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

Denim shirts aren’t great for hot weather but they’re an excellent way to add some style and warmth to fall or winter outfits if you do it right.

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

Some guys like to really stretch the boundaries of convention, even pairing denim shirts with suits, but we’re going to keep things relatively uncontroversial in this article so that the average guy can come away with solid advice.

I recruited two friends for this: a denimhead and a style guru, so you’ll be able to see a decent range of aesthetics. Most of our shirts are from Flint and Tinder’s USA-made range, but these tips will apply to any denim shirt you’re likely to find.

Why Denim Shirts?

• Thicker and warmer than most shirts; great for fall and winter
• Very durable; they’ll last you many seasons
• Improve with wear; the denim molds to the shape of your body and fades attractively the more you wear it

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 in 1873) denim shirts are just a really classically American piece of clothing.

Our Denim Shirt Style Experts

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.

But I recruited two other guys for this piece to round it out: Peter from Peter’s Prism, a banger YouTube channel about “style from a Gen X lens;” and Nick from the denimhead Instagram account Denimscapes.

I’m proud of putting together this trio because we all exist in slightly different spaces in the world of denim shirts.

Choose Your Weapon: Western vs Workwear Denim Shirts

Because it’s a rough and tumble casual material, there are two styles that you’ll see the most often: workwear and western.

I think if you’re getting your first denim shirt, I’d pick 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 Peter and I are wearing in these pics is Flint & Tinder’s Bone Button Western Shirt. It comes in a few different “washes” (levels of pre-distressed) and a black colorway that Peter’s sporting above. Like most denim shirts, the fabric weighs about 8 ounces per square yard: that’s about 30 percent lighter than your average jeans, but it feels pretty hefty for a shirt.

Peter’s workwear shirt is from the same brand, it’s Flint & Tinder’s Washed Denim Shirt. I’m wearing one of their older versions in some of these pictures, when its color was very uneven, but now it comes in a nice consistent light.

Workwear shirts are simpler and more versatile than Western shirts, usually coming with two pockets on the chest and no extra frills. In some of the photos I’m wearing a dark blue denim shirt from Benzak, but they seem to have stopped selling it.

Can’t decide between Western and workwear? Billy Reid‘s Shoal (above) is a famous denim shirt that has elements of both styles: snap buttons but no reinforced shoulders.

#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: Grown and Sewn’s fade like denim which is cool, Left Field’s have a roomier fit, Taylor Stitch for good value, and Naked & Famous for a wider range of fits.
• 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 henley works great under a denim shirt too. It’s a simple and stylish way to layer casually; mine are mostly from Buck Mason.

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 Grown & Sewn and Left Field, who do a great job of incorporating classic workwear materials with modern fits.

#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 a Wrangler denim shirt from Walmart, blue jeans, brown leather boots, and his jacket was the Waxed Canvas Trucker Jacket from Flint and Tinder.

My guest Nick from Denimscapes is very comfortable wearing a denim shirt with any kind of jeans. Personally, I’ll only do that if they’re very different washes.

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

Like I said in How to Style a Denim Jacket guide, the easies 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, or the way Joel does it: dark denim jeans with a faded denim shirt.

I’m not saying you’re not allowed to do a blue denim jacket with blue jeans like Nick Denimscapes in the picture above, I’m just saying that look stands out a little more — you need a little more confidence to do so, but if you’ve got that khutspe, go for it.

#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.

Chinos come in all shapes and sizes these days, but since denim shirts lean in the classic Americana direction, they work best with classic fit trousers: I’m talking high rise and roomy legs, like Buck Mason’s “Full Saddle” or Flint and Tinder’s “Classic” cut.

My personal recommendation: chinos with a classic cut and pleats.

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 (I’m wearing some suede derbies in the dressier fit on the left above).

#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: a 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 (particularly when they’re heavy), though this is a bit harder to do with a Western shirt; opt for a workwear style denim shirt if you’re going in the overshirt direction.

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 like this one — especially if you’re leaving it unbuttoned.

This plainer style of denim shirt is simply more versatile and more modern, plus 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.

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

• Wear a lighter colored denim shirt to keep the outfit feeling summery
• Try not to wear shorts that are thinner than the denim shirt (eg. linen)

Denim shirts are usually heavy and don’t look great with summery looks. But if the denim is faded and well worn, it can give enough of a breezy, relaxed vibe to make it work with shorts.

White sneakers, like the canvas ones from Nothing New, are my go-to. I thought about loafers, but denim workwear shirts have a rugged feel that isn’t quite as consistent with the vibe of loafers.

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.

#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 jeans 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 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 & Don’ts For Wearing a Denim Shirt

In all these examples, we’ve followed a few 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 Acid Washed Denim: Faded is fine, but leave acid washes in the 80s.

Keep it 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.