Twill Skirts

Twill skirts are your new wardrobe MVP, ready to take you from brunch dates to late-night adventures with style and ease. These beauties bring a little texture and a lot of flair, making sure you stand out in every crowd. Whether you're pairing them with your favorite graphic tee for a casual vibe or dressing them up with heels for that special occasion, twill skirts are the versatile staple every Windsor girl needs. So go ahead, strut your stuff and let these skirts do all the talking—because why blend in when you were born to stand out?

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Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

A black midi skirt featuring a high-rise fit, ruching, and an asymmetrical high-side slit.

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.

Windsor So Perfect Mid-Rise Pleated Denim Mini Skirt

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Windsor So Perfect Mid-Rise Pleated Denim Mini Skirt

$11.97 $36.90 68% off

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

Trendsetter Mid-Rise Belted Twill Skort in Olive

$34.90

An olive green twill skort featuring a belted mid-rise waist, bodycon fit, and four-pocket styling.

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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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

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Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural

$9.97 $32.90
70% off

(4)

Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades! Fit & FeaturesCrochet fabric, stretchy knit lining, High-rise elasticized waist, High front slit, Flowy maxi-length silhouette, Runs true to size , Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top Free Shipping on All Orders Over $75. | Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural | Size: L | Knit Fabric

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

Sale

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

Twill Skirts

When you’re ready to level up your style game, twill skirts are your go-to BFF—always down for whatever, always looking flawless. There’s just something about that crisp, structured fabric that adds instant polish to any look. Whether you’re running from class to coffee dates or plotting a spontaneous night out, a twill skirt has you covered. Picture this: you slip into a pleated midi twill skirt, tuck in your favorite graphic tee, and suddenly you’re serving main character energy with zero effort. That’s the magic of twill—effortless, versatile, and endlessly remixable. Twill mini skirts are just as iconic, giving you that perfect blend of flirty and fierce. Pair one with a slouchy sweater and chunky boots, and you’re ready to strut your stuff down the hallways, sidewalks, or wherever your day takes you. These aren’t just wardrobe staples—they’re confidence boosters, conversation starters, and the perfect excuse to take the long way around just to be seen.

Shopping for a twill skirt is all about finding your vibe and owning it. Maybe you’re all about that tailored look, cinched at the waist and pleated just right, or maybe you love the laid-back feel of a classic mini with deep pockets for your phone and lip gloss. Twill’s durability means you can live your life out loud without worrying about wear and tear—these skirts are built for adventure. They’re also the ultimate gift for your fashion-forward bestie or that sister who’s always “borrowing” your clothes. Imagine wrapping up a twill mini skirt with a handwritten note, knowing you’re giving her a piece she’ll wear on repeat. And let’s be real: twill skirts are made for making memories, whether you’re dancing at a festival, acing a presentation, or just snapping selfies with your crew. They transition seamlessly from day to night, from laid-back hangs to dressed-up moments, always keeping you one step ahead of the style curve.

For those who love to mix things up, don’t sleep on pairing your twill skirt with unexpected textures and layers—think ribbed knits, faux leather jackets, or even a bold pair of patterned tights. The beauty of twill is how it plays well with literally everything in your closet, letting you experiment and express your mood, no matter the occasion. If you’re craving even more ways to switch up your skirt game, check out our Tie Front Skirts for a fun twist on classic silhouettes. Whether you’re curating your own closet or looking for that standout piece to gift someone special, twill skirts are the ultimate power move—versatile, stylish, and always ready for the next adventure.

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