Comfortable Kitten Heel Shoes
Comfortable kitten heel shoes are your secret weapon for those days when you want to look effortlessly chic without sacrificing a single ounce of comfort. Whether you’re strutting into the office, dancing the night away, or just adding a little sass to your everyday vibe, these shoes have your back. Slip into a pair and let your confidence do the talking—because every Windsor girl deserves to feel unstoppable, one cute step at a time.
$28.90
A strappy pink faux leather kitten heel with a square toe and buckle accent for chic outings.
$28.90
A metallic silver faux leather kitten heel featuring asymmetric strappy design, thong strap, and padded insole.
$30.90
A camel faux leather slingback heel featuring rhinestone embellishments, a pointed toe, and stiletto kitten heel.
$24.90
A chic pair of black faux leather kitten heels featuring strappy design and adjustable ankle buckle closure.
$26.90
A chic pair of tan faux leather thong heels featuring a square toe and comfortable 2" kitten heel.
$28.90
A pair of black strappy kitten heels featuring a square toe and wrap-around adjustable ankle strap.
$30.90
A bold red faux leather mule featuring delicate straps, a square toe, and a comfortable 2.5" kitten heel.
$30.90
A chic silver slingback heel featuring a pointed toe, bold buckle strap, and cushioned insole.
$38.90
A white satin kitten heel featuring chiffon beaded flower accents, open square toe, and adjustable straps.
$30.90
A wine-colored faux leather kitten heel featuring a sleek strappy design and adjustable ankle strap.
$30.90
A white faux leather mule featuring rhinestone-accented straps, open square toe, and a chic kitten heel.
$24.90
A gold faux leather mule featuring a thong strap, buckle detail, and comfortable kitten heel design.
$9.97 $28.90 66% off
A sleek blue patent faux leather pump with a pointed toe, adjustable slingback strap, and kitten heel.
$9.97 $24.90 60% off
A chic pair of camel faux leather mules featuring criss-cross buckle straps and a comfortable kitten heel.
$30.90
A pair of black faux leather heels featuring a square toe, kitten stiletto heel, and adjustable ankle strap.
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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: 6 | 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 Kitten Heel Shoes
Let’s be real: life’s too short for shoes that slow you down or make you wince with every step. That’s why comfortable kitten heels are the secret weapon every Windsor girl needs in her closet. They’re the ultimate flex—effortlessly balancing that chic, put-together vibe with a low-key “I could walk across town and still look fire” energy. Whether you’re running from a coffee date to a last-minute invite or you’ve got a calendar that’s booked and busy, kitten heels are the MVPs that keep up with your every move. Think of them as the shoe equivalent of your favorite group chat: supportive, always there, and never letting you down. Slip into a pair and suddenly you’re gliding through the day—no backup flats needed, no bandaids in your bag, just pure confidence with every step. They’re the shoes you reach for when you want to look like you tried (but didn’t try too hard), and let’s be honest, that’s the vibe we’re all chasing.
Comfortable kitten heels aren’t just about keeping your feet happy—they’re about unlocking every outfit’s potential. That little lift does wonders, giving you a boost (literally and emotionally), elongating your legs, and adding just the right amount of sass to everything from denim to dresses. They’re the answer when your bestie texts, “dress cute, but comfy,” and you want to show up and show out without sacrificing an ounce of comfort. Gifting a pair? You’re basically handing someone an all-access pass to confidence and endless compliments. They’re perfect for the new grad stepping into her first big job, the friend who’s always on the go, or your mom who deserves to feel as fabulous as she looks. And if you’re treating yourself (because you absolutely should), you’ll find they become your go-to for everything—think brunches, date nights, or even those “I just want to look cute while running errands” days. The best part? The most comfortable kitten heels are designed to keep you moving, grooving, and living your best life, all while serving up major style points.
When you’re on the hunt for your next pair, pay attention to the details that make all the difference: cushioned insoles, sturdy straps, and a heel height that feels just right (not too high, not too low—Goldilocks would approve). Look for styles that play well with your wardrobe, whether you’re into bold colors, playful prints, or timeless neutrals. And if you’re craving a classic that goes with literally everything, check out our Comfortable Black Kitten Heels for that perfect blend of versatility and comfort. Trust, once you add these to your rotation, you’ll wonder how you ever lived without them. So, go ahead—step out, strut your stuff, and let your shoes do the talking. The world is your runway, and you’re owning every inch.