Kelsea Ballerini’s Season of Play

It’s an early morning in June and the caffeine from Kelsea Ballerini’s Starbucks latte is hitting. “Do you want me to frolic?” she asks on the set of her StyleCaster cover shoot, swaying between poses in a top-to-toe Valentino jumpsuit. Let’s try it with a wide-brim, patent leather hat, her stylist Molly Dickson suggests. Ballerini agrees. “It’s giving Beyoncé,” she says.

As she bounds and bends in front of the camera, pointing one foot forward with the other gracefully outstretched behind her, Ballerini’s whimsical and adventurous spirit is palpable. Not since before she hit puberty, she would tell me later, has the 29-year-old pulled out the moves she is today. Ballerini was a dancer for years—ballet, jazz, hip-hop—but then “got really long and lanky and I lost all my coordination,” she says. “I have miscellaneous bruises all over my body all the time because I can’t keep up with where my limbs are.” The camera flashes, and her glam team hoots and hollers as the shot appears on the monitor. Clearly, there’s still a dancer in there somewhere.  

Fast forward two hours, and Ballerini exits her dressing room in the final look of the day: a Carolina Herrera suit dress, thigh-high leather boots, and a floppy, pinstripe denim hat that her glam team wasn’t sure she’d be on board with. This is such a stylistic departure, they say, but that’s the point. “I feel like I could fly us all home in this hat,” Ballerini jokes. 

Ballerini has spent much of her decade-long career sheathed in varying degrees of sequins, leather fringing, and a healthy helping of yee-haw energy, but her aesthetic has evolved into what I’m defining as Highbrow Country. Don’t worry, the cowgirl boots haven’t gone anywhere, but when it comes to fashion—and life in general—Ballerini is up for anything. 

“You’re meeting me at a very interesting time in my life because I think that statement would not have been true a couple of years ago,” she says. “I always thought of myself as one thing, which was a glittery, palatable blonde that sings country music. I’ve realized over the last few years, as I’ve woken up to myself, and really stepped into my womanhood, that I’m really open to discovering more of myself.” She pauses. “I think that’s translating in a lot of different ways in my life, but certainly through fashion, to being open and also realizing that it’s another way to express yourself and play. I’m in such a season of play right now.”

At 19, the Knoxville-born star signed with Black River Entertainment touted as the Next Big Thing; a promising singer-songwriter who’d move on to drop four esteemed studio albums while earning Grammy nominations and mastering the equilibrium between pop and country—a feat only a handful of icons like Shania Twain, Taylor Swift, and Faith Hill have conquered. Ballerini is a music industry success story. But in the past year, her life—both personal and professional—reached a crescendo. 

Did I think I’d be living in Nashville, doing music in some capacity, with a dog, and feeling a lot of love in my life? Yes.

Kelsea Ballerini

2022 was punctuated with the end of her five-year marriage to fellow country music singer Morgan Evans, whom she wed at 24; he was 32. Then, on Valentine’s Day the following year, Ballerini released Rolling Up the Welcome Mat, an unexpected heartbreak EP as a way of processing the divorce. Soon after, in April, she went public with her sizzling romance with Outer Banks star and Gen Z heartthrob Chase Stokes. She’s been in headlines around the clock since. And as she edges toward 30 on September 12, dusting herself off from a “shitstorm” of a year (her words), Ballerini is rediscovering herself—and having a blast. 

A week after the shoot, Ballerini appears via Zoom from her home in Nashville, enjoying time off between the Pittsburgh and Santa Barbara dates of her Heartfirst tour. She apologizes for being a bit late. “Sorry, I was just coming back from the chiropractor,” she says. “When I’m on tour, my bones just seem to go in different directions so I try to stay on top of it.” It’s how she decompresses, literally and mentally, she says. 

