5 Cowboy Boot Outfits Any Guy Can Pull Off

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Let’s get this straight. You are a modern, stylish man who knows that lace-up footwear is not your only option! You’ve embraced open-back shoes like Birkenstock clogs, and classic loafers. Now, you’re itching for something new. So I’m going to throw something out there. Have you considered cowboy boots?

Okay yes. Maybe cowboy boot outfits feel too “out there,” like you can’t pull the look off. Or maybe you’re not sure you even want to?

But I am here to convince you that you — yes you! — can and should wear cowboy boots.

First thing’s first, you may be asking yourself:

Can I pull off cowboy boots?

modern cowboy boot outfit — source: @cowboybootsofnyc

Even if you’re firmly in the “I like all music but country” camp, don’t turn your back on cowboy boots! You can absolutely make this functional footwear built for durability work for your soft-living city style.

Just think of all the benefits! No laces to tie or trip over. Your ankles stable but not suffocated like they are in ski boots. Sturdy design crafted to last for years, if not decades.

And if you somehow find yourself astride a horse? Well, you’ll be ready.

Oh, and if you’ve added some of the wider silhouette workwear pants that are currently so trendy to your wardrobe? Great news, a cowboy boot is a great shoe style for this modern look!

What kind of cowboy boots are there?

Just like there are all kinds of sneakers, there are different types of cowboy boots.

You’ve definitely seen the traditional Western boots style that hits mid-calf, has a pointed or “snip” toe, a bit of a heel, and ornate detail on the shaft.

These are the standard when you hear “pair of cowboy boots” and they definitely make a statement.

The roper boot, designed for roping cattle, is a great option if you want to experiment in this look, but want something more subtle. Their heel is lower, their toe might be more square, their shaft is shorter, and plenty of brands make ropers with less flourishes than traditional cowboy boots.

Unless you’re doing actual cowboy work in them, what style you buy is totally up to you. No shade to cowboy hats, but IMO a cowboy boot is way more versatile in a modern man’s wardrobe.

Where do I buy cowboy boots?

tecovas store — Tecovas store in Nashville

You can’t go wrong picking up a pair from one of the long-standing heritage companies that specialize in cowboy boots: Lucchese, Ariat, Tony Lama, and Alvies.

Other shoe or leather brands you already love, like Barbanera, Stetson, and Thursday Boot Company, certainly won’t disappoint.

Since cowboy boots require so much leather, intricate stitching, and a whole lotta labor to craft, they can quickly enter into “investment piece” territory.

If you’re not sure you want to go all in on a pair of investment boots quite yet, consider scooping up a vintage or secondhand pair on a resale site like Etsy, eBay or Poshmark.

Mine are Acme, the most popular cowboy boot brand in the 50s, and cost $60—and I’ve definitely worn them well over sixty times.

Below, check out 5 men’s cowboy boot outfits to wear right now:

MONDAY

STYLING NOTES: Take your boots out dancing in a bomber jacket, camp shirt, and ’70s-esque pants.

Yes, they say these boots are made for walking, but they can make pretty great dance shoes, too! Whether you salsa, boogie, or just sway awkwardly at a more acoustic show, these can become your favorite night out shoes.

TUESDAY

STYLING NOTES: Comfort is key in this laid-back boot look.

A pair of boots is weirdly perfect for a casual outfit because you can throw them on like you’re slipping into a pair of well-loved sneakers and be out the door.

In warmer weather, swap the button-down for your favorite t-shirt.

WEDNESDAY

STYLING NOTES: This is an homage to an outfit I was wearing when I first pitched this story, and Megan was wearing basically the same exact outfit. Great minds!

You can make this Western staple more PNW GORP-core casual with a fleece and workwear pants.

THURSDAY

STYLING NOTES: Get ready to feel like an influencer when you wear cowboy boot outfits like the one above, because all your friends are going to want to copy them.

For this look to work, the light jacket is key.

Go with something sporty like the coach’s jacket above, or rugged but in a country gentleman way like a waxed jacket. From there, finish the whole thing off with boot-cut jeans, straight-leg jeans, or chinos in a relaxed fit.

Why? You don’t want the ankles bunching up around the top of the boot.

FRIDAY

STYLING NOTES: While you may not ever pair your boots with a suit, it can be done! So, consider at least experimenting with dressing up your black or brown cowboy boots.

Use the wrong shoe theory and pair a dressier outfit with rodeo-adjacent accessories for a look that leans more east coast ivy league than Yellowstone.