How I Shop: Kelsea Ballerini

We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what's "you"? These are some of the questions we're putting to prominent figures in our column "How I Shop."

When Kelsea Ballerini stepped onto the country music scene in 2014, she became known for her charming and melodious songwriting, as well as her sweet and playful girl-next-door style. Brightly colored mini dresses, princess-y high/low gowns and plenty of glitter defined Ballerini's appearance at the start of her career. Now, 10 years later, the 30-year-old is in an era of rebirth.

After a highly publicized divorce in 2022, an elegantly vulnerable EP and finding new love, Ballerini is channeling her renewed energy into a full-blown style evolution — as signified by her 2023 MTV Video Music Awards performance, during which she quick-changed onstage out of a white, bridal-y gown into a black Alexander McQueen mini dress.

"That performance outfit was symbolism of me shedding my skin and part of my life. I think there's been an evolution of the way I feel about myself and what I'm comfortable in. I feel comfortable enough in myself to explore different looks and fall in love with my body a little bit more," Ballerini tells Fashionista. "Learning to accept myself and learn the parts of my body that I like has been a really big part of my style evolution. Now I can be like, 'I am digging my legs this week, let's show 'em off.' It's all part of growing up and leaning into my womanhood."

Ahead, the Grammy nominee and Pantene brand ambassador reveals the recent red carpet looks that she's felt most beautiful in, her extensive (and sentimental) collection of Christian Louboutin heels, the one category she wants to "get better" at shopping for and more.

"My favorite pastime as an only child and little girl was playing dress up. Luckily, my mom is very girly, so I would just go into her closet and raid her dresses, scarves and anything glittery. Obviously, I was too young to understand what fashion was, but I've just always been really drawn to any form of self-expression — whether it be music, songwriting, hair, makeup or the way you dress.

"When I was first starting out, having long blonde hair was my look. I was touring all the time and constantly damaging it by coloring it and putting it through so much heat. Now, I've finally gotten it to a healthier place with Pantene's Miracle Rescue products and can experiment more with different hairstyles. Right now, I'm loving a slicked-back bun. That's been my go-to for any outfit — I think it makes everything look chic.

"My everyday style is very comfortable. My friends make fun of me because I used to just not leave the house unless I was glammed to the gods. I always had to wear chunky big heels, makeup and extensions. I think the reality was that I didn't feel super comfortable with who I was at that point. Now, I really don't mind leaving the house in a pair of baggy sweats or a good pair of jeans and a T-shirt.

"My favorite jeans are Agolde. I have a pair of high-rise ones with a little fray at the hem. My legs are kind of my whole body, so I really like a high-waist cut and, naturally, a crop top will hit right above that. So cropped T-shirts are definitely my go-to style.

"My onstage style is a lot more 'costume' than my everyday looks. The outfit is hyper-involved in the production and the music that I'm singing, so it's part of the show and the story I'm telling. I get to be more playful with my red carpet looks. I'm having a really fun time just exploring different ideas. For the 2023 CMA Awards, I wore a beautiful pink Christian Siriano gown and that was really fun.  For the 2023 VMAs red carpet, I wore something very showy — a Mônot gown. That was more grown up for me.

"I truly have no idea what I'm wearing to the [2024] Grammys. I'm in between albums right now, so I think just staying in that in-between is really important to me. When I introduce new music, I want it to feel like you're getting a whole color palette and a whole aesthetic shift. So before we jump into any ideas, I first like to make sure we start with a clean slate.

"I did New York Fashion Week last year. I went to Prabal Gurung's show and he put me in this look that I would have been terrified to wear a couple years ago. I loved it. I felt like such a badass. It was this bodysuit, latex gloves and sheer skirt — booty out. We did a smudgy, almost wet eye look and hair fully greased back. I ended up really loving it. I think that was a moment for me to recognize, 'Okay, that's growth.'

"Blake Lively and Gigi Hadid are two of my style icons. To me, Blake is always at the beginning of trends and sets a lot of them. But she's also approachable — there's nothing about her that feels like she's in a glass box. I think fashion can sometimes feel unapproachable, so I really like when there's people that are aligned with that world and make it feel like it can be for everyone.

"Every time something big happens — ending a tour, dropping a record, etc. — I buy a pair of red-bottom [Christian Louboutin] shoes. That's my favorite designer thing. I have them all on a shelf in my house and I can literally name what memory or accomplishment is attached to each pair of shoes. It's fun because when I do have my days where I just wear jeans and a T-shirt, I can still throw on a pair of those shoes and it feels special — tied to a memory.

"My first pair splurge was a pair of Louboutins. It was after I released 'Peter Pan.' They're black and they have silver studs and the tiniest, skinniest little heel you've ever seen in your life. I've worn them out so much that they're actually in the shop right now getting the heel replaced. My favorite pair I have are these really pretty, very Elle Woods in 'Legally Blonde', baby bubblegum-pink ones I got after I finished touring with the Jonas Brothers in 2022. Those are good. Very Barbie-core.

"Comfortable is king for me right now. I love Reformation. It's really good for well-made basics. I'm also making a new record right now, so I just want a soft pant that I can sit criss-cross applesauce on the floor in. My go-to recording outfit is a Cotton Citizen sweats set. There's also a boutique in Nashville called Posh that I really like.

"I'm trying to get better at getting good pieces of jewelry. I want to get better at knowing the good brands and having some staple pieces I can wear to elevate a more basic look. My favorite piece of jewelry I own is a ring that I wore when I was nominated for Best New Artist at my first-ever Grammys. It has so many diamonds missing, but I love it. I think it just has character. I don't know where it's from, but that's what makes it special.

"I'm hyper-involed in my merch to the point where everyone's like 'Kelsea, foot off the gas.' I think there should be two solid options for people. If you want a classic vintage-looking face T-shirt, we should have a really good option for you. If you want something that's not branded with a name or a face on it, but has a print of your favorite lyric or something that doesn't feel like it's concert merch, I want to have a good option for that, too. I love merch and it's going to be really fun designing new stuff.

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