Comfortable Skirts
Hey there, fashion maven! Ready to twirl into a world where comfort meets style? Our collection of comfortable skirts is here to make sure you never have to choose between looking fab and feeling great. Whether you're strutting your stuff down the street or dancing the night away, these skirts are your ultimate partner in crime. Think flowy fabrics and silhouettes that move with you, all while keeping those good vibes rolling. So go ahead, unleash your inner fashionista and let those skirts do the talking!
$29.90
A tan faux suede skirt with a high-rise waist and long fringe detailing for a festival-ready look.
$26.90
A black stretchy knit midi skirt with high-rise fit, ruching, and an asymmetrical high-side slit.
$44.90
A beige high-rise maxi skirt with delicate embroidery and a flirty high front slit.
$29.90
An airy orange woven midi skirt with a high slit, tie detail, and flowy slim-fit silhouette.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$36.90
An ivory floral print maxi skirt with a high-rise waist and flowy knit fabric.
$22.90
A black satin mini skort featuring a high-rise waist, ruched side seam, and adjustable drawstring.
$42.90
An ivory knit wrap skirt featuring a tie-waist and cascading fringe hem for a chic getaway look.
$26.90
A chic ivory lace mini skirt with a high-rise waist and eyelet lace trim.
$29.90
A brown midi skirt featuring floral flocked velvet, sheer mesh, and a high-rise waist with lace trim.
$9.97 $19.90 50% off
A trendy brown zebra print mini skirt with a high-rise waist and chic front slit.
$39.90
A breezy ivory lace maxi skirt with a high-rise waist, side slit, and asymmetric hem.
$32.90
An airy ivory lace maxi skirt with a high-rise waist and flowy hanky hem.
$29.90
An ivory knit skort with a high-rise waist, double bow detail, and pleated skater silhouette.
$36.90
A medium denim high-rise mini skirt with adjustable drawstring ties and a flared raw cut hem.
$29.90
A black pleated ponte skort with a high-rise waist and mini-length hem for a preppy look.
$39.90
An ivory lace maxi skirt with a high slit and flowy sheer hem for boho-inspired elegance.
$39.90
A charming white denim mini skirt with a bubble hem and mid-rise waist for a playful look.
$39.90
A khaki denim skort with a high-rise waist and ruched drawstring for a unique, cute look.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$34.90
A light denim chambray maxi skirt with a tiered design and high side slit for a western vibe.
$29.90
A black faux suede mini skirt with flirty fringe trim and a flattering bodycon fit.
$9.97 $34.90 71% off
A high-rise black bubble skirt with side stripes, featuring a nylon woven fabric and adjustable drawstring.
$24.90
A faux suede mini skirt in camel with a low-rise V-cut waist and bodycon fit.
$39.90
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$9.97 $16.90 41% off
A stylish black mini skirt with a high-rise waist and bodycon fit in textured knit fabric.
$34.90
A black bleach-dye denim mini skirt with a belted waist and form-hugging fit.
$34.90
A natural-colored mini skirt featuring lace embroidery, sheer mesh fabric, and a chic side slit.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$26.90
A bold brown mini skirt with a large floral print and sheer mesh for a flirty silhouette.
$26.90
A blush bodycon midi skirt with a high-rise waist and side ruched seams in stretchy knit.
$34.90
A dark denim cargo mini skirt with a mid-rise waist, removable belt, and side pockets.
$24.90
An ivory mini skort with airy sheer floral lace, ruched high waist, and asymmetric hanky hem.
$19.90
A chic black knit mini skirt with a high-rise waist and sultry side slit.
$34.90
A black acid-wash denim skort with a mid-rise waist and hidden fitted shorts for coverage.
$39.90
A sheer black lace maxi skirt with a high-rise waist, ruching, and a high front slit.
$34.90
A trendy dark denim mini skort with a mid-rise waist and bodycon fit for versatile styling.
$34.90
An olive cotton-blend cargo mini skirt with a belted design and form-fitting silhouette.
$39.90
A light denim skort with tiered ruffles and a flared silhouette over fitted shorts.
$29.90
An ivory lace skort with tiered ruffles and knit-fitted shorts for charming coverage.
$34.90
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$36.90
A chic ivory mesh maxi skirt featuring a flocked floral pattern and high-rise lace-trimmed waist.
$36.90
A medium denim high-rise skort featuring a ruffled mini skirt overlay and form-hugging fit.
$36.90
A medium denim skort with a dual slit overlay and form-hugging fit for chic styling.
$24.90
An ivory high-rise skort with a flattering A-line silhouette in smooth ponte knit fabric.
