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.
Home Stretchy Maxi Skirts
- Recommended
- Most Popular
- Price - Low to High
- Price - High to Low
$9.97 $32.90 70% off
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$9.97 $34.90 71% off
A sheer mesh zebra print maxi skirt in brown, perfect for vacation or going out.
$32.90
A sleek olive maxi skirt crafted from double-lined, stretchy knit fabric with a flattering bodycon silhouette.

Now Trending
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
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
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
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
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
Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural
$9.97 $32.90
70% off
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
Breezy Vibes Lace Mini Skirt in Ivory
$9.97 $26.90
63% off
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
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
Go With The Vibe Slit Midi Skirt in Rust
$9.97 $26.90
63% off
Embrace your daring side and let this midi skirt elevate your look. Its sleek high-rise waist and side slit highlight your confidence and flair, perfect for making a statement at any event. Pair with the matching top. Shop Matching Top: Go With The Vibe Halter Crop TopFit & FeaturesSlinky knit stretchy fabric, High-rise waist, Side pleated hip seam, High side slit, Form-hugging silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Go With The Vibe Slit Midi Skirt in Rust | Size: M | Knit Fabric/Stretchy Fabric
Strut It Out Abstract Zebra Maxi Skirt in Brown
$9.97 $34.90
71% off
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
Stretchy Maxi Skirts
When it comes to leveling up your wardrobe with comfort-meets-glam energy, nothing does it quite like a stretchy maxi skirt. These beauties are the ultimate ride-or-die for the girl who wants to look snatched while feeling like she’s basically wearing pajamas. Think about it: you’re running from brunch to late-night boba, maybe squeezing in a little window shopping (because, priorities), and you need something that moves with you—literally. That’s where the stretchy skirt comes in hot. With their buttery-soft fabrics and figure-hugging fits, stretchy maxi skirts deliver that just-right blend of confidence and ease, hugging your curves in all the best ways. Whether you’re tall, petite, curvy, or somewhere in between, there’s an extra long skirt or long stretch skirt out there ready to become your new closet MVP. And let’s be honest, nothing says “main character energy” like swishing into a room, hem trailing behind you, and not worrying for a second about comfort.
Stretchy maxi skirts are the low-key hero of any closet, especially when the weather’s doing its unpredictable thing. They’re perfect for layering—toss on a cropped sweater and boots for a little cozy drama, or keep it chill with a fitted tank and sneakers for that off-duty model vibe. The best part? They transition from day plans to night moves with zero effort. If you’re shopping for yourself (treat yourself, babe) or hunting for the ultimate gift for your bestie, a stretchy skirt is basically a love letter in outfit form. These skirts are made for every scenario: casual hangs, last-minute dates, family dinners where you want to look put together but still have room for dessert. And if you’re feeling bold, style a long stretch skirt with a statement belt and a leather jacket—suddenly, you’re the girl everyone’s asking for style tips. The stretch factor means you’re never stuck in that “ugh, too tight” moment, and the maxi length gives you all the drama with none of the fuss. They’re especially clutch for travel, since you can roll them up, toss them in your bag, and they’ll still look flawless when you land.
For the Windsor girl who loves to mix it up, stretchy maxi skirts are the ultimate canvas for self-expression. Play with prints, play with textures—go wild, because these skirts are down for whatever. If you’re obsessed with the long, flowy look but want to switch things up, don’t sleep on the mini version; our Stretchy Mini Skirts bring the same comfy, curve-loving magic in a shorter silhouette. Whether you’re gifting or getting, stretch skirts are the kind of piece that always sparks joy, inspires confidence, and keeps up with every plan you dream up. So go ahead, make space in your closet and your calendar—your stretchy maxi skirt era is about to begin, and it’s going to be iconic.