She’s speaking from the 1920s cottage she moved into in November, where the calming, sage-colored walls of her study serve as the backdrop. An elegant white peacock chair is nestled in the corner, but “what you’re not seeing in Zoom is the pile of random shit that I have in the corner because I don’t have a place for everything yet,” she says, sipping on a green juice. She’s makeup-free with her blonde hair styled in a messy half-up bun, her weight shifting between perching one foot up on her chair and not. Eight-year-old Dibs, her beloved dog who recently underwent a second ACL surgery, is snoozing in the background. 

Amid these last few months in her 20s, Ballerini tells me she’s mulling over her Saturn return, a cataclysmic astrological event where the planet Saturn aligns on the same ecliptic longitude that it occupied at the moment of a person’s birth. “There is this huge energetic shift within you where you shed your child self and become your adult self,” Ballerini explains. “It’s usually surrounded by a lot of friction and a lot of difficult conversations and losing people and that kind of stuff. But then you get to the other side—you’re like, ‘Oh, shit, here I am’.” 

Sure enough, the past 12 months have been filled with friction, difficult conversations, and loss. Her divorce from Evans was the ultimate tabloid fodder: He claimed he had no idea their relationship was doomed in a single titled “Over For You”; in response, Ballerini questioned whether he was trying to capitalize on their split in “Blindsided.” It was unpleasant and she doubles down on a phrase she’s uttered in previous interviews: “Who you marry is not who you divorce.” 

It was during some of these particularly dark days that Ballerini’s eyes were opened to the unfiltered and often cruel opinions of strangers on the internet. “I discovered Reddit in 2022 and I no longer go on Reddit,” she says bluntly. “I would read situations of what people had thought of me or what people had heard about me, or people’s interactions of meeting me, and they were negative. That guts me; that shit really gets to me.” 

But in 2023, Ballerini emerged on top. 

Rolling Up the Welcome Mat hit a nerve in a way that no one was expecting. Composed of six songs not initially intended for radio—let alone the stage—the critically-revered mishmash of country riffs, pop sensibilities, and sprinklings of hip-hop syncopation peaked at number 5 on the Billboard Independent Album charts. Such was its reception that Ballerini added a third leg to her Heartfirst tour, finessing the setlist to include new Welcome Mat favorites like “Penthouse” and “Leave Me Again,” prompting fans to belt the words back to her. With this pure emotional catharsis, her world began to heal.

I’ve done this for a decade. I’ve done the work. But the eyeballs on the rest of my life is new, so I’m giving myself a lot of grace.

Kelsea Ballerini

Unlike her previous release, 2022’s SUBJECT TO CHANGE, where she and her collaborators would each bring ideas to the table to see what stuck, producer Alysa Vanderheym observed Ballerini’s laser focus during the writing of Welcome Mat. From the beginning, Ballerini had a clear vision of the story she wanted to tell: Divorce is really fucking hard, and being in the public eye makes it all the more complicated. Some things were left unsaid, though, and Vanderheym says an extended version of the EP is underway. And Ballerini’s potential? Unfettered. 

“Kelsea has done an incredible job at positioning herself as the go-to of commercial country. She’s done a great job at dipping her toe in the pop world,” Vanderheym says. “No one’s ever told her what to do, and I think that’s really rare in country music, and anywhere really, to find someone that’s such a boss, who has such a vision and executes it.” 

With this resurrected confidence, Ballerini has found conviction to speak out in favor of polarizing social issues like gun reform and denounce her home state’s attempt at criminalizing drag, joining Maren Morris and Kacey Musgraves in a female-led movement to upend country music’s historically blue-collar bro culture. She’s a school shooting survivor herself, and as co-host of the 2023 CMT Music Awards in April, Ballerini dedicated the broadcast to those whose lives are changed by gun violence—the families, witnesses, and first responders that so often go unnoticed.

“I get why people don’t speak out because the pushback is so aggressive, so violent, and so dark and scary,” she says. “But, I didn’t for a long time. I didn’t say shit about shit for a long time because I was there. I was scared. And I guess I just had to rip [off] a couple of Band-Aids. As soon as you rip one, the rest get a little less scary.”

