Pointed Toe Stiletto Booties

Pointed Toe Stiletto Booties are your secret weapon for turning every sidewalk into a runway moment. These sleek, confidence-boosting kicks add just the right amount of edge to any outfit—whether you’re owning the dance floor or strutting into brunch like you own the place. Slip into your boldest self and let those Pointed Toe Stiletto Booties do all the talking—they’re here to make sure you never blend in, babe.

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Major Strut Faux Leather Knee-High Stiletto Boots in Black

$48.90

A sleek black patent faux leather knee-high boot featuring a pointed toe and 3" stiletto heel.

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.

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Ride or Shine Studded Cowboy Boots in Wine

$52.90

A pair of wine faux leather cowboy boots featuring studded details, Western embroidery, and a pointed toe.

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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

Pointed Toe Stiletto Booties

Pointed toe stiletto booties are the kind of shoe that instantly changes the tone of your whole look—think of them as the exclamation point at the end of your outfit. They’re the secret weapon you reach for when you want to turn denim and a sweater into something photo-worthy, or when you need to add a little edge to a floaty dress on a chilly night out. December is prime time for pointy stiletto boots: they’re sleek enough to slip under wide-leg trousers for the office holiday party, but bold enough to hold their own with a mini skirt and tights for your friend’s birthday dinner. The sharp silhouette of a pointed toe stiletto boot hints at confidence and a bit of mischief, perfect for those moments when you want to stride in and own the room—whether that’s a crowded bar or just the living room at a family get-together. If you’re shopping for yourself, it’s about finding that perfect pair that feels like it was made for your closet, but pointed toe stiletto boots also make a standout gift for the style-obsessed friend or sibling who’s always on the hunt for something that feels a little extra.

There’s a reason pointed toe stiletto boots have become a cold-weather staple—they’re as versatile as they are striking. The elongated toe and slim heel create a leg-lengthening effect that works with everything from skinny jeans to midi skirts, and they’re surprisingly easy to dress up or down. Think morning errands in an oversized blazer and straight-leg denim, or a last-minute date night where you need to pull together something that feels intentional but not overdone. The right pointed toe stiletto boot can handle it all. When you’re shopping, pay attention to the heel height and boot shaft—ankle-high pointed toe stiletto booties are perfect for everyday wear, while knee-high versions bring maximum drama for special occasions. Material matters, too: classic faux leather brings polish, while suede adds a touch of softness (and looks especially chic peeking out from under a long coat). If you’re gifting, consider the recipient’s style—do they live for bold statement pieces, or do they prefer something sleek and understated? Either way, pointed stiletto boots are a safe bet for anyone who loves to experiment with their look but still wants a piece that will go the distance season after season.

Practicality meets personality in every pair, and that’s what makes pointed toe stiletto boots such a no-brainer for winter wardrobes. They’re built for those back-to-back plans that December always brings: brunches, gift exchanges, impromptu nights out, and everything in between. And because they’re such an instant style upgrade, you’ll find yourself reaching for them even on days when you’re just running errands but want to feel a little more put-together. If you’re looking to expand your collection or searching for the pair that finally checks all your boxes, explore our curated selection of High Heel Pointed Toe Booties to find your new go-to. Whether you’re shopping for yourself or someone you want to spoil, these boots are a gift that keeps on giving—season after season, outfit after outfit.

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