How To Break In Cowboy Boots

Cowboy boots have risen and dipped in popularity throughout fashion’s hundred-some years of history. Iconized in the 30s, 40s, and 70s, the ‘spaghetti western’ aesthetic blended nicely with the vintage fuzz of early television. 

Unfortunately, the country-bumpkin fad began to falter during the 80s, when trendsetters traded their spurs for sneakers instead. With Y2K and minimalism taking the stage, it appeared that there was no more room for cowboys, at least—until today. 

Since 2020, we’ve seen a resurgence of old-country Western thanks to TikTok and Instagram. Its pointed-toe silhouette, sturdy shape, and intricate stitching are all markers of a well-made closet staple

Our rejection of fast-fashion trends has encouraged us to look at classic fads that managed to survive years of ‘style recycling,’ and cowboy boots have managed to make the list. 

If you copped yourself a brand-new pair from Ariat or Corral, you’re probably wondering how to break in cowboy boots.

Strap yur-selves in, as we’ll provide an ace-high guide for newbie Westerners. Make sure to stay tuned for the rest of this article, as we’ll also discuss:

  • How long does it take to break in cowboy boots 
  • How to break in cowboy boots fast 
  • How to stretch out cowboy boots 
  • Outfits that pair well with cowboy boots 

What Are Cowboy Boots?

Before we get this ‘how to break in cowboy boots’ train rolling, we thought it best to define the shoe first. Considered a staple in Nashville fashion, these kicks are typically worn as a stylish yet practical alternative to regular footwear. 

They’re made out of sturdy leather, which helps to maintain the shape of the boot itself. It comes with many different parts, including the pull strap, crown, front shaft, and vamp.

Some versions feature a spur for horse riding, but it’s common for modern alternatives to be free of them. 

History Of Cowboy Boots

Like an old-school spaghetti western, there’s a lone-stranger type of mystery surrounding the origin of cowboy boots.

Its birthplace is up for speculation, as some experts point to Texas while others suggest Kansas. The sole inventor of the shoes has yet to be discovered, but some attribute its classic silhouette to that of Charles Hyer. 

Nevertheless, most agree that its rise to popularity began in the 1800s when westerners needed a pair of sturdy kicks that would protect and secure their feet while horseback riding.

Partially inspired by the vaquero shoe of the 1600s, the cowboy made its final debut after the American Civil War. 

Riders had two designs to choose from: the Wellington and the Hessian. Both different in construction and silhouette, these cowboy boots were considered top-pick for silent-movie stars and cattle herders. 

Over the years, brands like Lucchese took to developing more styles for customers to try. Today, hundreds of different stores offer their own take on the classic cowboy boot. 

How To Break In Cowboy Boots

100% leather is both a blessing and a curse. On the one hand, you’re practically guaranteed long-term use. On the other hand, its stiff silhouette makes it painful to walk in. 

For those wondering how to break in cowboy boots, we’ve developed a helpful guide to help turn those wellingtons into a cloud nine dream. 

  • The ol’ walking method: If you’re wondering how to break in new cowboy boots safely, you can always opt for a leisurely stroll. After continued use, the footbed will slowly conform to the contours of your foot. Just be sure to wear socks and blister tape to prevent any rawness. 
  • Use a boot stretcher: Not up for a bit of walking? If you need your cowboy boots to be broken in ASAP, a wooden stretcher can help expand the shape of your new kicks. 
  • The freezer method: So, you’re probably wondering how to break in cowboy boots overnight. We suggest opting for the water bag method, which requires users to fill a ziplock bag of water, stuff it into their shoes, and let it cool for a couple of hours. Remember, water expands when it freezes! 
  • Use a hairdryer: Breaking in cowboy boots is a tough thing to do, especially if the leather is brand-new. We recommend heating the inside of your kicks with a hairdryer. This helps to loosen the stiff nature of the fabric. If you do decide to do this, make sure that the machine is at its lowest temperature setting. 

If you managed to loosen your kicks just a bit, it’s cause for celebration. Moving forward, we’ll share some ways to style your cowboy boots using 8 outfit ideas

8 Outfit Ideas With Cowboy Boots

It would be an insult to exclude an homage to Nashville fashion within our ‘how to break in cowboy boots’ guide.

I’ll admit it, this outfit is missing a few fundamental parts—that being a classic pair of jeans—but it definitely imbues the spirit of a western-borne country girl. 

Composed of a t-shirt dress, a pinch front chapeau, and a pair of flaming-hot kicks, this stylish OOTD is perfect for window shopping at the state flea market. Don’t forget to top the look off with a cute designer bag. 

For date-night line-dancing, we suggest swapping your vintage Levis for a more romantic number instead.

