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
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
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
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
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
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’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
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
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.
