8 Ways for Men to Style a Denim Shirt Any Time of Year

There are more denim shirt types, washes, and fits than you’d guess, from Western-yokes with snap buttons to two-pocket workwear styles, and some even wear them with suits. If you get the wrong denim shirt, and it’s easy to accidentally look a bit too Midnight Cowboy when you’re aiming for Ralph Lauren.

So, I’m here to answer the question of how to style a denim shirt.

But I’m not covering how to wear them with a suit because my aim is to provide the least controversial ways to wear a denim shirt. Nothing high fashion or experimental here, just basic tips for regular guys.

My denim shirts are from Flint and Tinder’s USA-made range, but we’ll include a few other styles at different pricepoints at the end of this article to save you some leg work.

Why Denim Shirts?

Denim shirts are thicker and tougher than most regular cotton shirts — of course, that’s why denim jeans are staples of workwear.

Denim shirts aren’t always as thick as jeans, but the hardy twill weave still means they last a long time and look better the more you wear them. The color also fades with wear and washes (again, like jeans), so they add a nice element of texture to an outfit.

Because these shirts are usually on the thicker side, they’re great pieces to wear in the cold and they can save you from needing a jacket in transitional seasons.

A big bonus: denim shirts don’t really need ironing because it’s a burly fabric designed for harder wear.

Plus, like jeans themselves (patented here in 1873) denim shirts are just a really classically American piece of clothing.

Our Denim Shirt Style Expert

I’ve been traveling the world learning about durable, casual apparel for over 6 years, making videos all along the way. That journey has included visiting denim artists, historians, boutique brands, and jean-fading factories, as well as hanging out with fans of the raw denim subculture in five countries and counting.

Choose Your Weapon: Western vs Workwear Denim Shirts

Because it’s a rough and tumble casual material, there are two classic styles you should look at: workwear and western.

I think if you’re getting your first Western shirt, you’ll want something in a darker color that will fade as you wear it. “Earning” your denim fades is a huge part of the fabric’s appeal — and it’s why denim is awfully hard to wear in business professional environs.

The Western shirt I’m wearing in these pics is Flint & Tinder’s Bone Button Western Shirt. It comes in six washes right now and I got the darkest I could, which they call “medium wash.” It’s just a tiny bit faded and it’s a nice, heavy 8-ounce weight. (That’s about 30 percent lighter than your average jeans, but it feels pretty hefty for a shirt.)

You can pick up similar Western shirts elsewhere:

• Wrangler is king of the budget Western shirts, all coming in under $60.
• Taylor Stitch‘s washed selvedge denim shirt is a great midway point between budget and luxury at $125.
• Wythe headlines the “luxury” Western shirt with indigo-dyed fabric and pearl snaps for a little over $200.

My workwear shirt is also from Flint & Tinder but they don’t sell it anymore. Workwear shirts are typified by being made of a hard wearing material (like denim) and having two button closure pockets on the chest.

You can pick up similar shirts elsewhere:

• Wrangler has a popular one for under $40.
• Lee sells a one-pocket denim workshirt for under $80.
• Todd Snyder leans higher end with their one-pocket denim shirt for $178.
• Imogene & Willie sells a premium, USA-made work shirt made on vintage shuttle looms for $235.

Can’t decide between Western and workwear? Billy Reid‘s Shoal is a good combo of the styles.

#1 Classic Workwear Style

Denim Shirt, Canvas Pants, and Leather Boots

• This combination gives a consistent workwear theme without repeating the same material

The first thing to know about denim is that it pairs well with canvas.

They’re both tough cotton fabrics with workwear origins but they’re made with different weaves, so you’re not wearing the same textile for your shirt and pants. (Not that there’s anything wrong with that, we’re just starting with the least controversial tip.)

Whether it’s a Western or workwear shirt, I recommend combining a denim shirt with canvas pants and leather boots. Simple. Handsome. Classic. Here are some recommendations:

• Canvas pants: Dickies and Carhartt for looser fits, Taylor Stitch (mine) and Naked & Famous for more fashion-oriented looks. You’re more likely to get 100% cotton with those last two brands, and that’ll age and breathe better.
• Service Boots: My favorite boot brands are here; I’m wearing Oak Street’s Field Boot but Thursday’s President looks pretty similar for half the price. If that’s too sleek, try Red Wing’s Blacksmith.
• Western boots: For a more Western workwear look, try Tecovas on the lower end or Chisos on the higher end.
• Watch: I like simple tool watches, and I found the best value to be Vaer; I’m in one of their field watches here.

Denim Shirt and Leather Jacket

And if it’s a little cold, nothing beats a leather jacket over a denim shirt and canvas pants — it’s all the classic American outdoor materials in one, no doubling up. (Bonus if you get wool in there, like I did with this beanie.)

My favorite leather jackets are from Schott and Satchel & Page, which is what I’m sporting above.

