How to Wear Cowboy Boots This Fall

Though I wouldn’t really call it a comeback since they’ve been in style for well over a century, cowboy boots The post How to Wear Cowboy Boots This Fall appeared first on The Everygirl.

  Lifestyle   Nov 3, 2025   0   7  Add to Reading List
How to Wear Cowboy Boots This Fall
how to wear cowboy boots

Though I wouldn’t really call it a comeback since they’ve been in style for well over a century, cowboy boots have recently adopted a following of fashion-goers that has prompted a resurgence of the Western staple for fall. The western boot, as a key element of Western-inspired fashion, is now celebrated for its versatility and ability to elevate both casual and tailored outfits. In years past, I probably wouldn’t have touched a pair of cowboy boots with a 10-foot pole out of fear that there was no other way to wear them than with a matching L.L.Bean flannel and a pair of Wranglers. Fast forward to today, I stand before you—a proud beneficiary of the Cowboy Carter effect—a changed woman. No, I may not be taking a trip to the Boot Barn any time soon, but if they’re metallic, studded, or happen to be from my favorite brand (Ganni) then sure, I’ll take a pair or two.

Now this next sentence may surprise you: I am from Nashville. I know—I probably just committed a crime in the great state of Tennessee by claiming that I once feared a pair of cowboy boots. But take it from me, a native Nashvillain, that I am now an expert when it comes to styling this spurred staple. Inspired by designers like Isabel Marant, fashion girls have played a big role in making cowboy boots and western boots both trendy and versatile. Luckily, there are now countless fashionable ways to wear cowboy boots, making them accessible and appealing to everyone. From country music stars to cowboy city-slickers and every bachelorette party in between, I’ve seen a thing or two. (And more than I care to admit—do not go to Broadway at 2 a.m.–just don’t).

SHOP: Western Fashion Pieces to Add to Your Wardrobe this Fall

Source: @ganni

Everything to Know About Cowboy Boots

Cowboy boots aren’t just a passing trend—they’ve been around long before the fashion girlies took them from the ranch to the streets of NYC. Cowboys may have needed sturdy footwear for long days in the saddle, but the fashion crowd needs stylish boots that can keep up with their night-out step count. Whether you have Southern roots or just can’t resist a good statement shoe, cowboy boots are a must for every closet. From casual outfits with a hint of Western edge to bold going-out looks, a great pair of cowboy boots can instantly elevate your look. With endless ways to style them, it’s no wonder cowboy boots have become the cool girl shoe for cowboys (or cowgirls) and beyond.

Choosing the Right Boots

When it comes to choosing the right cowboy boots, it’s all about finding the boots that align with your personal style. If you’re style icon is Sofia Richie and you love a more polished vibe, opt for a pair of black cowboy boots with a sleek finish. Whether you’re pairing them with your classic leather jacket or even stepping out of your comfort zone with an Aspen-inspired cowboy hat fit, they will get so much use in your closet. If you love a more relaxed, Dakota Johnson-esque look, reach for boots in brown or tan with a bit more personality. And of course, you need to consider arguably the most important part of styling boots—what jeans you’ll be wearing. Straight leg, bootcut, or even wide leg jeans can all bring out a different side of your cowboy boots. To take your look to the next level, you can also pair your boots with accessories like a cute cowboy hat or a statement belt. If you’re struggling to find your perfect pair of boots, don’t be afraid to try on a few different pairs until you find what works with your closet.

How to Style Cowboy Boots

Although it was hard to give up being neighbors with Dolly (well, not exactly, but I did live next door to her office), I’ve since become a New Yorker drawing from my Southern roots and laboring a new sense of sophistication when it comes to my personal style. I find it to be the perfect metaphorical example of how to style a pair of cowboy boots for fall.

You’ll want to avoid the slippery slope to cowboy cosplay by laying down your wide-brimmed hat and opting for a pair of boots with more subtle Western details—a stacked heel, rounded shaft, or soft stitching—and styling them with opposing pieces like a romanticized lace slip or an oversized blazer. The key to modernizing this trend is to go for a versatile, less-costumey pair worn with your usual closet essentials in place of other footwear go-tos like ballet flats or knee-high boots.

Ready to style a pair of your own? Here are nine ways to wear your cowboy boots this fall, plus my favorite 20 pairs to shop if you’re ready to dip your toe into the Western trend.

With Jeans and a Hoodie

Although, on paper, the idea of wearing jeans and a hoodie with a pair of cowboy boots could technically still read ranch-appropriate, it’s all about how you style them. As a stylist, I often use cooking examples to help clients better understand: Depending on the quality of ingredients used, you could either call your noodles and red sauce spaghetti or pasta pomodoro. My point? Choose your best jeans, a quality hoodie, and your favorite sunnies for a super chic, off-duty look rather than a ranch-ready ensemble. Consider opting for a relaxed fit or straight leg jeans, and look for a shorter inseam to prevent bunching around the feet and ankles. Headed out on an extra-chilly day? Add a classic trench or wool overcoat. Now we’re getting into Princess Diana territory.

With a Sweater Dress and Classic Trench

Sweater dresses are a versatile option for pairing with western boots, especially when you want to elevate your look with minimal effort. When I want to look like my most posh self, I throw on the ole’ tan trench that lives in the back of my closet. It’s not that I’ve purposefully left it to collect dust, it’s just that it’s hard to find ways to wear it other than my go-to pairing of jeans and some trusty sneakers. But after seeing this photo, my trench coat just earned itself a new spot in my rotation.

Though some might opt for fancy heels or ballet flats with dresses, I like that she went with the unexpected choice—some may even call it the wrong-shoe theory choice—of completing the look with a pair of western boots. This combination makes the outfit feel both chic and grounded, offering a stylish alternative to more traditional footwear.

With a Slip Dress

By choosing to style your boots with a slip dress, you help to counterbalance the usual heaviness that comes with any pair of boots—cowboys or not. The delicate femininity of the dress juxtaposed with the more masculine effect of the cowboy boots shows that chances are, you’re not heading to the rodeo in this look. The toe shape of the boots, especially if you opt for a modern style, can add a contemporary touch to the outfit. Pairing a slip dress with cowboy boots in dark washes can also create a more polished, elevated look.

READ: 4 Ways I Wear My Tecovas Boots

With It-Girl Accessories

This feminine styling approach has me swooning over a pair of studded, Western-style boots of my own. While we’re used to seeing images of cowboy boots worn by men with wide-brimmed hats and worn-out wranglers, this look is giving Western wear a girlish revival. From the coordinating rosette details to the evil-eye embroidered bag, this look is all about the details. Fringe accessories can add a Western touch, but it’s best to balance them with simpler pieces to avoid looking too costume-like.

SHOP: The Best Boots to Buy for Fall 2025 (Before They Sell Out)

With Boxer Shorts and a Blazer

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