Square Toe Stilettos

Step into the spotlight with square toe stilettos that are here to elevate your style game to new heights! These chic and edgy heels are the perfect blend of modern sophistication and timeless allure, ready to take you from day to night with ease. Whether you're strutting through the office or dancing under the stars, these statement-makers promise to keep your fashion-forward foot forward. Pair them with your favorite Windsor outfit, and let your inner diva shine bright. Because let's face it, darling—you're not just walking; you're making an entrance!

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Love Story Era Heart Rhinestone Thong Heels in Black

$28.90

A chic black faux leather stiletto heel featuring a rhinestone heart thong strap and square toe.

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Style Pop Square Toe Nubuck Stiletto Heels in Black

$28.90

A sleek black nubuck stiletto heel with a square toe and adjustable thin straps.

Classy Luxe Rhinestone Strappy Stiletto Mules Shoes in Gold

$32.90

A glamorous gold mule with rhinestone straps and a 3.5" stiletto heel for elegant occasions.

Fab Icon Butterfly Rhinestone Stiletto Heels in Silver

$32.90

A metallic silver stiletto heel featuring rhinestone butterfly accents and sparkling embellished straps.

So Much Personality Strappy Block Heels in Red

$28.90

A vibrant red strappy block heel crafted from faux leather with a cushioned insole for comfort.

Windsor Glam Bloom Flower Strap Kitten Heels in White

$38.90

A white satin kitten heel featuring chiffon beaded flower accents, open square toe, and adjustable straps.

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Smooth And Sleek Block Heels in Black

$26.90

(74)

Step out in style in these chic low block heels! Create the perfect stylish graduation outfit or gorgeous prom look in these comfortable heels. This open-toe design features a stylish ankle strap detail with a zipper-closed back on a trendy block heel. The lower heel silhouette creates a supportive and comfy fit, perfect to wear with a semi-formal gown or dressy pant outfit. Fit & FeaturesZippered closed back , Ankle strap strap, Open almond toe , Single strap over the toe, Low block heel , Faux leather and nubuck material , Luxe fit cushioned insole, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Smooth And Sleek Block Heels in Black | Size: 9 | Leather/Nubuck

Flirt Mode Activated Strappy Block Heels in White

$30.90

(8)

These heels understood the assignment—flirty, chic, and ready to turn heads. With strappy detailing and a comfy block heel, they’re made for rooftop hangs, brunch dates, and everything in between. Fit & FeaturesBlock heel, Open square-shaped toe, Asymmetric strappy design, Adjustable ankle strap with buckle detail, Faux leather material, padded insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt Mode Activated Strappy Block Heels in White | Size: 10 | Leather

Endless Glam Rhinestone Bow Block Heels in Silver

$36.90

(7)

Every step will look so glam in these rhinestone block heels featuring a statement bow and a luxe fit insole for comfort. Pair with a clutch. Fit & Features3" Block heel, Almond toe, Adjustable ankle strap, buckle closure, Luxe fit breathable cushioned insole, Rhinestones, Bow accent, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Endless Glam Rhinestone Bow Block Heels in Silver | Size: 8.5

Windsor So Much Personality Strappy Block Heels in Red

$28.90

(4)

Give your outfits some cuteness in these strappy block heels, perfect for pairing with your favorite bottoms or dresses! Fit & Features3" Round block heel, Square toe, Strappy design, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Much Personality Strappy Block Heels in Red | Size: 5.5 | Leather

Windsor Chic And Polished Pearl Satin Block Heels in White

$35.90

(4)

The kind of heels that take you from “just cute” to “can’t look away” in one step. With faux pearl embellished straps and a sleek block heel, they’re a dream for bridal celebrations and birthday soirees! Fit & Features3" Block heel, Square toe, Faux pearl embellished straps, Adjustable ankle strap with buckle closure, Satin material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic And Polished Pearl Satin Block Heels in White | Size: 8

Feeling Chic Thong Square Toe Heels in Wine

$26.90

(4)

From daytime outings to nights out, these thong heels are perfect for dressing up any look for every occasion! Fit & Features2" short kitten heel, Square toe, Thin thong toe strap, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Feeling Chic Thong Square Toe Heels in Wine | Size: 7 | Leather

Starlight Steps Strappy Block Heels in Gold

$34.90

(4)

