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 bold red faux leather mule featuring delicate straps, a square toe, and a comfortable kitten heel.
$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.
$32.90
A bold snake print block heel in faux leather with rhinestone chain accents and adjustable ankle strap.
$52.90
A dazzling pair of silver rhinestone booties featuring a pointed toe and sleek stiletto heel.
$42.90
A romantic pair of white stiletto pumps featuring sheer lace material and a classic pointed toe.
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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
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
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: 10 | 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: 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 chic patent faux leather stiletto pumps feature a criss-cross buckle strap design and a sleek slingback adjustable strap. Fit & FeaturesShort stiletto heel, Patent faux leather material, Closed pointed toe, Criss-cross buckle strap design, Sling-back adjustable strap, buckle detail, Cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Buckle Strap Sling-Back Stiletto Pumps in White | Size: 9 | Leather
Sharp, sleek, and totally unstoppable—these stiletto heels are the definition of glam power moves. With a chic ankle strap and gold buckle accents, they’re your go-to for a polished finish with a bold edge. Fit & FeaturesStiletto heel, Square toe, Hardware buckle strap accent, Adjustable ankle strap, buckle closure, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Strap In Luxe Stiletto Heels in Black | Size: 8 | Leather
These strappy stiletto heels were built for chic nights out. With sleek straps and a gold hardware toe ring accent, they’re the perfect balance of classy and cool for weeknight dinners to weekend RSVP's. Fit & FeaturesStiletto heel, Square toe with hardware toe ring accent, Strappy design, Adjustable ankle strap, buckle closure, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Luxe Minimalist Toe Ring Strappy Stiletto Heels in Ivory | Size: 8.5 | Leather
These sleek kitten stiletto heels with PVC straps and a glossy finish are ready to elevate your ‘fit, from brunch to date nights. Fit & Features3" Kitten stiletto heel, Square toe, PVC clear straps, Adjustable ankle strap with buckle closure, Luxe fit cushioned insole, Patent faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Strut Factor Patent Stiletto Kitten Heels in Beige | Size: 9 | Leather/Polyvinyl Chloride
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.