Date Night Heels
Get ready to strut into the spotlight, because date night heels are here to make sure you're unforgettable from the ground up! Whether it's a candlelit dinner or a spontaneous adventure under the stars, these heels are your secret weapon for turning heads and stealing hearts. With every step, you'll be serving confidence and charm, leaving a trail of enchantment wherever you go. So go ahead, slip into those show-stopping stilettos or flirty platforms, and let your shoes do all the talking. After all, life's too short for anything less than fabulous!
$28.90
A black block heel mule featuring a sheer floral-embroidered lace strap and cushioned linen insole.
$30.90
A chic pair of black faux nubuck platform heels with an adjustable ankle strap and block heel.
$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 thin straps.
$39.90
A silver chrome faux leather platform heel with rhinestone embellishments and an adjustable heel strap.
$28.90
A vibrant red strappy block heel crafted from faux leather with a cushioned insole for comfort.
$26.90
A chic pair of pink faux leather thong heels featuring a square toe and 2" kitten heel.
$30.90
A dazzling pair of silver criss cross platform block heels crafted from metallic faux leather.
$30.90
A beige faux leather mule featuring delicate strappy design, square toe, and comfortable 2.5" kitten heel.
$36.90
A white faux leather platform heel featuring rhinestone-embellished straps and an adjustable buckle closure.
$30.90
A vibrant yellow faux leather heel featuring asymmetric straps, a comfy block heel, and adjustable ankle buckle.
$28.90
A pair of black strappy kitten heels featuring a square toe and wrap-around adjustable ankle strap.
$32.90
A strappy silver block heel featuring asymmetrical rhinestone-embellished straps and metallic faux leather material.
$32.90
A black faux suede wedge heel adorned with rhinestone-embellished straps and an adjustable ankle buckle.
$39.90
A black faux leather block heel featuring rhinestone strappy design, adjustable ankle straps, and platform sole.
$32.90
A silver metallic faux leather wedge heel featuring rhinestone straps, open square toe, and adjustable ankle strap.
$32.90
A stylish pair of black platform block heels featuring a unique eyelet crisscross strap and adjustable ankle closure.
$32.90
A beige faux leather block heel featuring clear PVC straps adorned with rhinestone-embellished knotted accents.
$9.97 $24.90 60% off
A blue faux leather mule featuring criss-cross buckle straps, open square toe, and a chic kitten heel.
$9.97 $28.90 66% off
A sleek leopard print stiletto heel featuring an almond toe and adjustable buckle ankle strap.
$12.97 $28.90 55% off
A metallic silver faux leather stiletto heel featuring an open almond toe and adjustable ankle strap.
$40.90
A chic black ankle bootie with studded accents, criss-cross straps, and a peep toe design.
$24.90
A sleek white faux leather mule featuring a thong strap, buckle detail, and comfortable kitten heel.
$28.90
A bold red patent faux leather mule featuring dual strappy bands, open almond toe, and block heel.
$26.90
A bold gold jelly mule featuring a platform sole, block heel, square toe, and wide foot strap.
$30.90
A white faux leather mule featuring a block heel and H-shaped band adorned with faux pearl embellishments.
$26.90
A chic gold mule with a 2" block heel and faux leather wide toe strap.