Take, for instance, this outfit, which features a red summer dress with a 3-tiered skirt. Flirty, fun, and playful, this look will definitely bring all the cowboys to your yard. 

It’s further accentuated with a pair of leather wellingtons, a chunky black belt, and a set of cool shades. If you really want to imbue that Shania Twain attitude, there’s no shame in wearing a classic cowboy hat. 

Inspired by the late Princess Diana, this western take on a 1980s classic features a pair of black cowboy boots with a set of jeans, a white button-up tee, and a stylish plaid blazer.

The pants are rather baggy in silhouette, which helps exude the right amount of country edge to the entire look. 

Meanwhile, the Louis Vuitton bag and the dainty chain necklace keep things clean and sophisticated for casual use. This OOTD is by far the classiest ensemble within this ‘how to break in cowboy boots’ guide. 

Who says that cowboy boots can’t look classy? This outfit imbues the perfect balance between country-girl and collegiate student. It features a YSL blue button-up, a white collared shirt, distressed denim shorts, and a pair of white wellingtons. 

Accentuated with a set of sunglasses and a designer bag, this look definitely screams ‘country derby at 1:00 and brunching with the girls at 2:00.’

Guys, you don’t have to resort to the Clint Eastwood cowboy aesthetic. If you’re a fan of modern silhouettes, we suggest this updated take on spaghetti western. 

Composed of a sage green tee, white pants, paisley brown cowboy boots, and a matching Yankees baseball cap, this look strikes the perfect balance of contemporary and Nashville fashion.

For those keen on accessorizing, this ‘how to break in cowboy boots’ guide recommends a set of stacked necklaces and a crossbody bag. 

Western fashion can be romantic. Not convinced? This outfit is considered the perfect blend between Wes Anderson and Once Upon a Time in Hollywood.

It’s definitely a look for main character types, as it features a pair of dark-wash jeans, a cream tee, a blue plaid shirt, and a honey-colored corduroy jacket over top. 

Of course, the shoes make or break the ensemble, as it provides the right amount of western edge without going overboard. For accessories, this ‘how to break in cowboy boots’ guide recommends a set of silver stud earrings. 

Heading to Coachella? If so, it’s time to level up your fashion game. This bold and bright outfit features a pair of black pants, an orange fur coat, and a pair of snakeskin cowboy boots. 

We’re fully aware that Indio, California, is known to be notoriously hot, but hey—fashion demands sacrifice, right?

But if you can’t handle the humidity, you can always opt for a pair of distressed shorts instead. This ‘how to break in cowboy boots’ suggests topping the look with a classy embroidered fedora.

This old-western look is bound to make any cowgirl (or boy) swoon. Brown in hue, this outfit showcases a blend of deep espresso with rich chocolate in order to create a clean, cohesive fit. 

This monochrome ensemble comes with a button-down shirt, a white tee, pinstripe trousers, and a pair of matching cowboy boots. If this OOTD is too plain for your liking, we suggest blinging it out with a simple gold-toned necklace. 

What Type Of Cowboy Boots Can You Get?

The ‘how to break in leather cowboy boots’ is usually an afterthought for trendsetters.

First, you’ll need to decide what design to buy. With hundreds of styles sold on the market, it begs the ultimate question: what are some of the trendiest cowboy boots that you can currently get? 

To keep things easy to read, we’ve provided a short list of iconic silhouettes for fashionistas to consider. 

  • The traditional silhouette: Outfitted with a pointed-toe shape, pull tabs, paisley stitching, and spurs, this cowboy boot is typically made for horseback riding. 
  • Sweet and short: Otherwise known as cowgirl boots, these kicks feature a lower cut and exaggerated pointed toe. They’re mostly worn as statement pieces rather than functional footwear. 
  • Work boots: These kicks aren’t made for line dancin’. They usually come with added traction and a thicker outsole to help prevent slippage. 
  • The exotics: Made out of alligator, ostrich, deer, and other types of animal skins, these cowboy boots are designed to be shown off. This also includes intricately designed kicks that feature patchwork and stitching details. 

How To Choose The Best Cowboy Boots

Nothing screams quality craftsmanship than a pair of leather cowboy boots. I mean, half of the results on Google images feature a rugged set of well-made wellingtons. These kicks have a good rep for being sturdy, resilient, and practical for daily use. 

With that in mind, it’s rare to encounter a poorly-made version. But, with the onslaught of fast fashion trends, it may seem difficult to differentiate quality from quack for novice shoppers. 

There are 5 things to look out for in a pair of cowboy boots: price, quality, material, fit, and design. Of course, comfort is another point to consider—but given that these kicks take some time to break in, we thought to exclude it for the time being. 

