Trendy Midi Skirts

Ready to turn the sidewalk into your personal runway? Trendy midi skirts are here to elevate your style game, bringing that perfect blend of chic and effortless flair you’ve been dreaming of. Whether you're strutting into a brunch date or owning the dance floor, these skirts are your go-to for making every moment a fashion statement. With their versatile lengths and eye-catching designs, they’re the ultimate wardrobe staple for any Windsor girl who’s not afraid to stand out. Get ready to twirl, swirl, and make heads turn with these must-have pieces!

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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.

Windsor Trendy Moves Long Fringe Skirt in Black

$36.90

A black knit skirt featuring a high-rise waist, long flowy fringe, and built-in cheeky shorts.

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.

Wild At Heart Long Fringe Skirt in Black

$29.90

A trendy black faux suede skirt with a high-rise waist and long fringe detailing.

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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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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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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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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

Trendy Midi Skirts

Ready to live your main character moment? Midi skirts are your ticket to that sweet spot between easy-breezy and totally put-together. They’re the ultimate wingwoman—flirty enough for rooftop brunches, polished enough for big-deal meetings, and comfy enough for those spontaneous road trips with your ride-or-die crew. Picture yourself stepping out in a cool midi skirt, the kind that catches the light and every eye in the room, with a silhouette that flatters every curve and a vibe that says, “Yeah, I woke up like this.” The best part? Midi skirts are that rare find that works for every mood, every plan, and every last-minute change of heart. Dress one up with strappy heels and a fitted top to channel boss energy, or throw on your favorite sneakers and a graphic tee for a look that’s all about laid-back glam. Whether you’re gifting your bestie a little extra confidence for her birthday, surprising your sister with a wardrobe upgrade, or treating yourself (because, hello, you deserve it), midi skirts are the kind of present that keeps on giving—endless styling options, endless compliments, endless fun.

Let’s be real: nothing feels quite like the swish and sway of a midi skirt when you’re strutting down the street or twirling on the dance floor. There’s something about that length—it gives you coverage without cramping your style, lets you move freely, and always leaves room for a little leg reveal when you’re feeling cheeky. And if you’re all about versatility, midi skirts are your new BFF. Go for a sleek, body-hugging fit when you want to serve up some serious glam, or choose a flowy, pleated style for those days when you want to twirl & swirl windsor with zero effort. Midi skirts are also a dream for mixing and matching—pair them with crop tops, oversized sweaters, or even a sharp blazer for a look that’s as unique as your group chat banter. They’re the go-to piece for anyone who wants to look cute without trying too hard, and they’re perfect for those in-between plans when you’re not sure where the night will take you. And if you’re looking for something a little extra, don’t miss the chance to explore our Elegant Midi Skirts collection for styles that bring the drama and the dazzle.

Midi skirts are basically the secret sauce to a wardrobe that works as hard as you do. They’re the piece you’ll reach for when you want to feel unstoppable, whether you’re heading to a concert, a coffee date, or just living your best life out and about. They make amazing gifts for the fashion-obsessed friend who’s always ahead of the trends, the sister who loves a little extra flair, or anyone who appreciates the magic of a piece that’s equal parts classic and current. Slip into a midi skirt and you’re instantly ready for whatever the day throws your way—rain or shine, day or night, solo adventures or squad goals. Trust us, once you find your perfect midi, you’ll wonder how you ever lived without it.

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