Pointed Toe Booties

Step into the spotlight with pointed toe booties that are ready to strut their stuff! Whether you're heading out for a night on the town or just want to add a little sass to your everyday ensemble, these booties are your go-to for turning heads and breaking hearts. With their sleek silhouette and bold attitude, they’re designed for the Windsor girl who knows how to make an entrance and leave a lasting impression. So, slip into these beauties and let your feet do all the talking—because when it comes to style, you've got it on point!

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Windsor Up To No Good Rhinestone Fishnet Booties in White

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Windsor Up To No Good Rhinestone Fishnet Booties in White

$15.97 $42.90 63% off

A white nubuck ankle bootie featuring sheer rhinestone fishnet, pointed toe, and clear PVC trim.

Windsor Bedazzled Allure Rhinestone Stiletto Booties in Silver

$52.90

A dazzling pair of silver rhinestone booties featuring a pointed toe and sleek stiletto heel.

Windsor Daring Details Studded Ankle Booties in Black

$40.90

A black faux microsuede ankle bootie featuring criss-cross straps, metal buckles, and studded accents.

Windsor Glam Strut Rhinestone Cowboy Boots in Taupe

$54.90

A taupe faux suede cowboy boot adorned with all-over rhinestone geometric patterns and a stacked block heel.

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Totally Edgy Buckled Square Toe Boots in Black

$45.90

(12)

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

Windsor Steppin Up Block Heel Knee High Boots in Black

$48.90

(10)

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

Windsor Boot Scootin’ & Vibin’ Cowboy Boots in Camel

$52.90

(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: 8 | Faux Suede

Major Strut Faux Leather Knee-High Stiletto Boots in Black-2

$48.90

(7)

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

Sleek Stance Faux Leather Stiletto Boots in Brown

$46.90

(5)

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 Brown | Size: 7

Daring Details Studded Ankle Booties in Black

$40.90

(5)

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

Windsor Tough Love Platform Block Heel Booties in Black

$40.90

(5)

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: 9 | Leather

Windsor Gloss Effect Patent Stiletto Boots in Wine

$49.90

(4)

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: 9 | Leather

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: 5.5 | Faux Suede

Windsor Boss Moves Over-The-Knee Block Heel Boots in Black

$54.90

(3)

Power stance, but make it fashion. These sleek over-the-knee boots with a bold block heel bring instant confidence to every 'fit. Fit & Features4" Block heel, 10" leg opening, 23" shaft height, Faux leather material, Over-the-knee height, top back slit, Pointed toe, Partial inner zipper closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Boss Moves Over-The-Knee Block Heel Boots in Black | Size: 7.5 | Leather

Pointed Toe Booties

Pointed toe booties are the unsung heroes of fall wardrobes—the kind of shoe that can instantly elevate a basic jeans-and-tee combo or add a sharp finish to your favorite sweater dress. As soon as November chills start rolling in, these booties become the go-to for anyone who wants to keep their style game strong without sacrificing comfort. There’s something about that sleek, tapered toe and the just-right ankle height that feels both modern and timeless—a little bit city, a little bit country, and endlessly versatile. Whether you’re dashing out the door for coffee runs, clocking in at the office, or planning a night out with friends, pointed toe booties deliver that perfect mix of polish and edge. They’re the pair you reach for when you want to look put-together but not like you tried too hard. And let’s be honest—when holiday invites start piling up, having a reliable pair of windsor booties on standby is a game changer. They tuck seamlessly under wide-leg trousers, peek out from midi skirts, and play surprisingly well with everything from leather leggings to cozy knits.

Shopping for pointed toe booties is all about embracing your vibe and anticipating where your days (and nights) will take you. If you’re looking for something to gift, they’re a no-brainer for the fashion lover in your life—especially if she’s always on the hunt for that one piece that ties every outfit together. Think about the details that matter most: a block heel for all-day wearability, a stiletto for those dressier moments, or a western-inspired silhouette for a little extra attitude (hint: if that’s your style, check out our Pointed Toe Western Booties). Materials play a big role, too—faux suede brings a soft, luxe feel that’s perfect for autumn, while smooth faux leather adds a bit of shine and drama. Color is another way to make them your own: classic black is a no-fail staple, but don’t sleep on rich browns, taupes, or even bold statement hues that can turn a neutral outfit into a moment. And if you’re worried about comfort, look for cushioned insoles and flexible soles—you’ll thank yourself after a long day (or night) on your feet.

Pointed toe booties aren’t just about looking good—they’re about feeling ready for whatever the season throws your way. They’re for the girl who wants to walk into any room with confidence, the one who loves a little extra height without wobbling, and the friend who’s always up for a spontaneous plan. Maybe you’re styling them with slouchy socks and a plaid skirt for a bit of ‘90s nostalgia, or maybe you’re pairing them with tailored pants for a sleek, office-ready look. However you wear them, these booties are built to flex with your style, your schedule, and your mood. They’re the finishing touch that makes a last-minute outfit feel intentional, the secret weapon you’ll reach for again and again, and the kind of staple that keeps your closet rotation feeling fresh. This season, let pointed toe booties do the heavy lifting—they’re proof that you don’t have to choose between comfort, confidence, and seriously good style.

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