$39.90
A high-rise black knit skort with a preppy pleated silhouette and striped mini-length hem.
$24.90
A black knit mini skirt featuring a pleated wrap design and a mid-rise waist.
Now Trending
Windsor Slay It With Style Mini Skirt in Black
$18 $22.90
21% 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: M | 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 Black | Size: L | Faux Suede
Serve major style in this on-trend cargo mini skirt! Featuring a high-rise waist, vertical seam detailing, cargo-style side pockets, a mini-length hem, and a form-hugging fit, this skirt will level up your basic looks. The twill fabric offers minimal stretch. Style with a halter bodysuit and strappy mules. Fit & FeaturesHigh-rise waist, Belt loops, hidden front zipper, button closure, Vertical seams, Cargo side pockets, Mini-length hem, form-hugging fit, Twill fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Serving Style Cargo Mini Skirt in Brown | Size: M
This cute and trendy cargo mini skirt will step up this season's 'fits! It features a mid-rise waist, an included removable belt with a double grommet design, cargo-style side pockets, a mini-length hem, and a fitted silhouette. The denim fabric offers a moderate stretch. Style this denim skirt with a crop top and clear mules. Fit & FeaturesMid-rise waist, hidden front buttons, zipper closure, Included removable belt, double grommet design, Dual cargo-style side pockets, Mini-length hem, Fitted silhouette, Denim fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute And Trendy Cargo Mini Skirt in Dark Denim-2 | Size: S
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
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 Black | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric
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: M | Knit Fabric
This airy woven midi skirt will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric with a mini-length lining, it features a high waist with the cutest tie detail, a high-cut side slit to showcase some leg, and a flowy slim-fit silhouette. Style with the matching crop top for a fabulous 'fit! Shop Matching Orange Top: Sunny Vibes Bow Back Woven Crop TopFit & FeaturesWoven fabric with mini-length knit lining, minimal stretch, High-rise elasticized waist, Tie detail, High side slit, Flowy slim-fit silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunny Vibes High Slit Woven Midi Skirt in Orange | Size: S | Knit Fabric/Woven Fabric
Comfortable Skirts
When you’re on the hunt for the perfect comfy skirt, you know it’s not just about what looks good—it's about what feels good, too. Let’s be real, nothing beats the feeling of slipping into a skirt that hugs you in all the right places but never tries to steal the spotlight from your comfort. Whether you’re running errands, heading to brunch with your crew, or just living your best life, comfy skirts are your ticket to feeling put together without sacrificing that cozy, cloud-nine vibe. Think soft knits that move with you, breezy silhouettes that catch the light, and waistbands that stretch with your every mood. The beauty of a windsor skirt is that it works for every kind of day: the ones when you want to dress up a little, and the ones when you just want to keep it chill but still look like you totally planned your outfit. And let’s not forget, a comfy skirt is the ultimate BFF for travel days, long study sessions, or spontaneous adventures—just throw it on, add your favorite top, and you’re ready to slay, no matter what’s on the agenda.
Gifting a comfy skirt? Major win. It’s the kind of present that says, “I see you, I get you, and I want you to feel amazing.” Whether it’s for your fashion-forward bestie, your sister who’s all about that effortless style, or your mom who deserves a little extra comfort, skirts windsor are a thoughtful pick. They’re versatile enough to fit every personality—edgy, classic, or boho—so you can find something that matches their vibe. Plus, there’s just something about receiving clothing that’s as easy to wear as it is to style. Imagine the smile when they unwrap a piece that instantly becomes their new go-to, the one they reach for when they want to feel both cute and comfy. And hey, don’t sleep on the power of self-gifting, either. Treat yourself to a windsor skirt that makes you want to twirl in the mirror, snap a quick selfie, and take on the day with a little extra attitude. These skirts aren’t just wardrobe staples—they’re confidence boosters, conversation starters, and the secret ingredient to a look that’s as unique as you are.
When it comes to choosing the right comfy skirts, think about your favorite textures and fits. Maybe you’re all about buttery-soft jersey that feels like your favorite tee, or perhaps you lean toward ribbed knits that give a little structure without ever feeling stiff. Midi lengths are perfect for that just-right amount of coverage, while minis bring the flirty fun if you’re feeling bold. Don’t be afraid to play with prints, colors, and details—drawstring waists, side slits, or playful ruching can make all the difference. The best part? You can dress them up with a cute blouse and heels for a night out, or keep it low-key with sneakers and a crop top for a day of exploring. If you’re ready to level up your skirt game and discover even more inspo, check out the Best Skirts page for a curated selection that brings all the comfort and all the style, every single time.