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!

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Windsor Ride or Shine Studded Cowboy Boots in Wine

$52.90

A wine faux leather cowboy boot featuring studded embellishments, Western embroidery, and a sleek pointed toe.

Dust to Dawn Cowboy Boots in Brown

$54.90

A pair of brown faux leather cowboy boots with western stitch detailing and a sleek pointed toe.

Fringe Flirt Studded Cowboy Boots in Black

$46.90

A black faux suede cowboy boot featuring studded star accents, playful fringe, and a stacked block heel.

Windsor Glam Strut Rhinestone Cowboy Boots in Black

$54.90

A pair of black faux suede cowboy boots adorned with all-over rhinestone geometric embellishments.

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.

Windsor Fall For Me Wide Calf Knee-High Boots in Camel

$49.90

A pair of camel faux suede knee-high boots featuring a wide calf design and block heel.

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Steppin Up Block Heel Knee High Boots in Wine

$48.90

(25)

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, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Steppin Up Block Heel Knee High Boots in Wine | Size: 8.5 | Leather

Totally Edgy Buckled Square Toe Boots in Black

$45.90

(16)

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 Ride or Shine Studded Cowboy Boots in White

$52.90

(16)

Western, but make it glam. These faux leather cowboy boots mix classic embroidery with studded detailing and a sleek pointed toe—perfect for bachelorettes, country concerts, or costume parties. Fit & Features3.5” stacked block heel, 7.5” leg opening, 12.5” shaft, Pointed toe, side zipper closure, Studded and grommet embellishments, Western-inspired embroidery, Under-the-knee length, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ride or Shine Studded Cowboy Boots in White | Size: 9 | Leather

Sleek Stance Faux Leather Stiletto Boots in Black

$46.90

(12)

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 Black | Size: 7.5

Retro Rise Knee High Platform Boots in Brown

$48.90

(11)

A little vintage, a little modern—these knee-high boots are the ultimate outfit maker. With a smooth faux leather finish, a sturdy block heel, and a platform sole perfect for elevating any outfit. Fit & FeaturesBlock heel, Square toe, Side zipper closure, Knee-high shaft, Side zipper closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Retro Rise Knee High Platform Boots in Brown | Size: 8.5 | Leather

Windsor Cuffed Up Faux Fur Booties in Brown

$42.90

(10)

Your fall-to-winter uniform starts here. These faux fur booties keep things snug and stylish with a soft faux fur lining and a wear-everywhere flat sole. Perfect for morning coffee runs, lazy Sundays, or that “I just look effortlessly cute” vibe. Fit & Features7” leg opening, 8” shaft height, Round toe, Above-the-ankle length, Allover faux fur material, Soft fuzzy faux fur lining, Flat sole, traction bottom, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cuffed Up Faux Fur Booties in Brown | Size: 11

Windsor Major Strut Faux Leather Knee-High Stiletto Boots in Brown

$48.90

(8)

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 Brown | Size: 5.5

Windsor Drama Queen Faux Fur Boots in Ivory

$42.90

(6)

Go big, go fuzzy, go bold—these faux fur boots bring all the drama your outfit’s been waiting for. Perfect for stepping out, staying cozy, or just making every entrance feel like a moment. Fit & FeaturesPlush faux fur fabrication, Below-the-knee length, Round toe, Flat insole, Slip-on design, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Drama Queen Faux Fur Boots in Ivory | Size: 9

Windsor Point Taken Lace-Up Stiletto Boots in Brown

$58.90

(5)

Equal parts bold and refined. These foldover stiletto boots serve a major edge with a pointed toe, sleek faux leather finish, and lace-up back detail that ties the look together—literally. Perfect for taking your outfit from casual to captivating in one step. Fit & Features4” Stiletto heel, 7" leg opening, 16" shaft height, Pointed-toe, Foldover shaft with lace-up placket, Inner side zipper closure, Sleek faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Point Taken Lace-Up Stiletto Boots in Brown | Size: 8 | Leather

Windsor Tough Love Platform Block Heel Booties in Black

$40.90

(5)

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: 8.5 | Leather

Fall Cowboy Boots

When the air gets crisp and the leaves start crunching underfoot, there’s something about slipping into a pair of cowboy boots that just feels right—like you’re channeling your own main character energy, minus the theatrics. Fall cowboy boots aren’t just a trend; they’re a mood, a mindset, and honestly, a wardrobe essential for anyone who wants to walk out the door feeling pulled together with zero effort. Whether you’re headed to a city brunch, a concert, or just running errands with a PSL in hand, these boots bring a little western flair to any outfit without looking like you’re headed to a costume party. The beauty of Windsor cowboy boots is in their versatility: one day you’re pairing them with a floral midi dress and a chunky knit for that perfect blend of feminine-meets-rugged, and the next you’re tucking your favorite jeans into them for a classic, timeless look that reads equal parts cool and comfortable. And for the record, cowboy boots aren’t just for rodeos or festivals (though they absolutely shine on the dance floor)—they’re the secret weapon for making even the most basic outfit feel intentional and photo-ready.

If you’re shopping for yourself or scouting out a gift for the friend who’s always two steps ahead on trends, cowboy boots tick all the right boxes. They’re practical enough to handle unpredictable fall weather, but stylish enough to turn heads at just about any social event—think fairs, outdoor markets, or even a spontaneous road trip. The best part? They’re not a one-season wonder. With the right care, a great pair of boots will carry you from autumn leaves straight through winter chill and beyond. This season, you’ll spot everything from classic western silhouettes to bold animal prints and fashion-forward details like metallic finishes or subtle embroidery—each pair with its own personality, ready to match yours. If you gravitate toward neutrals or love a statement piece, there’s a cowboy boot out there with your name on it. And don’t underestimate the power of comfort: modern styles are designed for real life, so you can actually wear them all day (and night) without that “fashion sacrifice” regret. When you’re curating your closet, think about what you’ll reach for on those “I have nothing to wear” mornings—cowboy boots are the solve, every time.

Shopping for fall cowboy boots should feel as exciting as the first chilly day that calls for your favorite sweater. Look for details that speak to your vibe, whether that’s a sleek pointed toe, a stacked heel for a little extra height, or a pop of texture like faux snakeskin or embossed leather. If you’re gifting, consider sizing up for thicker socks or picking a neutral shade that goes with everything—trust, they’ll thank you later. And if you’re ready to level up your boot game, explore our curated selection of Chic Cowboy Boots for styles that blend trend-driven design with everyday wearability. No matter how you style them—dressed up, dressed down, or somewhere in between—cowboy boots are the ultimate fall staple that lets you show up exactly as you want to be seen.

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