Comfortable Evening Heels
Get ready to strut your stuff with a little extra flair and a whole lot of comfort, because when it comes to comfortable evening heels, we've got you covered! Whether you're hitting the dance floor or simply want to elevate your look for that special night out, these heels are here to ensure you feel fabulous without sacrificing an ounce of style. From chic soirées to casual dinners, let your feet do the talking while you embrace every unforgettable moment with confidence and ease. So go ahead, step into the spotlight and let those comfortable evening heels carry you through the night like the star you truly are!
$26.90
A chic black low block heel with a zippered back and ankle strap in faux leather.
$32.90
A silver low block heel with rhinestone accents and adjustable ankle strap for glamorous comfort.
$28.90
A sleek black nubuck stiletto heel with a square toe and adjustable ankle strap.
$30.90
A beige faux leather mule featuring delicate strappy design, square toe, and comfortable 2.5" kitten heel.
$30.90
A chic pair of black faux nubuck platform heels with an adjustable ankle strap and block heel.
$32.90
A glamorous gold mule with rhinestone straps, 3.5" stiletto heel, and cushioned insole.
$28.90
A vibrant red strappy block heel crafted from faux leather with a cushioned insole for comfort.
$26.90
A chic pair of tan faux leather thong heels featuring a square toe and 2" kitten heel.
$36.90
A white faux leather platform heel featuring rhinestone-embellished straps and an adjustable buckle closure.
$28.90
A black block heel mule featuring a sheer floral-embroidered lace strap and cushioned linen insole.
$32.90
A gold glitter block heel featuring rhinestone-embellished strappy design, clear PVC accents, and padded insole.
$28.90
A pair of black strappy kitten heels featuring a square toe and wrap-around adjustable ankle strap.
$30.90
A dazzling pair of gold criss cross platform block heels in metallic faux leather for formal occasions.
$32.90
A silver metallic faux leather wedge heel featuring rhinestone straps, open square toe, and adjustable ankle strap.
$38.90
A white satin kitten heel featuring chiffon beaded flower accents, open square toe, and adjustable straps.
$28.90
A bold red patent faux leather mule featuring dual strappy bands, open almond toe, and block heel.
$32.90
A chic pair of black platform block heels featuring a unique eyelet crisscross strap and adjustable ankle closure.
$30.90
A strappy wine-colored kitten heel crafted from faux leather with an adjustable ankle strap and square toe.
$26.90
A bold gold jelly mule featuring a platform sole, block heel, square toe, and wide foot strap.
$26.90
A chic pair of white faux leather block heels featuring a trendy toe ring and strappy design.
$24.90
A sleek black faux leather mule featuring a thong strap, buckle detail, and comfortable kitten heel.
$26.90
A chic gold mule with a 2" block heel, square toe, and faux leather material.
$9.97 $28.90 66% off
A sleek leopard print stiletto heel featuring an almond toe and adjustable buckle ankle strap.
$30.90
A chic black faux nubuck platform heel with criss-cross straps and a tall block heel.
$30.90
A white faux leather mule featuring a block heel and H-shaped band adorned with faux pearl embellishments.
$12.97 $28.90 55% off
A metallic silver faux leather stiletto heel featuring an open almond toe and adjustable ankle strap.
$32.90
A black faux suede wedge heel adorned with rhinestone-embellished straps and an adjustable ankle buckle.
