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The Only Cowboy Boots Styling Tips and Tricks You Will Ever Need

By Orgesta Tolaj


10 October 2023

cowboy boots styling tips

© Megan Bucknall / Unsplash

These boots were made for walking, and definitely not just for festivals! Cowboy boots have become the latest craze in the fashion industry at the moment. Who could blame them? They are versatile, stylish, and extremely comfortable. So it comes as no surprise that many are looking for ways to style them all year long. Having trouble doing that? No worries! We are here to offer you the only cowboy boots styling tips you will ever need. Yes, really! So buckle up (your boots as well!) and let’s find out how you can style your cowboy boots together.

What Are Cowboy Boots?

Cowboy boots are a distinctive style of footwear that originated in the American West and are characterized by several key features. This includes the pointed toes which originally allowed cowboys to easily slip their feet into stirrups while riding horses. Additionally, these boots often feature high, slanted heels that are designed to keep the rider’s foot securely in the stirrup while riding and to provide stability during activities such as roping and working with cattle.

Moreover, many cowboy boots feature intricate and decorative stitching patterns on the shaft and foot of the boot. These designs can vary widely and are often a distinctive feature of each boot.

Brief History of Cowboy Boots

The history of cowboy boots is steeped in legend and mystery, with no definitive originator, although most agree that the first pair was crafted by a shoemaker in either Texas or Kansas. The history begins in the aftermath of the Civil War in 1865 when cowboys found that their military boots were ill-suited for long hours on cattle trails, dealing with harsh terrain and the need for quick dismounting.

Around the 1870s, an ingenious cowboy visited a local shoemaker and requested a new type of boot. He desired a higher top for protection against snakes and thorns, scalloped edges for easy donning, loose tops for swift removal, pointed toes for effortless stirrup access, and high, slanted heels for a secure grip on stirrups during cattle drives.

What Were the First Cowboy Boots like?

These boots also featured thick leather to shield ankles from wooden stirrups and prevent chafing against stirrup leathers. Additionally, the stitching was placed outside to prevent leather from causing discomfort on the cowboy’s leg. Initially designed purely for function, the first cowboy boots were not known for their style but quickly gained popularity due to their practicality.

Cowboy boots were originally handcrafted and custom-fitted by cobblers, but as demand grew, efforts were made to streamline production. While mail-order boot companies emerged, custom-fit boots remained the preferred choice for those who could afford them.

How Cowboy Boots Became a Fashion Statement

Cowboy boots evolved from practical workwear into a fashion statement through a combination of cultural influences, media portrayal, and shifts in fashion trends. But, what made them so trendy to begin with? Western movies and TV shows that gained popularity in the mid-20th century, featuring cowboys and cowgirls, played a significant role in popularizing cowboy boots as a fashion item. Icons like John Wayne and Roy Rogers were often seen wearing them on-screen, making them seem adventurous and rugged.

cowboy boots styling
© freepik

Additionally, celebrities and musicians, particularly those associated with country and rock ‘n’ roll music, embraced cowboy boots as part of their signature style. Icons like Elvis Presley, Johnny Cash, and Dolly Parton made cowboy boots fashionable by incorporating them into their stage outfits.

Cowboy Boots Styling Tips and Tricks

Here are some ways to style your boots according to season:

Summer Fling

Sporting cowboy boots with a mini skirt during the summer season is a style choice that can both make a statement and exude a laid-back, casual charm. Cowboy boots have the versatility to complement and balance out the boldness of a mini-dress, making them an excellent alternative to traditional heels. So, the next time you find yourself struggling to find the right pair of heels to match your eye-catching mini-dress, consider opting for cowboy boots to effortlessly combine fashion and comfort for a chic summer look.

cowboy boots styling ways
© notsammishapiro / Instagram

Winter Wonderland

Cowboy boots styled with a winter jacket are a fashion choice that can channel an ’80s-inspired look, especially when paired with oversized blazers or A-line miniskirts. This ensemble delivers a sense of cool nostalgia, but you can put your own unique twist on it by substituting heels or loafers with cowboy boots. To maintain the preppy and retro vibe of this outfit, consider selecting cowboy boots in soft, pastel hues. This combination blends the classic and the unconventional, creating a stylish and edgy winter look that pays homage to the fashion trends of the past while adding a contemporary twist.

louisa_mazzurana / Instagram

Angelic Autumn

Autumn is a great way to show layered outfits, and this includes quiet luxury matches as well! Embracing cowboy boots during the autumn season can infuse your wardrobe with a blend of rugged charm and seasonal flair. As the leaves change and temperatures drop, cowboy boots provide a versatile and stylish option for your autumn outfits. Transitioning from summer to autumn doesn’t mean you have to retire your dresses and skirts. Cowboy boots can be the perfect footwear choice to give your feminine outfits a touch of Western-inspired flair. Flowy maxi dresses, midi skirts, or even floral prints can be balanced with the ruggedness of cowboy boots for a trendy autumn ensemble.

cowboy boots styling in autumn
© withameliataylor / Instagram

Spring Blossom

There is a growing trend in fashion where cowboy boots are becoming more casual and versatile, transitioning from statement pieces to essential wardrobe staples. And spring is the perfect time to experiment! Try to wear cowboy boots in a subtle and understated manner, similar to sneakers, to achieve an effortless look. This can be achieved by opting for shorter boot styles like ankle or mid-calf height and choosing muted colors such as beige, black, or brown. The overall aim is to make cowboy boots a more casual and adaptable choice for everyday wear.

cowboy boots styling in spring
© christina.alexia / Instagram

Cowboy Boots Styling: Things to Avoid

While you can absolutely wear whatever you like (and rock it!), there are certain styling choices to avoid to ensure your look remains fashion-forward and flattering. Here are some cowboy boot stylings you should avoid:

Don’t Match Your Outfit Colors

Avoid wearing cowboy boots that are too perfectly matched to the rest of your outfit. Instead of choosing boots in the exact same color as your clothing, opt for complementary or contrasting shades. This can help create visual interest and prevent a monotonous look.

Avoid Too Many Western-Inspired Accessories

While it’s fun to embrace a Western-inspired theme, be cautious not to overdo it with too many Western accessories. Avoid piling on cowboy hats, belts, buckles, and fringe all at once. Opt for one or two Western-inspired elements to keep your outfit balanced and avoid appearing costume-like.

Leave the Gym Clothes for, You Guessed It – The Gym!

Cowboy boots generally don’t pair well with athletic or gym attire. Avoid combining them with sweatpants, workout leggings, or athletic shorts, as the contrast in styles can look mismatched. It is best to reserve cowboy boots for fashion-forward and casual occasions where their unique style can shine.

What season do you like wearing cowboy boots in? Would you try our cowboy boots styling tips for your next outfit? Let us know in the comments below!

You might also want to read: What You Wear Changes the Way You Think

Orgesta Tolaj

Your favorite introvert who is buzzing around the Hive like a busy bee!