Square Toe Chunky Boots

Square Toe Chunky Boots are the statement-makers your closet’s been craving. Equal parts edgy and effortless, these boots instantly upgrade anything from your lived-in denim to your favorite mini dress. Whether you’re channeling throwback cool or just need a little boost for your everyday look, Square Toe Chunky Boots bring that perfect mix of attitude and versatility. Consider them your shortcut to turning every sidewalk into a runway—no outfit anxiety required.

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Totally Edgy Buckled Square Toe Boots in Brown

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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.

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Heavy Duty Cool Lug Boots in Black

$50.90

A pair of black faux leather boots featuring a chunky lug sole, square toe, and under-the-knee cut.

Sleek Confidence Over-The-Knee Boots in Black

$54.90

A striking black over-the-knee boot crafted from stretch knit and smooth faux leather with a block heel.

Best Seller

Statement Stomp Chunky Boots in Black

$44.90

A sleek black faux leather ankle boot with a chunky block heel, platform sole, and side zipper closure.

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Windsor Steppin Up Block Heel Knee High Boots in Wine

$48.90

(24)

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

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

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: 5.5 | Leather

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 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

Drama Queen Faux Fur Boots in Ivory

$42.90

(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

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: 5.5 | Leather

Windsor Dust to Dawn Cowboy Boots in Black

$54.90

(3)

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

Windsor 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: 7 | Faux Suede

Windsor Fray All Day Denim Booties in Black Denim

$40.90

(2)

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

Square Toe Chunky Boots

Square toe chunky boots are more than just a passing trend—they’re the ultimate cold-weather confidence boost, designed for the kind of season that calls for both style and stamina. Whether you’re navigating city sidewalks dusted with frost or making a statement at your annual friendsmas dinner, these boots deliver that rare combination of comfort and edge. There’s something about the squared-off toe—sleek, structured, a little bit unexpected—that instantly sharpens up any look, from oversized knits and mini skirts to tailored trousers and longline coats. And let’s not ignore the chunky heel: it’s the unsung hero that lets you clock in a full day (or night) without the “my feet might actually fall off” regret. The silhouette is modern but totally wearable, built for the girl who wants to look put-together without sacrificing her ability to sprint for the last train or dance until closing. If you’re shopping for yourself, think of these boots as an instant outfit elevator—one piece that can anchor your closet through every holiday gathering, last-minute coffee date, or spontaneous winter adventure. They’re also a foolproof gift for your most stylish friend, the one who’s always ahead of the curve but never too precious about her footwear. She’ll love how easily they transition from day to night, work to weekend, and everything in between.

When it comes to choosing the right pair, it’s all about balancing your personal style with practical details. Pay attention to the shaft height—ankle boots are endlessly versatile, perfect for pairing with cropped jeans or tights and minis, while mid-calf and knee-high versions bring a little more drama and warmth. Material matters, too: classic faux leather has that sleek, city-girl vibe, while suede or textured finishes feel softer and a touch more bohemian. If you’re someone who loves a little extra height but hates teetering, the chunky heel is your friend—steady, supportive, and surprisingly easy to walk in, even if you’re juggling shopping bags or weaving through a crowded holiday market. And let’s be real, winter weather isn’t always kind to your footwear, so look for features like sturdy soles and easy-to-clean uppers to keep your boots looking fresh all season long. Square toe chunky boots are made for mixing and matching, so don’t be afraid to experiment—layer them under wide-leg pants for a subtle peek of the squared toe, or let them take center stage with a bodycon dress and statement coat. If you’re craving even more ways to work this silhouette into your rotation, explore the full range of Square Toe Block Heel Boots for additional inspo and options that suit every mood.

Gifting these boots is a move that says, “I know your style, and I know you need something that works as hard as you do.” They’re perfect for the friend who’s always on the go, the sister who’s building her winter wardrobe, or even the mom who deserves a little everyday luxury. There’s a certain satisfaction in unboxing a pair that feels both on-trend and timeless—something she’ll reach for again and again, no matter what’s on her calendar. And for those moments when you’re standing in front of your closet, convinced you have nothing to wear, square toe chunky boots are the answer that pulls everything together. They add polish to casual fits, edge to feminine pieces, and a little bit of attitude to the basics you already own. With their bold lines and walkable heels, they’re the kind of boots that turn errands into events and everyday routines into runway moments. This season, let your boots do the talking—and the walking.

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