Pleated High Waist Skirts

Pleated high waist skirts are your new wardrobe BFFs, ready to add a touch of flair and finesse to any outfit you dream up. Whether you're strutting down the city streets or twirling at a garden party, these skirts have got your back, bringing that perfect blend of elegance and edge. With their flattering silhouette and playful pleats, they’re here to make sure every step you take feels like a runway moment. So get ready to turn heads and break hearts because when you slip into one of these beauties, you're not just wearing a skirt—you're making a statement.

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Cool-Girl Vibes Faux Leather Wrap Skort in Black

$22.90

A sleek black faux leather wrap skort with a high-rise waist and pleated detailing.

School's Out High-Rise Pleated Ponte Skort in Black

$29.90

A black pleated ponte skort with a high-rise waist and mini-length hem for a preppy look.

Style Game High-Rise Buckle Pleated Mini Skort in Black

$32.90

A black ponte mini skort with a high-rise waist and chic faux leather buckle accents.

Windsor Feeling Cool Pleated Faux Leather Mini Skort in Black

$32.90

A black faux leather mini skort with a high-rise waist and pleated silhouette for stylish outings.

Windsor Around The City Mid-Rise Pleated Skort in Brown

$32.90

A vintage-inspired brown faux leather skort with pleated overlay and stretchy knit shorts lining.

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Keep It Cool Mid-Rise Acid-Wash Denim Skort in Black

$34.90

(18)

Capture cool vibes in this on-trend acid-wash denim skort! Designed with a cotton-blend denim fabric, the skort offers a moderate stretch. The flattering mid-rise waist leads to a mini-length overlay over hidden fitted shorts for coverage. The skort features a classic five-pocket and belt loop design and a hidden front zipper and button closure. Style with a graphic tee and combat boots for an edgy-chic concert look. Fit & FeaturesAcid wash cotton-blend denim fabric, moderate stretch, Mid-rise waist, Five-pocket and belt loop design, hidden front zipper, button closure, Mini-length overlay, hidden fitted shorts, Form-hugging fit, Skort in size small has a 10" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep It Cool Mid-Rise Acid-Wash Denim Skort in Black | Size: XS | Cotton

Charming Allure Drop Waist Tiered Lace Skort in Ivory

$29.90

(9)

Look and feel charming in this lace skort designed with flirty ruffles and knit-fitted shorts for coverage. Pair with a jean jacket. Fit & FeaturesMesh floral lace fabrication, moderate stretch, Drop waist, Tiered-ruffles, Mini skirt-like overlay, Knit fitted shorts, Skort in size small has an 8" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Charming Allure Drop Waist Tiered Lace Skort in Ivory | Size: L | Lace Fabric

Buckle Down Denim Mini Skort in Brown

$39.90

(8)

This isn’t just a skort—it’s a serve. Buckle straps + a form-hugging fit = instant upgrade to your “I just threw this on”.Fit & FeaturesDenim fabric, stretchy shorts lining, Mid-rise waist, dual side buckle straps, Back zipper and hook-eye closure, Form-hugging fit, Skirt overlay with hidden snap-button closure, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Buckle Down Denim Mini Skort in Brown | Size: XL

Windsor Admirable Style High-Rise Ponte Mini Skort in Black

$24.90

(7)

Bring on the compliments in this high-rise skort featuring a flattering A-line silhouette and mini-length hem. The smooth ponte knit fabric offers a polished look and plenty of stretch. Fit & FeaturesPonte knit fabric, shorts lining, moderate stretch, High-rise waist, A-line silhouette, Mini-length hem, Skort has a 11.5” front rise with a 1.5” inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Admirable Style High-Rise Ponte Mini Skort in Black | Size: L | Knit Fabric

School's Out High-Rise Pleated Ponte Skort in Black

$29.90

(6)

Achieve a preppy look with this pleated ponte skort in a flattering high-rise waist and mini-length perfect for showing off boots or flats! Fit & FeaturesPonte knit fabric, shorts lining, High-rise waist, Pleated skirt overlay, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor School's Out High-Rise Pleated Ponte Skort in Black | Size: S | Knit Fabric

Polished Edge Ruffle Bouclé Skort in Black

$42.90

(6)

This bouclé lurex mini skort serves polished-but-playful energy — sparkly woven texture, gold button details, and a flirty ruffle hem that ties the whole “effortlessly chic” vibe together. It’s giving a holiday party, a gallery opening, and any night you want to look expensive without even trying. Shop The Matching Jacket: Polished Edge Crop Bouclé JacketFit & FeaturesBouclé lurex woven fabrication, sewn-in lining, Mini skort silhouette with flounce ruffle hem, Decorative button and pocket detailing, Hidden shorts for comfort, Back zipper and hook-eye closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Polished Edge Ruffle Bouclé Skort in Black | Size: L | Woven Fabric

