The Stunning Style Transformation Of Lainey Wilson

Lainey Wilson's music career has been built on her vocals, stage presence, and, of course, her bell-bottoms. After learning how to play the guitar from her father and spending a few years as a Hannah Montana impersonator, Wilson made the move to Nashville, Tennessee, in 2011, and hasn't looked back.

By 2014, Wilson would release her self-titled debut album. Its successor "Tougher" was released in 2016, and the country music singer was on her way to stardom. Before she knew it, she was performing at places like the Mercury Ballroom and attending events like the ASCAP Country Music Awards. Just as surely as Wilson began to gain notoriety, people started noticing a pattern with her outfits.

During her interview for People's StyleWatch for Summer 2023, she noted, "I'll probably be 90 years old and still wearing bell-bottoms — I don't think anybody's ever seen my ankles!" Hey, we're not mad about it. Take this as a sign to add a pair of flared jeans to your wardrobe. Wilson has perfected the art of a staple: Find a garment you love and feel comfortable in, and figure out creative ways to style it from there. Though the star said to People in September 2024 that she's worn the flared-out jeans "every single day," she never wears the same pair twice. Utilizing all kinds of material, textures, colors, and patterns, Wilson's look is classic and refined. That's not to say her style evolution hasn't made any strides; it still took her some time to find her footing in the fashion world. Let's unpack Lainey Wilson's stunning style transformation.

Lainey Wilson took her bell-bottoms to the stage when her career was taking off in 2016, but the singer-songwriter has always had a soft spot for that delicious denim. During the interview with People in September 2024, Wilson expressed that she had first discovered the classic Western piece when she was young, but it wasn't any accident that they landed back in her wardrobe. "I realized pretty quickly that as a decent female singer-songwriter, that's not enough. I needed to do something that made me stand out and stand apart," she remarked during the interview. Her signature look at the crossection between '70s vintage and cowboy couture was born.

During the first few years of her career, Wilson primarily stuck with classic denim, but her outfits were anything but boring. In December 2017, the "Heart Like a Truck" singer partook in a Christmas-themed photoshoot with her signature ensemble locked and loaded. She wore a white button-down, tied into a knot at the bottom, a burgundy coat thrown over her shoulder, a matching statement necklace, black bell-bottoms, and square-toe boots. Even back then, her fans still knew it was iconic, one writing under her Instagram post, "You bellbottomed bada**!" Another cheered her on with, "You go girl."

In June 2019, Wilson was named one of CMT's Next Women of Country and joined four others on stage at the Country Music Hall of Fame for a panel and live concert. Sitting with her acoustic guitar in her lap, Wilson wore a pair of dark-wash denim bell-bottoms and a patterned babydoll blouse. Even back in the day, she was taking notes from our ultimate guide to styling flared jeans. It gave toned-down coastal cowgirl, the perfect aesthetic for an event like this.

The year 2020 was a landmark one for Lainey Wilson, as she made her debut at the Grand Ole Opry in February. After several months of quarantine, she released her single "Things a Man Oughta Know" in August 2021, which later became her first single to reach number one on country radio. Significant strides in her career were a turning point for Wilson's style (aka her bell-bottoms), as she became more adventurous with her stage looks by incorporating different fabrics, textures, and accessories.

In September 2020, Wilson performed at The Basement in Nashville, Tennessee, and her look was the perfect elevation of the coastal cowgirl aesthetic, which is perfect for spring wardrobes as we know. The singer wore a red button-down shirt with a brown leather vest, pairing it with snakeskin bell-bottom pants. She finished off the look with an assortment of chunky necklaces, a brown beaded belt, and statement earrings. Perfectly bohemian, perfectly country.

The following years were when Wilson truly found her footing as an artist. In 2021, she won two ACM awards. In 2022, Wilson made her acting debut on "Yellowstone." By 2023, she swept the CMAs with five wins, partially due to the success of her album "Bell-Bottom Country." What can we say — the woman knows her brand. The look she wore to the event was another turning point for Wilson, as she debuted a Carolina Herrera black jumpsuit with ruffled bell-bottoms. She paired the garment with a black cowboy hat and lots of statement jewelry. Who said country couldn't also be glam?

Lainey Wilson was riding high in 2024, so much so that she nearly abandoned her signature ensemble. In September of that year, she attended the Carolina Herrera show at New York Fashion Week, but her outfit stole the show. The "Watermelon Moonshine" singer seemed to don a floral floor-length dress with a navy belt and gold jewelry. However, at a closer glance, it turns out that the "dress" was a jumpsuit all along. Though now in a slightly different silhouette for Wilson, this 'fit proves that pants will always be her first option.

Following the event, Wilson shared a carousel of photos on Instagram, writing how full circle it was to be at one of Herrera's shows. "I wore @carolinaherrera for last year's #CMAawards red carpet, and on the morning of the nomination announcement for the 2024 CMA Awards, I'm heading to my first fashion show for #NYFW, with none other than Carolina Herrera of course." She had been nominated for four CMA awards, and only a few days later, it would be announced that she would be joining Peyton Manning and Luke Bryan to host the event. "I think I could bring something to the CMA Awards that you ain't never had before ... Like humor. Like personality. Like style. A little bell-bottom flare," she said during the announcement video, and she did just that.

This year has been shaping up to be another phenomenal one for Lainey Wilson. At the ACM Awards in May, she brought home four wins, later writing on Instagram, "To the country music fans and to the country music community, thank you. All I've ever wanted to do is sing and write music. Y'all have given me a stage for my songs to be heard and I will never be able to tell you how thankful I truly am for just giving me a shot. Here's to 14 years in Nashville doing the only thing I know how to do. Love y'all to the moon."

For the event, Wilson gave us two stunning looks. For the red carpet, she opted for a monochromatic brown-suede look, with a vest and bell-bottoms with sewn-in chaps. She paired the outfit with a matching cowboy hat and a turquoise bolo tie to coordinate with the embellishments on her hat and top.

Later, she changed into a leather bustier with matching fringe armbands, a matching pair of bell-bottoms with lace embellishments, a black cowboy hat, and turquoise statement jewelry. In conclusion, Lainey Wilson is nothing less than a Western fashion icon.