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Lainey Wilson Brings Back Classic Mid-2000s Fashion in Leather, Cowboy Hat Look

The country superstar sported a throwback favorite while hanging out with Jelly Roll and Post Malone.

Allie Hayes

Lainey Wilson
Lainey Wilson / Kristina Bumphrey/Billboard/Getty Images

Lainey Wilson was a mid-2000s dream girl in her latest photo drop!

The 32-year-old Grammy-winning country music superstar took to social media this week to treat her 3.2 million Instagram followers with a look at her latest style choice, and it’s certainly bringing me (hi, it’s me, the human writing this article) and many of her fans crashing back to our high school days in the early aughts (yes, I’m ancient).

In the 11-photo carousel, which Wilson captioned “@jellyroll615 sure knows how to throw a party! Had so much fun last night at @billybobstexas with some of my buddies ❤️,” the singer sported a pair of hip-hugging low-rise leather pants, which she accessorized with several black and silver belts.

Though truth be told, the top was certainly the star of the outfit! Wilson opted for a mid-2000s classic in the form of a repurposed, bedazzled Ed Hardy tank with a unique halter-esque neckline. And of course, no country look would be complete without a hat, with Wilson donning a flat-brimmed black cowboy hat with silver accents to match her many belts. For footwear, the singer sported some daring black heels (seriously, I’ve somehow twisted my ankle just picturing trying to walk in them).

Her long, wavy blonde tresses were left down, cascading onto her shoulders from beneath the brim of her cowboy hat and providing a stark contrast against the otherwise dark ensemble. Her makeup was the perfect springtime into summertime transitional look, with natural, glowy skin, pink cheeks and nude lips being the name of the game.

But this fabulous outfit wasn’t the only star featured in Wilson’s latest photo drop, with the singer sharing several selfies alongside her friends and fellow artists Jelly Roll and Post Malone, who looked equally stylish for the evening event.

And of course, countless fans of the country superstar had plenty of love to share in her comment section, stopping by to praise her look—but namely, that throwback Ed Hardy top:

“Omg Ed Hardy throwback 👏👏,” one fan praised.

“I really want this shirt! ❤️,” another commenter added.

“🙌😍🤠,” one more fan simply wrote, using the perfect sequence of emojis.

Wilson has certainly had a busy 2025 so far, kicking off her appropriately named Whirlwind Tour back in March with dates going through Nov. of this year. She also recently graced the pages of Rolling Stone UK as their April/May cover star, where the magazine dubbed her “the cool girl of country.”

When discussing the importance of being able to “rest, reconnect and reflect,” Wilson opened up to the magazine, saying, “When I’m doing the things that make me feel like a sister, friend, daughter, girlfriend or dog mama, that’s what refills my cup [...] That way, I can go back out and pour out the way that I want to. I’ve tried pouring from an empty cup and it don’t work.”

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Allie Hayes
ALLIE HAYES

Allie Hayes is an experienced pop culture staff writer and editor specializing in movies, TV and celebrity news. Before joining the Sports Illustrated Swimsuit team as a Breaking/Trending News Editor, she worked at several outlets including BuzzFeed, The Daily Dot, and Newsweek. When she’s not writing for work (or writing for fun), you’ll find her curled up on the couch reading yet another romance novel, obsessively watching pro wrestling with her friends, or taking blurry photos of her two adorable cats.

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