Stretchy Maxi Skirts
Stretchy maxi skirts are your new wardrobe BFF, ready to take you from brunch to beach with a twirl and a wink. These beauties are all about comfort meeting style, hugging your curves in all the right ways while letting you move like the unstoppable force you are. Perfect for those days when you want to feel effortlessly chic and totally unstoppable, stretchy maxi skirts are here to elevate your style game without breaking a sweat. Whether you're dressing it up with heels or keeping it casual with sneakers, these skirts are the ultimate partner-in-crime for any fashion adventure.
$39.90
A sheer black lace maxi skirt with a high-rise waist, ruching, and a high front slit.
$32.90
A natural crochet maxi skirt with a high-rise waist and sultry front slit, perfect for vacations.
$34.90
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$26.90
A brown high-rise knit maxi skirt with an asymmetrical slit and form-hugging silhouette.
$34.90
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$36.90
A fierce leopard print maxi skirt with a high-rise waist and ruffled flowy silhouette.
$32.90
A black knit maxi skirt featuring a high front slit and a beachy starfish accent.
$39.90
A breezy ivory lace maxi skirt with a high-rise waist, side slit, and asymmetric hem.
$36.90
A white knit maxi skirt featuring a bold floral print, mid-rise waist, and flowy, hip-hugging fit.
$32.90
An airy ivory lace maxi skirt with a high-rise waist and flowy hanky hem.
$24.90
A magenta floral mesh maxi skirt with ruched sides and a form-hugging fit.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$34.90
A leopard floral maxi skirt in mesh fabric featuring a high-rise waist and dramatic side slit.
$36.90
A vibrant orange floral maxi skirt in chiffon with a high-rise waist and curve-hugging silhouette.
$34.90
A black mesh maxi skirt featuring a tropical floral print, high-rise waist, and form-hugging silhouette.
$24.90
A tropical print maxi skirt in black mesh with a high-rise waist and sultry side slit.
$34.90
A fuchsia abstract floral maxi skirt in sheer mesh with a form-hugging fit and back slit.
$39.90
A black tropical print maxi skirt in stretchy knit fabric featuring a high front slit and flowy silhouette.
$39.90
A taupe gingham woven maxi skirt featuring a high-rise elastic waist and a stylish front slit.
$39.90
A black floral mesh maxi skirt featuring a high-rise waist, dramatic front slit, and attached panty lining.
$36.90
A natural linen-blend maxi skirt with a tiered design, high-rise waist, and thigh-high side slit.
$34.90
A white woven maxi skirt featuring a high-rise waist, front slit, and tiered flowy silhouette.
$42.90
A whimsical white floral maxi skirt with a high-rise waist and flowy ruffled slit.
$39.90
A boho-inspired ivory lace maxi skirt featuring a high slit and flowy sheer hem.
Now Trending
Slay It With Style Mini Skirt in Black
$9.97 $22.90
56% 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: L | 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 Tan | Size: XS | Faux Suede
Windsor Cute And Trendy Cargo Mini Skirt in Dark Denim-2
$13.97 $34.90
60% off
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
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: 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
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
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
With this flirty midi skirt for celebrations or date night, you'll stun with the ruched detailing and high-cut side slit. Pair with the matching crop top to complete the look. Shop Matching Top: Flirty Ways Halter Lace Trim Crop TopFit & FeaturesStretchy smooth knit fabric with lining, High-rise waist, Ruching, Asymmetric high-side slit, Midi-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirty Ways Ruched High Slit Midi Skirt in Ivory | Size: L | Knit 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: L | Knit 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: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Stretchy Maxi Skirts
Let’s be real—stretchy maxi skirts are the unsung heroes of every closet, the low-key MVPs you reach for when you want to feel like you’re living your best life, no matter what’s on the agenda. Picture this: you’re running late for brunch with your girls, hair still wet from the shower, but you throw on a long stretchy skirt, add a cute crop top, and suddenly you’re giving main character energy without even trying. That’s the magic of a stretch skirt—it moves with you, hugs in all the right places, and never judges if you decide to go back for seconds (or thirds) at the dessert table. These skirts are made for the girl who wants to look put-together but also wants to dance, twirl, and maybe even climb over a fence or two if the night calls for it. Whether you’re heading to a rooftop party, a casual date, or just running errands, a stretchy skirt is your ride-or-die for comfort and style. And if you’ve ever found yourself wishing your favorite jeans felt as good as your yoga pants, long stretchy skirts are your new style soulmate.
Stretch skirts aren’t just for you, either—they’re the ultimate gift for your bestie who’s always on the go, your sister who just started her first job, or your cousin who loves to travel light and look cute doing it. Trust, they’ll thank you every time they slip into that maxi skirt stretchy and realize they can actually breathe, sit cross-legged, and still look like they spent hours curating their outfit. These skirts play nice with everything in your wardrobe, from oversized graphic tees for a chill vibe to a fitted bodysuit when you want to turn heads. And don’t even get us started on how easy they are to pack—just roll them up, toss them in your bag, and you’re ready for spontaneous adventures or last-minute plans. When you want to go from casual coffee run to dinner with zero outfit changes, these stretch skirts have your back. Plus, let’s not forget the confidence boost that comes from a skirt that flatters your curves and lets you move like you own the place. If you’re vibing with the whole stretchy, comfy, and effortlessly chic look, you might also want to check out our Stretchy Maxi Dresses for even more options that keep the good times rolling.
When you’re picking out your next maxi skirt stretchy, think about what makes you feel unstoppable—maybe it’s a bold print that matches your wild side, a classic solid that goes with literally everything, or a little side slit for that extra touch of drama. Look for details like elastic waistbands (hello, comfort), soft fabrics that drape just right, and lengths that make you feel like you’re gliding through life. Whether you’re tall, petite, curvy, or anywhere in between, there’s a stretchy skirt out there that’s basically tailor-made for you. And honestly, don’t be surprised if you start collecting them in every color—once you experience the freedom and flair of a long stretchy skirt, you’ll wonder how you ever lived without it. From spontaneous road trips to lazy days at home and everything in between, these skirts are your ticket to feeling fabulous with zero effort. Go ahead, embrace the stretch and let your style do the talking—you’ve got places to be and memories to make, and your skirt is right there with you, every step (and twirl) of the way.