/27 Best Denim Shirts for Men in 2022: These Sturdy Button-Ups Are a Cheat Code for Good Style

27 Best Denim Shirts for Men in 2022: These Sturdy Button-Ups Are a Cheat Code for Good Style

Dennis Hopper, Paul Newman, Marvin Gaye—what do these style icons all have in common? A great denim shirt. But only the best denim shirts for men will give you a clear path to fashion glory. See, what those dudes understood was that the right denim shirt won’t just make you look rugged and handsome and all kinds of confident (to be clear, it will do that), it’ll also solve virtually any wardrobe-related dilemma that comes your way. For instance:

  • You’ve got yet another wedding this fall, your sixth of the season, and your tiny little fashion brain is all maxed out on shirt-and-tie combos. Pull out a denim shirt and pair it with your tired flannel suit to instantly supercharge it with rugged sex appeal. Boom.
  • The algorithm got you good and you just dropped an irresponsible amount of dough on some insanely loud pants that have a hard time getting along with the rest of your closet. A classically handsome denim shirt will tame the beast.
  • It’s the weekend and you’re lazy as hell. But you’re not so insouciant that you don’t care about looking good—you just don’t want have to exert so much energy into pulling together a good outfit. Denim shirt, white T-shirt, black jeans, can’t lose.
  • Giving an important presentation at work when your trousers embarrassingly split right down the seat? Okay, well, a denim shirt probably can’t help you there. That’s when you ask yourself question number two: What’s my tailor’s phone number again?

The Best Denim shirts Shopping Guide 

So, yeah: Denim shirts are useful. Like, having-a-sibling-who’s-a-contractor useful. They’re an American classic and a menswear staple that deserves a space (or two) in your closet. And the two most useful kinds of denim shirts are button-down and Western, which you’ll probably want in a medium-to-light wash for maximum versatility. But should you want to freak it, who are we to stop you? Designers are going buckwild with their denim fantasies and you can join in on the freaky denim shirt fun. As gaudy as they can get these days, there’s still some sort of magic in an indigo-dyed shirt that gives it a sartorial flexibility that other garments just can’t seem to match. Here are 23 of the best men’s denim shirts that’ll help to really tie your fits together.

The Gold Standard Denim Shirt

Levi’s Barstow western denim shirt

You knew it was coming: More than 160 years into their run, it’s hard to picture anybody angling for Levi’s’ crown. The first name in denim still makes one of the best Western shirts you’ll find anywhere—the fit is just right for layering, the details are on point, and the fabric of this particular version is made sustainably, using way less water than regular denim. Add in a super-reasonable $80 price tag, and you’ve got yourself a wardrobe staple for the ages. 

The Daily Driver Denim Shirt

Orslow button down collar denim shirt

Remember Dennis Quaid in The Parent Trap? The perfectly louche way his shirts hung? How beautifully washed-out the denim was? We wouldn’t be surprised for a second if we saw the guy in Orslow’s moodboard when it came up with this pitch perfect shirt. It hits all the right notes: all-cotton Japanese denim; a natural, lived-in wash that steers well clear of over-the-top whiskering; handsome off-white buttons; comfortable, relaxed (but not sloppy!) fit. Wear it with a thick thermal shirt, or layer it over a light sweater like you would an overshirt. Nearly $300 bucks might sound like a lot for a denim shirt (it is), but Orslow’s high reputation for artisanal denim and next-level construction means you’ll have still have this shirt in 2043, when the next remake of The Parent Trap comes out.

The “Technically, It’s Chambray” Denim Shirt

J.Crew organic cotton chambray shirt

If you’re not really picky about semantics, a chambray shirt qualifies as a denim shirt. (If you’re curious, the difference is mainly that it’s a plain weave as opposed to denim, which is a twill). And in this category, J.Crew’s the best of the lot. The chambray is lightweight and breezy but by no means tissue thin. The tailored fit is perfect for tucking into pants or even wearing with a sharp suit for some casual Friday vibes.

The OG Western Shirt

Rockmount denim floral Western embroidered cowboy shirt

You know those pearly snap buttons on the front of every yeehaw-ready Western shirt you’ve ever worn? You can thank Rockmount Ranch Wear for them. The Denver outfitter’s original snap-front long-sleeves have been worn by everyone from Bob Dylan (during his Presidential Medal of Freedom ceremony, no less) to the entire cast of Brokeback Mountain. The label makes their fair share of frill-free denim numbers, too, but ornate embroidery is a part of Rockmount’s essential DNA. So if you’re gonna go for it, why not really go for it?

The A-List Denim Shirt

Brunello Cucinelli Western chambray denim button-down shirt

Ever see paparazzi snaps of dudes like Brad Pitt or Ryan Gosling and wonder how their seemingly regular clothes always look so damn crisp and impeccably just-so? Well, for starters, they’re much, much better-looking than you. That tends to help. But the good genetics also extend to their wardrobes: Guys like that can afford shirts like this one, exactingly engineered by Italian tailoring god Brunello Cucinelli to make anyone—even mere mortals like you—look and feel like a matinee idol. The chambray is the ideal weight—light enough to be comfortable, thick enough for some structure—and the cut is trim and sharp like a dress shirt, which means you can wear it tucked in with a suit, or rolled up and rumpled with chinos, and it’ll never not radiate perfectly imperfect movie-star cool.

