Chunky Heel Winter Boots
Chunky Heel Winter Boots are the secret weapon for cold-weather style that doesn’t compromise on confidence. Think bold, walkable heights that instantly elevate your outfit (and your mood), all while keeping things cozy enough for every winter plan on your calendar. Whether you’re pairing them with a sweater dress for brunch or denim and an oversized coat for city strolls, these boots bring just the right amount of edge to any look. Ready to step up your winter wardrobe? Let’s make every sidewalk your runway.
$48.90
A sleek black faux leather knee-high boot featuring a comfy block heel and almond toe design.
$48.90
A pair of brown faux leather knee-high boots featuring a block heel, platform sole, and side zipper.
$49.90
A pair of camel faux suede knee-high boots featuring a wide calf design and block heel.
$45.90
A pair of black faux leather calf-length boots featuring buckled side accents and a square toe design.
$54.90
A pair of brown faux leather cowboy boots with western stitching, pointed toes, and stacked block heels.
$46.90
A black faux suede cowboy boot featuring studded star accents, flirty fringe, and a stacked block heel.
$40.90
A pair of black distressed denim booties featuring a slouchy fit, raw edge finish, and block heel.
$48.90
A sleek black faux leather ankle bootie featuring a chunky platform sole and elastic gore design.
$11.97 $36.90 68% off
A pair of pink western boots featuring classic stitching, a pointed toe, and a stacked block heel.
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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, 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: 6 | 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
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: 5.5 | Leather
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
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
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: 11
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: 5.5 | Leather
Classic western, modern edge. These cowboy boots feature stitched detailing and a sleek pointed toe that brings a bold finish to denim, minis, or your favorite fall layers. Fit & FeaturesStacked block heel, Pointed-toe, Western-inspired stitch detailing, Pull-on design with pull tabs, Under-the-knee length, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dust to Dawn Cowboy Boots in Black | Size: 7 | Leather
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: 7 | Faux Suede
Jeans for your feet? Basically. These distressed denim booties bring all the grunge-girl energy with a slouchy fit and raw edge finish. Perfect for concerts or themed parties! Fit & Features3” block heel, 6.5” leg opening, 8” shaft height, Pointed toe, Foldover denim with distressed accents, Hidden side zipper closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fray All Day Denim Booties in Black Denim | Size: 8