Every Christmas Eve, Kelsea Ballerini and her mom, Carla, go all out with their holiday style, especially when it comes to their pajamas.
"My mom does Christmas PJs every year [and] we have to wear them no matter where we go," the two-time CMA winner tells PEOPLE of the mother-daughter ritual.
Though she admits there have been some "embarrassing" looks throughout the years, the Unapologetically singer says it's always a shoo-in when she unwraps a pajama set from Aerie. Simply put: "If they're cute, they're Aerie."
Pajamas, like this plaid pair, may be a mainstay in the Ballerini household, but this year, the Aerie brand ambassador is also decking out her closet with the coziest apparel from the brand, including a pair of comfortable pants to get into the festive mood.
"When I get off the road, I am like, soft pants or bust," Ballerini tells PEOPLE of her post-tour tradition while celebrating Aerie's Holiday Shopping Party event at its New York City flagship.
"I really want to be cozy, and I want to have pants that let me eat all the Christmas cookies," she says. That's why the high-waisted, waffle-knit flare leggings from Aerie's OFFLINE range, with their supportive silhouette and ruched waistline, are on the top of her wishlist.
She also loves to go "stretchy and oversized," which is where the Buttercream Crew Sweater (in Cappuccino), the Longline Lace Bralette (in Green Alpine) and the Tassel Trapper Hat (Ballerini's favorite is the white-and-blue knit), come into play.
"Super glammed up and glittery" is the singer's M.O. when she's on the road. Winding down and getting comfy is her game plan during the holidays, though, because, as the "half of my hometown" singer admits, she's a "homebody" at heart.
Ballerini joined the Aerie family last year, due in part to her love for the brand's clothing. But it was also the company's unfiltered authenticity that made an ongoing partnership a perfect fit through and through.
"I love that Aerie's all about empowering us to be as we are and to embrace the realness. It was a really beautiful alignment to be able to partner with a brand that really just wants everyone to feel good in their skin," says Ballerini, who also strives to bring relatability in her work, whether it's through her songs or being mindful about what she posts online.
A part of that vulnerability has been learning to stand in her confidence — from owning her style to performing in front of a crowd — which has come with its challenges as well as its rewards.
"Giving myself grace has been the biggest lesson I've learned," Ballerini says of how she's overcome bumps in the road.
Like many, she has days when she feels "really empowered" in her body as well as moments when she feels "tired or bloated or sad." She's worked through the ups and downs, though, by allowing herself to feel confident "without shame."
"To be fully in that when I feel it, allows the days where I feel confident to feel much sweeter," she says.
The holidays are leading up to a jam-packed year for Ballerini, who is ready to "cannonball" back into touring and to bring her new music to life.
While she's at it, she's ready to bring her own style to the table and to redefine what it looks like to be a woman in country music, one stage and one red carpet at a time.
"I just love playing with fashion," she says. "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."
Kelsea Ballerini and Shania Twain
Ballerini made red carpet headlines in August, wearing Twain's 1999 Grammy gown to the Academy of Country Music Honors. While it certainly impressed many, the fashion moment was only a part of the women-to-women collaborations Ballerini takes part in.
"I've really had to recalibrate my answer to this. When people ask me, 'What does it mean to be a woman supporting women?' Early [on] I was like, 'Oh my God, we all have to be best friends and have sleepovers.' That's not my answer anymore," Ballerini states.
"It's not just lifting up other female artists — it's going behind the scenes where people don't see it and involving women in every aspect of my career. To be able to lift women up on the front line, you have to step back first and get it from the roots," adds Ballerini, whose "whole team is basically women."
Michael Loccisano/Getty Kelly Clarkson, Kelsea Ballerini and Carly Pearce
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Subject to Change, which was released in September, is Ballerini's fourth studio album. Now 29, and with many career milestones, there's one piece of advice she'd pass along to her 19-year-old self who was just starting out.
"Stay curious — I think that's been really valuable. I really don't ever want to get comfortable. I want to always be wondering how to be better at my craft and how to expand into things that make me uncomfortable, and just how to grow as a person," she concludes.