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?
$42.90
A clear PVC stiletto pump adorned with sparkling rhinestones, faux pearls, and a patent faux leather slingback.
$30.90
A rhinestone-embellished camel heel featuring a pointed toe, slingback strap, and faux leather insole.
$30.90
A bold red slingback kitten heel featuring a pointed toe, trendy buckle strap, and cushioned insole.
$28.90
A sleek black nubuck stiletto heel with a square toe and adjustable thin straps.
$30.90
A mocha faux leather stiletto heel featuring asymmetric skinny straps, adjustable buckles, and a padded insole.
$30.90
A glossy white patent faux leather pump featuring a block heel and adjustable buckle sling-back straps.
$9.97 $28.90 66% off
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.
$30.90
A bold red faux leather mule featuring delicate straps, a square toe, and a comfortable kitten heel.
$42.90
A romantic pair of white stiletto pumps featuring sheer lace material and a classic pointed toe.
$52.90
A dazzling pair of silver rhinestone booties featuring a pointed toe and sleek stiletto heel.
$32.90
A bold snake print block heel in faux leather with rhinestone chain accents and adjustable ankle strap.
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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: 5.5
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 Blue | Size: 6 | Leather
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
Step out boldly in these chic faux leather heels. Featuring a sleek square toe and a sleek kitten stiletto heel, these shoes blend poise with polished style, perfect for any occasion. Fit & FeaturesStiletto kitten heel, Square toe, Adjustable ankle strap, buckle closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Strides Kitten Stiletto Heels in Black | Size: 10 | Leather
The slingback stiletto heels that instantly make every outfit hotter. Sleek, minimal, and endlessly wearable, they’re the pair you’ll reach for on repeat for day or night looks. Fit & FeaturesStiletto heel, Square toe, Slingback ankle strap, cutout side design, Cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Strut Ready Sling Back Stiletto Pumps in Black | Size: 9
These metallic strappy heels are sleek, chic, and made to level up any look. Perfect for weddings, nights out, or any occasion when you want to shine. Fit & FeaturesStiletto heel, Square toe, Strappy design, Adjustable ankle strap with buckle closure, Cushioned insole, Metallic material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Shine Hour Metallic Strappy Stiletto Heels in Gold | Size: 9
Not your average plus-one—these stilettos were made to steal the spotlight. With skinny straps and a sleek heel, they’re your go-to for everything from rooftop drinks to dance floor moments. Fit & FeaturesStiletto heel, Faux leather material, Open square-shaped toe, Asymmetric strappy design, Adjustable ankle and heel straps with buckle detail, Padded insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Afterparty RSVP Strappy Stiletto Heels in Mocha | Size: 10 | Leather
A showstopping stiletto heel adorned with a whimsical rhinestone butterfly accent on sleek metallic that turns heads! Fit & FeaturesStiletto heel, Square toe, Rhinestone-embellished twist toe straps, Rhinestone-embellished ankle support strap, Adjustable ankle strap, buckle closure, rhinestone butterfly accent, Metallic faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fab Icon Butterfly Rhinestone Stiletto Heels in Silver | Size: 7 | Leather/Rhinestone
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.