Comfortable Pointed Toe Heels
Ready to strut your stuff without sacrificing comfort? Comfortable pointed toe heels are here to level up your look and keep you feeling unstoppable from day to night. Whether you're making power moves at work or dancing until the lights come on, these heels bring all the style with none of the drama. Slip into a pair that’s as fierce as you are—because who says you can’t have it all?
$30.90
An elegant ivory lace stiletto with a slingback strap and cushioned insole for ultimate comfort.
$30.90
A chic ivory pump with a 4" stiletto heel and stylish inner cutout design.
$30.90
A chic black nubuck slingback pump with a trendy buckle strap and sleek pointed toe.
$30.90
A sleek black faux leather stiletto pump featuring a pointed toe and trendy circular buckle accents.
$32.90
A sleek white patent faux leather stiletto pump with criss-cross buckle straps and slingback design.
$28.90
A sleek blue patent faux leather pump with a pointed toe, slingback strap, and low kitten heel.
$30.90
A wine-colored patent faux leather pump featuring a block heel, pointed toe, and chic buckle details.
$42.90
A clear PVC stiletto pump adorned with sparkling rhinestones, faux pearls, and a patent faux leather slingback.
$30.90
A sleek silver slingback kitten heel featuring a bold buckle strap and cushioned insole for comfort.
$30.90
A rhinestone-embellished camel heel featuring a pointed toe, slingback strap, and faux leather insole.
$28.90
An elegant olive green satin stiletto pump featuring a pointed toe and lace-up ankle strap.
$34.90
A chic pair of beige stiletto pumps featuring sheer mesh and faux leather with a pointed toe.
$32.90
A silver low block heel with rhinestone-studded straps and an adjustable ankle strap for comfort.
$28.90
A sleek black nubuck stiletto heel with a square toe and adjustable thin straps.
$32.90
A glamorous gold mule with rhinestone straps and a 3.5" stiletto heel for any event.
$30.90
A glossy white patent faux leather pump featuring a block heel and adjustable buckle sling-back straps.
$30.90
A chic white patent faux leather stiletto pump featuring a pointed toe and adjustable sling-back strap.
$28.90
A sleek pair of leopard print stiletto heels featuring an almond toe and adjustable buckle ankle strap.
$32.90
An ivory straw stiletto pump featuring a pointed toe, faux pearl accent, and adjustable ankle strap.
$42.90
A romantic pair of white stiletto pumps featuring sheer lace material and a classic pointed toe.
$30.90
A bold red faux leather mule featuring delicate straps, a square toe, and a comfortable kitten heel.
$32.90
A bold snake print block heel in faux leather with rhinestone chain accents and adjustable ankle strap.
$30.90
A mocha faux leather stiletto heel featuring asymmetric skinny straps, adjustable buckles, and a padded insole.
$52.90
A dazzling pair of silver rhinestone booties featuring a pointed toe and sleek stiletto heel.
$28.90
A sleek tan faux leather pump featuring a pointed toe and a 3.5-inch block heel.
$36.90
A brown faux leather stiletto heel featuring rhinestone-embellished sheer mesh straps and a pointed toe.
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Step out looking like a mythical babe in these statement stiletto heels for a truly exclusive look! These heels are designed with a sleek almond toe, sparkling rhinestone spiral strap adorned with butterfly printed organza appliques, and a sleek stiletto heel. Made from iridescent metallic material, these heels will add a touch of magic to any outfit! Complete the look with a fab skater dress for a party! Fit & Features 4.5" Stiletto heel, Almond toe, Rhinestone embellished spiral straps, Butterfly printed organza appliques, Iridescent metallic material, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Mythical Babe Butterfly Rhinestone Spiral Stiletto Heels in White | Size: 8
Step into style with these lace stiletto pumps perfect for wedding guests, brides, or any dressy occasion! They feature a closed pointed-toe, an elasticized slingback strap adorned with a side bow accent, a luxe fit cushioned insole for ultimate comfort, and a stiletto heel. Complete the look with a clutch. Fit & Features4" Stiletto Heel, Closed pointed-toe, Elasticized slingback strap, side bow accent, Luxe fit cushion insole, Lace material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Cuties Lace Slingback Stiletto Pumps in Ivory | Size: 8
Make your style pop in these heels featuring a square toe and thin straps for a sleek look finished with a stiletto heel. Perfect for elevating your everyday outfits. Fit & Features3.5" Stiletto heel, Black is nubuck, red is patent material, Square toe, Thin straps, adjustable ankle strap, buckle closure, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Style Pop Square Toe Nubuck Stiletto Heels in Black | Size: 5
Perfect your glam game with sparkly stride metallic spiral strap stiletto heels. Featuring rhinestone embellishments and a chic spiral design, these stilettos are your new go-to for dazzling nights. Fit & Features4" Stiletto heel, Metallic faux leather material, Open almond-shaped toe, Thin toe strap, thin strap across the foot, thin spiral strap design, Rhinestone embellishments, rhinestone heart accents, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sparkly Stride Metallic Spiral Strap Stiletto Heels in Silver | Size: 8 | Leather/Rhinestone