She’s come a long way from life on the farm. Growing up in rural Tennessee, Ballerini’s childhood was wholesome. She remembers listening to Savage Garden with her mom and Norah Jones, Dean Martin, and Frank Sinatra with her dad. Occasionally, she’d sing at church on Sundays and afterward, there would be a big family cook-up. “I lived literally next door to my aunt, my uncle, my cousins, with all this big room to run around and animals and bare feet,” she says. “It was very country music.”

Ballerini’s parents divorced when she was 12 and, as an only child, she learned a special kind of resilience that has served her well into adulthood. Metamorphosis has been a theme of her life, she observes, and music has always been a refuge from conflict. So at 15, her mom agreed to pack up their life and move to Nashville, where Ballerini could pursue her craft seriously. “She’s been my ride-or-die ever since,” she says.

It’s hard to believe that a decade into her career, Ballerini hasn’t had her “made it” moment, not as far as she’s concerned anyway. She considers Welcome Mat her big break. “I’m like, ‘Why now’? And the answer I keep getting is because when you honor yourself—and you do the right thing for everyone—but you’re really honoring yourself, you create the space within your soul and your body and your heart to welcome what’s meant for you,” she says. “So I do feel like there’s some kismet stuff happening just because I have space for it now.” 

The success of Welcome Mat intensified public interest in Ballerini’s personal life, which is uncharted territory for her. “I’ve done this for a decade. I’ve done the work. But the eyeballs on the rest of my life is new, so I’m giving myself a lot of grace,” she says, explaining that, of the two options to put up a barrier or maintain an openness with fans, she chooses the latter. “All the things that I’ve always done are because that’s actually who I am at my core. [But] I am actively working to protect the normalcy.”

In January, fans began speculating that Ballerini was in a relationship with Chase Stokes after some flirty social media interactions caught everyone’s eye in the comments section: He would leave a single red heart emoji, and she would reciprocate. You can’t hide anything from the internet for long, though, and after gossip reached boiling point, Ballerini confirmed she wasn’t single with a coy “um… nope” on the podcast Call Her Daddy. A little over a month later, Stokes and Ballerini hard-launched their coupledom on the red carpet of the CMT Music Awards. 

Stokes nor Ballerini had talked about how, and if, they would reveal their relationship to the world beforehand, but they have since. “The thing that we’ve decided, and to each their own, is when you’re with someone that you feel secure with and that you’re proud to be with, why not share it?” she says. “He’s also a Virgo; we’re both Labrador Retrievers in human form. It doesn’t take much conversation to be on the same page. It’s been half a year and it’s been great.”

Still, it’s Ballerini’s relationships with her girlfriends that she considers the “most important” in her life; they’re her “built-in sisterhood.” Most are a couple of years older, and since she’s supported them through various rites of passage, it’s her turn to get messy. “I’ve gotten them through all their 30th birthdays and now I’m like, ‘You’re gonna have to hold my hair’,” she jokes.

With an unwavering group of friends, a blossoming romance, and a sky’s-the-limit career trajectory, Ballerini’s life is quite together, but I do have one final question: Has she become the person she thought she would? “I’ve always had a knowingness that this is what I was going to do,” she says. “But did I think I’d be living in Nashville, doing music in some capacity, with a dog, and feeling a lot of love in my life?” Without pause or hesitation: “Yes.” Then, quite unceremoniously, Ballerini’s green juice explodes all over her desk. She laughs, because how else do you move on from a mess?

Several days later, she’s back on the road for Heartfirst and participates in an “Ask Me Anything” segment on IG. A fan asks if she’s happy. She thanks them for the question and writes, “I am indeed.”

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Photographer: George Chinsee
Stylist: Molly Dickson
Hair & Makeup Artist: Kelsey Deenihan for CoverGirl
Nail Artist: Mo Qin