Western-style riding boots are just about as American as it gets. They exist somewhere between functional work clothes, pop culture faves, and Western-style folk art. Everybody from presidents to actors has worn them, with varying degrees of success.
How to style cowboy boots? The answer to this question proves tricky. After all, few symbols are more iconic or laden with stereotypes.
Yes, you can most definitely wear them, even if you’re not a cowboy. But you’ll need to follow some basic rules to pull off this look without giving off a Woody in Toy Story vibe. With that in mind, here’s what you need to know about the best cowboy boots for you.
Why You Need a Pair of Cowboy Boots in Your Closet
Just because you’re after a pair of Western-style boots doesn’t mean you have to learn how to dress like a cowboy. Of course, if you’re after a cool “Should’ve Been a Cowboy” look, there’s no better way to channel it than with a well-executed boot investment.
Think of cowboy boots as the ultimate fashion weapon. While they exemplify a high-quality pair of leather shoes from a distance, they have distinctive flair and styling upon closer inspection. Their unique shape can also add height to any look.
They often feature gorgeous decorations, and you’ll find a style for every fashion preference imaginable. From contrast-color stitching to bright vegetable dyes and leather tooling, the best boots to wear represent veritable works of art like these alligator boots.
Yet, this special footwear only has to be as visible as you’d like. For example, the bottoms may peek out from underneath a well-fit pair of trousers, or women may wish to showcase them with a maxi dress.
Finding the Best Boots to Wear
You’ll need to be aware of some terminology before shopping for the best cowboy boots. As a first-time boot buyer, you could feel overwhelmed by the wide selection and many options, but a little research ahead of time will give you a better sense of what to look for.
That said, a few universal elements help identify the unique look of a Western-style boot. For example, true cowboys boots should feature a Cuban heel that’s underslung and angled by at least a half-inch. They should also feature a high shaft that typically comes up to the mid-calf area.
Boot tops may have a rounded, plain opening, or they may culminate in decorative cutouts. Either way, classic Western boots tend to measure between ten and 14 inches at the shaft. You’ll also notice that proper boots never have laces.
Types of boots include:
- Western work
The stockman and cowboy styles share many similarities, although the heels will be broader and shorter on a stockman. This stockier heel makes the stockman ideal for long days on your feet.
Ropers also have a broader heel and a more rounded toe. Shaped more like your typical Western-style work boots, these features render them ideal for rodeo use.
As for Western work boots? They look very much like ropers but come with a larger toe box and non-slip rubber soles.
Last but not least, show riders typically wear buckaroo-style boots because they feature elaborate details. They also have tall shafts, often well past 14 inches, making them a flashy choice.
How to Style Cowboy Boots
Wearing Western-style riding boots doesn’t have to relegate you to dressing like a cowboy. But if that’s your thing, more power to you. That said, if you aren’t a tried and true horseman or horsewoman, we recommend a less conventional approach to styling this footwear.
Tips for Styling Men
What’s a rule of thumb we swear by? Never have more than one piece of Western-themed attire per outfit. In other words, put cowboy boots with a jacket and sleek belt rather than a bolo tie and a ten-gallon hat.
What else will help you look like a stylish dresser as opposed to someone who should accessorize with a sheriff’s star? Forego light-colored denim work jeans in favor of close-fitted, dark denim, and never tuck jeans in your boots. That is unless you’re preparing to muck stalls.
Or avoid denim altogether with a nice set of dress trousers or a casual suit. Stay away from decorative belt buckles, or you’ll look like you’re attempting to “cowboy up.” And almost always wear boots with a jacket as it balances the casual style of the shoes in a way that most shirts can’t do alone.
Tips for Styling Women
For women, avoid stereotypical pieces such as overalls and prairie dresses. Instead, go with an edgy contrast such as an animal print maxi dress. You should also avoid piled-on accessories and hats in favor of simple outfits and polished pieces.
Leave the streetwear at home. But do take the time to dress up boots to channel a decidedly elegant, chic look. Must-try pieces when it comes to cowboy boot pairings include jeans with a turtleneck or t-shirt.
Minimalism is key here. So, stay away from the fringe, sequins, and anything else that looks like you’re about to take the stage at Dollywood. Instead, make the boots the focal point of your outfit (without theming your entire outfit around them) to pack the biggest fashion punch.
Fashion Forward Cowboy Boot Pairings
Fashion is an awful lot like wine tasting. You must know what to pair with each bottle to fully appreciate it. As you can see from the tips above, it’s easier than you think to dress in a way that complements wearing cowboy boots.
When it comes to how to style cowboy boots, don’t fall into the Halloween category and attempt to pair your footwear with other Western-inspired apparel. Otherwise, you’ll end up looking like you’re auditioning for the latest Billy the Kid documentary.
Instead, go with polished pieces that have a minimalist appeal, and don’t be afraid to let the boots get all of the attention. When you find the right pair, they represent a work of art, so show them off accordingly.
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