Strut with icy flair in these rhinestone kitten stiletto heels to dress up your look. Fit & FeaturesKitten stiletto heel, Square toe, Rhinestone embellished straps, Adjustable ankle strap, buckle closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Icy Rhinestone Kitten Stiletto Heels in Black | Size: 7
Sparks will fly with every step you take in these glitter mesh stiletto heels perfect for dressed up date nights or formal soirees! Fit & Features3.5" Stiletto heel, Square toe, Glitter toe strap, Adjustable ankle strap, buckle closure, Luxe fit cushioned insole, Glitter mesh material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sparks Fly Glitter Mesh Stiletto Heels in Silver | Size: 10 | Mesh Fabric
Be prepared for many compliments when you step out in these lace-up stiletto heels that add a bold touch to any look. Fit & Features4" Stiletto heel, Square toe, Thin strappy design, Lace-up ankle straps, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Major Moment Lace-Up Stiletto Heels in Pink | Size: 5.5 | Leather
Step out in glamour in these gorg metallic heels with a sleek stiletto design. Perf for parties and nights out! Fit & FeaturesStiletto heel, Faux leather material, metallic sheen, Open almond-shaped toe, wide toe strap, Thin adjustable ankle strap, buckle detail, Closed back, Cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glam Steps Metallic Stiletto Heels in Silver | Size: 6 | Leather
Tie your look together with these statement stiletto heels! Perfect for brides, graduates, birthday babes, or any occasion, these heels showcase a pretty tulle back bow and a sparkling rhinestone trim toe strap. Fit & FeaturesStiletto heel, Square toe, rhinestone-embellished toe strap, Closed ankle, back tulle bow accent, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Tied With A Bow Stiletto Heels in White | Size: 7.5 | Leather/Rhinestone
Edge up your look in these sleek stiletto heels with a trendy buckle accent perfect for dressing up jeans or a dress! Fit & Features4" Stiletto heel, Square toe, Buckle accent toe strap, Adjustable ankle strap, buckle closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Buckled Up Stiletto Heels in Black | Size: 8 | Leather
Comfortable Pointed Toe Heels
Let’s be real—finding a pair of pointed toe heels that don’t leave you limping home is basically the holy grail of shoe shopping. But you know what? Your search for comfortable pointy heels is about to get a serious upgrade. Imagine slipping into a pair that feels as good as they look, ready to take you from boardroom boss moves to late-night dance floors without a single “ouch.” These aren’t your average heels—they’re made for the girl who refuses to compromise on style or comfort, who wants to turn heads and keep the good times rolling all night long. Whether you’re heading to a big presentation, brunch with your ride-or-die crew, or a date you’ve been hyping up in your group chat, comfortable pointed toe heels are your secret weapon. They’re perfect for anyone who lives for those spontaneous plans—think last-minute invites, impromptu photo ops, and the kind of adventures you’ll be laughing about for weeks. The magic is in the details: plush insoles, flexible soles, and just the right amount of support to keep you strutting with confidence, no matter how many blocks you have to conquer.
These heels aren’t just for you, either—think of them as the ultimate gift for your bestie who’s always on the go, your sister who’s leveling up her work wardrobe, or even your mom who deserves to feel as fabulous as she looks. Gifting a pair of comfortable pointy heels is like handing someone a ticket to their next main character moment. It’s about giving the gift of confidence, of knowing she can own every room she walks into, all while feeling totally at ease. And if you’re the one treating yourself (as you should), you’ll love how these shoes blend seamlessly into every part of your life. Pair them with tailored trousers for your 9-to-5 grind, a flirty dress for dinner downtown, or even your go-to jeans and a graphic tee for that perfectly undone vibe. The pointed toe is classic and chic, elongating your silhouette and adding instant polish to any outfit, while the comfort features make them a must-have for marathon days and unforgettable nights.
When you’re picking your next pair, pay attention to those little things that make a big difference—like cushioned footbeds, adjustable straps, and materials that move with you. Look for options with a bit of give in the toe box and a heel height that matches your energy, whether you’re all about a subtle lift or you want to go full glam. The best part? You don’t have to sacrifice your feet just to look fierce. There’s a whole world of styles out there that prove you can be both unstoppable and comfortable. If you’re ready to find your new favorite heels, check out our curated collection of Comfortable Heels and get ready to strut like you mean it. No more kicking off your shoes under the table or stashing flats in your bag—these are the heels you’ll actually want to keep on, from your morning coffee run to that “just one more” round at your favorite rooftop bar.