Why Carrie Underwood Slipped Back into Her Old American Idol Looks as Judge and More Season 23 Style Facts (Exclusive)
Carrie Underwood is wrapping up her debut season as a judge on a popular music competition on May 18. The singer’s return to the show marks 20 years since she won season 4. Here, Underwood, along with her stylists Marina Toybina and Courtney Webster, share insights into the creation of her outfits for each episode.
Carrie Underwood holds a special place in the show’s history. As the season 4 winner, she’s become an integral part of its legacy.
Two decades after appearing as a contestant on the program in 2005, the country singer, 42, came back to where it all began, but in a new role as a judge! On March 9, Underwood began this new chapter alongside seasoned judges Luke Bryan and Lionel Richie, consistently delivering stunning looks week after week.
“I absolutely love fashion and getting to play dress-up for my job,” Underwood shared before the season’s conclusion on May 18.
She didn’t undertake the task of styling a new outfit each week alone. With the help of her stylists Marina Toybina and Courtney Webster, the “Good Girl” singer assembled a wardrobe of gowns, suits, minidresses, and more that balanced “comfort, functionality, and fun.”
“Designing for the show felt like a natural extension of our previous work together,” Toybina and Webster said. “Each look needed to embody her strength, grace, and star power. We adopted a more refined, editorial approach for television, allowing her authenticity to shine in a seated setting, while still retaining that signature Carrie brilliance.”
What makes a look distinctly “Carrie”? It’s about bold femininity and drama expressed through “refined embellishment” and pieces that highlight her figure. “It’s that quiet confidence woven into every thread,” they explained.
Here are more style details from Underwood and her stylist team.
**Blast from the Past**
Throughout the season, Underwood included nods to her 2000s outfit choices.
“There are definitely a lot of things I still have, like my original finale dress and the jacket I wore when I originally performed ‘Alone,’ both of which I loved bringing back this season,” Underwood said.
Beyond re-wearing iconic pieces — such as the low-cut leopard-print dress from 2005 — she incorporated references to many of her past looks. “I love that we gave a nod to my original audition outfit with the pink dress I wore on the first day as a judge,” she added, referring to the bright pink cape dress she wore for the season premiere.
Discussing how her personal style has evolved, Underwood continued: “Well, back then, we were wearing our own clothes and the few things we were able to buy with a very modest wardrobe budget. Even then, I always wanted to be comfortable, and I did get to play around a little with different looks and hairstyles in that first season.”
Referencing her past was meaningful for Underwood in several ways. “I owe my career to the show. It has been such an important part of my life, and I will always be grateful for that. Coming back as a judge 20 years later is such a special full-circle moment for me, and it’s meant a lot to share that journey with the people that have been there from the beginning, as well as a whole new generation of fans.” Stay tuned for more updates from Eternal Pen.
Toybina and Webster shared that seeing Underwood revisit her archives was incredibly nostalgic and significant. “Watching her step back into those moments with such grace reminded all of us how far she’s come — and yet how grounded and true to herself she’s remained.”
**Setting the Bar**
The stylist duo mentioned that there wasn’t a particularly “risky” outfit chosen. They aimed to experiment with diverse aesthetics for each show, always striving to present their best work.
“We did take a few bold, creative leaps, especially when aligning wardrobe with the themed episodes. It was a careful balance between pushing fashion boundaries and honoring the theatricality of the themes, all while preserving the integrity of Carrie’s personal style. Every choice was intentional, and Carrie carried each look with effortless poise and confidence,” they said.
Underwood also noted that wardrobe malfunctions were avoided. “We’ve had a couple behind the scenes, but the team is always quick to address them. Thankfully nothing too major. Definitely fewer chances of that happening here than when I’m performing live on stage for two hours with multiple wardrobe changes.”
**Prep Time**
Putting together such an extensive collection of outfits from various sources — including Underwood’s own closet — requires considerable preparation on the part of Toybina and Webster.
“Preparing for the season took months of planning and creative development. Given Carrie’s demanding schedule, we split fittings into multiple sessions to ensure flexibility and the ability to thoughtfully curate each look. Once the hero option was selected, it typically took about a week leading up to each episode to perfect the details, from tailoring and custom embellishments to accessories and final styling. Every ensemble was crafted with intention, aligning with the week’s theme while staying true to Carrie’s elevated and ever-evolving aesthetic.”
Underwood was also an effortless collaborator. “Carrie has an innate understanding of who she is, both as an artist and a woman. She’s collaborative, open, and deeply respectful of the creative process. Her trust, humility, and radiant spirit make every moment of working together a privilege.”
**The Favorites**
Underwood “loved all of the looks,” but some definitely stood out. “The Rock & Roll Hall of Fame episode was definitely a favorite,” said the singer, who wore her own leather jacket and a custom kilt for the taping.
“I also loved the gown I wore to perform ‘How Great Thou Art’ for the Easter show. And, of course, who doesn’t want to dress like a Disney princess, so looks inspired by Alice in Wonderland and Rapunzel were a lot of fun.”
As for Toybina and Webster, they favored the multicolored beaded column dress that she wore on the “Iconic Women” episode. “The refined elegance of its silhouette, combined with the striking, architectural intricacy of the hand-beaded embellishments, made it both visually captivating and artistically exceptional.”
**Standing Ovation for the Glam**
Of course, Underwood elevated her glam to complement her fashion. Makeup artist Melissa Schleicher consistently created Underwood’s signature glossy lip, while hairstylist Lorenzo Martin styled her hair in diverse ways.
“It’s fun to play, but I always want to look like me,” Underwood said of her look. “In the same way we like to bring the rhinestones and sequins and fringe to the fashion, we always love to bring ‘more’ to the glam too — more lashes, more hair and more sparkle!”
The season 23 finale of the music competition aired May 18.
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