Pleated Fashion Skirts

Pleated fashion skirts are having their moment, and let’s be real, they’re here to stay! Whether you're strutting down the street or twirling on the dance floor, these skirts add that extra flair to your every move. Perfect for channeling those effortlessly chic vibes, pleated skirts are the ultimate wardrobe staple that can take you from day to night without missing a beat. From playful minis to elegant midis, these skirts are all about embracing fun and fearless style. So go ahead, unleash your inner fashionista and let those pleats do the talking!

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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.

Preppy Please Striped Pleated Knit Skort in Black

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Preppy Please Striped Pleated Knit Skort in Black

$11.97 $39.90 70% off

A high-rise black knit skort with a preppy pleated silhouette and striped mini-length hem.

So Perfect Mid-Rise Pleated Denim Mini Skirt

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So Perfect Mid-Rise Pleated Denim Mini Skirt

$11.97 $36.90 68% off

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

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.

Fierce And Trendy Mid-Rise Leopard Mini Skort

$36.90

A leopard print denim mini skort featuring a belted mid-rise waist and pleated skirt overlay.

Style Game High-Rise Buckle Pleated Mini Skort in Black

$32.90

A chic black mini skort with a high-rise waist, faux leather buckles, and pleated hem.

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.

Flirt Alert Plaid Lace-Up Mini Skirt in Navy Blue

$39.90

A navy blue plaid mini skirt featuring a lace-up high waist and flouncy woven fabric hem.

Adorably Chic Pleated Linen Mini Skort in Natural

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Adorably Chic Pleated Linen Mini Skort in Natural

$9.97 $36.90 73% off

A natural linen-blend skort featuring a pleated A-line mini overlay and hidden fitted shorts.

Talk About Me Mid-Rise Pleated Denim Skort in Med Denim

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Talk About Me Mid-Rise Pleated Denim Skort in Med Denim

$9.97 $39.90 75% off

A medium denim skort featuring a pleated mini skirt overlay and edgy exposed pockets.

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.

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

$34.90

(16)

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: XL | Cotton

Charming Allure Drop Waist Tiered Lace Skort in Ivory

$29.90

(8)

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

Windsor It-Girl Sparkle Rhinestone Denim Skort in Black

$44.90

(7)

Built for the spotlight, this rhinestone denim skort gives it-girl after-hours energy. With its high-rise waist and body-hugging fit, it’s your go-to when you want all eyes on you. Shop Matching Top: It-Girl Sparkle Rhinestone Denim Halter TopFit & FeaturesDenim fabrication with rhinestone embellishments, Mid-rise waist, Mini-length skort design with back shorts lining, Front zipper and button closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor It-Girl Sparkle Rhinestone Denim Skort in Black | Size: M

Buckle Down Denim Mini Skort in Brown

$39.90

(7)

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

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

Windsor Casual Look Denim Mini Skort in Brown

$34.90

(6)

Hop into this denim mini skort in brown and flaunt your style! With a high-rise waist and cheeky front slits, this skort is your go-to for a fab, form-hugging fit. Fit & FeaturesDenim fabric, High-rise waist, Back zipper closure, Dual short front slits, Mini-length overlay, fitted shorts, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casual Look Denim Mini Skort in Brown | Size: XL

Admirable Style High-Rise Ponte Mini Skort in Black

$24.90

(5)

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: S | Knit 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

Fierce And Trendy Mid-Rise Leopard Mini Skort

$36.90

(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

Pleated Fashion Skirts

There’s just something about pleated skirts that feels like instant polish—no overthinking required. Maybe it’s the way those crisp folds catch the light, adding movement to every step, or how a pleated silhouette can play both sides: classic and cool, preppy and playful, romantic and rebellious. Pleated fashion skirts are the kind of wardrobe MVPs that work overtime, especially when the calendar flips to December and your social life suddenly demands a little extra effort. Whether you’re dressing for a holiday dinner, a last-minute office party, or just trying to look put together for a coffee run (because “cozy” and “cute” are not mutually exclusive), pleated skirts style your look with zero fuss. There’s a reason they’ve never really gone out of style—they’re endlessly adaptable, universally flattering, and somehow always just right for the moment.

When you’re thinking about adding a windsor pleated skirt to your closet, the first thing to consider is how you want it to move with your life. If you’re after something with a little edge, a double pleated mini skirt brings that extra volume and bounce—perfect for pairing with chunky boots or a fitted turtleneck and tights when the weather calls for layers. For those who love a bit of drama, a midi or maxi pleated skirt swishes with every step, making even a grocery run feel like a main character moment (without ever saying it out loud). Sizing is key with pleated skirts: size small is a great starting point if you love a more tailored fit, but don’t be afraid to try different lengths and rises to find your sweet spot. Pleats have a way of flattering curves, skimming over hips, and giving just enough structure to feel intentional but never stiff. And if you’re gifting? Pleated skirts are a thoughtful pick for anyone who loves to experiment with their style or needs a closet refresh—think sisters, best friends, or even a fashion-forward mom who isn’t afraid to try something new. They wrap up beautifully and feel a little more special than your average sweater.

Styling pleated skirts is where the fun really starts. There’s no one way to wear them: tuck in a slouchy knit for that effortless winter brunch vibe, layer with a cropped jacket for a night out, or keep it simple with a fitted tee and sneakers for everyday errands. The beauty is in the mix—textures, prints, and even the pleat width can change the whole mood of your outfit. If you’re feeling bold, try a double pleated skirt for extra dimension, or go for metallics and jewel tones that pop against neutrals during the colder months. Pleated skirts also transition seamlessly from day to night, making them a smart investment for your wardrobe rotation. And if you’re building your collection, or just need a little more inspiration, you can always browse the full range of Pleated Skirts for even more ways to make the trend your own. However you wear them, pleated skirts are the answer to those “I have nothing to wear” days—bringing a little movement, a lot of style, and just the right amount of confidence to every occasion.

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