Kaitlyn Frey
February 08, 2018 09:00 AM

Dierks Bentley doesn’t consider himself to be a “really big fashion guy.”

The 13-time Grammy Award nominee and country superstar favors a good pair of broken-in jeans, a flannel and vintage tees both on and off-stage over fancy suits and ties, so when Flag & Anthem (a brand known for its casual wear made for real guys) wanted to work with the star on his debut clothing collection, Bentley quickly jumped on-board with a “really big yes.”

“I can’t say I’m overly fashion-oriented,” Bentley admitted. “So I think that is something unique about our thing. It is not meant for fashion people. It is meant for people like me, that when they were 17 years old, they saved up enough money to go buy a pair of Lucky jeans because they were the cool jeans to have back then.”

The assortment of vintage-washed t-shirts, button-ups, hoodies, jeans and jackets (the first batch of items are available now online!) not only reflect Bentley’s “utilitarian” sense of style, but also the kinds of clothes he sees his fans in.

Courtesy of Flag & Anthem

“I kinda dress like my audience in some way,” Bentley told PeopleStyle of the collection, which he designed with the help of his longtime stylist Annie Psaltiras. “Not on purpose! It’s just who I am. Guys come to the show with their girl and they want to wear something that looks nice, but also something that their guy friends aren’t going to make fun of them for wearing. I think we do a good job of balancing that.”

Flag & Anthem

The team of designers at Flag & Anthem made sure to hone in on exactly what Bentley envisioned for the collection — all the way down to the tiny details.

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“I feel like those guys really just went out of their way to dial in on what I like as far as the way jeans look broken in and feel, a lot of the flannels, the kind of vintage t-shirts, that whole vibe,” he said.

Courtesy of Flag & Anthem

And surprisingly, the country crooner even found the design process to be quite similar to when he writes music. “Just like in song, it’s all in the details. In country music at least, there’s not one word that doesn’t matter,” Bentley said. “These guys are relentless when it comes to details, which I would say is very similar to country music songwriting.”‘

Flag & Anthem

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As someone who loves wearing “comfortable, regular guy clothes,” Bentley admits he doesn’t worry too much about what he puts on in the morning.

Flag & Anthem

“Kind of like in Kris Kristofferson’s song ‘Sunday Morning Coming Down,’ where he talks about just grabbing a shirt off the ground that looks clean — your cleanest dirty shirt,” he described. “Why not? I’m not overly picky.”

Even when it comes to performing onstage, Bentley’s motto is, the more holes, the better.

Courtesy of Flag & Anthem

“All of our guitars are hand-me-downs and I like shirts that are hand-me-downs too,” he said. “It just kind of feels broken in and a little more beat up. I like clothing that has a story to tell.”

In terms of the rest of Bentley’s on-stage look? He goes for a pair of vintage Vietnam-era boots (“They’re really helpful because you can lace ’em up tight so you can run around on-stage.”) and a good pair of jeans. “I’m such a jeans guy. I just wear the same ones I wear off-stage,” he said. “Well, I mean, I have a couple for on-stage that just might be a little tighter. But not like crazy tight!”

Tim Mosenfelder/Getty

As much as the country star loves wearing denim, he does keep a tight edit on the number of jeans in his closet as opposed to owning 100 pairs. “People think I have a ton of guitars. I have three. Same with my closet. I have like, five pairs of jeans,” Bentley told us. “I am really a creature of habit. When I find something I like, I wear the heck out of it. Plus, simplifying it down a bit makes for a much easier morning.”

With his less-is-more philosophy in mind, Bentley definitely already has a few pieces from his own collection he hasn’t been able to stop wearing. “I love this black-and-red check soft flannel shirt. You can’t go wrong with a red flannel. It just always looks good and rock n’ roll,” he said. “With the weather being the way it is, I’ve been wearing that every day.”

Although the multi-platinum artist is used to seeing his albums sitting on shelves in stores, the moment he spots a fan wearing his clothing in public will be something the star will never forget.

“It would be kind of surreal,” Bentley told us. “Actually seeing someone wear it at a show, that would just bring a really big smile to my face. I’d have to find that person and give ’em a beer…or at least a high five!”

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