Shine with every step—these strappy block heels bring the glam with glittery straps and a sturdy heel that’s perfect for dancing all night. Chic, comfy, and totally party-approved. Fit & FeaturesBlock heel, Almond toe, Rhinestone-embellished straps, Closed ankle, back zipper closure, Luxe fit cushioned insole, Glitter material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Starlight Steps Strappy Block Heels in Gold | Size: 6.5 | Rhinestone

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Windsor Sweet Attraction Toe Ring Strappy Block Heels in White

$9.97 $26.90
63% off

(3)

A pair of strappy block heels with a trendy toe ring trim that gives every outfit a sweet look! Fit & Features2.5" Block heel, Square toe, Strappy design, Toe ring trim, Luxe fit cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Attraction Toe Ring Strappy Block Heels in White | Size: 10 | Leather

Ultra Luxe Rhinestone Short Block Heels in Pearl

$32.90

(3)

Ultra-luxe rhinestones embellish the asymmetrical toe straps on these chic short block heels perfect for brides, birthday babes, or dressy events! Pair with a clutch. Fit & Features2" short block heel, Square toe, Rhinestone embellished asymmetrical toe straps, Closed ankle with adjustable strap, buckle closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ultra Luxe Rhinestone Short Block Heels in Pearl | Size: 8 | Leather/Rhinestone

Chic Crush Strappy Block Heels in Wine

$36.90

(3)

Bold, sleek, and made to steal the spotlight—these strappy heels bring the drama with a deep red shine and chic block heel. Perfect for everything from cocktail nights to holiday parties. Fit & FeaturesBlock heel, Square toe, Asymmetrical strappy design, Luxe fit cushioned insole, Adjustable ankle strap with buckle closure, Patent faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Crush Strappy Block Heels in Wine | Size: 8 | Leather

Square Toe Stilettos

There’s something about square toe stiletto heels that instantly elevates your outfit—and your confidence. Maybe it’s the way that sharp, geometric edge peeks out from beneath a tailored trouser or the way it anchors a floaty dress with a bold, modern finish. Square toe stilettos are the shoes you reach for when you want to look polished but not predictable, sophisticated but with a little edge. They’ve got that perfect blend of architectural cool and classic femininity, making them a go-to for everything from spontaneous dinner dates to those “I need to look like I have my life together” meetings. If you’re someone who loves to mix trends with timelessness, these are the heels that let you do both—effortlessly. And if you’re gifting, trust that square toe stilettos are a crowd-pleaser for the fashion-forward friend, the sister who’s always experimenting, or even the mom who appreciates a fresh twist on a classic silhouette. They’re versatile enough to work year-round, but there’s something about slipping into a pair in January, when the world feels fresh and full of possibility, that just feels right—especially when paired with a sleek coat or a cozy knit dress.

When you’re shopping for square toe stiletto heels, it’s all about finding that sweet spot between style and comfort. Look for cushioned insoles and sturdy heel construction if you’re planning to wear them all night (or all day—no judgment). The square toe gives your toes a little more room to breathe than a pointy toe, making them a smart pick for anyone who’s tired of sacrificing comfort for style. And let’s talk color: while black and metallics are always safe bets, don’t sleep on the understated power of windsor plain nude high heels open toe square styles. Nude tones have a way of elongating your legs and going with literally everything in your closet, from winter whites to moody jewel tones. They’re the shoes you’ll forget you’re wearing—until someone stops you to ask where you got them. Whether you’re styling them with cropped jeans and a blazer for a coffee run or going full glam with a mini dress and statement earrings, these heels adapt to your vibe and your plans. They’re also a secret weapon for wedding season, formal events, or any moment when you want to look put-together with minimal effort. The best part? Square toe stilettos aren’t just a fleeting trend—they’re a modern classic that keeps your look fresh without feeling overdone.

For anyone building a shoe wardrobe that can handle last-minute invites, unpredictable weather, and every mood swing in between, square toe stilettos are a must. They’re the finishing touch that makes your outfit feel intentional, even if you got dressed in five minutes. And if you’re still exploring different shapes and heel heights, check out our full collection of Square Toe Heels for even more options to fit your style (and your calendar). Whether you’re shopping for yourself or searching for a gift that feels personal and on-point, these heels deliver on style, comfort, and versatility—because your shoes should work as hard as you do.

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