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 knit midi skirt with high-rise fit, ruching, and an asymmetrical high-side 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.

Windsor Soft Allure Asymmetrical Midi Skirt in Navy Blue

$26.90

A navy blue stretch knit midi skirt featuring ruched detailing, an asymmetrical hem, and a side slit.

Swipe Right High Slit Midi Skirt in Black

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Swipe Right High Slit Midi Skirt in Black

$29.90

A black knit midi skirt featuring a high-rise waist, flowy silhouette, and dramatic high front slit.

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Wild At Heart Long Fringe Skirt in Tan

$29.90

(36)

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: XS | 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: S

First Take Micro Slit Mini Skirt in Black

$14.90

(10)

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 Sleek Status Faux Leather Mini Skirt in Black

$19.90

(9)

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

Windsor Trendy Moves Long Fringe Skirt in Black

$36.90

(7)

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: XS

Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue

$36.90

(6)

A maxi skirt that feels like slipping into vacation mode without even trying. The soft floral print mesh hugs just right, giving you that effortless “I’m ready for whatever” confidence—day plans or date nights included. Shop Matching Top: Vacay Bloom Floral Mesh Halter TopFit & FeaturesSheer mesh fabric with knit lining, high stretch, Large floral print, High-rise waist, Ruching, High-cut side slit, Maxi-length hem, form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Throwback Cool Denim Cargo Mini Skirt

$39.90

(5)

Low-rise nostalgia meets modern street style—this denim cargo mini skirt is made for layering with baby tees, tanks, or oversized fits. The pocket detail gives it that effortless “just stepped out of an early 2000s music video” energy. Fit & FeaturesDenim fabric with color fade effect, Mid-rise waist, Cargo-style front and side pockets, Fitted mini-length hem, Front button closure, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Throwback Cool Denim Cargo Mini Skirt | Size: XL

Windsor After Dark Flutter Mini Skirt in Black

$29.90

(5)

Sleek with a little edge, this mini skirt is made for plans that don’t end early. The smooth knit finish and subtle butterfly detail bring just enough intrigue, while the side slit keeps things flirty without trying too hard. Fit & FeaturesSmooth knit fabric with stretch, Low-rise waist, High front slit with subtle butterfly detailing, Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor After Dark Flutter Mini Skirt in Black | Size: S | Knit Fabric

Sweet Like Summer Crochet Maxi Skirt in Ivory

$46.90

(4)

Sweet like summer, this crochet maxi skirt was made to flirt. With a high-rise waist, scalloped trim, and high-cut side slit, it's your new go-to for coastal vibes. Style with the matching bralette top. Shop Matching Top: Sweet Like Summer Crochet Bralette TopFit & FeaturesSheer crochet knit fabric, moderate stretch, High-rise waist, scalloped trim, Adjustable tie-front drawstring, Thigh-high side slit, Maxi-length fitted silhouette, scalloped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Like Summer Crochet Maxi Skirt in Ivory | Size: M | Knit Fabric

Life Of The Party Lace-Up Mini Skirt in Brown

$42.90

(4)

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: S | Leather

Midi Skirts For Fall

There’s something about fall that makes you want to slow down, savor the air, and—let’s be honest—completely reinvent your closet. If you’re feeling that seasonal urge for a style refresh, midi skirts for fall are the ultimate power move. These skirts are the sweet spot between effortless and elevated, giving you room to play with textures, layers, and all those rich autumnal hues that suddenly feel right again. Picture yourself in a cozy coffee shop, wrapped in a chunky knit, your favorite midi skirt swishing just above a pair of knee-high boots. Or maybe you’re heading to a friend’s birthday dinner, pairing a suede midi with an oversized blazer and a pop of gold jewelry. This is the kind of piece that carries you from crisp mornings to golden-hour hangs, no outfit change required. Fall midi skirts aren’t just about looking good—they’re about feeling ready for whatever the day throws at you, whether that’s a spontaneous road trip, a last-minute office meeting, or an impromptu brunch that turns into a whole afternoon out.

When you’re shopping for a midi skirt for fall, it’s all about versatility and texture. Think buttery faux leather, plush knits, or structured denim—each one brings its own vibe, and you get to decide how you want to show up. Deep, saturated colors like burgundy, olive, and camel instantly set the mood for the season, while pleated styles add movement and slip skirts bring a touch of understated glam. If you’re gifting, midi skirts are a genius choice for the friend who’s always layering or the sister who claims she “never has anything to wear.” They’re universally flattering and easy to style, so you know they’ll get real use—plus, they’re a dream for anyone who loves to mix and match. Pair with ankle boots for a downtown edge, or go classic with pointed-toe heels for a leg-lengthening effect. Tuck in a turtleneck, throw on a cropped jacket, and you’re set. The best part? Midi skirts are seasonless staples that transition seamlessly from the first hint of a chill right through those early spring days when you’re still not ready to ditch your boots.

If you’re building out your fall wardrobe or just want one piece that does the heavy lifting, midi skirts are as practical as they are photogenic. They’re made for those in-between temps and unpredictable forecasts—layer up with tights and a sweater, or keep it simple with a fitted tee and a denim jacket. From romantic pleats to modern cargo styles with pockets (because yes, we need them), fall midi skirts meet you wherever your style lands. And if you’re ready to explore even more ways to wear this closet MVP, take a look at our Midi Length Skirts collection for endless inspiration. Whether you’re planning outfits for cozy nights in or statement-making days out, these skirts are your ticket to feeling pulled-together, comfortable, and totally yourself—no matter how many times you hit snooze.

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