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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Cuffed Up Faux Fur Booties in Brown

$42.90

A pair of brown faux fur booties featuring a soft lining, round toe, and flat traction sole.

Windsor Drama Queen Faux Fur Boots in Ivory

$42.90

A plush ivory faux fur boot with a below-the-knee length and easy slip-on design.

Instant Edge Platform Ankle Booties in Black

$48.90

A sleek black faux leather ankle bootie featuring a chunky platform sole and elastic gore design.

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Windsor Snuggle Steps Faux Sherpa Platform Booties in Tan

$11.97 $28.90 59% off

A cozy tan microsuede platform bootie featuring faux sherpa lining and a stylish side hoop accent.

Windsor Western Chill Embroidered Suede Boots in Oatmeal

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Windsor Western Chill Embroidered Suede Boots in Oatmeal

$11.97 $46.90 74% off

An oatmeal faux suede boot with western-inspired embroidery, fuzzy faux fur lining, and a traction lug sole.

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.

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Windsor Steppin Up Block Heel Knee High Boots in Wine

$48.90

(24)

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: 6 | Leather

Totally Edgy Buckled Square Toe Boots in Black

$45.90

(16)

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

(16)

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

Retro Rise Knee High Platform Boots in Brown

$48.90

(11)

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

Windsor Major Strut Faux Leather Knee-High Stiletto Boots in Brown

$48.90

(8)

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 Brown | Size: 5.5

Drama Queen Faux Fur Boots in Ivory

$42.90

(5)

Go big, go fuzzy, go bold—these faux fur boots bring all the drama your outfit’s been waiting for. Perfect for stepping out, staying cozy, or just making every entrance feel like a moment. Fit & FeaturesPlush faux fur fabrication, Below-the-knee length, Round toe, Flat insole, Slip-on design, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Drama Queen Faux Fur Boots in Ivory | Size: 11

Windsor Point Taken Lace-Up Stiletto Boots in Brown

$58.90

(5)

Equal parts bold and refined. These foldover stiletto boots serve a major edge with a pointed toe, sleek faux leather finish, and lace-up back detail that ties the look together—literally. Perfect for taking your outfit from casual to captivating in one step. Fit & Features4” Stiletto heel, 7" leg opening, 16" shaft height, Pointed-toe, Foldover shaft with lace-up placket, Inner side zipper closure, Sleek faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Point Taken Lace-Up Stiletto Boots in Brown | Size: 5.5 | Leather

Windsor Dust to Dawn Cowboy Boots in Black

$54.90

(3)

Classic western, modern edge. These cowboy boots feature stitched detailing and a sleek pointed toe that brings a bold finish to denim, minis, or your favorite fall layers. Fit & FeaturesStacked block heel, Pointed-toe, Western-inspired stitch detailing, Pull-on design with pull tabs, Under-the-knee length, Faux leather material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dust to Dawn Cowboy Boots in Black | Size: 7 | Leather

Windsor Fall For Me Wide Calf Knee-High Boots in Brown

$49.90

(3)

Seasonal staple unlocked—these faux suede boots pair effortlessly with oversized knits, flowy dresses, or denim for all your autumn to winter plans! Fit & Features3.5" Block heel, 9" leg opening, 12" shaft height, Almond toe, Knee-high shaft silhouette, Wide calf design, Faux suede material, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fall For Me Wide Calf Knee-High Boots in Brown | Size: 7 | Faux Suede

Windsor Fray All Day Denim Booties in Black Denim

$40.90

(2)

Jeans for your feet? Basically. These distressed denim booties bring all the grunge-girl energy with a slouchy fit and raw edge finish. Perfect for concerts or themed parties! Fit & Features3” block heel, 6.5” leg opening, 8” shaft height, Pointed toe, Foldover denim with distressed accents, Hidden side zipper closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fray All Day Denim Booties in Black Denim | Size: 8

Women's Round Toe Booties

There’s something about round toe booties for women that just works—no matter the season, no matter the mood. Right now, as December settles in and winter wardrobes get their annual upgrade, these booties are the secret weapon your closet craves. They’re the kind of shoe you reach for when you want to look put-together but still feel like yourself: comfy, current, and totally ready for whatever the day throws your way. Maybe you’re heading out for a holiday market crawl, braving the cold with your favorite oversized sweater and a hot chocolate in hand, or maybe you’re simply trying to make your everyday jeans-and-tee combo feel a little less… expected. Windsor booties with a round toe silhouette are the answer—softening up structured looks, adding a playful twist to tailored pieces, and somehow making even the most thrown-together outfit look intentional. The rounded front isn’t just a style choice; it’s a comfort move, giving your toes a little breathing room (because let’s be real, nobody’s got time for pinched feet during marathon shopping sessions or late-night catch-ups with friends).

When it comes to gifting, round toe booties are that rare find that hits the sweet spot between “I totally thought this through” and “I know your style.” They’re universally flattering, easy to fit, and versatile enough to suit everyone from your trend-obsessed sister to your always-on-the-go best friend. Think of them as the wardrobe MVPs—perfect for those who want to stay on-trend without sacrificing comfort, or for anyone who needs a reliable pair of shoes that can handle everything from spontaneous dinner plans to a full day at the office. They’re especially great for those transitional moments—when your calendar is packed with events and you need a shoe that can keep up, or when the weather can’t quite decide if it’s winter or spring. And if you’re curating your own rotation, round toe booties slip seamlessly into every style story: paired with bare legs and a sweater dress for a cozy-chic vibe, or layered up with tights, a midi skirt, and a chunky scarf when the temperature drops. The best part? They’re made for movement, with sturdy soles and walkable heels that let you actually live in your look, rather than just posing for it.

Shopping for booties isn’t just about picking a pair that looks good on the shelf—it’s about finding the ones that feel like you. Pay attention to the details: the height of the shaft, the texture of the material, the color that makes your heart skip a beat. Maybe you gravitate toward classic neutrals that go with everything, or perhaps you’re drawn to statement shades that turn the sidewalk into your own personal runway. If you love a little extra edge, consider mixing up your collection with different finishes—think smooth faux leather, soft suede, or even a hint of metallic for a festive twist. And if you’re someone who likes to play with proportions, round toe booties are the perfect counterpoint to more angular pieces in your closet. Of course, if you’re feeling a little adventurous, you might want to explore other silhouettes too—something a bit sharper, perhaps? You can always check out our Womens Pointed Toe Booties for a fresh take on the trend. No matter your vibe, round toe booties are a style staple that adapts to you—ready to take on busy days, big nights, and every little moment in between.

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Women's Round Toe Booties

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Women's Round Toe Booties

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