Classic Skirts
Classic skirts are your timeless wardrobe heroes, ready to add that extra flair to your everyday and special occasions. Whether you're twirling into a meeting or stepping out for brunch with the squad, these skirts have got you covered. From chic pencil styles that mean business to flirty A-lines perfect for a night out, classic skirts are all about versatility and style. So go ahead, strut your stuff and let those hems do the talking—because when it comes to making an entrance, you're always on point!
$29.90
A trendy black faux suede skirt with a high-rise waist and long fringe detailing.
$34.90
A brown high-rise cargo mini skirt with vertical seams and side pockets in twill fabric.
$34.90
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$26.90
A black lace mini skirt featuring a high-rise waist, adjustable side ties, and a ruffled hem.
$26.90
A high-rise black maxi skirt with a flocked floral pattern and a dramatic side slit.
$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.
$29.90
A black faux suede mini skirt with flirty fringe trim and a flattering bodycon fit.
$39.90
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$34.90
A black bleach-dye denim mini skirt with a belted waist and form-hugging fit.
$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.
$9.97 $34.90 71% off
A black high-rise bubble skirt with side stripes, featuring a nylon woven fabric and adjustable drawstring.
$44.90
A beige high-rise maxi skirt with delicate embroidery and a flirty high front slit.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$36.90
A chic ivory mesh maxi skirt featuring a flocked floral pattern and high-rise lace-trimmed waist.
$36.90
An ivory floral print maxi skirt with a high-rise waist and flowy knit fabric.
$29.90
A tan faux suede mini skirt with a high-rise waist and stylish front slit.
$9.97 $39.90 75% off
An adorable beige pleated mini skirt with a mid-rise waist and side button closures.
$36.90
A sheer brown lace maxi skirt with a high-rise waist and romantic high slit.
$34.90
A trendy denim mini skirt featuring a flattering mid-rise waist and chic pleated silhouette.
$29.90
An ivory pleated mini skirt with eyelet lace trim and a high-rise waist for charming elegance.
$9.97 $32.90 70% off
A khaki cotton-blend mini skirt with a high-rise waist and flirty pleated hem.
$9.97 $39.90 75% off
A black ruffled mini skirt in ponte knit with a high waist and bodycon fit.
$36.90
A medium denim high-rise mini skirt with adjustable drawstring ties and a flared raw cut hem.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$9.97 $26.90 63% off
A charming black plaid mini skirt with a mid-rise drop waist and dual bow accents.
$34.90
A light denim chambray maxi skirt with a tiered design and high side slit for a western vibe.
$39.90
A natural crochet knit midi skirt featuring a high-rise waist and bodycon fit for stylish outings.
$26.90
A black woven skort with a floral polka dot pattern and ruffled mini-length skirt overlay.
$26.90
A mauve satin skater skirt with a high-rise waist and flirty faux wrap overlay.
$34.90
A sassy pleated mini skirt in dark denim with a high-rise waist and trendy flair.
$34.90
A denim pleated mini skirt with a mid-rise dual belted waist and back zipper closure.
$9.97 $29.90 67% off
A dark denim high-rise mini skirt with front pockets and a form-hugging fit.
$36.90
A dark denim mini skirt with a mid-rise waist, bodycon fit, and frayed hem for vintage charm.
$44.90
A natural-colored knit midi skirt featuring a wavy striped pattern and high center back slit.
$9.97 $36.90 73% off
A tan corduroy mini skirt with a high-rise waist and bubble hem design.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$39.90
A medium denim cargo mini skirt with a mid-rise waist and functional side string pockets.
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: S | 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
Classic Skirts
Classic skirts are the ultimate ride-or-die when it comes to building a wardrobe that’s equal parts timeless and totally you. These are the pieces that make you feel like the main character, whether you’re strutting into a big presentation, hitting brunch with your crew, or heading out for a spontaneous date night. Classic skirts for women are all about versatility—think tailored pencil skirts that mean business, pleated numbers that bring a little prep to your step, and those endlessly chic A-lines that flatter every vibe and body type. The magic of a classic skirt is that it never tries too hard; it just gets you. You know the drill: you grab your favorite windsor black skirt, pair it with a crisp white tee or a flirty crop top, and suddenly you’re ready for whatever the day throws at you. That’s the power move. And if you’re in the mood to gift a little confidence boost, classic skirts make the sweetest surprise for your bestie, your sister, or anyone who deserves to feel like their most unstoppable self.
Picking out the perfect classic skirt is all about knowing your mood and your moves. Are you looking for something that nails the “effortlessly polished” look for work and still turns heads at happy hour? Or maybe you want a black skirt Windsor style—sleek, bold, and ready to anchor every outfit from Monday meetings to Friday nights out. The beauty of classic skirts is how they play well with literally everything in your closet. Tuck in a slinky cami for a little glam, throw on a chunky knit for those chillier nights, or keep it simple with a graphic tee and sneakers for that off-duty model energy. If you’re on a mission to figure out how to build a timeless wardrobe, start here: invest in a few classic skirts in neutral shades (black, navy, beige), sprinkle in a fun print or two, and watch as your outfit options multiply like magic. These are the go-to pieces that never let you down, no matter what’s on your calendar.
Classic skirts are more than just a fashion staple—they’re a confidence booster, a style chameleon, and the ultimate canvas for showing off your personality. Whether you’re dressing up for a special occasion or just want to bring a little extra sparkle to your everyday, classic skirts have your back. And if you’re itching for a refresh or want to scope out the latest trends, check out the Latest Skirts for even more inspo. Trust us, with the right skirt in your arsenal, you’ll always have a reason to twirl.