Tailored Skirts

Tailored skirts are the ultimate game-changer for your wardrobe, giving you that sleek, polished look with a twist of fierce flair. Whether you're strutting into the boardroom or owning the dance floor, these skirts are your ticket to looking effortlessly chic and fabulously put-together. Picture yourself in a silhouette that hugs in all the right places, making you feel like the unstoppable force you truly are. It's time to embrace the tailored life and let your style do all the talking.

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Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

A black stretchy midi skirt featuring ruching and an asymmetrical high-side slit for chic occasions.

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.

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.

Windsor Luxe Allure Flocked Floral Knit Mini Skirt in Black

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Windsor Luxe Allure Flocked Floral Knit Mini Skirt in Black

$9.97 $26.90 63% off

A black knit mini skirt with a velvet flocked floral pattern and a high-rise waist.

So Perfect Mid-Rise Pleated Denim Mini Skirt

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So Perfect Mid-Rise Pleated Denim Mini Skirt

$11.97 $36.90 68% off

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

Windsor City Chic Faux Leather Belted Mini Skirt in Black

$32.90

A chic black faux leather mini skirt featuring a belted waist and side flap pockets.

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.

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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 Iconic Getaway Tie-Waist Wrap Fringe Skirt in Ivory

$9.97 $42.90
77% off

(5)

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: L | Knit Fabric

First Take Micro Slit Mini Skirt in Black

$14.90

(5)

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

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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

Sale

Breezy Vibes Lace Mini Skirt in Ivory

$9.97 $26.90
63% off

(3)

Show off a breezy chic vibe in this airy lace mini skirt featuring a high-rise waist and a short form-hugging fit. Style with the matching tie-front top for a weekend getaway. Shop Matching Top: Breezy Vibes Lace Tie-Front TopFit & FeaturesSheer lace fabric with lining, High-rise waist, eyelet lace trim, Mini-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Breezy Vibes Lace Mini Skirt in Ivory | Size: L | Lace Fabric/Sheer Lace 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

Tailored Skirts

There’s something about a tailored skirt that feels instantly transformative—the way it skims, hugs, and sharpens your silhouette, turning even the most thrown-together top into a full-on look. As autumn leans into winter and your calendar fills with everything from last-minute coffee runs to impromptu office parties, a tailored skirt is that secret weapon you reach for when you want to look put-together with zero fuss. The beauty of these skirts is all in the details: crisp pleats, sharp seams, and just the right amount of structure to keep you feeling polished but never restricted. Whether you’re a devotee of classic pencil styles or you love a modern twist with a wrap or asymmetrical hem, the tailored skirt is endlessly versatile—ready to anchor chunky knits, sleek bodysuits, or even that oversized blazer you’ve been living in since the first chilly breeze hit.

Tailored skirts aren’t just for the office (though they absolutely deliver when you’re heading into a big meeting or interview). They’re the kind of piece you can dress up for a dinner date or dress down for a casual weekend vibe, all without missing a beat. Think of them as the sartorial equivalent of a great cup of coffee: reliable, energizing, and always a good idea. If you’re shopping for yourself, consider fit and fabric first—look for pieces that move with you but hold their shape, especially as layering season kicks in. A high-waisted tailored skirt can work wonders for your proportions, especially when paired with a tucked-in turtleneck or a cropped sweater. And if you’re on the hunt for a gift that feels thoughtful but not over-the-top, a tailored skirt is a smart choice for anyone who loves to mix up their wardrobe staples. It’s the kind of piece that says, “You’ve got this,” whether she’s heading to her first internship or just wants to elevate her everyday rotation.

As the days get shorter and your social calendar picks up, tailored skirts offer that rare blend of style and substance—easy to personalize, impossible to ignore. Don’t be afraid to play with textures, especially as the temperatures dip: wool blends, tweeds, and even vegan leather bring a cozy sophistication to your look and make the transition from desk to dinner totally seamless. And if you’re all about comfort (without sacrificing style), keep an eye out for options with a hint of stretch or a soft lining—because nothing ruins a killer outfit faster than a scratchy waistband. For those who want to explore even more ways to stay warm and stylish, check out our curated collection of Lined Skirts for extra comfort and coverage. At the end of the day, a tailored skirt is more than just a wardrobe staple—it’s a style foundation you can build on, reinvent, and make entirely your own, season after season.

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