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.

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Keep A Secret Lace Slit Maxi Skirt in Black

$39.90

A sheer black lace maxi skirt with a high-rise waist, ruching, and a high front slit.

Breezy Boho Sheer Lace Asymmetric Maxi Skirt in Ivory

$39.90

A breezy ivory lace maxi skirt with a high-rise waist, side slit, and asymmetric hem.

Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural

$32.90

A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.

Windsor Floral Sensation High Rise Maxi Skirt in Pink

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Windsor Floral Sensation High Rise Maxi Skirt in Pink

$14.97 $34.90 57% off

A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.

Boho Babe Lace Hanky Hem Maxi Skirt in Ivory

$32.90

An airy ivory lace maxi skirt with a high-rise waist and flowy hanky hem.

Windsor Strut It Out Abstract Zebra Maxi Skirt in Brown

$34.90

A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.

Windsor Romance Me Floral Jacquard Maxi Skirt in Pink

$39.90

A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.

Windsor The One High-Rise Slit Maxi Skirt in Brown

$26.90

A brown high-rise maxi skirt with an asymmetrical slit and form-hugging knit silhouette.

On The Prowl High-Rise Slit Leopard Maxi Skirt

$36.90

A fierce leopard print maxi skirt with a high-rise waist and dramatic front slit.

Island Muse Tropical Floral Maxi Skirt in Black

$34.90

A black mesh maxi skirt featuring a tropical floral print, high-rise waist, and form-hugging silhouette.

Windsor She Came to Slay Floral Maxi Skirt in Fuchsia

$34.90

A fuchsia abstract floral maxi skirt in sheer mesh with a back slit and form-hugging fit.

Windsor Resort Calling Mesh Slit Maxi Skirt in Black

$39.90

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

Windsor Under The Sun Tropical Slit Maxi Skirt in Black

$39.90

A black tropical print maxi skirt in stretchy knit fabric featuring a high front slit and flowy silhouette.

Windsor Gorgeous Getaway Tropical Print Maxi Skirt in Black

$24.90

A tropical print maxi skirt in black mesh with a high-rise waist and sultry side slit.

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Slay It With Style Mini Skirt in Black

$9.97 $22.90
56% off

(42)

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

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

Serving Style Cargo Mini Skirt in Brown

$34.90

(19)

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: XL

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

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

Keep A Secret Lace Slit Maxi Skirt in Black

$39.90

(6)

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

Flirty Ways Ruched High Slit Midi Skirt in Ivory

$26.90

(6)

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

Windsor First Take Micro Slit Mini Skirt in Black

$14.90

(5)

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

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

Stretchy Maxi Skirts

Let’s be real—there’s just something about a stretchy maxi skirt that makes you feel like you could take on the world (or at least the dance floor). These aren’t your average skirts; they’re your secret weapon for those days when you want to look effortlessly put-together without sacrificing one ounce of comfort. Picture yourself gliding through a brunch date, running errands, or vibing at a rooftop party—all while feeling like you’re wrapped in your favorite cozy blanket, but looking like an absolute goddess. Stretchy skirts are the ultimate “get you a skirt that can do both” moment: they hug in all the right places, move with you (not against you), and somehow manage to make every top in your closet look like it was made to match. Whether you’re a queen of the minimalist look, obsessed with bold prints, or somewhere in between, long stretchy skirts are your ticket to endless outfit possibilities. They’re a closet staple for everyone from the campus trendsetter juggling classes and coffee runs to the boss babe making power moves at the office, and even the chill girl who just wants to keep things cute and comfy for movie night with the squad.

Gifting a stretch skirt? You’re officially the MVP of any birthday, celebration, or just-because surprise. Stretchy maxi skirts are that rare find that works for everyone—your bestie who lives for statement jewelry, your cousin who’s always on the go, or your mom who deserves to feel fabulous every day. They’re the kind of gift that says, “I get you, and I want you to feel amazing.” And let’s not forget how these skirts play well with literally everything: crop tops for a little sass, oversized sweaters for a cozy-chic vibe, or even a fitted blazer for those “I’m the boss” moments. The beauty of a stretch skirt is in its versatility—dress it up with heels and a clutch for a night out, or keep it low-key with sneakers and a denim jacket for a casual day adventure. The stretchy waistband is basically a love letter to comfort, making it easy to slip on and off, and perfect for those days when you want to look good without putting in extra effort. If you’re all about maximizing your wardrobe, these skirts are your new BFF. And if you’re loving the whole stretchy, comfy, and cute aesthetic, you’ll be obsessed with our Stretchy Maxi Dresses collection too—trust, it’s a vibe you won’t want to miss.

Let’s not sleep on how these stretch skirts are the ultimate travel companions. Rolling up a long stretchy skirt into your weekender bag? Zero wrinkles, zero worries, and a million outfit combos just waiting to happen. They’re a lifesaver for those spontaneous plans that pop up—think last-minute road trips, impromptu beach days, or a quick change after work when you’re heading out with friends. And for those days when you’re feeling a little extra, pair your stretchy maxi skirt with bold accessories and a killer attitude, and you’ll be serving main character energy wherever you go. No matter your shape, style, or mood, stretchy skirts are designed to celebrate you exactly as you are—confident, comfortable, and ready for anything. So go ahead, make some room in your closet (and your life) for the skirt that does it all.

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