Let’s talk about fabrics first. Premium cowboys boots are typically made out of sturdy leather and exotic animal skins. A brand new pair should offer a small amount of flexibility. Knockoffs are usually constructed out of synthetic textiles, which are usually flimsy when worn. 

A good pair of cowboy boots should feel tailored in silhouette. It’s common for brand-new kicks to feel constrictive after first use, but don’t take it as an excuse to throw them away. 

If you’re wondering how long to break in cowboy boots, it can take a couple of weeks if worn continuously. Design is another factor to consider, as we recommend choosing a simplistic style to ensure long-term wear

So, how much are we talking about here? A pair of well-made cowboy boots can range from $200 to $700, depending on the brand. Yep, it’s a high price to pay for quality, but you can at least relax knowing that you won’t run into any rips or dips along the way. 

How To Style Cowboy Boots

Congrats! You finally know how to break in cowboy boots. For those looking for new ways to style their new kicks, we’ll share some tips worth considering.

From cowboy hats to neck scarves, we’ve rounded up a few recommendations to finesse your final fit. Trust me, you’ll want to show off your fashion prowess at the next county derby. 

  • The cowboy hat: No Nashville-inspired outfit is complete with a cowboy hat. Offered in various cuts, shapes, and colors, it’s an easy way to transform any casual look into a yeehaw moment. 
  • The printed scarf: Considered a super versatile accessory, the scarf can be used as a necktie, a headscarf, or as a hat decoration. 
  • Embellished bootstraps: Instead of opting for flimsy anklets, we recommend a sturdy metal bootstrap as a better alternative. 
  • Engraved heel guards: In need of additional bling? If so, why not add a metal guard to the heel of your cowboy boots? They come in a variety of designs and finishes, including gold and silver.  
  • High-waisted jeans: Levi’s and cowboy boots are the bread and butter of Nashville fashion. If you’re not a fan of midi skirts and shorts, there’s no shame in opting for this classic combo. 

Fashion Tips To Avoid With Cowboy Boots

Like any core aesthetic, country fashion comes with some good and some bad. On the one hand, it’s a romantic style that harbors on old-school classics with modernized Shania Twain. 

On the other hand, it can be a stereotypical stock image of cheesy trends. If you prefer the latter vibe, here are some fashion tips to avoid with cowboy boots. 

  • Assless chaps: To be fair, this unusual garment can work in a Coachella setting. In terms of casualwear, its strange silhouette can often lead to some unwarranted snickers and giggles. 
  • Unnecessary harnesses: Wearing cowboy boots and a cowboy hat doesn’t qualify you as an expert rider. On top of that, gun holsters are considered a completely impractical accessory if you’re not Clint Eastwood.  
  • Spurs: Trust me, your calves and butt will thank you later. There’s nothing more painful than an accidental jab. 
  • Athleticwear: Nashville fashion and athletic wear are considered polar opposites of the fashion spectrum. You should never swap your Levis for leggings, no matter how comfortable they are. 

How To Take Care Of Cowboy Boots

So, you finally know how to break in cowboy boots. Now it’s time to initiate some basic care and maintenance. For those who can’t be bothered to visit an in-store professional, we’ll share some ways to clean your new kicks at home. 

  • Use a microfiber cloth or a brush to get rid of surface-level dirt 
  • Apply a damp rag or a magic eraser to stains and blemishes 
  • To maintain the shine of your cowboy boots, we suggest a leather conditioner and polisher 
  • Stuff your cowboy boots with a foot shaper or newspaper to help preserve their shape 
  • Stay away from mud, water, and other types of treacherous terrain to help prevent excessive wear and tear 

Best Places To Buy Cowboy Boots

Before this ‘how to break in cowboy boots’ guide ends, we thought it best to leave our readers with some recommendations.

If you’re in need of some brand-new wellingtons, here are some places to check out:

  • Ariat 
  • Bootmaster
  • Frye 
  • Lucchese
  • Durango boots
  • Tecovas 

Final Thoughts

There’s a cheesy yet romantic nature found in a pair of cowboy boots. For some casual dressers, it’s reminiscent of line-dancing, cow-tipping, and other Western-bound stereotypes. 

But, if you were to ask a Nashville native, it’s a closet staple that speaks volumes about their heritage and fashion traditions. If anything, cowboy boots imbue a vintage aura that can’t be found in a pair of combat boots or Uggs. 

Consider yourself briefed in the ‘how to break in cowboy boots’ debacle. We also left you with a selection of fashionable outfits to wear. From county fairs to horseback riding trips, there’s a pair of well-made wellingtons fit for every occasion. 

Looking to broaden your fashion horizons? We’ve got you covered:

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