Carrie Underwood has worn bold looks throughout her career.Hubert Vestil/WireImage/Getty ImagesCarrie Underwood returned to "American Idol" as a judge on Sunday.Since first appearing on the show in 2005, she's been pushing fashion boundaries on red carpets.Here are the singer's most daring looks of the last 20 years.It's been two decades since Carrie Underwood took the stage and was crowned the fourth winner of "American Idol."Since then, Underwood, 41, has become one of the most successful contestants on any reality show, not just "American Idol." She has dozens of awards to her name, including eight Grammys, 10 People's Choice Awards, and 25 CMT Music Awards — and now she's back on "American Idol," but this time as a judge.She's also become a fashion risk-taker. Underwood has worn many bold styles across her career and rarely plays it safe.We've chosen 38 of the most daring looks she's worn since winning "American Idol" 20 years ago — take a look.After she won "American Idol" in May 2005, Underwood walked the red carpet in a bold animal-print dress with a jade-and-red belt."American Idol" winner Carrie Underwood posed in the press room in 2005.Frederick M. Brown/Getty ImagesUnderwood beat the other finalist, Bo Bice, to become the champion of season four of "American Idol." She's since become one of the most successful contestants of all time.She went full Old Hollywood glam at the 2006 Academy of Country Music Awards in May 2006.Carrie Underwood at the 41st Annual Academy Of Country Music Awards.Kevin Winter/Getty Images for ACMAUnderwood opted for a satin champagne-colored dress with another low-cut neckline for her first ACM Awards. She accessorized with a silver necklace featuring a large black pendant.At the 2006 CMA Music Festival in June, Underwood paired pinstripe shorts with a denim corset top and cowboy boots.Carrie Underwood at the CMA Music Festival.Tony R. Phipps/Contributor/Getty ImagesThis look proves that Underwood wasn't — and still isn't — afraid to mix patterns, materials, and aesthetics on the red carpet.At the 2006 CMA Awards, Underwood wore this backless white fit-and-flare gown.Carrie Underwood at the 40th Annual CMA Awards.Peter Kramer/Getty ImagesWhile her piecey updo is very 2006, this dress has stood the test of time — Sabrina Carpenter wore a similar look to the 2025 Grammys.Later that month, Underwood paired princess glam with some rock 'n' roll edge at the 2006 American Music Awards.Carrie Underwood performed onstage at the 2006 American Music Awards.Ethan Miller/Getty ImagesUnderwood wore a bold, black ball-gown skirt over gray shorts with a matching gray and black top to perform a medley of her biggest hits at the time: "Jesus, Take the Wheel," "Don't Forget to Remember Me," and "Before He Cheats."Underwood wore a canary-yellow gown that was almost entirely backless at the 2008 CMA Awards.Carrie Underwood at the 42nd Annual CMA Awards.Bryan Bedder/Getty ImagesThis gown was designed by Roberto Cavalli.Underwood switched it up a little for a 2009 Grammys event by channeling disco divas in a black polka-dot minidress with bell sleeves.Carrie Underwood at a 2009 Grammy event.Steve Granitz/WireImage/Getty ImagesUnderwood ditched her usual country vibes for this event by channeling '70s disco glam.At a 2010 Grammys event, Underwood wore this one-shouldered dress that's criss-crossed with pearls and sequins.Carrie Underwood at a 52nd Annual Grammy Awards event.Steve Granitz/WireImage/Getty ImagesHer look was designed by Jenny Packham.Underwood looked like she was wearing a watercolor painting at the ACM Awards in April 2010.Carrie Underwood backstage at the 45th Annual Academy of Country Music Awards.Christopher Polk/ACMA2010/Getty Images for ACMAThe strapless dress featured a satin lavender belt around her waist.Later that year, at the CMA Awards in November, Underwood wore a bold gray dress featuring an oversize peplum waist.Carrie Underwood at the 44th Annual CMA Awards.Michael Loccisano/WireImage/Getty ImagesThe gun-metal gray was a new look for the singer, as was the tulle, but the rose detail at the waist is pure Underwood. The