If you’ve got one, a white henley works pretty well under a denim shirt as well. It’s a simple and stylish way to layer casually. Mine’s from Hnly, but I own a lot from Buck Mason as well.

Style Tip: Mix Twill (Denim) & Canvas

Wool and leather are great but if you’re pairing denim with another cotton fabric, canvas is ideal.

They’re both really tough cotton materials with origins in workwear. A twill weave has diagonal lines in it (called wales) while canvas is a plain weave with more of a cross-hatched look to it. These two looks complement each other.

Most of my canvas pants are from Taylor Stitch, who do a great job of incorporating classic workwear materials with modern fits.

For looser fits, you can get canvas pants from Carhartt and Dickies. Just note that most of their canvas pants aren’t 100% cotton, so while they’re usually stretchier, they don’t wear or drape exactly the same as traditional canvas. It’s up to you if that matters or not, but I prefer the look of 100% cotton.

#2 Dress Like Joel From The Last of Us

• Pedro Pascal wore blue jeans, a Wrangler denim work shirt, and a tan canvas trucker jacket

The next workwear-inspired outfit is my recreation of Joel’s outfit from The Last of Us on HBO.

He had Wrangler denim shirt from Walmart, blue jeans, brown leather boots, and his jacket is the Waxed Canvas Trucker Jacket from Flint and Tinder.

(Flint and Tinder didn’t sponsor this article; if they had, I wouldn’t be able to recommend all the other brands I’ve discussed. Still, I own a lot of their gear because they sit right in that Americana workwear sweet spot.)

Style tip: Can You Wear a Denim Shirt With Jeans?

Like I said in How to Style a Denim Jacket guide: the ideal way to wear two kinds of denim is if they contrast.

The two least controversial ways to pair denim and denim are: black jeans with a blue denim shirt/jacket and the way Joel does it: dark denim jeans, faded denim shirt, and a tan canvas jacket.

I’m not saying you’re not allowed to do a blue denim jacket with blue jeans, I’m just saying that look stands out a little more — and this article is about the most uncontroversial ways to wear a denim shirt.

#3 Denim Shirt & Chinos

• Chinos are made from cotton twill
• All denim is twill but not all twill is denim; chinos are more uniform in appearance

Another simple way to wear a denim shirt is with chinos, casual trousers made from sturdy cotton twill that were popularized as work pants in the military.

In the picture above, I’ve gone a little vintage military by adding a brown leather flight jacket and leather boots (my girlfriend says it looks like I’ve just come home from the war), but chinos are casual trousers and you’d be fine wearing them with sneakers.

A hair less casual than canvas pants, you can dress chinos up fairly easily with a sport jacket and business casual shoes if you so choose. You wouldn’t normally combine those with the casual denim shirt, but we’ll explore one famous example of a tweed-and-denim pairing later in this article.

#4 Streetwear: Black Jeans, Denim Shirt, White Sneakers

• This simple and modern look works better with a workwear denim shirt than a Western one, but either is acceptable

For a more modern look, you absolutely can and should mix blue denim with black denim: blue shirt on black jeans with white sneakers. It’s a really easy, perfectly modern way to wear a denim shirt.

Unbuttoned denim shirts often work as an overshirt as well, and especially when you’re doing this more streetwear-friendly look, you can add an element of layering by tossing one over a white t-shirt if it’s cold.

A black leather jacket here is king for topping off streetwear. Mine’s from Schotts NYC.

Styling Tip: Workwear Style Denim Shirts Are More Modern

If you’re going in this more modern direction with the denim shirt and you have the choice of a Western and a non-Western denim shirt, I’d suggest non-Western — especially if you’re leaving a shirt open.

A plainer style of denim shirt is simply more versatile and more modern, and I prefer pairing western denim shirts with more earthy tones for a more consistent country theme. (Oh man, what a ridiculous sentence I just wrote.)

#5 Corduroy Pants & Denim Shirt

Corduroy is another solid fabric to mix with denim, and while you can definitely wear this somewhat retro fabric with earthy tones and leather shoes, you can also make it a bit more modern by pairing the cozy corduroy with some nice leather sneakers. I’ll often wear the outfit above with some blue suede sneakers from Beckett Simonon.

#6 Denim Shirt & Shorts

• Try not to wear shorts that are much thinner than the denim shirt (eg. linen)

Rolling up your sleeves and pairing your denim shirt with green or cream colored shorts creates a casual, summer-friendly outfit. To be honest, I prefer single pocket shirts like Todd Snyder’s if I’m rocking shorts but since this two-pocker shirt is a lighter wash, it fits the summer vibe.

White sneakers, like the canvas ones from Nothing New, are my go-to here. I thought about loafers, but denim shirts have a rugged feel that aren’t quite as consistent with this ultra casual theme.

