Classic Skirts

Classic skirts are your timeless wardrobe heroes, ready to add that extra flair to your everyday and special occasions. Whether you're twirling into a meeting or stepping out for brunch with the squad, these skirts have got you covered. From chic pencil styles that mean business to flirty A-lines perfect for a night out, classic skirts are all about versatility and style. So go ahead, strut your stuff and let those hems do the talking—because when it comes to making an entrance, you're always on point!

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Windsor Fringe Attitude Faux Suede Mini Skirt in Black

$29.90

A black faux suede mini skirt with flirty fringe trim and a flattering bodycon fit.

Windsor Delightful Duo Polka Dot Ruffle Skirt in Black

$36.90

A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.

Windsor So Perfect Mid-Rise Pleated Denim Mini Skirt

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Windsor So Perfect Mid-Rise Pleated Denim Mini Skirt

$7.97 $36.90 78% off

A trendy denim mini skirt featuring a pleated silhouette and flattering mid-rise waist.

Windsor Radiant Sweetie Floral Polka Dot Ruffle Skirt in Black

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Windsor Radiant Sweetie Floral Polka Dot Ruffle Skirt in Black

$9.97 $26.90 63% off

A black woven skort with a floral polka dot pattern and ruffled mini-length skirt overlay.

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Windsor Wild At Heart Long Fringe Skirt in Tan

$29.90

(34)

Channel your western side with this trendy-chic skirt that will level up your festival look! It features a high-rise waist, an asymmetric mini-length hem with a form-hugging fit, and long fringe detailing that cascades to your ankles. The stylish fringe design will dance with you to your favorite band! Complete your 'fit with a cropped graphic tee and cowboy boots. Fit & FeaturesHigh-rise waist, Back zipper, hook and eye closure, Asymmetric mini-length hem, Form-hugging fit, Long fringe design, ankle-length hem, Faux suede fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild At Heart Long Fringe Skirt in Tan | Size: S | Faux Suede

Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

(14)

Fit & FeaturesStretchy smooth knit-lined fabrication, High-rise fit, Ruching, Asymmetrical high-side slit, Midi length hem, Runs true to size, Shop Matching Crop Top: Bold Staple Long Sleeve Crop Top Free Shipping on All Orders Over $75. | Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black | Size: L

Sleek Status Faux Leather Mini Skirt in Black

$19.90

(8)

Level up your sleek status with this chic mini skirt made with smooth faux leather fabric to elevate your casual 'fits. It features a high-rise waist, a side slit accent at the hem, and a form-hugging silhouette to highlight your stunning curves. Fit & FeaturesFaux leather fabric, plenty of stretch, High-rise elasticized waist, Side slit, Mini-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Status Faux Leather Mini Skirt in Black | Size: XS

First Take Micro Slit Mini Skirt in Black

$14.90

(5)

Step out looking like goals in this micro mini skirt with a flirty side slit and bodycon fit that'll get you noticed! Fit & FeaturesStretchy knit fabric, High-rise waist, Side slit, Bodycon silhouette, Micro mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor First Take Micro Slit Mini Skirt in Black | Size: S | Knit Fabric

Windsor Trendy Moves Long Fringe Skirt in Black

$36.90

(4)

Make major trendy moves in this long fringe skirt featuring a high-rise waist, a flowy fringe design, and cheeky fitted shorts for coverage. Style with a crop top and boots for a country concert. Fit & FeaturesKnit fabric, high stretch, High-rise elasticized waist, Ruched side seams, Long flowy fringe design, Cheeky fitted shorts, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendy Moves Long Fringe Skirt in Black | Size: M

City Chic Faux Leather Belted Mini Skirt in Black

$32.90

(2)

Dare to dazzle in this faux leather belted mini skirt. With a mid-rise waist, metal grommets, and side pockets, it's your go-to for a fierce and fabulous look. Fit & FeaturesCoated faux leather fabrication, Mid-rise waist, Belted waist with metal grommets, Side pockets with flap closure, Mini length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor City Chic Faux Leather Belted Mini Skirt in Black | Size: S

Shake It Up Fringe Maxi Skirt in Tan

$29.90

(2)

