Comfortable Black Dress Heels
Comfortable black dress heels are the ultimate ride-or-die for every Windsor girl who’s ready to slay from brunch dates to dance floors—no outfit changes required. When you want all eyes on you (and your killer moves), these heels have your back, letting you own every moment without missing a beat. Ready to step up your style game and keep it comfy? Slip into a pair and let the compliments roll in—your next-level confidence starts from the ground up.
$28.90
A sleek black nubuck stiletto heel featuring a square toe and adjustable thin straps.
$28.90
A chic pair of black faux leather block heels featuring a strappy design and cushioned insole.
$28.90
A sophisticated pair of black strappy kitten heels featuring a square toe and wrap-around adjustable ankle strap.
$30.90
A chic black faux nubuck platform heel with an adjustable ankle strap and cushioned insole.
$34.90
A chic black faux leather mule featuring a stiletto heel, square toe, and trendy buckle accent.
$24.90
A chic pair of black faux leather kitten heels featuring strappy design and adjustable ankle buckle closure.
$28.90
A black block heel mule featuring a sheer floral lace strap and cushioned insole for chic comfort.
$24.90
A sleek black faux leather mule featuring a thong strap, buckle detail, and comfortable kitten heel.
$39.90
A black faux leather block heel featuring rhinestone strappy design, adjustable ankle straps, and platform sole.
$30.90
A chic black platform heel with criss-cross straps and a cushioned insole in faux nubuck.
$32.90
A chic black platform block heel featuring a unique eyelet crisscross strap and adjustable ankle buckle.
$9.97 $24.90 60% off
A chic pair of black faux leather mules with criss-cross buckle straps and a kitten heel.
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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, Free Shipping on All Orders Over $75. | Windsor Smooth And Sleek Block Heels in Ivory | Size: 8 | 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
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: 7.5 | Leather
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 White | Size: 8 | 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
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 Tan | Size: 9 | 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
Comfortable Black Dress Heels
When it comes to nailing that “effortlessly put-together” vibe, nothing works harder for you than a pair of comfortable black dress heels. Whether you’re racing from a last-minute work presentation to a rooftop dinner with your girls, or slipping away to a spontaneous date night after a day of errands, these heels are your secret weapon. They’re the ultimate chameleons—sleek enough for formal events, but with the right details, a total vibe for brunches, birthdays, or that one friend’s engagement party you RSVP’d “maybe” to but are now definitely attending. The magic of black dress heels is all in the details: think plush insoles, sturdy block heels, and straps that actually stay put, so you can dance, strut, and live your best life without the dreaded “I need to sit down” moment. For anyone who’s ever had to do a quick-change in the back of an Uber or sprint across a crosswalk with coffee in hand, you already know—comfort isn’t a luxury, it’s a non-negotiable.
Shopping for comfortable black heels isn’t just about ticking a box for style—it’s about saying yes to every invite, every adventure, and every “let’s go!” text that pops up. These aren’t just for the girl who’s got a calendar full of galas and fancy dinners (though, if that’s you, we see you!). They’re for the boss babe who wants to slay her 9-to-5 and still have enough energy to hit happy hour, the bestie who’s always down for a spontaneous night out, or even the thoughtful friend hunting for the perfect gift that says, “I know you, and I want you to look fire and feel amazing.” Black dress black heels are the go-to for anyone who refuses to compromise—on comfort, on style, or on living life to the fullest. And if you’re the queen of mixing and matching, you already know that fun heels for black dress moments are a must, turning any LBD into a whole main character mood.
Pro tip from your ride-or-die: sometimes, the most iconic looks start from the ground up. Picture this—you’re in your favorite black mini, hair on point, and your heels? Not just cute, but so comfortable you forget you’re even wearing them. That’s the energy we’re manifesting. And if you’re all about finding those perfect in-between heights, don’t miss our curated collection of Comfortable Black Kitten Heels—because sometimes a little lift is all you need to take your look (and your confidence) to the next level. Whether you’re gifting, treating yourself, or building your capsule wardrobe, investing in comfortable black dress heels means you’ll always have that one pair ready to go—no matter where the night (or your group chat) takes you.