How to Wear Western Shirts Even If You’re Not a Cowboy

I wasted so much time feeling self conscious about wearing Western shirts, and I don’t want you to make the same mistake.

They’re awesome. A rare balance of casual, durable, and stylish, you’ll never feel more American than you will in a Western shirt — but trust me, you don’t have to go full cowboy to be able to wear one. In fact, they have a lot of subtle benefits that a lot of people (including myself) can miss.

Since I was a little new to this genre of shirt, I invited two menswear guys from two different areas of menswear to help me figure out the right way to wear denim and not-denim Western shirts. Stirrups not included.

Meet Our Experts

I’m quite proud of the trio I put together for this because we all have different approaches to clothes.

First, there’s me: I’ve traveled the world exploring boots and jeans, but here I’m a little out of my depth, so I’m sort of the average guy’s stand-in: I like to look “not bad” without too much effort, but I also don’t know much about Western shirts.

Then we have Peter from Peter’s Prism on YouTube; his channel’s tagline is “Style from a Gen X Lens” and he has an enormous reservoir of knowledge about all kinds of Americana-style apparel to match his enormous wardrobe of said apparel.

With a background rich in the fields of design, history, and philosophy, Peter’s the guy with PhD-level knowledge of the “rules” of menswear — and, of course, he knows how to break them just right.

Lastly, there’s the resident denimhead: Nick from @Denimscapes on Instagram. That’s a menswear subculture that revolves around vintage denim and workwear. Denimheads often source them from obscure Japanese workshops where they’ve painstakingly recreated garments of old, down to using the kind of vintage looms that are way too inefficient for any big brand to use today.

But purists like Nick love them — and the kind of fades you can only get from dedicated, un-fake-able wear.

How to Recognize a Western Shirt

• Snap buttons
• Shoulders reinforced with pointed yokes
• Slim fits and usually long (so they can stay tucked in)
• Traditionally long sleeved to protect from sunburn and snags

“Typically, a Western shirt has snap buttons and that distinctive angular yoke on the shoulders,” says Nick. “You’ll often see them in tough and burly fabrics like denim and corduroy, but there are some lighter weight flannels and cottons out there.”

Snap Buttons

Why snap buttons?

1. They’re super durable: they’re way less likely to pop off your shirt than normal buttons, and no cowboy wants to be camping for four weeks and needing a needle and thread to make his shirt wearable.

2. They bust open easily: That’s actually ideal: if your shirt gets caught on a panicky horse’s reins, it’s easier to tear the shirt off so you don’t get carried away.

“Snaps are also easy to take off compared to fiddling with tiny buttons,” adds Nick. “That’s actually favored by a lot of farmers because their hands can feel stiff and sore after a long day of farm work.”

You’ll find some interesting kinds of snap buttons: Nick’s are mother of pearl and Peter’s are made of charred bone.

Reinforced Shoulders

The iconic pointed yokes on the shoulders are there because big pieces of fabric were put over the shoulders to reinforce them.

Note that Western shirts don’t have the easily-bustable seam running along the top of your shoulder in all your other shirts. (Cowboys tended to use cross-body messenger bags or satchels as well, so the reinforced shoulders help to limit the abrasion .)

Slim, V-Shaped Fits

The yokes actually make your shoulders look a little bigger, plus Western shirts tend to fit slim in general. The combination of those two elements means Western shirts have a pretty flattering, V-shaped fit.

“The reinforced shoulders and heavier fabric let you wear it slightly looser up top and a bit tighter through the torso,” says Nick. “They help create that illusion — in my case it’s an illusion — of a V-shaped torso.”

Slim fits are unusual for workwear, which usually fits pretty loose to allow for more movement.

But the Western shirt’s fit is to reduce the chances of the cowboy getting snagged on thorns, fences, bridles, and buckles throughout his day. (“Not getting snagged” is also a reason Western shirts have snap buttons and are cut long so you can keep them tucked. Cowboys did not like getting snagged on things!)