Styling Tip: Know Your Earth Tones From Cool Tones

I’m not a gigantic devotee of color theory, like a lot of style guys who look at color wheels to decide what tones to wear today.

But I do dress (and pack for a trip) according to whether I want to wear earth tones or cooler tones.

• Earth tones: green, brown, orange, tan
• Cool tones: Gray, black, burgundy, pink

Blue and white fit into either.

“Pink and burgundy aren’t cool?” Yeah, maybe not, but the point is pink and burgundy work better with black and blue than brown and tan, you get me? Look in awe at how I style my one-of-a-kind pink Red Wing boots.

#7 Denim Shirt and White Jeans

When I said denim on denim should contrast, I wasn’t just talking about black jeans. You can also pair a denim shirt with white jeans for a carefree summer look. A lighter wash shirt is preferable, and some canvas sneakers, like Chuck Taylors, can complete the look.

A pair of nice black leather sneakers like Thursday’s can add a little more class to this outfit than beat up old Chucks.

#8 Denim Shirt and Tweed Sports Jacket

• Ralph Lauren made this look popular
• An ode to how America popularized outdoor apparel like denim, tweed, and boots as office wear

I guess I like outfits to be thematically consistent — you wouldn’t wear a silk dress shirt with work pants either — and if we’re looking at the journey of the denim Western shirt we have to look at an extremely, iconically American way to wear it: with a tweed sports jacket.

Popularized by Ralph Lauren as well as Dustin Hoffman and other 70s icons, all these fabrics are casual, except they aren’t. But they are.

What I mean is that tweed, denim, and suede boots were historically for hardy outdoor use — tweed, a dense wool, is actually very weather resistant and started out as the go-to hunting jacket material in England.

To the horror of the British, Americans made tweed and denim fairly common in business casual settings. Mixing a denim shirt with a tweed sports jacket and cowboy boots is a great example of America unselfconsciously dragging workwear up to smart casual and the American love of thumbing their noses at the British gentry. Isn’t that what being an American is all about?

Dos & Dont’s For Wearing a Denim Shirt

In all these examples I’ve followed some basic dos and don’ts:

Do:

Contrast: Do make your shirt contrast with your pants or jacket. Ideally that’s in terms of color and with fabric (eg. denim on canvas).

Avoid Crazy Faded Denim: Stick to a dark or medium wash for your first denim shirt.

Keep it Casual: Keep things casual to smart casual. Some guys experiment with denim shirts with a suit and tie, but it takes a lot of thought and I prefer to keep things simple around here.

Pick an Earthy or Cool Color Palette: This is an uncomplicated, totally binary way to help you match your colors.

Don’ts:

Wear Complicated Designs: Don’t go for complicated designs, embroidery, patches, or acid washes on your denim shirts.

Default to Levi’s Denim Shirts: These days, their fits and quality are pretty inconsistent.

Wear Denim on Denim: Not if you want to be as uncontroversial as possible. Do it if you don’t care and you love it.

Wrapping Up How to Style a Denim Shirt for Men

That was a quick guide to styling the two main kinds of denim shirts with a variety of styles, fabrics, and motifs.

I hope this gives you some inspiration on how to incorporate denim shirts into your wardrobe. Let me know your thoughts and how you like to wear denim shirts in the comments, and subscribe to my YouTube channel for more on durable, casual style.

FAQs: How to Style a Denim Shirt

How Men Should Wear a Denim Shirt?

A denim shirt can be paired with chinos for a relaxed yet put-together look, canvas trousers and boots for a more rugged look, or black jeans and white sneakers for a more modern one.

Should Denim Shirts Be Tucked In or Out?

If you’re leaning in the direction of Western style, it’s not uncommon to tuck a denim shirt into jeans. If your denim shirt is a more common button up, it’s usually left untucked unless you’re going smart casual with chinos and business casual shoes. The key is to ensure the shirt’s length is appropriate for wearing untucked; it should not extend beyond the mid-fly of your jeans.

What Color Jeans to Wear with a Blue Denim Shirt?

The best color for a blue denim shirt is black jeans. Otherwise, common advice is to make sure your denims contrast: a faded blue shirt with darker blue jeans, for instance. Matching denim colors will give you more of a Western look — but if that’s what you’re after, go for it.

Are Denim Shirts Still in Style?

Yes, denim shirts remain in style. The Western denim shirt is more often seen as a throwback in major cities, but two-pocket or single pocket workwear style denim shirts can easily be worn by anyone with chinos, canvas pants, or black jeans.

Is a Chambray Shirt the same as Denim?

No. Both are usually cotton and combine blue and white or undyed yarn, but denim is a twill weave and chambray is a plain weave. This just means when you look closely at it, the surface of denim looks like a series of diagonal lines while chambray has more of a cross-hatched appearance. Both are tough fabrics with origins in workwear, but chambray is usually lighter in weight, so it’s seldom used for pants.