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.

Swipe Right High Slit Midi Skirt in Black

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Swipe Right High Slit Midi Skirt in Black

$29.90

A black knit midi skirt featuring a high-rise waist, flowy silhouette, and dramatic high front slit.

Windsor Soft Allure Asymmetrical Midi Skirt in Navy Blue

$26.90

A navy blue stretch knit midi skirt featuring ruched detailing, an asymmetrical hem, and a side slit.

Going Somewhere Wrap Slit Maxi Skirt in Black

$29.90

A sleek black knit maxi skirt featuring a high-rise fit and dramatic front wrap slit for movement.

All Dressed Up Satin Lace Trim Mini Skirt in Off White

$34.90

An off-white satin mini skirt featuring a high-rise fit and delicate eyelash lace trim hem.

Edgy Glam High-Rise Buckle Maxi Skirt in Black

$54.90

A black faux leather maxi skirt featuring a high-rise waist, dual front buckles, and a dramatic front slit.

Chic Allure High-Slit Midi Skirt in Burgundy

$29.90

A burgundy knit midi skirt featuring a high-rise waist, front ruching, and an asymmetric high-cut side slit.

Windsor Downtown Chic Faux Leather Mini Skirt in Black

$44.90

A sleek black faux leather mini skirt featuring a low-rise waist, pleated silhouette, and buckled belt.

Top Tier Tailored Pinstripe Denim Mini Skort in Charcoal

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Top Tier Tailored Pinstripe Denim Mini Skort in Charcoal

$9.97 $39.90 75% off

A charcoal pinstripe denim mini skort featuring a mid-rise waist, belt loops, and hidden fitted shorts.

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Wild At Heart Long Fringe Skirt in Tan

$29.90

(36)

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

(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: S

First Take Micro Slit Mini Skirt in Black

$14.90

(10)

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: S | Knit Fabric

Windsor Sleek Status Faux Leather Mini Skirt in Black

$19.90

(9)

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

Windsor Trendy Moves Long Fringe Skirt in Black

$36.90

(7)

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: XS

Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue

$36.90

(6)

A maxi skirt that feels like slipping into vacation mode without even trying. The soft floral print mesh hugs just right, giving you that effortless “I’m ready for whatever” confidence—day plans or date nights included. Shop Matching Top: Vacay Bloom Floral Mesh Halter TopFit & FeaturesSheer mesh fabric with knit lining, high stretch, Large floral print, High-rise waist, Ruching, High-cut side slit, Maxi-length hem, form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric

Throwback Cool Denim Cargo Mini Skirt

$39.90

(5)

Low-rise nostalgia meets modern street style—this denim cargo mini skirt is made for layering with baby tees, tanks, or oversized fits. The pocket detail gives it that effortless “just stepped out of an early 2000s music video” energy. Fit & FeaturesDenim fabric with color fade effect, Mid-rise waist, Cargo-style front and side pockets, Fitted mini-length hem, Front button closure, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Throwback Cool Denim Cargo Mini Skirt | Size: XL

Windsor After Dark Flutter Mini Skirt in Black

$29.90

(5)

Sleek with a little edge, this mini skirt is made for plans that don’t end early. The smooth knit finish and subtle butterfly detail bring just enough intrigue, while the side slit keeps things flirty without trying too hard. Fit & FeaturesSmooth knit fabric with stretch, Low-rise waist, High front slit with subtle butterfly detailing, Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor After Dark Flutter Mini Skirt in Black | Size: S | Knit Fabric

Sweet Like Summer Crochet Maxi Skirt in Ivory

$46.90

(4)

Sweet like summer, this crochet maxi skirt was made to flirt. With a high-rise waist, scalloped trim, and high-cut side slit, it's your new go-to for coastal vibes. Style with the matching bralette top. Shop Matching Top: Sweet Like Summer Crochet Bralette TopFit & FeaturesSheer crochet knit fabric, moderate stretch, High-rise waist, scalloped trim, Adjustable tie-front drawstring, Thigh-high side slit, Maxi-length fitted silhouette, scalloped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Like Summer Crochet Maxi Skirt in Ivory | Size: M | Knit Fabric

Life Of The Party Lace-Up Mini Skirt in Brown

$42.90

(4)

This faux leather skirt gives life to the party vibes! It has lace-up sides that demand attention, a high-rise waist, and a flattering form-hugging fit that shows off your figure. Fit & FeaturesFaux leather fabric, High-rise waist, Back zipper closure, Side lace-ups , Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Life Of The Party Lace-Up Mini Skirt in Brown | Size: S | Leather

Tailored Skirts

There’s something about a tailored skirt that just gets it—a kind of quiet confidence that doesn’t have to shout to make an entrance. Whether you’re navigating back-to-back meetings, brunching with friends, or mapping out your next city adventure, a great tailored skirt is the wardrobe hero you’ll reach for on repeat. The clean lines, sharp silhouettes, and thoughtful details of these pieces do more than elevate your look—they give you options. Pair a high-waisted pencil skirt with a tucked-in turtleneck for that “I’ve got my life together” vibe (even if you hit snooze three times this morning), or opt for an A-line cut with a chunky knit for an outfit that balances structure and comfort. Tailored skirts are seasonless, but there’s a special kind of satisfaction in styling them for January: think cozy tights, knee-high boots, and oversized coats that make stepping out into the cold feel like a style statement, not a survival tactic. And if you’re gifting? A skirt windsor moment is a chic, practical pick—perfect for the friend who’s always ahead of the curve or the sister who’s building her post-grad wardrobe one investment piece at a time.

Shopping for windsor skirts is about finding pieces that fit not just your body but your lifestyle. The beauty of a tailored skirt is its versatility: it’s the foundation for endless outfit formulas, from nine-to-five polish to after-hours ease. Look for details that work for you—adjustable waistbands, subtle slits, pockets (because yes, we all care), and linings that add that extra layer of comfort and confidence. If you’re someone who loves the feel of luxe fabrics against your skin or needs a little extra warmth in the winter months, don’t skip the Lined Skirts collection, where style meets substance in the best way. Tailored skirts also make a thoughtful gift for anyone stepping into a new role, celebrating a milestone, or just in need of a closet refresh. There’s an ease to gifting a classic piece that can be styled up or down—one that says, “I see your potential, and I support your style evolution.”

Tailored skirts are for the planner and the improviser, the trendsetter and the minimalist, the one who loves a capsule wardrobe and the one who’s always experimenting. They’re the answer to those “nothing to wear” mornings and the secret weapon for last-minute plans that pop up on your calendar. The right skirt transitions seamlessly from winter layers to spring’s lighter touch, making it a true year-round staple. And let’s be honest—there’s a certain magic in slipping into a skirt that fits just right, hugging your curves in all the right places and moving with you, not against you. That’s what makes a tailored skirt more than just a piece of clothing—it’s a mood, a mindset, and a reminder that style should always feel like it was made for you.

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