Noticing the Western shirt’s flattering silhouette, Peter remarked that it was the last refuge of the Millennial slim fit. If you’ve been missing the slim fits of the 2010s, Western shirts are waiting for you!

Great Pants for Western Shirts

“What I appreciate the most about the Western shirt is that it pushes you to style yourself in a way that’s different to how you’d style any other shirt,” says Peter. “I would just not throw this on with any random stuff in my closet — you’ve got to put a look together.”

So let’s talk about styling Western shirts.

Jeans

It’s a no-brainer to pair the most American work shirt with the most American work pants.

Keep in mind that Western shirts are cut slimmer than most work shirts, and for all the same reasons we listed above, a cowboy’s jeans aren’t baggy. They might be boot cut but you should get a well fitting pair of straight leg jeans.

“I went horseback riding in Wyoming this summer, and everyone was wearing Wrangler jeans,” says Nick. “Jeans must be the least pretentious thing you can wear with a Western shirt.”

Chinos

Chinos are great with a Western shirt. Given how thoroughly they’ve infiltrated business casual spaces, some guys might think of chinos as too dressy, but they actually originated as workwear in the military.

How do you pick the right chinos for a Western shirt? Pick a pair with a roomy leg, a higher rise, and — if you have the option — pleats. Pleats might sound dressy, but they actually dress down your pants because they give you more range of motion.

Corduroy

“I think corduroy is a fantastic fabric to pair with Western shirts,” says Peter.

Corduroy probably hit its peak in the 1990s and if that’s when you grew up, you might think of it as a smart casual fabric. But (like chinos) it originated as workwear, is remarkably tough, and remains a mainstay fabric for Western shirts and trousers in particular.

Great Jackets for Western Shirts

Western shirts are their own form of workwear. You might have noticed that theme in the trousers we recommended, and it’s reflected in the jackets too — with a couple of exceptions.

Leather Jackets With Western Shirts

All three of us tried leather jackets with our Western shirts, but they were all different kinds of leather jackets. Some work better than others.

I wore what’s called a delivery jacket on the far right of the picture above. I like how simple it is, but delivery jackets are cut a little longer than most, which I don’t think hit the right “workwear” or “Western” tone of the cowboy shirt.

“My Buco leather jacket is cropped right at the belt line, which is a really classic silhouette,” says Nick. “It also softens things up compared to the black motorcycle jacket Peter wore, which can feel like a pretty strong statement piece.”

“Mine’s a modernized motorcycle jacket,” says Peter. “I love mixing genres like that: Ivy, preppy, motorcycle, Western. It’s all Americana, and when you freshly blend those influences, that’s styling gold.”

Leather jackets are the coolest casual jackets, but they aren’t always workwear. To best match a Western shirt, try a shorter leather jacket like those called trucker, mechanic, or rancher jackets.

Canvas and Denim Trucker Jackets With Western Shirts

These are simply the best jackets for a Western shirt. On the left and right above I’m in Flint and Tinder’s waxed canvas trucker jacket and Nick’s in one from Mister Freedom. There’s no better pairing than denim and canvas.

And if you’re inclined toward the Canadian tuxedo, Nick has “no hesitation.”

“The full Canadian tuxedo brings pure cowboy energy,” he says. “You get all your fades developing at once, so there are bonus points for efficiency. If you want the most balanced look, I’d say try to match the fade levels. Or you can lean in with a significant difference in wear between the jeans and jacket — what you don’t want is the near miss.”

“Yeah, that’s like wearing dark navy with black,” adds Peter. “It doesn’t quite land.”

Tweed It Up: Dressing Up a Cowboy Shirt with a Sports Jacket

“This is a classic Ralph Lauren move, who really championed denim shirting as part of a modern man’s wardrobe,” says Peter, who also noted that Dustin Hoffman wore a couple versions of this outfit in Kramer vs Kramer, a movie that earned his character quite a few accolades for his style.

