High Rise Midi Skirts
High rise midi skirts are the ultimate wardrobe must-have for every Windsor girl ready to own her style game. These skirts are your go-to for creating effortlessly chic looks that transition seamlessly from brunch dates to dance floors. With their flattering fit and versatile length, they’re perfect for pairing with everything from crop tops to cozy sweaters. Whether you're strutting into the office or twirling at a garden party, these skirts bring that perfect mix of sophistication and sass. Time to elevate your fashion vibe and let those high rise midi skirts do the talking!
$26.90
A red stretchy knit-lined midi skirt with ruching and an asymmetrical high-side slit.
$26.90
A rust-colored, high-rise midi skirt crafted from double-lined, stretchy knit fabric with a sultry side slit.
$16.97 $39.90 57% off
A natural crochet knit midi skirt featuring a high-rise waist and bodycon fit for stylish getaways.
$29.90
A tan tropical print midi skirt featuring a high-rise waist, mesh overlay, and form-hugging silhouette.
$44.90
A brown striped crochet knit midi skirt featuring a high-rise waist, thigh-high side slit, and form-hugging fit.
$18.97 $44.90 58% off
A natural-colored knit midi skirt featuring a wavy striped pattern and high center back slit.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$9.97 $39.90 75% off
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$34.90
A black high-rise midi skirt crafted from stretchy knit fabric with a flattering column silhouette.
$28.90
A flirty pink knit midi skirt featuring ruffle trim, side slit, high-rise waist, and bodycon fit.
$29.90
A tan faux suede skirt with a high-rise waist and long fringe detailing for a festival-ready look.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$26.90
A mocha knit midi skirt featuring a high-rise bodycon fit, double lining, and a center back slit.
$36.90
A leopard print maxi skirt with a high-rise waist and ruffled flowy silhouette.
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Slay It With Style Mini Skirt in Black
$9.97 $22.90
56% off
Elevate your going-out looks in this sleek faux leather mini skirt! This high-waist mini skirt features a sexy front slit and hidden back zipper for a seamless look at every angle. Make this faux leather mini skirt your wardrobe must-have for date night or clubbing with your party squad. Pair this flirty mini skirt with a beaded bustier top or long-sleeve satin tie-front top for a sexy and fierce night-out look. Fit & FeaturesHigh-rise fit, Vertical seam details, back zipper, Front slit accent, Form-hugging fit, Mini-length hem, Unlined faux leather fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Slay It With Style Mini Skirt in Black | Size: L | Leather/Satin Fabric
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
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
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
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
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: L | Knit Fabric
Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, adjustable drawstring, High side slit, Asymmetric maxi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Breezy Boho Sheer Lace Asymmetric Maxi Skirt in Ivory | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Get ready for an iconic getaway with this tie-waist wrap fringe skirt perfect for days spent under the sun or sipping on drinks poolside! Fit & FeaturesCrochet knit design, sewn-in knit lining, Wrap-tie waist, Back zipper and hook-eye closure, Cascading fringe hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Iconic Getaway Tie-Waist Wrap Fringe Skirt in Ivory | Size: S | Knit Fabric
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
Call Me Cutie Floral Eyelet Mini Skirt in White
$9.97 $39.90
75% off
Get ready for everyone to call you cute in this floral mini skirt designed with a flirty layered ruffle that captures attention and a mini-length hem that lets you flaunt your figure. Pair with the matching top. Shop Matching Top: Call Me Cutie Lace-Up Floral Eyelet Corset TopFit & FeaturesFloral print, eyelet woven lined fabric, Stretchy smocked high-rise waist, Layered ruffle , Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Call Me Cutie Floral Eyelet Mini Skirt in White | Size: L
High Rise Midi Skirts
Let’s be real—there’s nothing quite like slipping into a high rise midi skirt and feeling instantly unstoppable. Whether you’re strutting into brunch with the girls, acing that big presentation, or just living your main character moment on a random Tuesday, these skirts are the ultimate power move. The magic of a high waisted midi skirt is all in the details: a waist-cinching silhouette that serves hourglass vibes, a length that says “I’m classy, but I’m here to play,” and endless styling potential that’ll have your closet working overtime. Think about it—pair with a sleek bodysuit and mules for date night, or throw on a graphic tee and sneakers for errands that somehow turn into an impromptu photo shoot. And if you’re the friend who’s always on the hunt for the perfect birthday gift or just want to treat your ride-or-die bestie, a high waist midi skirt is a foolproof pick. It’s the kind of piece that flatters every body, matches every mood, and instantly upgrades any wardrobe from “meh” to “major.”
Let’s talk about the real-world perks. High rise midi skirts are the go-to for anyone who wants to look put together with zero fuss. Got a last-minute invite to a rooftop party? Grab your favorite high rise midi skirt, add a cropped jacket, and you’re golden. Heading into the office and need to keep things polished? Tuck in a button-down, slip on some ankle boots, and you’re serving CEO energy. These skirts are also a total lifesaver when you’re between sizes or just want a little more comfort—hello, forgiving waistbands and breezy fabrics that move with you, not against you. And for those who love a little drama (the good kind, obviously), a high waisted midi skirt is the perfect canvas for bold colors, flirty prints, and all the accessories your heart desires. You can even make it a family affair—your mom, your sister, your best friend, and yes, even your cool aunt who’s always ahead of the trends, will all find a way to make it their own. It’s the gift that keeps on giving, season after season, because high rise midi skirts truly never go out of style.
Confidence, comfort, and a dash of that “I woke up like this” energy—that’s what you’re signing up for with every high rise midi skirt. You get to play with proportions, show off your favorite shoes, and twirl through your day with a little extra bounce in your step. And if you’re on the hunt for even more inspo or want to see the latest must-haves, check out our Trendy Midi Skirts page for all the freshest looks. Whether you’re dressing up, dressing down, or just doing you, these skirts are here to hype you up and keep the good vibes rolling.