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.
$29.90
A tan faux suede mini skirt with a high-rise waist and stylish front slit.
$29.90
A brown midi skirt featuring floral flocked velvet, sheer mesh, and a high-rise waist with lace trim.
$39.90
A black satin midi skirt featuring a polka dot print, high-rise waist, and side slit.
$39.90
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$42.90
A black satin midi skirt featuring a high-rise waist, faux buttons, and a front high slit.
$9.97 $32.90 70% off
A black high-rise pleated denim mini skirt with a flattering fit and minimal stretch.
$34.90
A chic black faux leather wrap midi skirt featuring a high-rise waist and high-slit design.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$34.90
A brown cargo mini skirt with a high-rise waist, vertical seams, and cargo-style pockets.
$34.90
A black satin mini skirt with a high-rise waist and dual side flap pockets.
$26.90
A black stretchy knit midi skirt with high-rise fit, ruching, and an asymmetrical high-side slit.
$36.90
A chic ivory mesh maxi skirt featuring a flocked velvet floral pattern and flared hem.
$34.90
A plum mesh midi skirt with a flocked velvet floral pattern and a high side slit.
$26.90
A brown high-rise maxi skirt with an asymmetrical slit and form-hugging knit silhouette.
$24.90
A black knit mini skirt featuring a pleated wrap design and moderate stretch for a perfect fit.
$29.90
A chic black ribbed knit midi skirt with a high side slit and bodycon fit.
$26.90
A black knit mini skirt with a velvet flocked floral pattern and a high-rise waist.
$36.90
A fierce leopard print maxi skirt with a high-rise waist and dramatic front slit.
$13.97 $32.90 58% off
A taupe faux suede mini skirt with a high-rise waist and sleek button-down design.
$34.90
A black denim mini skirt with a bleach-dye design and trendy belted waist for edgy style.
$34.90
A trendy denim mini skirt featuring a flattering mid-rise waist and chic pleated silhouette.
$26.90
A sleek brown faux leather mini skirt with a high-rise fit and stylish front slit.
$29.90
An ivory pleated mini skirt with eyelet lace trim and a high-rise waist for charming elegance.
$34.90
A mid-rise pleated denim mini skirt with a dual belted waist and back zipper closure.
$9.97 $34.90 71% off
An edgy black denim mini skirt with a belted wrap-front design and form-hugging fit.
$17.97 $42.90 58% off
A rose floral velvet burnout midi skirt with a high-rise waist and ruched seams.
$26.90
A black satin mini skirt with a lace trim slit and form-hugging high-rise fit.
$26.90
A mauve satin skater skirt with a high-rise waist and flirty faux wrap overlay.
$9.97 $39.90 75% off
An orange ruffled mini skirt in ponte knit with a high waist and bodycon silhouette.
$34.90
A sassy pleated mini skirt in dark denim with a high-rise waist and trendy flair.
$9.97 $36.90 73% off
A tan corduroy mini skirt with a high-rise waist and bubble hem design.
$44.90
A natural-colored knit midi skirt featuring a wavy striped pattern and high center back slit.
$16.97 $39.90 57% off
A trendy dark denim bubble skirt featuring a mid-rise belted waist and flared silhouette.
$9.97 $44.90 78% off
A black faux leather mini skirt featuring a high-rise waist and a side statement bow.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
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
Tailored Skirts
When you slip into a tailored skirt, you’re not just getting dressed—you’re setting the tone for your whole day. These pieces are the MVPs of any wardrobe, blending sharp, clean lines with a little bit of that main character energy. Whether you’re strutting into an interview, owning your spot at brunch, or just feeling yourself on a coffee run, a tailored skirt is the ultimate power move. The beauty of a tailored skirt lies in its versatility: it plays nice with everything from your favorite band tee to a crisp button-up, and it’s always down to be styled up or down. Picture this: you’ve got a last-minute invite to a rooftop hang, you’re staring at your closet, and boom—your tailored skirt is there to save the day. Add a crop top, a blazer, or even that statement belt you bought on a whim, and suddenly you’re serving looks with zero stress. If you’re shopping for someone else, these skirts make a killer gift for the friend who’s always on the go, the one who loves a little structure in her life (or at least in her outfit), or even for the grad who’s about to take on the world. Because honestly, who doesn’t want a piece that works overtime to keep up with every spontaneous plan?
When you’re picking out a tailored skirt, it’s all about finding that perfect fit and fabric that feels like it was made for you. Think about the details: a high waist that cinches you in just right, a subtle slit that lets you move (and dance) with ease, or pockets deep enough for your lip gloss and phone. Tailored skirts come in all the best silhouettes—pencil, A-line, mini, midi—so you can match your vibe, your mood, or even your calendar. If you’re all about comfort without sacrificing style, check out options with a little stretch or soft lining. And speaking of lining, if you love that extra layer of luxe, don’t sleep on our Lined Skirts for a smooth, flawless finish that feels as good as it looks. These skirts aren’t just for the office, either. They’re your go-to for date nights, gallery strolls, or even that spontaneous road trip when you want to look put together but still feel like yourself. And let’s be real—there’s something about a tailored skirt that just makes you walk a little taller, like you’re ready to take on whatever the day throws at you.
Tailored skirts are that rare combo of classic and bold, making them a must-have for anyone who loves to mix things up. They’re the pieces you reach for when you want to feel unstoppable, whether you’re nailing a presentation or just catching up with your crew. If you’re gifting one, it’s a thoughtful pick for anyone who’s leveling up their style game—think birthdays, new jobs, or just because. And if you’re treating yourself (as you should), you’ll find that a tailored skirt has a way of making every outfit feel intentional and elevated, no matter how you style it. So go ahead, embrace the structure, play with textures, and let your tailored skirt do the talking. Because when your outfit’s got this much attitude, the world can’t help but pay attention.