Fall Cowboy Boots

Saddle up, darling, because fall cowboy boots are here to kick up your autumn style! Whether you're two-stepping through pumpkin patches or strutting down city streets, these boots are your ticket to a season of fearless fashion. With every step, you're channeling that irresistible blend of rustic charm and modern flair. So go ahead, unleash your inner cowgirl and let those fall cowboy boots do all the talking—because when it comes to making a statement, these boots were made for more than just walking. Yeehaw!

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Made For Dancing Laser Cut Cowboy Boots in Taupe

Sale

Windsor Made For Dancing Laser Cut Cowboy Boots in Taupe

$19.97 $46.90 57% off

A taupe cowboy boot with a laser cut design, stacked block heel, and knee-high shaft.

Windsor Glam Strut Rhinestone Cowboy Boots in Black

$54.90

A black faux suede cowboy boot adorned with all-over rhinestone geometric patterns and a stacked block heel.

Totally Edgy Buckled Square Toe Boots in Brown

Best Seller

Totally Edgy Buckled Square Toe Boots in Brown

$45.90

A pair of brown faux leather calf-length boots featuring buckled side accents and a square toe design.

Now Trending

Totally Edgy Buckled Square Toe Boots in Black

$45.90

(11)

Step into these edgy statement faux leather boots with a buckled side accent and a calf-length fit perfect for pairing with bottoms or dresses. Fit & Feature2” in heel, 7.5” leg opening, 11.5” shaft , Square toe, Buckled side accents, Calf height shaft, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Totally Edgy Buckled Square Toe Boots in Black | Size: 8.5 | Leather

Windsor Steppin Up Block Heel Knee High Boots in Black

$48.90

(10)

Big boot energy only—these tall babes instantly elevate any 'fit. A sleek silhouette with a comfy block heel makes them perfect for day-to-night flexing. Fit & Features3" Stacked block heel, 8" leg opening, 12" shaft height, Platform sole, Round toe, Complete inner zipper closure, Knee-length shaft, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Steppin Up Block Heel Knee High Boots in Black | Size: 7 | Leather

Major Strut Faux Leather Knee-High Stiletto Boots in Black-2

$48.90

(7)

Fit & Features3" Stiletto heel, 7.5" leg opening, 13.5" shaft height, Patent faux leather material, Knee-high design, Pointed toe, Complete inner zipper closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Major Strut Faux Leather Knee-High Stiletto Boots in Black-2 | Size: 5.5

Windsor Boot Scootin’ & Vibin’ Cowboy Boots in Camel

$52.90

(5)

Giddy up, but make it fashion. These cowboy boots bring rodeo realness with a side of city-girl sass—perfect for concerts, content days, or just stomping through life like it’s your personal runway. Fit & FeaturesStacked block heel, Almond toe, Western-inspired pattern, Inner zipper closure, Knee-length shaft height, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Boot Scootin’ & Vibin’ Cowboy Boots in Camel | Size: 7.5 | Faux Suede

Daring Details Studded Ankle Booties in Black

$40.90

(5)

Make a bold statement with the daring details studded ankle booties. Featuring a block heel, peep toe, and criss-cross straps with metal buckles, these booties are your new go-to for standout style. Fit & FeaturesBlock heel, Ankle-length fit, Faux microsuede material, Peep toe, Criss-cross straps with metal buckles, Studded accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Daring Details Studded Ankle Booties in Black | Size: 10

Windsor Edgy Essential Platform Lug Boots in Black

$38.90

(4)

An absolute edgy essential, these faux leather boots elevate your outfit with a platform lug sole and under-the-knee length shaft, perfect for styling with jeans or a skort! Fit & FeaturesRound toe, Platform lug sole, Inner zipper closure, Under-the-knee length shaft, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Edgy Essential Platform Lug Boots in Black | Size: 7.5 | Leather

Windsor Tough Love Platform Block Heel Booties in Black

$40.90

(3)

Walk tall and with edgy confidence in these faux leather booties, and elevate your outfit! They feature a platform sole for stylish height and a stacked block heel. Fit & Features3.5" Stacked block heel, Square toe, Inner zipper closure, Platform sole, Luxe fit cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Tough Love Platform Block Heel Booties in Black | Size: 7 | Leather