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Step out in style in these chic low block heels! Create the perfect stylish graduation outfit or gorgeous prom look in these comfortable heels. This open-toe design features a stylish ankle strap detail with a zipper-closed back on a trendy block heel. The lower heel silhouette creates a supportive and comfy fit, perfect to wear with a semi-formal gown or dressy pant outfit. Fit & FeaturesZippered closed back , Ankle strap strap, Open almond toe , Single strap over the toe, Low block heel , Faux leather and nubuck material , Luxe fit cushioned insole, Runs true to size, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Smooth And Sleek Block Heels in Black | Size: 5.5 | Leather/Nubuck
Amp up the glamour while still keeping it comfortable in these low block heels featuring an open square-shaped toe, a thin asymmetric strappy design accented with mini rhinestone embellishments for a pretty sparkle, and an adjustable ankle strap. Pair with your fave clutch! Fit & Features2.5" Low block heel, Open square toe, Asymmetric strappy design, mini rhinestones, Adjustable ankle strap with buckle detail, Closed back, faux leather padded insole, Black heels are faux nubuck, Gold and silver heels are faux leather, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glam Up Rhinestone Strappy Low Block Heels in Silver | Size: 6 | Leather/Faux Nubuck/Rhinestone
Every step will look so glam in these rhinestone block heels featuring a statement bow and a luxe fit insole for comfort. Pair with a clutch. Fit & Features3" Block heel, Almond toe, Adjustable ankle strap, buckle closure, Luxe fit breathable cushioned insole, Rhinestones, Bow accent, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Endless Glam Rhinestone Bow Block Heels in Silver | Size: 8
Make everyone starstruck when you're in these block heels showcasing rhinestone embellished straps for a glamorous look! Fit & Features2.5" Block heel, Square toe, Rhinestone embellished strappy design, Closed ankle, adjustable ankle strap, buckle closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor A-List Glam Rhinestone Strappy Block Heels in Gold | Size: 6.5
The perfect glam block heels for the girl who loves to sparkle! They feature sparkling rhinestone embellished asymmetrical straps and a luxe fit cushioned insole. Complete the look with a clutch. Fit & Features3.5" Block heel, Almond toe, Rhinestone embellished straps, Back zipper closure, closed ankle, Luxe fit cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Love To Sparkle Rhinestone Strap Block Heels in White | Size: 9 | Leather/Rhinestone
Perfect for any occasion, these block heels add the prettiest allure to your look! These stunning heels feature a delicate chiffon bow and a sleek satin finish. Fit & Features2" Block heel, Square toe, wide toe strap, Back chiffon bow, Closed ankle, adjustable ankle strap, rhinestone buckle closure, Satin material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Pretty Chiffon Bow Satin Block Heels in Blue | Size: 7 | Chiffon/Rhinestone/Satin Fabric
Show off a fabulous strut in these sleek strappy kitten heels with a trendy gold metal ring accent. Fit & Features3" Kitten stiletto heel, Faux leather material, Open square-shaped toe, Thong strap design, gold metal ring accent, Adjustable ankle strap, buckle detail, Padded insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fabulous Strut Strappy Kitten Heels in Black | Size: 10 | Leather
Give your outfits some cuteness in these strappy block heels, perfect for pairing with your favorite bottoms or dresses! Fit & Features3" Round block heel, Square toe, Strappy design, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Much Personality Strappy Block Heels in White | Size: 7 | Leather
From daytime outings to nights out, these thong heels are perfect for dressing up any look for every occasion! Fit & Features2" short kitten heel, Square toe, Thin thong toe strap, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Feeling Chic Thong Square Toe Heels in Pink | Size: 9 | Leather
Tie your look with these strappy kitten heels, perfect for styling day or night! Fit & FeaturesKitten heel, Square toe, Strappy design, Adjustable ankle strap, buckle closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Tied Together Strappy Kitten Heels in Gold | Size: 7 | Leather
Comfortable Evening Heels
When the sun dips and the city lights flicker on, it’s your cue to step out and glow up—literally from head to toe. But let’s be real: nothing kills a vibe faster than a pair of heels that make you want to call it a night before the party even starts. That’s where comfortable evening heels come in, and girl, trust—these are the secret weapon your closet’s been begging for. Whether you’re heading to a rooftop soiree, twirling across a dance floor, or just want to look next-level for a dinner date, the right pair of evening shoes can turn every step into a strut. Think plush insoles, supportive straps, and silhouettes that serve style without the sting. For anyone who’s ever found herself barefoot by midnight or stashing a pair of flats in her bag “just in case,” it’s time to upgrade. Comfortable formal heels mean you can make an entrance, own the room, and shut it down—without sacrificing your feet to the fashion gods.
These aren't just shoes—they're your plus-one for every RSVP, that finishing touch that takes your look from cute to iconic. Black evening shoes comfortable enough to last all night are basically the holy grail, perfect for the girl who wants her style to be as effortless as her confidence. And if you’re shopping for someone else? Comfortable evening shoes make a genius gift for the friend who’s always on the guest list, the sister who never misses a gala, or even the mom who deserves to sparkle without the ouch. No matter who’s slipping them on, the right pair of evening heels can turn every celebration into a memory, from weddings to girls’ nights out and every spontaneous adventure in between. Look for details like padded footbeds, adjustable ankle straps, and block heels that promise both stability and sass. And don’t think you have to play it safe—metallics, embellishments, and bold hues are all fair game when comfort has your back.
If you’re chasing that glass-slipper moment—where you feel unstoppable and look it, too—start with shoes built for both the dance floor and the afterparty. With comfy, chic options, there’s no need to compromise on style or stamina. Whether you’re drawn to strappy numbers, classic pumps, or statement stilettos, there’s a pair out there that’s just waiting to become your new favorite. And if you’re ready to see what’s possible when comfort meets glam, check out our curated collection of High Heel Evening Shoes for even more inspo. Because every Windsor girl deserves to own the night—and look flawless doing it.