Perfection High-Rise Ruffled Mini Skort in Black

$34.90

(5)

The perfect ruffled skort that will turn heads with every wear! Fit & FeaturesKnit fabric, High-rise waist, Ruffled mini-length skirt overlay, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfection High-Rise Ruffled Mini Skort in Black | Size: S

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Fierce And Trendy Mid-Rise Leopard Mini Skort

$9.97 $36.90
73% off

(4)

Unleash your fierce and trendy side in this leopard mini skort! The belted waist and pleated skirt overlay create a trendy look while the mini hem shows off your legs. Fit & FeaturesLeopard print, denim fabric, Mid-rise belted waist, belt loop accents, Pleated skirt overlay, side zipper closure, Shorts lining, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fierce And Trendy Mid-Rise Leopard Mini Skort | Size: M

Style Game High-Rise Buckle Pleated Mini Skort in Black

$32.90

(4)

Level up your style game in this ponte mini skort this weekend! This skort features a high-rise waist with faux leather buckle accents, adding a touch of chic edginess. The pleated mini-length hem adds flirty movement, while the shorts lining ensures comfort and coverage. Complete the look in a cute graphic tee and sneakers. Fit & FeaturesPonte knit fabric, stretchy knit shorts lining, High-rise waist with faux leather buckle accents, Pleated mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Style Game High-Rise Buckle Pleated Mini Skort in Black | Size: L | Leather/Knit Fabric

Windsor Simple And Chic Ponte Knit Mini Skort in Black

$27.90

(4)

Simple and chic, this ponte knit mini skort will elevate your casual looks. It features a mid-rise waist, a mini-length overlay with a double slit design, and hidden shorts for coverage. Fit & FeaturesPonte knit fabric, moderate stretch, Mid-rise waist, Mini-length overlay, Double slit side design, Hidden fitted shorts, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Simple And Chic Ponte Knit Mini Skort in Black | Size: XS | Knit Fabric

Pleated High Waist Skirts

There’s a reason the pleated high waisted skirt has never truly left the style conversation—it’s the ultimate wardrobe chameleon, ready to transform with you from season to season, mood to mood. Right now, as winter settles in and layering becomes an art form, these skirts are the unsung heroes of cold-weather dressing. Picture this: soft knits tucked into a high-waisted pleated skirt, tights and boots adding warmth, and a tailored coat thrown over your shoulders for a look that’s equal parts cozy and polished. Whether you’re braving frosty mornings on campus, dashing off to a last-minute dinner, or just want to feel a little more put together for a coffee run, the pleated silhouette brings movement and dimension that makes even the simplest outfit feel intentional. The high waist flatters every curve, cinching you in just right and letting you play with proportions—crop tops, oversized sweaters, fitted turtlenecks, you name it. If you’re shopping for yourself or scouting a gift for that friend who’s always ahead of the trend curve, a windsor pleated skirt is the kind of present that doesn’t just get worn once for the ‘gram—it gets lived in, loved, and styled on repeat.

When it comes to purchase considerations, versatility is the name of the game. A pleated high waisted skirt is that rare piece that looks as good with sneakers as it does with heels, and transitions seamlessly from day to night with a quick change of accessories. Think about fabric—lightweight chiffons and airy satins add a touch of romance, perfect for layering over tights or under chunky knits in December, while structured materials like faux leather or heavier crepe bring a modern edge and extra warmth. Length is another detail to play with: a mini high waist pleated skirt feels playful and flirty, while a midi or maxi length channels effortless sophistication (and pairs beautifully with knee-high boots). These skirts aren’t just for one aesthetic, either; they work for preppy, edgy, vintage-inspired, and minimalist wardrobes alike. If you’re gifting, consider the recipient’s style—do they love a dramatic twirl moment, or are they more about subtle texture? Either way, the high-waisted pleated skirt is a thoughtful choice that feels personal without being prescriptive. It’s the kind of piece that says, “I see your style, and I know you’ll make this your own.”

Styling a high waist pleated skirt is all about self-expression. Some days call for a crisp button-down and loafers for that “I’ve got my life together” energy; other days, it’s all about a slouchy sweater and combat boots for a little attitude. The beauty lies in the details—belt it for extra definition, layer with a statement jacket, or let the skirt’s movement do all the talking. And let’s be real: December is peak “what do I wear to this?” season, with holiday parties, family gatherings, and spontaneous nights out filling up the calendar. A pleated skirt takes the guesswork out of getting dressed, giving you endless options without the stress. It’s also a lifesaver for those “I have nothing to wear” mornings, because it instantly elevates your basics and makes even a simple tee look intentional. If you’re ready to explore even more ways to style and shop this timeless favorite, check out our full collection of Pleated Skirts for inspiration that’ll carry you through every season, every vibe, and every last-minute invite.

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