Shake and shimmy at concerts and festivals in this showstopping fringe maxi skirt with your fave cowboy boots! Fit & FeaturesFaux suede fabric, High-rise waist, back zipper and hook-eye closure, Fringe silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Shake It Up Fringe Maxi Skirt in Tan | Size: S | Faux Suede

Sultry Eye Candy Floral Velvet Mesh Mini Skirt in Black

$29.90

(2)

Be the sultry eye candy in this floral velvet mesh mini skirt! The high-rise waist and bodycon fit add a touch of allure and a flattering fit. Pair with the matching top. Fit & FeaturesFlocked floral velvet pattern, mesh-lined fabric, High-rise waist, Bodycon silhouette, Mini-length hem, Runs true to size, Shop The Matching Top: Sultry Eye Candy Floral Velvet Mesh Bustier Free Shipping on All Orders Over $75. | Windsor Sultry Eye Candy Floral Velvet Mesh Mini Skirt in Black | Size: S | Mesh Fabric

She's Irresistible Faux Leather A-Line Mini Skirt in Black

$39.90

(2)

A faux leather mini skirt like this will make you simply irresistible! This high-rise skirt flaunts side button details for an edgy vibe and a flirty a-line silhouette perfect for pairing with heels or boots. Fit & FeaturesSleek faux leather fabric, High-rise waist, Side snap-button and zipper closures, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor She's Irresistible Faux Leather A-Line Mini Skirt in Black | Size: M

Cue The Sparkle Rhinestone Fishnet Maxi Skirt in Silver

$89.90

(2)

Cue the sparkle—this rhinestone fishnet maxi skirt was made to own the night. With a thigh-skimming slit and trendy shine, it'll give off effortless cool-girl glam. Shop Matching Top: Cue The Sparkle Rhinestone Fishnet Halter TopFit & FeaturesRhinestone-embellished, mesh-lined fabric, High-rise fit with subtle stretch, High side slit design, Form-hugging silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cue The Sparkle Rhinestone Fishnet Maxi Skirt in Silver | Size: S

Classic Skirts

When you’re building a wardrobe that’s equal parts iconic and effortless, nothing delivers like classic skirts. These are the ride-or-die pieces that have your back on every adventure, from spontaneous coffee runs to late-night dance floors. There’s just something about the clean lines and timeless silhouettes that make you feel instantly put together—like you woke up with your life in order, even if you totally hit snooze three times. Classic skirts are the ultimate closet chameleons, ready to flex for any vibe: pair a crisp A-line with a tucked-in tee for instant boss energy, or throw on an elegant midi and suddenly you’re channeling main character at a rooftop soirée. They’re the pieces you reach for when you want to look like you tried (without actually trying), and trust, they never let you down.

Shopping for a classic skirt is like finding your signature scent—it’s all about what makes you feel most like *you*. Maybe you’re after a sleek pencil skirt that means business (and knows how to have fun after hours), or a pleated number that twirls with every step, giving you that movie-moment magic. Think about your go-to shoes, your favorite jackets, and even your wildest accessories—classic skirts play well with all of them, making your wardrobe work harder and smarter. And if you’re on the hunt for the perfect gift, these skirts are a total win for your bestie, your sister, or anyone who loves a wardrobe staple that never goes out of style. Imagine the look on her face when she unwraps a piece that’s equal parts chic and versatile—now that’s how you earn best gift-giver status. Whether you’re dressing for a big presentation, a first date, or just want to stroll through the city with a little extra pep in your step, classic skirts are your go-to for confidence and comfort.

Let’s be real, trends come and go, but a classic skirt is forever. It’s the piece you’ll reach for when you need to feel powerful, playful, or just plain gorgeous. The best part? Styling possibilities are endless, whether you’re layering up with cozy knits or keeping it breezy with a simple cami. Don’t be afraid to play with textures, colors, or even a little sparkle—classic doesn’t mean boring, babe. If you’re ready to level up your skirt game and discover the pieces that’ll have you serving looks on repeat, check out our Best Skirts page for even more inspo. Because when you find that skirt that hugs you just right, it’s not just fashion—it’s a whole mood.

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