Comfortable Booties

Step into the spotlight with our collection of comfortable booties that are as chic as they are cozy. Whether you're strutting down the city streets or dancing the night away, these booties have your back (and your feet) every step of the way. Imagine slipping into a pair that feels like a warm hug but looks like a million bucks—yes, please! From casual outings to glam nights out, these booties are ready to elevate every outfit and mood. So go ahead, darling, let your feet do the talking and make comfort your new fashion statement!

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Windsor Bedazzled Allure Rhinestone Stiletto Booties in Silver

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Windsor Bedazzled Allure Rhinestone Stiletto Booties in Silver

$11.97 $52.90 77% off

A dazzling pair of silver rhinestone booties featuring a pointed toe and sleek stiletto heel.

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Steppin Up Block Heel Knee High Boots in Black

$48.90

A sleek black faux leather knee-high boot featuring a comfy block heel and inner zipper closure.

Fringe Flirt Studded Cowboy Boots in Black

$46.90

A black faux suede cowboy boot featuring studded star accents, flirty fringe, and a stacked block heel.

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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

Comfortable Booties

When it comes to curating a wardrobe that works as hard as you do, comfortable booties are the real MVPs—always ready for whatever your day (or night) throws at you. Picture this: you’re running from brunch with your besties to a spontaneous shopping spree, then somehow find yourself at an impromptu rooftop hangout, all without missing a beat. That’s the magic of comfort booties—they’re the go-to for girls who want to look put together without sacrificing a single ounce of comfort. These aren’t just shoes; they’re a vibe, a confidence boost, a little secret weapon for making power moves and owning every step. Whether you’re styling them with your favorite flowy skirt, edgy leather pants, or that dress you’ve been dying to wear, comfort booties have your back (and your feet), making every outfit feel like a main character moment. And if you’re the friend who’s always gifting the best finds, trust—comfortable booties are the kind of present that’ll have your crew talking about your taste for months. They’re perfect for birthdays, “just because” surprises, or even that friend who’s about to start a new job and needs a little extra pep in her step.

Boots Windsor girls love aren’t just about looks (though, let’s be real, they’re always on point)—it’s about the little details that make a big difference. Think plush insoles that feel like walking on clouds, supportive soles that keep you dancing all night, and versatile silhouettes that go from casual coffee runs to late-night adventures. When you’re shopping for comfort booties, pay attention to the fit around your ankle, the flexibility of the sole, and how easy they are to slip on and off—because nobody has time for a shoe struggle when there’s fun to be had. And don’t sleep on the power of a block heel, either; it gives you that extra boost without the wobble, letting you strut with confidence from sunrise to last call. If you’re looking to up your style game even more, check out our curated collection of Comfortable Block Heel Booties—they’re the ultimate blend of fashion and function, perfect for leveling up your everyday looks.

The best part? Comfortable booties are the timeless staple that never lets you down, no matter what’s on your calendar. They’re made for the girl who’s always on the move, the one who says yes to every invite and turns every sidewalk into a runway. From casual hangs to special occasions, these booties are the definition of versatile—pair them with jeans for a laid-back vibe, or dress them up with a mini and a bold lip for instant main character energy. And if you’re gifting a pair, you’re basically giving the gift of confidence, comfort, and endless outfit possibilities. Every Windsor girl deserves that “I can take on the world” feeling, and with comfort booties in your rotation, you’ll always be ready for your next adventure.

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