look was designed by Talbot Runhof.Underwood wowed in this red gown with a thigh-high slit at the American Country Awards in December 2010.Carrie Underwood at the 2010 American Country Awards.Ethan Miller/Getty ImagesThe beaded cummerbund and sheer overlay on the shoulders of this Georges Chakra gown really add to the glam.Underwood wore this artfully draped fuchsia gown at the 47th ACM Awards in 2012.Singer Carrie Underwood at the 47th Annual Academy Of Country Music Awards.Christopher Polk/ACMA2012/Getty Images for ACMAs we've seen, Underwood is never one to shy from a daring neckline.We can't tell if it's Underwood or Cinderella on the red carpet of the Billboard Music Awards in May 2012.Carrie Underwood at the 2012 Billboard Music Awards.Jon Kopaloff/FilmMagic/Getty ImagesUnderwood landed on many best dressed lists in this gray/blue ball gown that's fit for a princess and designed by Oscar de la Renta.Underwood wore a white gown with sheer panels and golden leaves and accessorized with husband Mike Fisher at the 2012 CMA Awards.Carrie Underwood and Mike Fisher at the 46th Annual CMA Awards.Taylor Hill/WireImage/Getty ImagesThe sheer panel on this dress goes all the way down to just above her belly button.At the 2013 CMA Awards, Underwood rocked a skin-toned dress with a sheer skirt.Carrie Underwood at the 47th annual CMA Awards.Larry Busacca/WireImage/Getty ImagesThe elegant rose-gold look was designed by Ralph & Russo.In May 2014, the "Smoke Break" singer walked the Billboard Music Awards red carpet in this electric-yellow dress with a silver bodice and low neckline.Carrie Underwood at the 2014 Billboard Music Awards.Frazer Harrison/Getty ImagesThe intricately detailed gown was designed by Oriett Domenech.Later that night, she strutted the red carpet with her award in this shimmery gown with a slit and a cutout.Carrie Underwood, winner of the Milestone Award, posed in the press room during the 2014 Billboard Music Awards.Frazer Harrison/Getty ImagesUnderwood won the Milestone Award that year, and she showed it off while in this stunning dress with a bold golden belt.Her heels feature miniature golden crocodiles, too.She wore a white dress covered in pink and black flowers with a similar silhouette to the 2014 CMT Music Awards.Carrie Underwood at the 2014 CMT Music Awards.Mike Coppola/WireImage/Getty ImagesThe dress, which features a keyhole cutout, was designed by Roberto Cavalli.Underwood wore a sparkly blush-colored mini dress with a bedazzled cape at the 2015 American Music Awards.Carrie Underwood at the 2015 American Music Awards.Axelle/Bauer-Griffin/FilmMagic/Getty ImagesUnderwood, who took home the favorite country female artist award, was adorned in Yas Couture.For the (original) "American Idol" series finale in April 2016, Underwood wore a feathery gown with a see-through bodice and skirt.Carrie Underwood at Fox's "American Idol" finale in 2016.Alberto E. Rodriguez/Getty ImagesThe look was designed by Yanina Couture.She continued her bold choices at the 2016 American Country Countdown Awards with this structured white gown.Carrie Underwood at the 2016 American Country Countdown Awards.Kevork Djansezian/Getty Images for dcpYou might not be able to see them, but the Gauri & Nainika gown actually features white shorts underneath.When Underwood and her husband attended the CMT Music Awards in 2016, she wore a dress with a slit all the way up to her hip.Mike Fisher and Carrie Underwood at the 2016 CMT Music Awards.Sara Kauss/FilmMagic/Getty ImagesUnderwood's dress features a cutout just below her shoulder, too.To walk the red carpet of the 2017 Grammys, Underwood wore this blood-red gown with a keyhole cutout and a center slit.Carrie Underwood at the 59th Grammy Awards.Frazer Harrison/Getty ImagesThe dramatic long-sleeved dress was designed by Elie Madi.Underwood wore a skin-colored high-neck gown with crystal embellishments for the ACM Awards in April 2017.Carrie Underwood at the 52nd Academy of Country Music Awards.Allen Berezovsky/WireImage for Fashion Media/Getty ImagesThis sparkly, shimmery look was designed by LaBourjoisie.She wore a beige