Denim shirts are a cheat code for good style

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

  • You’ve got another fall wedding, your sixth of the season, and your little fashion mind is full of shirt-and-tie combos. Pull out a denim shirt and pair it with your tired flannel suit for instant 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 matching the rest of your closet. A classic handsome denim shirt will tame the beast.
  • It’s the weekend and you’re lazy as hell. But you’re not so inflexible that you don’t care about looking good – you just don’t want to have to spend so much energy putting together a good outfit. denim shirt, white T-shirt, black jeanscan’t lose.
  • Are you giving an important presentation at work when your pants embarrassingly split right down the seat? Okay, a denim shirt probably won’t help you there. That’s when you ask yourself question number two: What’s my tailor’s phone number again?

The ultimate shopping guide for denim shirts


So yes: denim shirts are useful. Like having-a-sibling-who-is-an-entrepreneur useful. They are an American classic and a piece of menswear that deserves a place (or two) in your closet. And the two most useful kinds of denim shirts are button-down and Western, which you’ll likely want in a medium to light wash for maximum versatility. But should you want to freak out, who are we to stop you? Designers are going wild with their denim fantasies, and you can join in the fun denim shirt fun. As flashy as they can get these days, there’s still a kind of magic in an indigo-dyed shirt that gives it a sartorial flexibility that other garments just can’t match. Here are 23 of the best denim shirts for men to help tie your fits together.

Denim shirt in gold standard

Levi’s “Barstow” western shirt

You knew it was coming: More than 160 years into their run, it’s hard to imagine anyone lusting after Levi’s crown. The first name in denim remains 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 in this version is made sustainably using far less water than regular denim. Add in a super-affordable $70 price tag, and you’ve got yourself a wardrobe for the ages.

The best everyday denim shirt

J.Crew Casual Midweight Denim Shirt

Remember Dennis Quaid in Parenting the trap? How did his shirts hang perfectly? How beautifully washed was the denim? Based on this shirt, we’re guessing everyone’s favorite Napa Valley vintner was all over J.Crew’s mood board this season. It hits all the right notes: all-cotton denim; a natural, built-in sink; beautiful white buttons; comfortable, roomy fit. Wear it with a thick thermal shirt, or layer it over a light sweater as you would an overshirt. Don’t be afraid to get drunk Canadian tuxedoeither, or team it with a white T-shirt and wide leg twill chinos to relive the oh-so-good 90s J.Crew catalog atmosphere.

AND the Western shirt

Rockmount Denim Floral Western Embroidered Cowboy Shirt

You know those pearly snaps 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 brand also has their fair share of no-frills denim numbers, but ornate embroidery is part of Rockmount’s essential DNA. So if you want to go for it why not really go for it?

The A-List denim shirt

Brunello Cucinelli Western chambray denim shirt with buttons

Ever see paparazzi photos of guys like Brad Pitt or Ryan Gosling and wonder how their seemingly ordinary clothes always look so damn crisp and flawless? For starters, they look much, much better than you. It usually helps. But the good genetics also extend to their wardrobes: Such guys can afford shirts like this one, precisely 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 trimmed and sharp like a shirt, meaning you can wear it tucked into a suit or rolled up and gathered with chinos. .. and it will never exude perfect 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 dressy nights out. Fresh from the ironing board, it will clean up well with a suit and tie or a sport coat and jeans. But the shirt really shining on a Sunday morning, left slightly crumpled 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 Naples. What more could you ask for?

The denim shirt with the Absolute Grail

Kapital boro western shirt

Kapital’s boro western shirt is a work of art, period. It comes from the renowned denim brand’s Kapital Kountry sub-line, famous for its meticulous use of Japanese boro fabrics, over-the-top distressing and obsessive craftsmanship. It takes dozens and dozens of hours of hand sewing to achieve this level of detail, a perfect mashup of traditional Japanese techniques and dyed Americana style.

The best budget denim shirt

Now that you’ve taken a few seconds to calm down from the sticker shock of that Kapital joint, let’s take a hard pivot. The rugged good looks, the Ivy flair, the dialed-in silhouette that stands the test of time and space – you can have it all without shaking your bank account. Uniqlo is good at many things, but the brand’s denim range is one of its highlights. Made from 100% cotton, this one feels sturdy enough to go toe-to-toe with some of the beefier options on this list, but is still soft enough that you don’t have to worry about any break-ins. It’s also casual enough to wear as a top, but tame enough to tuck in. And with the right shabby suit, it can easily play dress-up. For only $40, it doesn’t get much better.


Plus 17 more denim shirts we love

Sid Mashburn Western shirt in cotton chambray

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

Alex Mill indigo-colored Easy shirt

Crafted from seasonal scraps, this special edition Alex Mills eponymous shirt is cut from a delightfully smooth and crisp cotton poplin. While it’s obviously not denim, the natural plant indigo overdye brings out the fabric’s tones to a T.

Polo Ralph Lauren shirt in classic fit in denim velvet

It’s the little finishing touches that really make a great garment. In this case, the velvet collar takes an already good denim shirt and sends it into the stratosphere.

Buck Mason M024 Denim Work Shirt

Y/Project denim shirt with button panel

Y/Project’s denim wizardry is an endless bag full of indigo tricks and treats. Like, who asked for a denim shirt with removable panels? None! But hey – before 2007, no one asked for the iPhone either.

Fear of God Essentials denim shirt

Jerry Lorenzo’s popular Essentials brand offers some hall of fame-style per-dollar averages. And while this oversized denim shirt might not be the most classic, it’s not too trendy either. Throw it over a hoodie or rock it with a cardigan and a graphic tee underneath for some high-level layering.

Stussy boxy western denim shirt

You could pass Stussy off as a quality brand because of its humble streetwear background. But make no mistake: these are some of the best quality products for the price. For example, this oversized denim shirt that uses a BEEFY denim. We’re talking 14-ounce denim. That’s the same amount as a pair of Levi’s and more than twice as much as most other denim shirts.

Gitman Vintage Button Down Denim Shirt

Gitman Vintage has been making very good shirts for decades, so you know their buttons are top notch. This one features a meaty denim fabric with clean, tonal stitching and off-white buttons that all match a denim shirt, perfect for keeping it casual – or dressing it up with a blazer and tie.

Wales Bonner “Miles” Denim Shirt

You could dig into vintage store after vintage store hoping to stumble upon a gem like this. Or you could save your shillings and buy this 70s-inflected Wales Bonner grail instead.

Western shirt with flint and Tinder bone button

Rugged seven-ounce denim in a versatile medium wash? We listen. What is it you say? Natural bone snaps? Now that’s music to our ears.

Studio Nicholson Prince denim shirt

Sometimes one giant pocket is all you need.

Pilgrim Surf + Supply “Ivan” LS shirt

Other times, thaw Giant pockets are actually what you need.

Todd Snyder Japanese chambray work shirt

Not all denim shirts are blue.

Wrangler western long sleeve work shirt with pressure washed finish

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

Red Cape deluxe denim shirt for men

A durable workhorse of a denim shirt.

RRL work shirt in indigo denim

All the trappings of a workwear grail, like triple needle stitching, cat-eye buttons, hand-loading and Japanese denim.

Warehouse “Longhorn” denim shirt

For hardcore DIY denimheads.

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