Lainey Wilson's Biggest Fashion Disasters

Lainey Wilson's stunning transformation from singer-songwriter to "Yellowstone" star has pushed her adventurous style onto carpets and stages across the globe. Always pairing bold patterns with each other or opting for more loud and proud colors, the country performer has donned more than her fair share of funky ensembles in attendance at many high-profile events. Wilson described her approach to her personal style in an interview with People's StyleWatch: "I feel like I get to get up every single morning just like writing a song I get to express myself however I am feeling that day," she said with a smile (and her signature bell-bottoms). 

Bell-bottoms are one of the few staples in Wilson's wardrobe. This love runs deep too. In 2023, she claimed that she had worn bell-bottoms every day for eight straight years. She joked with People, "I'll probably be 90 years old and still wearing bell-bottoms — I don't think anybody's ever seen my ankles!" Outside of this pillar in her closet, we have Dolly Parton, Stevie Nicks, and Janis Joplin to thank for Wilson's out-there style. While it's great to see such a powerful force in the country music space take on a daring approach to the world of fashion, especially one so inspired by music greats before her, Wilson's creative style has landed her in some iffy outfits over the years. 

For the 2025 Emmys, Lainey Wilson joined the carpet in an all-white ensemble, topped with a cowboy hat and bedazzled sheer pants. From her signature cowboy hat to the wrapped goddess-like design of the halter top, the outfit is incredible. But as attention is drawn downward in the look, the 'fit falls apart. 

The billowing sheer train of Wilson's top is far too long and outdated, made of a light, soft material that cannot compete with the harshness of her sequined pants. The pattern created by the sewn-on sequins is reminiscent of a tapestry hung in college dorms. 

One of the worst dressed at the 2025 Academy of Country Music Awards, the country music singer wore an all-black look for the red carpet, of course styling her go-to hat and bell-bottom pants. Wilson's outfit is bogged down by chunky jewelry pieces — a huge necklace and large pointed earrings — that fight for attention with her intricate jacket. 

There's just one too many elements to the suit coat. Snaking silver stones, 3D flower details, a lace train, and cut-outs, these features by themselves are very interesting, but all together create an overwhelmed piece that drowns under the weight of each design. 

A surprisingly simple look for the singer-songwriter who loves to go big or go home, Wilson sported this getup on the red carpet of the CMT Music Awards in 2024. The asymmetrical top adds some much-needed dimension to this ensemble, but its shimmering metallic material gives the impression of being a fast fashion purchase. 

Her pants feature a polka dot pattern made out of rounded silver mirror material, giving Wilson the appearance of a deconstructed disco ball. The wide-brim cowboy hat comes in to save the day, looking sophisticated and clean as ever on the "Yellowstone" actor. 

"Yellowstone" actor Lainey Wilson joined the star-studded carpet of the 2023 Macy's Fourth of July celebration in a blue cheetah pant and black lace top. Wilson's blouse is an overly complicated piece, overwhelmed by a combination of a tie waist, necktie detail, and lace sleeves.

The blue cheetah print bell-bottoms were certainly a choice ... a questionable choice, but if Wilson wanted to stick to her beloved bell-bottoms than she may have been better off with a simpler top. Like Wilson's CMAs jacket, there's simply too much going on here.

Lainey Wilson performed at the Country to Country 2023 concert event in a pair of yellow gold bell-bottoms with silver sequined stars. Paired with the bold toned pants was a unique polka dot patterned blouse. 

You have to give it to Wilson for her daring fashion sense, but unfortunately for the country singer, this look did not pay off. The yellow gold comes off as tacky under the lights of the stage, and the polka dot top struggles to complement the aesthetic of the pant. 

Attending Dolly Parton's album release party in 2023, Lainey Wilson leaned hard into her country background. This outfit screams cowboy — unfortunately it also just screams. The cheetah print blouse with the polka dot scarf, tucked underneath a heavily designed suede jacket, each piece individually is very cowboy, but also just too much. 

With all that, at least it can be said that Wilson holds true to her inspirations for her sense of style. With the layers of dangling fringe and scarf accessory, the singer's Stevie Nicks inspo is very obvious. 

In 2024, Lainey Wilson strutted her stuff on the carpet for the Billboard Women in Music event. Donning her iconic wide-brim black hat, which paired perfectly with her black jacket, her outfit turned heads with her choice to wear this loud jumpsuit. 

The piece sucks the attention away from the incredibly detailed elements of the look with its garish print. Her metallic and turquoise belt disappears against the jumpsuit, as do Wilson's many silver rings. It's even hard to enjoy the attention to detail put into pairing the turquoise elements of the belt to the beaded breast pocket of the jacket.