Midi Length Pleated Skirts

Midi Length Pleated Skirts are having a major moment—and honestly, it’s about time. Effortlessly polished with just the right amount of movement, these skirts bring instant energy to any outfit, whether you’re dressing for brunch, work, or that last-minute night out. Pair them with your favorite sneakers for a laid-back vibe or heels when you want to turn up the drama—either way, you’ll nail that sweet spot between classic and current. Ready to give your closet the refresh it deserves? Midi Length Pleated Skirts are here to make getting dressed feel easy (and a little more fun).

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Windsor Slip Into Elegance Satin Lace Midi Skirt in Burgundy

$49.90

A burgundy satin midi skirt featuring a high-rise waist, lace side panel, and flared hem.

Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

A black stretchy knit midi skirt with high-rise fit, ruching, and an asymmetrical high-side slit.

Windsor Untamed Bloom High-rise Slit Midi Skirt in Leopard

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Windsor Untamed Bloom High-rise Slit Midi Skirt in Leopard

$7.97 $36.90 78% off

A bold leopard mesh midi skirt featuring a high-rise waist, floral accents, and a flirty side slit.

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Sweet Stroll Ruched Midi Skirt in Black

$7.97 $39.90 80% off

A black cotton-blend midi skirt featuring adjustable side ruching and a relaxed, mid-rise silhouette.

Quiet Drama Pleated Midi Skirt in Black

$49.90

A black faux leather midi skirt featuring accordion pleats and a high-rise, A-line silhouette.

Chic Confidence High Slit Mesh Midi Skirt in Black

$26.90

A black mesh midi skirt featuring a ruched waist, high-rise fit, and dramatic thigh-high front slit.

Chic Allure High-Slit Midi Skirt in Burgundy

$29.90

A burgundy knit midi skirt featuring a high-rise waist, front ruching, and an asymmetric high side slit.

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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

Windsor 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: S

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So Perfect Mid-Rise Pleated Denim Mini Skirt

$7.97 $36.90
78% off

(2)

The perfect denim mini skirt will elevate your everyday style with a trendy pleated silhouette and a flattering mid-rise waist. Complete the look with a graphic tee. Fit & FeaturesDenim fabric, minimal stretch, Mid-rise waist with seam detailing, Front button and hidden zipper closure, Pleated silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Perfect Mid-Rise Pleated Denim Mini Skirt | Size: M

Life Of The Party Lace-Up Mini Skirt in Brown

$42.90

(2)

This faux leather skirt gives life to the party vibes! It has lace-up sides that demand attention, a high-rise waist, and a flattering form-hugging fit that shows off your figure. Fit & FeaturesFaux leather fabric, High-rise waist, Back zipper closure, Side lace-ups , Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Life Of The Party Lace-Up Mini Skirt in Brown | Size: M | Leather

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

Windsor 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: L

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Windsor Wild Card Leopard Floral Print Maxi Skirt

$14.97 $36.90
59% off

(2)

This skirt’s got plot twist energy—sweet florals meet fierce leopard in a ruffled maxi made for your wild side. Let the bold print and thigh-high slit steal the spotlight from brunch to beach nights. Fit & FeaturesSheer mesh fabric with mini-length knit lining, high stretch, Leopard and floral multi-print pattern, High-rise waist, Ruching, hip-hugging fit, Thigh-high side slit, ruffled hem, Maxi-length hem, flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild Card Leopard Floral Print Maxi Skirt | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Windsor 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: L

Windsor Chic Confidence High Slit Mesh Midi Skirt in Black

$26.90

(2)

When subtle isn’t the move, this mesh midi skirt delivers. With a thigh-high slit and ruched waist, it’s the kind of style that owns the night and brings the confidence. Fit & FeaturesSheer mesh fabric with knit lining, high stretch, High-rise waist, ruching, Ultra-high front slit, Asymmetric midi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Confidence High Slit Mesh Midi Skirt in Black | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Midi Length Pleated Skirts

Midi length pleated skirts are the unsung heroes of a modern closet—equal parts classic and effortlessly current, with just enough movement to make every step feel cinematic. There’s something about the way pleats catch the light and sway with you that turns even a simple sidewalk stroll into a main character moment (without the cliché). If you’re shopping for yourself, think of a midi pleated skirt as your go-to for those days when you want to look polished but not precious. They’re the ultimate “throw it on and go” piece: tuck in a turtleneck and add boots for a winter-ready look, or pair with a cropped sweater and sneakers when you’re running late but still want to look intentional. The midi length does wonders for all heights and body types, hitting that sweet spot between playful and put-together. It’s long enough to keep you covered on chilly December mornings, but breezy enough to layer over tights or under a statement coat. Pleated skirts also have a way of making even your simplest tops feel instantly elevated—like you just know what you’re doing, even when you’re winging it.

If you’re on the hunt for a gift that’s both personal and universally flattering, a midi pleated skirt is a low-risk, high-reward option. It’s the kind of piece your best friend will text you about after her first wear, or your sister will “borrow” and never return. For the friend who’s always overdressed (in the best way), it’s a canvas for her boldest accessories. For the minimalist, it’s a chance to play with texture and subtle shine without straying from her comfort zone. Even if you’re shopping for someone whose style changes with the weather—or their mood—pleated midis are adaptable enough to keep up. Picture her styling it with a cozy knit and ankle boots for holiday brunch, or swapping in a graphic tee and denim jacket when spring finally rolls around. And if you’re curating your own wardrobe, this is the kind of staple you’ll reach for year after year, no matter how your style evolves. The beauty of pleated skirts lies in their versatility: they’re equally at home at office parties, family dinners, or last-minute coffee dates, making them a smart addition to any rotation.

When you’re weighing your options, pay attention to the details that matter most to you. Fabric choice can totally shift the vibe—think metallics for a hint of drama at winter gatherings, or soft satins for a more romantic, everyday feel. A defined waistband can work wonders for highlighting your shape, while an elastic waist gives you that all-day comfort (and room for dessert, just saying). If you’re all about a tailored silhouette, check out styles with a structured high waist for a little extra polish; our Pleated High Waist Skirts page is a great place to start if that’s your vibe. Don’t be afraid to mix it up with prints or unexpected color—pleats are surprisingly forgiving, and a bold skirt can be the anchor for so many different looks. Whether you’re building a capsule wardrobe or just looking for a fresh way to update your winter style, midi length pleated skirts are the kind of piece that works as hard as you do. They’re proof that practical doesn’t have to mean boring, and that a little movement in your outfit can go a long way in making every day feel a bit more special.

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