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 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 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 Luxe Allure Flocked Floral Knit Mini Skirt in Black

$26.90

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

So Perfect Mid-Rise Pleated Denim Mini Skirt

$36.90

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

Retro Chic Wavy Striped Crochet Midi Skirt in Natural

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Retro Chic Wavy Striped Crochet Midi Skirt in Natural

$9.97 $44.90 78% off

A natural-colored knit midi skirt featuring a wavy striped pattern and high center back slit.

Windsor Resort Calling Mesh Slit Maxi Skirt in Black

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Windsor Resort Calling Mesh Slit Maxi Skirt in Black

$16.97 $39.90 57% off

A black floral mesh maxi skirt featuring a high-rise waist, dramatic front slit, and attached panty lining.

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Iconic Moves Ruffled Ponte Knit Mini Skirt in Black

$9.97 $39.90 75% off

A black ruffled mini skirt in ponte knit with a high waist and bodycon fit.

Windsor Heavenly Match Floral Slit Midi Skirt in Brown

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Windsor Heavenly Match Floral Slit Midi Skirt in Brown

$14.97 $34.90 57% off

A brown floral mesh midi skirt with a high-rise waist and sultry front slit.

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Wild At Heart Long Fringe Skirt in Tan

$29.90

(33)

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

Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

(10)

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

Windsor Coastal Breeze Linen High Slit Maxi Skirt in Natural

$36.90

(9)

Channel that coastal chic vibe with this breezy linen maxi skirt featuring a tiered design, high-cut side slit, and flowy A-line silhouette. Fit & FeaturesLinen-blend fabric, High-rise waist, Tiered design, Thigh-high side slit, Flowy A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Coastal Breeze Linen High Slit Maxi Skirt in Natural | Size: L

Keep A Secret Lace Slit Maxi Skirt in Black

$39.90

(7)

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

(6)

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

Breezy Boho Sheer Lace Asymmetric Maxi Skirt in Ivory

$39.90

(5)

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

Windsor Iconic Getaway Tie-Waist Wrap Fringe Skirt in Ivory

$42.90

(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: S | Knit Fabric

Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural

$32.90

(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

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Boho Babe Lace Hanky Hem Maxi Skirt in Ivory

$13.97 $32.90
58% off

(4)

Live out your boho era in this airy sheer lace maxi skirt with a mini-length lining for a chic look. The long flowy silhouette will create that effortlessly cool vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, High-rise waist, Hip-hugging fit, Maxi-length hanky hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Boho Babe Lace Hanky Hem Maxi Skirt in Ivory | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric

Breezy Vibes Lace Mini Skirt in Ivory

$26.90

(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

Tailored Skirts

Tailored skirts are the ultimate closet chameleons—your go-to for those “I mean business but I still want to look cute” moments. Whether you’re strutting into a big presentation, heading out for a power brunch, or just want your outfit to scream “I woke up like this (but with style),” tailored skirts for women have your back. Picture this: a crisp, structured silhouette that hugs you just right, paired with your favorite blouse or a cheeky graphic tee. That’s the magic of a tailored skirt—it does all the heavy lifting, letting you focus on making memories and catching compliments. They’re the piece you reach for when you want to feel unstoppable, like you could run your world and still make it to happy hour without missing a beat. And if you’re shopping for your bestie, your sister, or that friend who’s always on the move, a tailored skirt is the kind of gift that says, “I see your hustle, and I’m here to make sure you do it in style.”

Let’s talk about the details that set tailored skirts apart. It’s all about the fit—the way the fabric glides over your curves, the clean lines that make you feel instantly polished, and those little design touches (hello, high waistbands and subtle pleats) that take your look from basic to unforgettable. These skirts are made to move with you, whether you’re twirling on the dance floor or sprinting to catch the train. And when it comes to versatility, nothing beats a tailored skirt. Dress it up with a blazer and heels for that big-deal meeting, or keep it chill with sneakers and a cropped sweater for a day out with your crew. The best part? They’re just as perfect for gifting as they are for treating yourself—because every girl deserves a piece that makes her feel like the main character. If you’re all about that luxe-on-a-budget vibe, you’ll love how tailored skirts let you play with textures, patterns, and lengths without breaking the bank. And for those who crave an extra layer of comfort (or just want to keep things smooth and sleek), check out our collection of Lined Skirts for a little extra polish.

When you slip into a tailored skirt, you’re not just wearing a piece of clothing—you’re stepping into your power. These skirts are the secret weapon for anyone who wants to look effortlessly put together, no matter what the day (or night) throws at them. They’re perfect for students leveling up their campus style, young pros making their mark, or anyone who loves a little structure with their sass. Picture yourself heading out for a late-night adventure, your tailored skirt catching the city lights, or making an entrance at a family gathering with a look that’s equal parts timeless and totally you. With tailored skirts for women, you’re always ready for the next big thing—because when your outfit is this on point, the world is yours for the taking.

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