The Office-Ready Denim Shirt

Sid Mashburn slim-fit cotton-chambray shirt

Sid Mashburn’s crisp chambray shirt is the best way to bring all the utility and character of denim with you to work and on dressy nights out. Fresh off the ironing board, it’ll clean up well with a suit and tie or a sport coat and jeans. But the shirt truly shines on a Sunday morning, left a little rumpled with a few buttons undone—you’ll feel like a wise, old Italian man sipping an espresso and smoking a cigar on the streets of Napoli. What more could you ask for?

The Absolute Grail Denim Shirt

Kapital 8oz denim studs western shirt

There aren’t many other brands that sit on the same level as Kapital, especially when it comes to denim. With an obsession for details and a healthy mix of playfulness, humor, and straight up badass design, Kapital’s got a library of denim shirts that could easily snag this spot and it’s hard to choose just one. From the absolutely insane boro denim shirt that sells for nearly $2k on secondhand sites to the Instagrammable bone-embroidered denim shirts, we could make a top 10 list comprised of just Kapital. One of the coolest out there right now is actually more tame for the brand and features a studded spiderweb motif, a nod to vintage studded leather belts popular amongst American motorcycle and rockabilly culture.

The Budget Denim Shirt

Lee relaxed fit worker denim button-up shirt

Now that you’ve taken a few seconds to settle down from the sticker shock of that Kapital joint, let’s do a hard pivot. The rugged good looks, the Ivy flair, the dialed-in silhouette that withstands time and space—you can have all of that without having to shake down your bank account. When it comes to work-style denim shirts, Lee’s is straight-ahead and the exact picture that comes to mind. Twin chest pockets, chalk-white buttons, and a light wash that’ll only get better with some elbow grease put into it. While it’s not the cheapest option on this list, it’s certainly the best value. So if you can hang on for a bit and save some scratch, we think it’s worth the wait.

Plus 19 More Denim shirts We Love

Flint and Tinder bone button western shirt

Denim doesn’t have to be blue!

The Armoury cotton denim spread collar shirt

Denim may be workwear, but everyone’s got a different job, right? Tastefully tailored with a #menswear-approved spread collar and French placket, this is the type of shirt you’d wear with a knit tie and a soft sportcoat for your fancy design job.

Adsum denim premium buttondown

If that Orslow joint is out of your budget, Adsum’s denim shirt is a near dead-ringer for about a hundred bucks less.

Gap denim pocket shirt

Gap got its start not with khakis, despite what its famous 90s commercials would lead you to believe, but with denim. So it’s safe to say that the stuff that got the mall brand off its feet is still very, very good.

Polo Ralph Lauren flap-pocket denim overshirt

We just got off a Teledoc and apparently we don’t have vertigo—we are indeed seeing four pockets and one shirt.

Buck Mason denim one pocket shirt

Buck Mason’s 7-ounce denim shirt is hefty enough to inspire confidence and tailored enough to inspire some clean fits.

Rick Owens DRKSHDW Jumbo denim shirt

The undisputed goth-king of menswear has a soft spot for denim, but of course, it’s often not in the usual indigo shade you’d expect of others. Ditto about the proportions.

Sophnet moisture-wicking denim shirt

Normally, denim wouldn’t be considered a technical fabric, but Sophnet’s figured out a way to bring it to the future with moisture-wicking properties.

Diesel D-OCEAN-OVER-SC Man western shirt with misaligned print

Tromp l’oeil has been a major trend over the past few years and brands like Diesel are using the concept to great effect. In this case, The shirt is actually a plain white button-up shirt with a high-fidelity print of a western shirt on top

RRL indigo chambray workshirt

Indi + Ash sawtooth western shirt

Handwoven denim dyed with a combo of iron, acacia tree bark and tea? Doesn’t get much more artisanal than this.

Todd Snyder Japanese raw selvedge indigo overshirt

Is it really a surprise to anyone that Todd Snyder also makes great denim?

Acne Studios relaxed fit denim shirt

With a pair of jorts and you’ve got yourself the perfect summer Canadian tuxedo.

Sid Mashburn cotton-chambray Western shirt

Look, we know that you’re not the Brunello Cucinelli guy (probably). But in the likely event that you’re an average Joe with above average taste, this Sid Mashburn Western shirt is a GQ-approved alternative.

Alex Mill indigo-dyed Easy shirt

Made from seasonal leftovers, this special edition of Alex Mill’s eponymous shirt is cut from a delightfully smooth and crisp cotton poplin. While that’s obviously not denim, the natural plant indigo overdye evokes the tones of the fabric to a T.

Wrangler western long sleeve snap washed finish work shirt

This western staple has satisfying snaps and even more satisfying denim.

Red Kap deluxe men’s denim shirt

A hard-wearing workhorse of a denim shirt.

Warehouse “Longhorn” denim shirt

For the hardcore DIY denimheads.