Women's Round Toe Booties

Women’s Round Toe Booties are the secret weapon your closet’s been waiting for—effortlessly cool, endlessly versatile, and ready to take on whatever you have planned. Whether you’re running from coffee dates to last-minute plans or just want a low-key upgrade for your go-to jeans, these booties are the answer. Think of them as your style safety net: easy to dress up, down, or somewhere in between. If you’re looking for that perfect mix of comfort and confidence, consider this your sign.

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Windsor Snow Glow Platform Rhinestone Booties in Tan

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Windsor Snow Glow Platform Rhinestone Booties in Tan

$9.97 $34.90 71% off

A tan faux suede platform bootie adorned with rhinestones and lined in plush faux fur for cozy glamour.

Sleek Strut Under-The-Knee Moto Boots in Ivory

$50.90

A pair of ivory faux leather under-the-knee moto boots with block heel, buckle accents, and zipper closure.

On Repeat Under-The-Knee Boots in Natural

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On Repeat Under-The-Knee Boots in Natural

$46.90

A pair of natural faux leather under-the-knee boots featuring a stacked block heel and round toe.

Windsor Fray All Day Denim Booties in Black Denim

$40.90

A pair of black distressed denim booties featuring a slouchy fit, raw edge finish, and block heel.

Built To Stomp Faux Leather Lug Boots in Black

$46.90

A pair of black faux leather under-the-knee boots with chunky lug soles and cushioned insoles.

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Steppin Up Block Heel Knee High Boots in Wine

$48.90

(28)

Big boot energy only—these tall babes instantly elevate any 'fit. A sleek silhouette with a comfy block heel makes them perfect for day-to-night flexing. Fit & Features3" Stacked block heel, 8" leg opening, 12" shaft height, Platform sole, Round toe, Complete inner zipper closure, Knee-length shaft, Faux leather material, Luxe fit cushioned insole, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Steppin Up Block Heel Knee High Boots in Wine | Size: 8.5 | Leather

Totally Edgy Buckled Square Toe Boots in Black

$45.90

(21)

Step into these edgy statement faux leather boots with a buckled side accent and a calf-length fit perfect for pairing with bottoms or dresses. Fit & Feature2” in heel, 7.5” leg opening, 11.5” shaft , Square toe, Buckled side accents, Calf height shaft, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Totally Edgy Buckled Square Toe Boots in Black | Size: 8.5 | Leather

Ride or Shine Studded Cowboy Boots in White

$52.90

(21)

Western, but make it glam. These faux leather cowboy boots mix classic embroidery with studded detailing and a sleek pointed toe—perfect for bachelorettes, country concerts, or costume parties. Fit & Features3.5” stacked block heel, 7.5” leg opening, 12.5” shaft, Pointed toe, side zipper closure, Studded and grommet embellishments, Western-inspired embroidery, Under-the-knee length, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Ride or Shine Studded Cowboy Boots in White | Size: 5.5 | Leather

Sleek Stance Faux Leather Stiletto Boots in Black

$46.90

(13)

Cold-weather dressing just got elevated. These faux leather boots bring timeless polish with a pointed toe and sleek under-the-knee cut, with a stiletto heel that pairs effortlessly with fall layers. Fit & Features3” stiletto heel, 7.5” leg opening, 15” shaft, Pointed-toe, Side zipper closure, Under-the-knee length, Sleek faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Stance Faux Leather Stiletto Boots in Black | Size: 9

Retro Rise Knee High Platform Boots in Brown

$48.90

(13)

A little vintage, a little modern—these knee-high boots are the ultimate outfit maker. With a smooth faux leather finish, a sturdy block heel, and a platform sole perfect for elevating any outfit. Fit & FeaturesBlock heel, Square toe, Side zipper closure, Knee-high shaft, Side zipper closure, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Retro Rise Knee High Platform Boots in Brown | Size: 8.5 | Leather

Moving Along Studded Cowboy Boots in Taupe-2

$50.90

(10)

Scoot and move it in true Western style at festivals and concerts in these studded cowboy boots! Fit & Features3.5" Stacked block heel, Pointed toe, Western-inspired pattern, studded trim, Mid-shaft length, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Moving Along Studded Cowboy Boots in Taupe-2 | Size: 10 | Faux Suede

Major Strut Faux Leather Knee-High Stiletto Boots in Black

$48.90

(9)