Windsor Fringe Worthy Cowboy Knee High Boots in Brown

$52.90

(3)

Cue the country playlist—these boots were made for dancing, strutting, and stealing the spotlight. The swishy fringe and sleek western shape make every step feel like a stage walk. Fit & Features3.5” heel height, 8” leg opening, 12.5” shaft height, Pointed toe, Inner zipper closure, Fringe trim detailing, Knee-high silhouette, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fringe Worthy Cowboy Knee High Boots in Brown | Size: 8.5 | Faux Suede

Sleek Stance Faux Leather Stiletto Boots in Brown

$46.90

(3)

Cold-weather dressing just got elevated. These faux leather boots bring timeless polish with a pointed toe and sleek under-the-knee cut, with a stiletto heel that pairs effortlessly with fall layers. Fit & Features3” stiletto heel, 7.5” leg opening, 15” shaft, Pointed-toe, Side zipper closure, Under-the-knee length, Sleek faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Stance Faux Leather Stiletto Boots in Brown | Size: 7

Fall For Me Wide Calf Knee-High Boots in Brown

$49.90

(3)

Seasonal staple unlocked—these faux suede boots pair effortlessly with oversized knits, flowy dresses, or denim for all your autumn to winter plans! Fit & Features3.5" Block heel, 9" leg opening, 12" shaft height, Almond toe, Knee-high shaft silhouette, Wide calf design, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fall For Me Wide Calf Knee-High Boots in Brown | Size: 10 | Faux Suede

Fall Cowboy Boots

When the air turns crisp and the leaves start to crunch under your boots, there’s just something magnetic about stepping out in a pair of fall cowboy boots. These aren’t just shoes—they’re a whole vibe, ready to take on pumpkin patch adventures, rooftop concerts, or spontaneous road trips with your besties. Whether you’re a city girl who loves to add a little Western edge to her look or you’re living out your countryside daydreams, fall cowgirl boots are the ultimate statement piece. They’re the kind of boots you throw on when you want to feel unstoppable, whether you’re pairing them with a flowy dress for that boho-meets-bad-girl energy or rocking them with distressed denim and a graphic tee for a look that says “I woke up like this.” For the Windsor girl, boots are more than just an accessory—they’re the exclamation point at the end of her outfit, the secret ingredient that turns a basic look into a full-on main character moment.

Windsor cowboy boots are built to keep up with your wildest plans and boldest moods. They’re the perfect pick for anyone who loves to mix a little Southern sass into their everyday style or wants to channel that fearless, festival-ready attitude all year round. Gifting a pair of Windsor cowgirl boots? You’re basically giving someone a ticket to their own personal hoedown—ideal for birthdays, holidays, or just because your bestie deserves to feel like a rockstar. And let’s be real: there’s no better way to celebrate a new season of adventures than with a killer pair of boots that are as ready to dance as you are. Whether you’re shopping for yourself or playing fairy godmother for your squad, boots like these have a way of turning “just another day” into a memory worth making. Picture this: golden hour, your favorite playlist bumping, and you strutting down Main Street with your crew—all eyes on your windsor cowgirl outfits, every step serving attitude and confidence.

Choosing the right pair is all about finding your perfect match—think about the heel height that makes you feel like you can conquer the world, the details that speak to your style (hello, embroidery and metallic finishes), and the fit that feels just right from the first step. Windsor cowgirl boots are designed for comfort and durability, so you can slay from brunch to bonfire without missing a beat. Whether you’re a boot newbie or a seasoned collector, you’ll find options that fit your personality—classic silhouettes for the understated queen, bold colors and patterns for the trendsetter, and everything in between. And if you’re looking to level up your boot game even more, check out our curated collection of Chic Cowboy Boots for inspo that’ll have you dreaming up outfits for every adventure on your calendar. No matter how you style them, your boots are your ride-or-die, ready to hype you up and carry you through every unforgettable moment.

Reset Your Password

Email Sent

Order Status

Fall Cowboy Boots

Home Fall Cowboy Boots

Now Trending

Fall Cowboy Boots

Related Collections