"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. 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.
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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. 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).
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 2024.
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 eight ways to style 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. 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
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 it would have made more sense to pair the preppy coat and dress with a pair of ballet flats or knee-high boots, 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-style boots.
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.
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.
With Boxer Shorts and a Blazer
Lucky for those of us who have hopped on the boxer short trend, they deliver a chic, unexpected look when paired with cowboy boots. Combine them with a blazer that hits near the hem of your shorts for a complement-earning combo that the cowboys never saw coming.
With a Denim Midi and Cool Sunnies
You don’t have to own lilac cowboy boots in order to embody this ultra-cool look. Achieve a similar effect by pairing you neutral boots with a pair of colorful sunglasses and a colorful, printed top, and I promise you’ll look just as stylish.
With a Matching Set
I may be a little biased because her boots are red and her bag is silver—two trends that pull at the strings of my maximalist heart—but this look is it. At first glance, it’s hard to even recognize that these are cowboy boots—proof that Western wear doesn’t always have to scream Americana. This is a prime example of how to take a pair of cowboy boots from country to city.
With an Airy Dress and Oversized Blazer
The fastest way to get me into a pair of cowboy boots is if it involves pairing them a blazer of any kind. I live for a blazer. (No, that is entirely false. I live for my french bulldog named Willow. Someone has to pay her vet bills). What I love about the unexpected pairing of an oversized blazer and a pair of cowboy boots is that they come from two totally different categories, yet somehow completely compliment each other.
Shop 2024’s Best Cowboy Boots
Tinsley Crisp, Fashion & Beauty Staff Writer
Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.