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 19 of the best men’s denim shirts that’ll help to really tie your fits together.
The Gold Standard Denim Shirt
How could we not include Levi’s? And at the very top, no less. Over a century and a half since they first opened shop, 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 silhouette is tailored enough to look clean but has enough room to layer a thick thermal shirt underneath and it comes in a handful of washes so you can opt for a fade-it-yourself, deep indigo or expedite the process and snap up an expertly-faded light wash. Add in a super-reasonable $80 price tag, and you’ve got yourself a wardrobe staple for the ages.
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 transcends time and space—you can have all of that without shaking down your bank account. Despite what its famous ’90s commercials would lead you to believe, Gap got its start hawking denim, not khakis. So it’s safe to say that the stuff that got the mall brand off its feet is still very, very good. It’s got a single chest pocket, chalk-white buttons with a button-down collar, and a light wash that’ll only get better with some elbow grease put into it. While it’s not quite the cheapest option on this list, it’s certainly the best value, especially since you can count on Gap’s frequent sales to knock down that starting price.
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 like most people, you’re not really picky about semantics and 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 made of organic cotton that’s lightweight and breezy but by no means tissue-thin. It comes in five different fits—classic, slim, slim untucked, tall, and relaxed—which makes it a great option for most people. With a press of the iron, a proper necktie, and a suit, you could easily stroll into the office without garnering unwanted attention from your boss. Toss it over a pair of wide-leg (dare we suggest Giant) chinos and some loafers for an Ivy look. Or tuck it underneath a thick wool sweater with the collar peaking out for a winter look.
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? Details like the spread collar and lack of a chest pocket give it a dressier feel on top of the long hem which allows you to tuck it into your trousers.
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 versions right now is actually a bit more subtle for the off-beat brand. This cowboy-style shirt features a thick fabric commonly used for martial arts uniforms and is dyed with natural indigo and two different tones. On top of that, it’s accented with more traditional denim throughout.
Plus 14 More Denim Shirts We Love
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