Midi Skirts For Fall

Midi Skirts For Fall are totally having a moment, and you’re about to be the main character. Whether you’re plotting your next coffee run or turning sidewalks into your personal runway, these midi skirts are ready to level up your vibe. From brunch dates to last-minute adventures, get ready to twirl, strut, and sashay through the season with major confidence. Your closet’s new MVP? You just found it.

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Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

A black stretchy midi skirt featuring ruching and an asymmetrical high-side slit for chic occasions.

Windsor Trendy Match Chevron Knit Midi Skirt in Natural

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Windsor Trendy Match Chevron Knit Midi Skirt in Natural

$9.97 $39.90 75% off

A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.

Heavenly Match Floral Slit Midi Skirt in Brown

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Heavenly Match Floral Slit Midi Skirt in Brown

$9.97 $34.90 71% off

A brown floral mesh midi skirt with a high-rise waist and sultry front slit.

Daydream Flow Plaid Chiffon Skirt in Brown

$39.90

A brown plaid chiffon skirt featuring a flowy A-line silhouette and an asymmetrical handkerchief hem.

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-cut 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

$11.97 $36.90 68% off

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

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Sweet Stroll Ruched Midi Skirt in Black

$11.97 $39.90 70% off

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

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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

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: XS

Keep A Secret Lace Slit Maxi Skirt in Black

$39.90

(9)

Make a statement in this lace slit maxi skirt. With sheer lace, ruching, and a high slit, it's your go-to for that effortlessly chic vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, High front slit, Maxi-length hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep A Secret Lace Slit Maxi Skirt in Black | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric

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: L

Windsor Trendy Moves Long Fringe Skirt in Black

$36.90

(3)

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

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Strut It Out Abstract Zebra Maxi Skirt in Brown

$9.97 $34.90
71% off

(3)

Perfect your vibe with the strut it out abstract zebra maxi skirt. This sheer mesh beauty flaunts a zebra print and mid-rise waist for a fierce look. Pair it with the matching top for ultimate style. Fit & FeaturesSheer mesh fabrication lined with stretchy knit, Mid-rise waist, Zebra print, Maxi length hem, Runs true to size, Shop Matching Top: Strut It Out Abstract Zebra Tie-Front Top Free Shipping on All Orders Over $75. | Windsor Strut It Out Abstract Zebra Maxi Skirt in Brown | Size: L | Mesh Fabric/Sheer Mesh Fabric

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Go With The Vibe Slit Midi Skirt in Rust

$9.97 $26.90
63% off

(3)

Embrace your daring side and let this midi skirt elevate your look. Its sleek high-rise waist and side slit highlight your confidence and flair, perfect for making a statement at any event. Pair with the matching top. Shop Matching Top: Go With The Vibe Halter Crop TopFit & FeaturesSlinky knit stretchy fabric, High-rise waist, Side pleated hip seam, High side slit, Form-hugging silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Go With The Vibe Slit Midi Skirt in Rust | Size: M | Knit Fabric/Stretchy Fabric

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Serving Prep & Sass Bubble Mini Skirt in Light Blue

$9.97 $32.90
70% off

(2)

This skirt said “main character energy” and meant it. With a playful bubble mini hem and classic pinstripe print, she’s made for casual hangs, day dates, and being the moment. Fit & FeaturesPinstriped print, cotton woven fabric, sewn-in woven lining, High-rise waist, Side zipper and hook-eye closure, Flouncy bubble mini hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Serving Prep & Sass Bubble Mini Skirt in Light Blue | Size: L | Cotton/Woven Fabric

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

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: L | Leather

Midi Skirts For Fall

As the crisp air settles in and the leaves start showing off, there’s something about a fall midi skirt that just feels right. It’s the sweet spot between breezy summer minis and bundled-up winter maxis—offering that effortless transition from sun-drenched afternoons to sweater-weather evenings. Whether you’re dashing out for a pumpkin spice run, heading to class, or mapping out your next apple orchard photo op, midi skirts are the low-key MVPs of your autumn wardrobe. They’re the kind of piece you reach for when you want to look put together without trying too hard, pairing just as easily with chunky knits and ankle boots as they do with sleek turtlenecks and your favorite sneakers. The magic is in the versatility: a fall midi skirt can handle a morning meeting, a cozy dinner date, and everything in between—no outfit change required. It’s the not-so-secret weapon for those “I have nothing to wear” mornings, especially when you want a look that’s equal parts comfort and cool.

Gifting a midi skirt for fall? It’s a move that says you really get her style—and her schedule. These skirts make thoughtful presents for sisters, best friends, or roommates who are always on the go and need pieces that flex with their plans. They’re also a smart pick for anyone building a capsule wardrobe, since midi skirts layer beautifully with tights and jackets as the weather shifts. Think about the friend who’s always mixing up her look, or the one whose closet is a masterclass in neutral layering—she’ll appreciate a midi that goes from campus to coffee dates to weekend getaways without missing a beat. Even if you’re just treating yourself, a fall midi skirt is basically an investment in outfit options. It’s the piece that lets you play with proportions, textures, and patterns—think cozy ribbed knits, soft suedes, or bold autumn florals—while still keeping things practical for real life. And let’s be honest: there’s something about the way a midi skirt moves that just makes you want to twirl, even if it’s just in your living room.

When you’re shopping for midi skirts this season, pay attention to the details that make a difference—like a comfortable waistband, a flattering silhouette, and fabric that holds up to both spontaneous plans and repeat wears. Look for styles that feel true to you, whether that means a classic A-line, a flowy pleated number, or something with a little edge like a faux leather finish. Midi skirts are all about balance: they give you coverage for chillier days but still show off a bit of leg, especially when paired with boots or statement socks. Don’t be afraid to mix and match textures, layer up with oversized sweaters, or add a belt for a little extra definition. The best part? Midi skirts are made to move with you, offering the perfect blend of style and ease for everything autumn throws your way. If you’re ready to explore even more options and discover styles that fit your unique fall vibe, check out our curated collection of Midi Length Skirts—your next go-to look is waiting.

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