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Country Star Kellie Pickler’s Style Transformation: From Ball Caps to Ball Gowns [Photos]

Style

Nov 14, 2023 11:19 am·

By Whitney Danhauer

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The world first met Kellie Pickler on the humble stage of the American Idol audition room during season 5. She wowed the judges with her vocals and quickly became a fan favorite. While Simon Cowell ultimately believed Kellie should take home the prize, it went to Carrie Underwood instead. However, that didn’t stop Kellie from paving her own way in the music industry.

Over the years, audiences have watched Kellie’s style change. From the short spiky hair in 2008 to throwing on a baseball cap with a T-shirt and jeans, Kellie always manages to look effortlessly cool and beautiful.

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2005

Kellie first charmed Simon Cowell, Paula Abdul, and Randy Jackson in her 2005 audition on American Idol. The Georgia native sang a song by fellow American Idol alum, Kelly Clarkson. Her long amazing voice and infectious attitude earned her a spot in the competition where she made it all the way to sixth place.

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2008

While she might not have won American Idol, it was only three short years later that Kellie was officially in the big league and attending the Academy of Country Music Awards. Her flirty black dress, headband and short, spiky hair was definitely on trend in 2008. Kellie was nominated for the New Artist of the Year award, but lost it to her friend, Taylor Swift.

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2009

In 2009, Kellie found herself back at the Academy of Country Music Awards, but this time she went for a much sleeker look. Sporting a smooth shoulder length bob and a form fitting gold dress, Kellie was an eyecatcher with that svelte figure.

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2012

Kellie hit the stage at the Arizona Country Thunder music festival in 2012. Flaunting toned arms while wearing a black tank top and jeans while she performed, Kellie was part of a lineup that included Big & Rich, Dierks Bentley, Alan Jackson, and more.

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2016

It was a big year for Kellie as she was inducted into the North Carolina Music Hall of Fame. At this point, Kellie was married and settling into life with late husband, Kyle Jacobs. She showed up at the Viacom Kids and Family Group Upfront event wearing a wine-red dress and loose waves in her blonde hair.

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Kellie Pickler crossing the finish line at the St. Jude Rock 'n' Roll Nashville Marathon.

2017

Kellie successfully completed the St. Jude Rock ‘n’ Roll Nashville Marathon in 2017. The “I Wonder” singer has been a longtime supporter of St. Jude. When she visited Pennington Elementary School in 2007, Kellie said, “When you’re able to give back to your communities and organizations like St. Jude, it’s a great thing,” Pickler said. “It’s been a great experience, and I encourage anyone and everyone to help.”

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2019

Kellie was one of several celebrities who visited the Hallmark Channel’s “Home & Family” event at Universal Studios Hollywood in 2019. She stunned in a form-fitting black dress, silver heels and long blonde hair.

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Stormy Warren, Ashley Cooke, and Kellie Pickler at SiriusXM's The Music Row Happy Hour Live on The Highway from Margaritaville

2022

During day 1 of The Music Row Happy Hour Live On The Highway From Margaritaville In Nashville in 2022, Kellie proved she doesn’t need to get all glammed up and still turn heads. She looked casually cool in a T-shirt and jeans alongside Storme Warren and Ashley Cooke on stage.

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Buzz Brainard (L) and Kellie Pickler (R) pose for a photo onstage with Lauren Alaina during SiriusXM's The Music Row Happy Hour Live On The Highway From Margaritaville

2022

Kellie continued her lowkey look on day 2 of SiriusXM’s The Music Row Happy Hour Live On The Highway From Margaritaville In Nashville wearing a ball cap and a T-shirt that read, “Nevertheless, she raises some hell.” Good for you, Kellie!