Lainey Wilson Outfits That Left Us Scratching Our Heads

Country music comes with a certain image that many artists emulate. Cowboy hats and boots are musts, while a generally laidback vibe and possibly some beachy hair waves complete the puzzle. But Lainey Wilson has cultivated her own unique look while still ticking the country-music boxes. She loves her Westerncore essentials as much as the next singer from Louisiana, but she also knows how to stand out on the red carpet. 

Having reached new career heights in the 2020s, the "Wildflowers and Wild Horses" singer has become known for her country couture looks, one of the more feminine takes on Western fashion. Her claims to fame? Seriously flared jeans and flowy tops. The artist calls on vintage inspirations (typically right out of the '70s) and is quickly becoming synonymous with her go-to platform shoes and textures, including feathers, fringe, and leather. She loves bright palettes (and looks unbeatable in all black), and also has a soft spot for the usual country conventions like denim, vests, and blazers. Of course, that courage to go against the grain and find her own style naturally lends itself to a few fashion misses. 

Wilson doesn't often end up in downright awful looks on the red carpet (though she did end up on our list of worst-dressed celebs at the 2025 Academy of Country Music Awards), but she has occasionally left us confused. From colors that blurred outfit lines to bits of material that seemed like safety hazards, the following Wilson outfits are head-scratchers. 

We love Lainey Wilson's signature style: the high-waisted flared pants, the flowy capes and skirts, and the cowboy hat. But when an outfit like this is worn to the 2025 Emmys, we have to wonder whether the "Somewhere Over Laredo" singer knew where she was going. For a performance at the CMTs, this would have landed, but on a prestigious red carpet where the majority of stars are in formal wear, this came off as costumey. Also, that white sheer material being dragged on the carpet is just asking for trouble. We're glad Wilson didn't trip, but we can imagine the fabric was dirty by the end of the night.

You have to admire Lainey Wilson for consistently experimenting on the red carpet. Her bold choices very often pay off, but every now and then, they don't. At the Academy of Country Music Awards in 2025, she chose chaos with an embellished blazer that came with a lacy train and cutouts. We usually love her signature bell bottoms and cowboy hat, but thrown together with this maximalist blazer, it was all a bit puzzling. It's a shame because Wilson usually kills it in all black. 

Obviously, Lainey Wilson prefers a maximalist look over minimalism or quiet luxury, and to each their own. But even a country star known for going big and bold can push things too far. If you've already got interest in your outfit with a leather-look finish, a bright belt, and an embellished cowboy hat, you don't need a bulky necklace that drapes chains of bling literally down to your thighs. Wilson wore this to the June 2025 launch of her Golden West Boots line, so it was also a missed opportunity to show off her boots instead of muddling things with the necklace.

Within a millisecond of viewing Lainey Wilson's look from the 2024 Tortuga Music Festival, you know exactly what's wrong with this 'fit. The wet-look finish can elevate any outfit, and when placed elsewhere, it probably would have livened up this simple jeans-and-vest combo. Unfortunately, the specific area of Wilson's jeans that seems drenched is bringing up an iconic scene from "Billy Madison." Let's just say the effect did her no favors! But if she wants to try this style again, maybe she can pair it with the popular wet-hair look for some cohesion. 

We wanted to love this snakeskin suit, truly. But rather than falling in love with it, we're questioning why the bottoms are sort of flared but not really, or what exactly is going on with the chainmail around the chest. When Lainey Wilson wore this to the ASCAP Country Music Awards in 2018, she didn't look like her proud, comfortable self in it. Her unsure stance almost hints that she knows the forgettable silhouette doesn't fit the bold snakeskin. We're definitely glad she's found her sense of style since then!

We love you, Lainey Wilson, but this look from the 2021 CMAs is one big yikes. Let's just begin with the clashing colors: The patterned dark blazer looks like it comes from one outfit, while the tiger-striped bell bottoms seem to come from another one entirely. Then, there's the fact that the flared bottoms are too long, and the "Hang Tight Honey" singer looked like she was going to trip any second. We know she has a thing for elastane pants, but the material looked cheap and Halloween-ish when paired with the more sophisticated blazer. 

It seems that 2021 was Lainey Wilson's era of mixing and matching unexpected tops and bottoms. This look from a pre-CMAs party definitely carried the theme of dressier blazer and spandex bell bottoms, but on a much bigger scale. The colors are the biggest clash here, even though we do appreciate the flow from the bling-y blazer to the sequin stars on the pants. And while the blazer is sparkly, it looks like tweed from faraway, which made us stamp this with an immediate "nope." Honestly, there's just too much mental work required to process this ensemble, and we hope to never see it again.

Another day, another Lainey Wilson look that forces our brains to overheat as we work out exactly what's going on. On the plus side, this mustard-toned outfit (it reads tiger-orange in some photos) that Wilson wore to the 2022 CMT Artists of the Year ceremony was creative. On the downside, the pants may or may not have come from the bedspread of your grandma's house. They're eyesore enough, but then there's the snakeskin shirt, knotted up for good measure, the fringed brown vest, and the feathers on the hat. All of those textures and the all-over yellow palette still make it hard to distinguish what is what. 

This look that Lainey Wilson wore to the April 2023 Axios After Hours event made us scratch our heads at first, but now we've worked it out: She went to disco in the '70s, stopped off at after-dinner drinks with the girls, and then finished at a ranch before walking the red carpet. In all seriousness, the contrast between lace and elastane (or maybe it's the marrying of black and bubble-gum blue) is blowing our minds here, and that's before we can even factor in the hat. But once again, this was a necessary misstep for Wilson to finally find her fashion voice.

Lainey Wilson's love for flowy materials sure makes it difficult to understand her outfit sometimes. We're most likely looking at a top and pants here at the 2024 Academy of Country Music Honors, but the blurry, skin-toned pattern threw us. Then, there are the bell sleeves that, at times, made the singer look like some kind of bird. This outfit is by no means ugly, but it is confusing, especially when you consider the patches of pink that look like unfortunately placed cutouts. But ultimately, Lainey Wilson has had a stunning style transformation, and oddball looks like this have just made the journey all the richer.