gown with a tulle overlay, red flowers, and a deep-V neckline at the 2018 ACM Awards.Carrie Underwood at the 53rd Academy of Country Music Awards.Jeff Kravitz/ACMA2018/FilmMagic for ACMUnderwood looked like a woodland fairy in this Berta gown — this evening was also her first performance after an accident that led to her getting 40 stitches in her face, per Us Weekly.She wore an ornate beige and bronze dress with a periwinkle train on the red carpet of the 2019 CMA Awards.Carrie Underwood at the 53rd annual CMA Awards.Jason Kempin/Getty ImagesThis glam dress — one of nine looks she wore that evening — was designed by Elie Madi.Underwood wore this deep-purple sequined gown with a high slit at the American Music Awards in November 2019.Carrie Underwood at the 2019 American Music Awards.Rich Fury/Getty ImagesThe asymmetrical gown was from Stello by Stephanie Costello.She went for this edgy black dress with buckle details for the ACM Awards in September 2020.Carrie Underwood at the 55th Academy of Country Music Awards.John Shearer/ACMA2020/Getty Images for ACMThe sparkling, belted dress was designed by Marina Hoermanseder.For the Latin American Music Awards, she chose beachy waves and a sunset-colored ombré dress.Carrie Underwood at the 2021 Latin American Music Awards.Aaron Davidson/Telemundo/NBCU Photo Bank via Getty ImagesThis butterfly-inspired look was designed by Iris van Herpen.Underwood made sure everyone stayed 6 feet away in this one-shouldered dress covered in silver spikes at the 2021 CMA Awards.Carrie Underwood at the 55th annual Country Music Association Awards.John Shearer/Getty Images for CMAThe bold look was designed by Jean-Louis Sabaji.Underwood was dressed for a celebration at the 2022 ACM Awards, wearing this silver confetti-inspired minidress.Carrie Underwood, winner of the single of the year award, posed in the press room during the 57th Academy of Country Music Awards.Mindy Small/WireImage/Getty ImagesAnd celebrate she did in this Rami Kadi dress — she won single of the year for her duet with Jason Aldean, "If I Didn't Love You."Underwood wore a gold ombré ball gown with a crystal bodice to the 2022 Grammys.Carrie Underwood at the 64th Annual Grammy Awards.Jeff Kravitz/FilmMagic/Getty ImagesThe bold look was designed by Dolce & Gabbana. That evening, she performed her song "Ghost Story" and won the Grammy for best roots gospel album for "My Savior."The "Cry Pretty" singer wore a purple chain-mail leopard-print minidress at the CMT Music Awards in April 2022.Carrie Underwood at the 2022 CMT Music Awards.Terry Wyatt/WireImage/Getty ImagesShe paired the mini with a pair of sky-high black pumps.She took a Canadian tuxedo to a whole new level at the 2022 iHeartCountry Festival.Carrie Underwood posed backstage during the 2022 iHeartCountry Festival.Bob Levey/Getty Images for iHeartRadioIn a nod to her album "Denim & Rhinestones," she picked a denim vest, purple acid-washed denim shorts, and rhinestone-encrusted denim boots for her performance.At the 2022 CMA Awards, she wore a dramatic off-the-shoulder blue gown with a long train and high slit.Carrie Underwood at the 56th Annual CMA Awards.Sara Kauss/FilmMagic/Getty ImagesThis look came from La Metamorphose, a French couture brand.A few weeks later, Underwood walked the 2022 American Music Awards red carpet in a fringed pink gown with another slit.Carrie Underwood attends the 2022 American Music Awards.Tommaso Boddi/WireImage/Getty ImagesThe Tony Ward dress was a pastel pink with silver trim and blue, pink, yellow, and green fringe.To attend the 2023 CMT Awards in April, Underwood was decked out in crystals.Carrie Underwood at the 2023 CMT Music Awards.Hubert Vestil/WireImage/Getty ImagesThe all-silver tailcoat and shorts were designed by Dolce & Gabbana and were entirely encrusted in Swarovski crystals.She kept the metallic silver look going for the Songwriters Hall of Fame induction ceremony in June 2024.Carrie Underwood at the Songwriters Hall of Fame 2024 induction.ANGELA WEISS/AFP/Getty ImagesThis unique Rafik Zaki strapless dress featured a chrome breastplate and a crinkled high-low skirt.
