. The garment's lapels were encrusted with rhinestones, which matched the sparkling strapless bandeau Ballerini wore beneath the jacket. 

For accessories, the "Peter Pan" singer chose transparent pointed-toe heels with rhinestone-embellished bows on the uppers. Ballerini also donned a few silver rings and a large pair of diamond hoop earrings. Her blond locks were styled in tousled waves gathered in a loose half-updo, and her makeup included her signature bronze smokey eye and glossy nude lips.

Kelsea Ballerini shared an extremely special moment with her inspiration-turned-friend, Shania Twain, at the 2022 ACM Honors. The "This Feeling" singer wore an ethereal white gown previously donned by Twain at the 1999 Grammys, where the revered musician won an award for "You're Still the One." The floor-length garment is so iconic that it was displayed in the Grammys Museum before Ballerini's epic re-wear. 

The long-sleeved gown, designed by Marc Bouwer, featured a turtleneck and a fitted silhouette that flared into a mermaid skirt with a flowing train. The cream-colored material was adorned with iridescent sequins that subtly shimmered under the lights. Ballerini paired the look with silver pointed-toe heels and diamond stud earrings, keeping all of the attention on the show-stopping dress. Her hair was styled in a sleek updo with a wavy strand framing her face, and her makeup was a soft glam that enhanced her natural beauty. The two country singers even posed for a few photos together, making Ballerini's re-wear all the more exciting.

While in New York City for Fashion Week in February 2023, Kelsea Ballerini wore an eye-catching hot pink ensemble with playful details. The singer donned a strapless sateen midi dress for Carolina Herrera's runway show, and she looked like a Barbie brought to life in the charming number. The calf-length dress featured an asymmetrical hem with a thigh-high slit and figure-flattering ruching at the hips. Two heart-shaped appliqués were adorned on her chest, adding a kittenish factor to the vibrant ensemble. Though Ballerini didn't wear it during the fashion show, she donned a luxurious shawl-style coat atop the fitted dress in the same fuschia color while walking the NYC streets. 

For accessories, the country musician chose strappy hot pink heels, a magenta-colored clutch, and dangling diamond-embellished heart-shaped earrings. Ballerini's golden mane was parted down the center and pulled into a low updo, and a section of her bangs hung in a loose wave along the side of her face. "The Other Girl" singer's makeup incorporated pink tones as well, including rosy eyeshadow, blush, and lip gloss. This Barbie is a fashion icon, that's for sure!

Kelsea Ballerini rang in her 30th birthday at the 2023 MTV VMAs, and she did so in major style. The award-winning singer looked red hot in a cherry-colored floor-length gown designed by Mônot. The ruby red silk dress featured a strappy halter neckline, an oblong cutout between the breasts, a plunging open back, and a fitted silhouette that flared into a mermaid-style skirt with a fishtail train. The vibrant fabric flowed over Ballerini's frame for a sexy, seamless appearance — perfect for the first chapter of her "30, flirty, and thriving" era! 

The "Legends" crooner accessorized with pointed-toe heels and several chunky gold bangles on each wrist. Her blond locks were cut shorter than usual, fanning around her shoulders in piecey waves. Ballerini's makeup brought out the metallic gold tones of her bracelets, with an edgy bronze smokey eye and rich bronzer swept across her facial features.

Kelsea Ballerini made another sexy splash with her sultry ensemble at the 2023 Time100 Next Gala. The country music star walked the red carpet in a jaw-dropping Stella McCartney gown with two oblong keyhole cutouts across the torso of the black garment. The skin-baring sections ran diagonally from Ballerini's shoulder to her opposite hip, with the gown held together by a small strip of fabric below the bust. Additionally, two oversized metallic knots sat atop the singer's shoulder and hip, respectively. The floor-length, long-sleeve dress also featured a hip-high slit that showed off Ballerini's legs and strappy black heels.

The designer gown was such a statement on its own that the award-winning musician opted to keep her accessories simple, wearing a few slim rings and a pair of diamond stud earrings. Ballerini's hair was styled in a suave ponytail, and her makeup included sunkissed bronze tones on her eyes, cheeks, and lips.