High Heel Pointed Toe Boots

High heel pointed toe boots are your secret weapon for turning every sidewalk into a runway. Whether you’re strutting into brunch or owning the dance floor, these boots bring instant main character energy to any outfit. Ready to level up your style game? Slip into a pair of high heel pointed toe boots and watch your confidence soar—because you deserve to stand tall and stand out, babe.

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Bedazzled Allure Rhinestone Stiletto Booties in Silver

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Bedazzled Allure Rhinestone Stiletto Booties in Silver

$11.97 $52.90 77% off

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

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.

Chic Buckle Strap Sling-Back Stiletto Pumps in White

$32.90

A sleek white patent faux leather stiletto pump with criss-cross buckle straps and slingback design.

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Steppin Up Block Heel Knee High Boots in Wine

$48.90

(25)

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: 8.5 | 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

Windsor 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: 9 | Leather

Sleek Stance Faux Leather Stiletto Boots in Black

$46.90

(12)

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: 7.5

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 Cuffed Up Faux Fur Booties in Brown

$42.90

(10)

Your fall-to-winter uniform starts here. These faux fur booties keep things snug and stylish with a soft faux fur lining and a wear-everywhere flat sole. Perfect for morning coffee runs, lazy Sundays, or that “I just look effortlessly cute” vibe. Fit & Features7” leg opening, 8” shaft height, Round toe, Above-the-ankle length, Allover faux fur material, Soft fuzzy faux fur lining, Flat sole, traction bottom, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cuffed Up Faux Fur Booties in Brown | Size: 11

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

Windsor Drama Queen Faux Fur Boots in Ivory

$42.90

(6)

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: 9

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: 8 | Leather

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: 8.5 | Leather

High Heel Pointed Toe Boots

There’s something undeniably powerful about slipping into a pair of high heel pointed toe boots—the kind of power that transforms a routine Monday or a last-minute dinner invite into a full-blown style moment. If you know, you know: the sharp silhouette, the leg-lengthening magic, the way a pointed toe commands attention without ever trying too hard. January’s chill might have you reaching for a cozy coat, but underneath, it’s these boots that do the talking—peeking out from under tailored trousers, elevating a sweater dress, or adding edge to your favorite jeans. They’re the ultimate confidence boost for anyone who wants to feel a little more put-together, even when the weather (or the calendar) says otherwise. Maybe you’re a serial outfit repeater looking for that one accessory to switch up your winter rotation, or maybe you’re the friend who always gets asked for style advice—either way, pointed toe boots are your not-so-secret weapon. They’re also the kind of gift that feels thoughtful and personal, whether you’re shopping for a sister who lives in her black skinnies or a best friend who’s always on the hunt for her next statement piece.

When it comes to choosing the perfect pair, the details matter—think about heel height, material, and how much drama you want to bring. Pointy heel boots with a sleek stiletto are all about after-dark energy, ready for rooftop cocktails or a spontaneous night out, while a chunkier heel makes even the busiest days feel a little less ordinary (and a lot more comfortable). Don’t underestimate the versatility of neutral shades—classic black, rich brown, or creamy taupe—but don’t be afraid to lean into bold colors or textures when you want your boots to do the talking. Windsor booties and windsor heel boots are designed for those moments when you want to look like you tried (even if you got dressed in five minutes flat). And if you’re navigating icy sidewalks or marathon shopping days, a pointed toe doesn’t have to mean sacrificing comfort; just look for styles with a supportive insole or a block heel for extra stability. For even more options that blend sharp style with all-day wearability, check out our Pointed Toe Block Heel Boots collection—because sometimes, you really can have it all.

High heel pointed toe boots aren’t just a winter staple—they’re a year-round style solution for anyone who loves a little extra polish without the fuss. Picture yourself heading from the office to dinner, swapping sneakers for windsor boots that instantly pull your look together. Or maybe you’re styling a mini skirt in early spring, letting your boots do the heavy lifting when the weather can’t make up its mind. The beauty of pointed toe boots is how easily they transition: dress them up with a satin slip for date night, or keep it casual with oversized knits and denim for a weekend coffee run. They’re the kind of piece that adapts to your mood, your schedule, and your ever-changing aesthetic. Whether you’re gifting them (and earning serious best-dressed points) or treating yourself to a little mid-season refresh, these boots are an invitation to step up and stand out—no matter where you’re headed or how you like to wear them. With the right pair, every sidewalk becomes a runway, and every outfit feels a little more intentional.

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High Heel Pointed Toe Boots

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