"In 2020, I found myself entrenched with the then-trending cottagecore aesthetic. The pandemic was at its height and I, like so many others, was turning to romanticism as a means to mentally escape and find joy and peace in the often-simple routine of life at home.
It was at this time, pregnant and then postpartum with my first child, that I fell in love with quintessential cottagecore pieces, including smocked floral dresses and—much to my own surprise—cowboy boots. While the shoe had previously been intimidating to me, as a new mom, I found myself gravitating toward bolder styles, no longer self-conscious in regard to what others thought. I didn’t initially know how to style the aforementioned herding and roping shoe—but I was eager to find out.
Over the past several years, I’ve found myself slowly adding cowboy boot after cowboy boot to my shoe rack. To date, I own five pairs as well as a handful of modern, western-inspired boots whose silhouette and construction mimic those worn by cattlemen. While that may sound excessive (and well, maybe it is, but I’m not sure I care), I’ve surprised even myself with just how often I’ve worn these shoes. Keep reading for everything I’ve learned about styling this new-to-me fashion staple, plus a few cowboy boots outfits to get you started.
How to Style Cowboy Boots
Over the past four years, I’ve learned that cowboy boots are multi-seasonal, practical, and possibly the most fun shoe to style. They truly go with everything, so long as you’re open-minded to their potential. Whether you’re simply intrigued by the cowboy boot craze (thank you, Taylor and Beyonce both) or have owned these boots for years and are looking for new ways to style them, these are some of my personal favorite ways to wear them.
Cowboy Boots Outfit Ideas
With a Plaid Skirt and a Cable Knit Sweater
If Practical Magic is your chosen autumnal vibe, I can’t recommend this outfit formula enough. A soft cable-knit sweater worn with a mom-friendly midi or maxi skirt is a cozy pairing that still feels put-together. This combo is also a perfect foray into cowboy boot styling if it’s something you’re interested in but are not yet comfortable with.
My favorite boot to pull out for this formula is my We the Free Montage Tall Boots in Bone—the true-to-form narrow toe and cognac piping feel witchy in the fall months but in a mild gather-herbs-in-the-meadow kind of way.
Shop this look:
1. skirt | budget-friendly option
2. sweater | similar option
3. boots
4. hair bow
5. bag | similar option
With a Puff-Sleeve Midi Dress
When the sun is shining during the summer and fall, I love nothing more than throwing on a dress and calling it a day. Whether it’s a denim jumper or a romantic floral number, a pair of cowboy boots complements the look and will—I promise—earn you compliments in return on every single wear.
If you’re feeling bold, dabble with a brightly-hued boot. A few years ago, I added a pair of beautiful blue Tecovas The Annie to my wardrobe, and they are—without a doubt—one of my favorite pairs of shoes. And trust me: That’s saying a lot. The fit, quality, and color are all so good that I very truly and often plan my outfits around them. To style a colorful boot, look for and add corresponding pops of color to the rest of your outfit.
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With Jeans and a Sweater
For a cozy, casual, easy-to-throw-on fit, grab for your favorite sweater and jeans. Short boots or booties work well for layering under jeans, but I’ve also been known to style tall-shaft boots under baggy-fit denim. A classic belt can tie the look together.
While this look is basically begging to be worn to a tailgating event, campfire gathering, or pumpkin patch, you can easily upgrade to “office-ready” by swapping the top out for a business casual blouse or button-up.
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With a Matching Set
Cowboy boots have a way of just working with whatever set you throw on—whether it’s basic cotton, knit, or quilted. I’ve personally styled my cowboy boots with romantic cotton sets, printed in floral and gingham. But I am looking to add a modern quilted set to my wardrobe this fall.
Shop this look:
1. jacket
2. skirt
3. white tee
4. boots
5. bag | budget-friendly option
With a Sweatshirt and Skort
A skort styled with a sweatshirt is the active-lifestyle-friendly, pulled-together combo every mom needs in her arsenal. As a fan of balletcore, this fall, I’ve been particularly fond of overly feminine pieces that speak to the insurgence of all things girly (cue sparkles, pleats, and ribbons).
This outfit can be styled with either a traditional cowboy boot or a tall, western-inspired boot that toes the line between classic and modern. A monochromatic palette adds to the soft, romantic aesthetic.
Shop this look:
1. sweatshirt
2. skort
3. earrings
4. boots
5. bag
With Denim Shorts and an Oversized Tee
I can’t tell you how many times I reached for this outfit formula this past summer. With my kids’ daycare closed three days a week, I found the combination to be comfortable and practical, with the cowboy boots also adding a fun, unexpected element that helped me feel like myself on my “mom days.” Knowing that the fall will inevitably include at least a few warmer-than-I’d-like days, I know I’ll be reaching for this formula in the weeks to come. The combo can also be adapted for cooler weather by choosing longer hem shorts, tall boots, and a cozy cardigan.
Shop this look:
1. denim shorts
2. oversized tee
3. boots
4. bag
5. cardigan
With Tailored Shorts and a Button-Down
There’s a part of me that will always love overly preppy, Twee-esque fashion. And if you also harbor a similar penchant, I know you know exactly what I mean. While a combo of tailored shorts and tall boots may not be everyone’s cup of tea, I’ve found this outfit to be particularly well-suited for my current “toddler mom” life phase.
I recently added a pair of Sézane Gabrielle Low Boots to my wardrobe and am very excited to style them with tailored shorts and preppy tops all fall long. The silhouette of the boot is reminiscent of the wild west but is more understated—positioning it to pair well with “all the fall.” A sweater vest and a messenger bag add to the autumnal aesthetic.
Shop this look:
1. shorts
2. button-down
3. sweater-vest
4. boots
5. headband
6. bag | budget-friendly option
With a Knit Dress and Trench Coat
For a cozy-chic outfitting option, style a knit dress with a classic trench coat and a pair of sleek Western-inspired boots. While kitten heels are more common in this situation, blocky cowboy boot heels make the look entirely more practical for life with kids. Wear to the office or to work from your favorite coffee shop with a stylish tote bag that holds all your essentials and then some.
Shop this look:
1. dress
2. boots
3. trench coat
4. earrings
5. bag
Shop More of Our Favorite Cowboy and Western-Inspired Boots
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The Everygirl Media Group has brought valuable content to our readers for 12+ years. In 2018, The Everymom set out to ensure that all moms know they’re not alone. If you find yourself seeking advice on how to style the latest fashion trend or searching for the best kid-friendly coffee table, we have the answers. And if you’re wondering what’s actually worth it from a sale or looking for a review of the hottest new kids’ product, we’ve got that covered too. From our annual Registry Awards and beloved holiday gift guides to the shopping round-ups you find on our site every day, The Everymom commerce team is well-versed in sifting through thousands of products to curate a digestible list for you. We combine our own experience with in-depth research to bring you a selection that meets our high standards for both fashion and function.
Emilee Janitz, Contributing Writer
Emilee is an accomplished communications strategist and lifestyle journalist. She currently works on the content team at Enterprise SEO company Terakeet where she creates and executes reputation management strategies for Fortune 500 companies. She is a Contributing Fashion Writer for The Everygirl and has additionally been published on POPSUGAR, Motherly, MSN, and Yahoo.