Fit & Features3" Stiletto heel, 7.5" leg opening, 13.5" shaft height, Patent faux leather material, Knee-high design, Pointed toe, Complete inner zipper closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Major Strut Faux Leather Knee-High Stiletto Boots in Black | Size: 7

Windsor Sleek Strut Under-The-Knee Moto Boots in Ivory

$50.90

(5)

Show off a sleek strut in these edgy under-the-knee moto boots featuring a stacked block heel, buckle strap accent, and inner zipper closure. Fit & Features3” block heel, 7.5” leg opening, 13” shaft, Round toe, Under-the-knee height, Faux leather material, Circular buckle strap accent, top buckle strap, Inner zipper closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Strut Under-The-Knee Moto Boots in Ivory | Size: 7.5 | Leather

Windsor Tough Love Platform Block Heel Booties in Black

$40.90

(5)

Walk tall and with edgy confidence in these faux leather booties, and elevate your outfit! They feature a platform sole for stylish height and a stacked block heel. Fit & Features3.5" Stacked block heel, Square toe, Inner zipper closure, Platform sole, Luxe fit cushioned insole, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Tough Love Platform Block Heel Booties in Black | Size: 8.5 | Leather

Windsor Higher Standards Kitten Heel Boots in Brown

$58.90

(5)

When subtle meets statement. These faux suede over-the-knee boots add instant polish to any look—with a sleek pointed toe and low kitten heel that keeps it chic and comfy. Perfect for date nights, coffee runs, and everything in between. Fit & Features2.5” Kitten heel, 8" leg opening, 21" shaft height, Pointed-toe, Scrunched over-the-knee length, Pull-on/off styling, Smooth faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Higher Standards Kitten Heel Boots in Brown | Size: 5.5 | Faux Suede

Women's Round Toe Booties

There’s a reason women’s round toe booties have become the unsung heroes of transitional style—especially as March teases us with a little bit of everything: chilly mornings, sun-soaked afternoons, and the occasional spring shower. These are the pairs you reach for when you want comfort that doesn’t compromise on polish, the ones that slip seamlessly into your daily routine and still manage to elevate even your most thrown-together outfits. Whether you’re dashing from work to weekend brunch or plotting a spontaneous day trip, round toe booties are that rare blend of practical and put-together. The softly curved toe feels relaxed but intentional, making them a no-brainer for everything from cropped jeans to midi skirts. And let’s not pretend you haven’t eyed them as the solution for those “I want to wear a dress, but it’s not quite sandal weather” days. The beauty of this silhouette is its versatility—casual enough for coffee runs, sharp enough for the office, and just edgy enough to anchor a floral dress or give a little attitude to your favorite leggings.

If you’re shopping for yourself, consider the details that make a pair feel like it was made for your closet. Think about heel height—block heels offer stability for all-day wear, while low-profile soles keep things easy and unfussy. Materials matter too: classic faux suede brings a soft, luxe vibe that looks equally at home with bare legs or tights, while smooth faux leather is your go-to for a little extra edge and weather resistance. Zippered styles make for quick changes (because who has time for laces when you’re running late?), and subtle embellishments—think tonal stitching or a hint of metallic hardware—add just enough interest without overpowering your look. If you’re the type who lives in neutrals, taupe, black, and cognac are endlessly wearable, but don’t sleep on a pop of color or a textured finish to shake things up. And if you’re gifting, round toe booties are a thoughtful pick for friends, sisters, or anyone who loves a wardrobe workhorse. They’re the kind of gift that feels personal—especially if you know her style—and practical enough to guarantee they’ll get plenty of mileage.

As you scroll through options, keep in mind that the best round toe booties are the ones that fit your life, not just your feet. Maybe you need a pair that can handle unpredictable weather (hello, March puddles), or you’re on the hunt for something that makes your everyday denim feel a little more intentional. Windsor booties are designed with real life in mind—think cushioned insoles, walkable heels, and silhouettes that play well with everything from slouchy knits to structured blazers. And because we know style is personal, you’ll find pairs that let you dial up the drama or keep things low-key, depending on your mood. If you’re ready to expand your rotation or just want to see more styles that hit that sweet spot between comfort and style, check out our full selection of Women's Round Toe Boots for even more inspiration. Whether you’re curating your spring wardrobe or searching for the kind of boots that make you feel instantly more put-together, round toe booties are the answer to those “what do I even wear today?” moments—no overthinking required.

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Women's Round Toe Booties

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Women's Round Toe Booties

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