It works because denim, boots, and tweed all originated as workwear and have slowly crept into the business casual space. They all “don’t belong” in the same way that they do belong.

Big Chunky Cardigans With Western Shirts

Make sure you don’t forget this classic look. Maybe an outdoorsy shirt and a cozy-fireplace-evoking cardigan seem incongruous, and yet this is an especially beloved way to wear the Western shirt. Look at that guy in the button below wearing Iron and Resin’s!

Best Shoes and Boots for Western Shirts

Obviously, cowboy boots are the natural choice, but there are other options that work just as well.

Cowboy Boots vs Chelsea Boots vs Engineer Boots

“Cowboy boots are obviously great, but I think you can get a similar vibe with any laceless boot, like engineers or Chelseas,” says Peter. “They all give you that simple, clean vamp and almond-shaped toe sticking out from under your jeans.”

We made this content for non-cowboys looking to try a shirt, so our recommendation is a brown suede Chelsea boot. It’s probably the most versatile footwear a guy can own (which is why I put it in my capsule wardrobe.)

Sneakers With Western Shirts?

“I’d never wear sneakers with a Western shirt,” says Peter. “Especially athletic sneakers, running shoes. It’s the wrong vibe, like wearing sweatpants with one.”

I agree that it’s hard to wear sneakers that feel congruous with a Western shirt, but I found one pair in my collection that I thought worked: minimalist brown suede sneakers.

It’s just the ideal balance of earthy, textured, smart, and casual.

Loafers With Western Shirts?

“I like mixing genres, so I love loafers with this kind of look,” says Peter. “Preppy, Western, and biker — all different flavors of Americana.”

As the resident guy-who-doesn’t-want-to-put-a-ton-of-thought-into-his-outfits, I think that even though Peter pulls this off, it’s easy for an amateur like me to get loafers with a Western shirt wrong.

The solution? Brown suede. Yes, that’s been the conclusion of every kind of footwear in this section. If you want to try loafers with a Western shirt, do brown suede.

Yes, there are other leathers that work for cowboy shirts. But especially if you’re wearing something near the borderline, like sneakers or loafers, choosing a brown suede variant will bring you closer to the Western side of footwear.

Accessories to Wear With Western Shirts

Besides a nice belt that’s a good 1.5 inches wide, here are some other pieces we found ourselves wearing with our Western shirts.

Hats

Stetson is the end all, be all of cowboy hats. (Or you can try Akubra from Australia, a country that had its own authentic Wild West.)

Just make sure you’re getting an appropriately outdoorsy hat and not a fedora that was designed for urban professional wear.

Stetson’s Open Road (2.75-inch brim) is a famous choice that will work fine (thanks to its cattleman’s crown), but I’ve learned that ensuring your brim is a good 3 inches wide is a good way to keep people from questioning the point of your hat!

Handkerchiefs, Neckerchiefs and Bandanas

“Having a bandana around your neck at all times is actually very handy because you can wipe your brow with it, you can wipe your hands with it, you can mop up something that needs it,” says Peter.

“And when you keep it around your neck and not in your pocket like a handkerchief, it catches the sweat coming off your head before it hits your shirt,” adds Nick. “It’s to keep your shirt… marginally cleaner.”

Bags

One reason the Western shirt’s shoulders are reinforced is because they tended to sling a cross body bag over it — casual satchels were the cowboy’s bag of choice.

The trick is to make sure your messenger bag isn’t too dressy for the use case. Fortunately, we designed a super rugged one that also saves American farms.

Final Thoughts

Like Peter says: Western shirts do require you to dress a little differently. If you toss one on with cargo shorts and running shoes, it just won’t really hit — the Western shirt is many things, but it’s not versatile the way a white t-shirt is.

But that doesn’t mean you need to go full urban cowboy if you want to rock a Western shirt. With the tips in this article, you can put together a fit that’s subtle, modern, and congruous with the shirt all at the same time.

Oh, make sure you follow Peter’s YouTube and Nick’s Instagram. Thanks for your time, guys!