Casual Booties
Step into your power with our collection of casual booties, designed for the Windsor girl who knows that life is her runway. Whether you're strutting down city streets or dancing under the stars, these booties are your go-to for turning heads and breaking hearts. Effortlessly chic and endlessly versatile, they're the perfect match for every outfit in your closet. So go ahead, slip into something that makes you feel unstoppable, because with these booties, every step is a statement.
Home Casual Booties
- Recommended
- Most Popular
- Price - Low to High
- Price - High to Low
$40.90
A chic black ankle bootie with studded accents, criss-cross straps, and a peep toe design.
$50.90
A sleek pair of ivory faux leather under-the-knee boots with a square toe and thin block heel.
$52.90
A dazzling pair of silver rhinestone booties featuring a pointed toe and sleek stiletto heel.

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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
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
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
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
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
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: 6
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
The kind of boot that owns every room. These patent stiletto knee boots serve glossy drama with a sculpted pointed toe and sleek silhouette—made for statement looks and confident strides. Fit & Features 3.5” stiletto heel, 7.5” leg opening, 15” shaft height, Pointed-toe, Inner zipper closure, Knee-length shaft, Glossy patent faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Gloss Effect Patent Stiletto Boots in Wine | Size: 6 | Leather
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
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: 6 | Faux Suede
Casual Booties
When it comes to building a wardrobe that works as hard as you do, casual booties are the undisputed MVPs. They’re the shoes you reach for when you want to look put-together but not like you tried too hard—the perfect in-between for running errands, catching up with friends, or making a coffee run feel like a mini fashion moment. As the days get shorter and the air picks up that unmistakable November crispness, there’s something about slipping into a pair of windsor booties that just feels right. They’re the answer to unpredictable weather and even more unpredictable plans. Think low heels for all-day comfort, cushioned soles that keep you moving from brunch to the bookstore, and easy-on designs (hello, Chelsea booties) that mean you’re out the door in seconds, not minutes. Neutrals like taupe, tan, and classic black are your best friends here—versatile enough to go with everything from denim to sweater dresses, and durable enough to handle whatever the day throws your way. Leather and suede options add that touch of texture and warmth that just feels right for fall, while still being breathable enough for those days when winter hasn’t quite settled in.
Gifting casual booties is a little like giving someone a style superpower. They’re thoughtful without being over-the-top, practical without ever feeling boring. Whether you’re shopping for your sister who’s always on the go, your roommate who’s mastered the art of the last-minute outfit change, or treating yourself to a seasonal refresh, these are the pairs that get real mileage. Picture them as the finishing touch to a cozy oversized sweater and leggings, or as the grounding element in a flowy midi skirt and cropped knit. They’re the shoes that can take you from a laid-back office vibe to a spontaneous dinner invite without missing a beat. And if you’re looking to expand your collection, don’t overlook the power of a bold, classic hue—our Black Booties edit is packed with options that go with literally everything. With the right pair, you’re not just ready for the season—you’re ready for anything your calendar (or your mood) throws at you. Whether you’re dressing up or down, casual booties are the style solution that feels as effortless as it looks, every single time.









