How to Dress Like a Cowboy: All the Fashion Tips You Need to Know

If you want to learn how to dress like a cowboy, you should check out these fashion tips. Click here to learn all about dressing like a cowboy.

Whether it’s the look of Leonardo DiCaprio’s Jake Cahill in Quentin Tarantino’s latest, “Once Upon A Time In Hollywood,” or Garth Brooks’ natural country music star vibe, cowboy threads, hats, belts, boots, and other gear have been in style for real and urban cowboys alike since long before Jon Voigt hit the screen in “Urban Cowboy” or Johnny Cash played the Grand Ole Opry.

While Garth has his hot Nashville style down pat and Tarantino had the help of costume designer Arianne Phillips to nail the cowboy look, how to dress like a cowboy isn’t obvious to all gents but always looks super when done right.

But how do you do the cowboy thing so it looks stylish but not over the top, you ask?

To help, we’ve put together some cowboy dress pro tips. Keep reading for what rugged style is on-trend right now in cowboy wear and gear, whether you’re an urban dude or actually rolling through on horseback doing the real ranch deal.

Know How to Dress Like a Cowboy the Cool Way

Okay, you know you’re thinking about those boots and that hat. Who wouldn’t be? That’s where the shizzle is.

But listen close, Marlboro Men! Don’t overdo it here with all the flashy gear at once unless you’re actually on a horse and roping cattle.

Half-cowboy/half-not is what you’re aiming for. 

So if you’re sporting the rugged denim jeans and your favorite steel-tip boots, put on a simple tee and a flannel up top and skip the hat and Western jewelry.

If you go with the cowboy shirt and bolo tie, stay away from the flashy steel-toes and hat. Think about simple cowboy boots and no hat.

If you’re itching to wear a hat, go with the jeans, white tee, and a sweater or flannel. Boots should be simple.

Hats do look snazzy with blazers for a formal look just keep the rest really simple.

Go Tried-and-True With Western Shirts and Blue

The All-American urban cowboy look you can wear any time is all about mens Western shirts and denim. Pair with solid everyday boots and a belt and you’re set.

Cowboy Jeans

Skip the skinny jeans, the low riders, the floods, the cuffs, the hipster street ankle bands, and the flairs, and go for durable, comfortable boot cut jeans so they fit just right over your boots.

Expect to get the inseam about two inches longer than you usually wear. This is because the boots give you those extra inches and you want them to stack some over those dogs of yours.

Your cowboy jean mantra is: Tough but relaxed, loose in the legs and long enough.

Cowboy Shirts

Keep these shirts classy, Guys, and you’ll be good to go. By classy, we mean button-down Western shirts with short or long sleeves.

Prints are hip and classy but don’t add flash if you go with a print. This means no over-the-top designs or embroidery on the print. Keep design and embroidery simple and more for the solids.

We’re keen on those pearly snaps and some embroidery though on single-color fabrics or subtle prints.

Pair Shirts and Jeans With the Right Hardware

This is where you remember that 50-percent cowboy look and keep your accessories and gear simple. Let’s take a look at how to do that.

Cowboy Hat

When picking a hat, you’re looking at what material the hat is made of and its shape.

Cowboy hats are typically made of felt or straw. Felt hats are pricier and look more dressy.

Stick with a brand that’s known. The brand assigns Xs to their hats. The more Xs the higher the quality. Compare Xs within brands not between them.

Go with a rabbit-beaver blend rather than wool.

You can find great-looking straw hats too. Again, go for the higher quality. A very light or white straw looks snazzy. Straw has ventilation so it’ll keep you cooler in hot temperatures.

Try on a variety of shapes to find the one that looks best and you feel comfortable in.

Cowboy Belt

A real cowboy boasts that silver 3-piece belt buckle like a trophy — because it is a trophy if you’re a rodeo rider. Don’t pretend to be one of those but do wear a simple silver 3-piece buckle.

Stay away from any other flashy buckles unless you find a fun one and are in for the irony when you match it with plain worn cowboy jeans, standard boots, and a simple T-shirt. Also, stylishly designed (read: top-notch quality) initials or other personal insignia are also a “yes.”

The belt itself should be leather in brown or black. No bling at all.

Cowboy Boots

The boot you’re looking for that’s simple and cool for your urban non-flashy cowboy dress is called a “roper” boot. Opt for a flat heel.

Toes should be round or square. Square seems to be on-trend right now. A lot goes into the process of making cowboy boots.

Do the Double-Denim Deal With Different Washes

Always wear two types of denim rather than one. This means that if your jeans are lookin’ smart and crisp with indigo blue, go with a lighter more-worn wash for the shirt or jacket.

Also, rugged and simple is a dark but worn pair of jeans with a darker but less-worn shirt unbuttoned and worn like a jacket over a simple white T-shirt.

Grab Your Hat and Saddle Up That Cowboy Look

Now that you got the goods on how to dress like a cowboy and keep it real, rugged, and dapper at the same time, you’re ready to grab some threads and step out in style. You might even try the two-step while you’re at it. The ladies will be lookin’ to fill their dance cards with your name.

Stick to the shops with the quality Western wear and gear to keep your fashion top notch.

Also, you might want to check our Clothing & Fashion posts for other guy gear and wear tips, like how to wear that simple white tee — always great under a Western shirt or with those double denim cowboy looks.