Women's Chunky Heel Booties
Turn every sidewalk into your personal runway with Women's Chunky Heel Booties that bring the attitude and the edge. These bold beauties are made for late-night adventures, brunches that turn into shopping sprees, and anywhere you want to show up with a little extra sass. Whether you're channeling main character energy or just looking to level up your everyday vibe, Women's Chunky Heel Booties are your go-to for instant confidence and non-stop compliments. Time to step out, stand tall, and let your shoes do all the flirting.
Home Women's Chunky Heel Booties
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- Price - High to Low
$45.90
A pair of black faux leather calf-length boots featuring square toes, buckled side accents, and block heels.
$40.90
A chic black ankle bootie with studded accents, criss-cross straps, and a peep toe design.
$26.90
A pair of tan faux leather block heels featuring a trendy toe ring and strappy design.

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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
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
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-2 | Size: 8
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
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
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
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: 8.5 | Leather
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
Women's Chunky Heel Booties
Chunky heel booties are the unsung heroes of every winter wardrobe—equal parts statement-maker and everyday staple, designed for women who want a little lift without the wobble. There’s something about that sturdy, blocky heel that brings instant confidence: you can actually keep up with your group chat’s plans, whether that means dashing across icy parking lots or dancing through a holiday party without plotting your next escape to the nearest chair. The beauty of chunky heel booties is in their versatility; they’re the ultimate chameleons, ready to anchor cozy sweater dresses, add edge to tailored trousers, or give your favorite jeans a fresh, modern spin. Think of them as your go-to for those “I want to look put-together, but I also want to feel like myself” moments. The extra support from the wider heel base means you’ll stay comfortable from brunch to last call—no backup flats required. And if you’re shopping for someone else? Chunky heel booties are a foolproof gift for the friend who’s always on the move, the sister who never misses a trend drop, or the mom who deserves a little more style in her step. They’re a thoughtful upgrade for anyone who’s ready to swap out their worn-in sneakers or wants a little more polish without going full-on stiletto.
When it comes to choosing the right pair, it’s all about balancing style with practicality. Look for details that fit your vibe: sleek Chelsea silhouettes for a minimalist mood, lace-up fronts for a dash of downtown cool, or platform soles if you’re feeling bold. Material matters, too—faux suede brings a soft, luxe texture that plays well with chunky knits, while smooth faux leather is a classic for rain-or-shine reliability. And don’t sleep on color; while black and taupe are timeless, a pop of burgundy or olive can transform your entire look (and make those winter neutrals feel less predictable). If you’re styling them for everyday, try tucking skinny jeans or leggings into ankle-height booties for a streamlined finish, or pair them with midi skirts and oversized sweaters for a mix that reads both effortless and intentional. For nights out, chunky heel booties are a power move with tailored jumpsuits or bodycon dresses—just enough height to elongate your legs, but stable enough to actually enjoy yourself. If you’re already eyeing something a little sleeker or want to compare heel shapes, Windsor’s collection of Women's High Heel Booties is full of options that bring extra drama without sacrificing wearability.
Chunky heel booties have a way of making every outfit feel a bit more interesting, and every plan feel a bit more doable. They’re the shoes you reach for when you want to look like you tried (even if you just rolled out of bed), and the secret weapon for anyone who refuses to choose between comfort and style. Whether you’re gifting them or grabbing a pair for yourself, these booties are built to keep up with real life—holiday shopping sprees, spontaneous nights out, or just your daily commute in unpredictable weather. They’re not just a trend; they’re a lifestyle upgrade, ready to carry you through the season and beyond.