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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: 7 | Leather/Faux Nubuck/Rhinestone
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 Black | Size: 7.5 | Leather
A pair of strappy block heels with a trendy toe ring trim that gives every outfit a sweet look! Fit & Features2.5" Block heel, Square toe, Strappy design, Toe ring trim, Luxe fit cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Attraction Toe Ring Strappy Block Heels in White | Size: 10 | Leather
These rhinestone strap mules are topped with a whimsical butterfly detail for that perfect mix of dainty and glam, ready to float from dinner dates to dance floors. Fit & FeaturesStiletto heel, Square toe, Rhinestone-embellished straps, butterfly accents, Metallic faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Butterfly Kisses Rhinestone Metallic Heels in Gold | Size: 8 | Leather/Rhinestone
Bring all the glamour in these block heels that shimmer with rhinestone embellishments and metallic trim! Fit & FeaturesBlock heel with rhinestone embellishments, Square toe, Rhinestone-embellished strap design, Cushioned insole, Adjustable ankle strap, buckle closure, Metallic material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Bring The Glam Rhinestone Block Heels in Gold | Size: 7
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 Black | Size: 7 | Leather
Minimal straps, max impact. These block heel mules are made for everything from rooftop drinks to girls’ night glam, with a shiny toe ring detail that adds a unique flair. Fit & Features3" Block heel, Square toe, Toe ring strap detail, Sleek strappy design, Cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Walking Pretty Toe Ring Heels in White | Size: 6 | Leather
These heels understood the assignment—flirty, chic, and ready to turn heads. With strappy detailing and a comfy block heel, they’re made for rooftop hangs, brunch dates, and everything in between. Fit & FeaturesBlock heel, Open square-shaped toe, Asymmetric strappy design, Adjustable ankle strap with buckle detail, Faux leather material, padded insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt Mode Activated Strappy Block Heels in Light Blue | Size: 7.5 | Leather
Designed to dazzle, destined to be noticed. These glitter block heels bring high-shine elegance with rhinestone bows that add the perfect luxe touch to any night-out moment. Fit & FeaturesBlock heel, Glitter mesh material, Open almond-shaped toe, Multi-strap design, rhinestone bow accent, Thin adjustable ankle strap, buckle detail, closed back, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Starlit Glam Rhinestone Bow Glitter Block Heels in Silver | Size: 6 | Rhinestone/Mesh Fabric
Date Night Heels
Date night is all about serving main character energy, and the right pair of date night heels is basically your co-star. Whether you’re heading out for a rooftop dinner with city lights as your backdrop, catching a late-night movie with your crush, or just grabbing drinks with your besties, your shoes set the tone for the whole night. Picking out date night shoes isn’t just about matching your outfit (though, let’s be real, that’s half the fun). It’s about how you want to feel—powerful, flirty, playful, or maybe a little bit mysterious. Think about those moments when you slip on a strappy stiletto and instantly feel like you could conquer the world, or when you go for a sleek block heel that’s made for dancing till last call. Date night heels aren’t just an accessory—they’re the secret weapon that takes your confidence from “cute” to “can’t stop, won’t stop.” And if you’re gifting a pair to your ride or die, your sister, or your favorite coworker who’s finally saying yes to that Bumble date, you’re basically giving them a ticket to their best night ever.
Don’t just settle for any heel—date night is your time to shine, and your shoes should be as bold as your plans. Maybe you’re the type who loves a classic pointed toe for that sharp, boss energy, or maybe you’re all about a pop of color and a little sparkle to catch the light (and everyone’s attention). The best date heel is the one that makes you want to take the long way around the block just so you can strut a little longer. Comfort matters too, because nothing kills the vibe faster than sore feet before dessert. Look for cushioned insoles, adjustable straps, and heel heights that let you actually enjoy every minute, from the first flirty hello to the last goodbye. And if you’re planning a surprise for someone special, date night shoes are the ultimate “I see you” gift—they’re thoughtful, fun, and guaranteed to make any outfit feel like a celebration. If you’re feeling the open-toe vibe and want something just as swoon-worthy but a little breezier, check out our Date Night Sandals for more inspo.
Every Windsor girl knows the magic of slipping into the perfect pair of heels before a night out. There’s a reason we obsess over the details—ankle straps that hug just right, metallic finishes that shimmer under the city lights, or platforms that give you that extra boost (literally and figuratively). Date night heels are more than just footwear; they’re the finishing touch that says you showed up for yourself. Whether you’re dressing up a classic LBD, adding edge to a denim mini, or going full glam in a bodycon dress, your shoes are the exclamation point on your look. And if you’re treating yourself to a new pair, remember: these aren’t just shoes, they’re memories waiting to happen. So go ahead—choose the pair that makes you feel unstoppable, because every unforgettable night starts with the perfect date heel.