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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Bold Simplicity Bodycon Dress Maxi Skirt in Olive

$32.90

An olive green maxi skirt crafted from double-lined, slinky knit fabric with a bodycon silhouette and ruched sides.

Eyes On You High Slit Maxi Skirt in Neon Pink

$36.90

A neon pink maxi skirt featuring a high side slit, ruched details, and hardware accent in stretchy knit.

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Windsor Wild At Heart Long Fringe Skirt in Tan

$29.90

(34)

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

Sleek Status Faux Leather Mini Skirt in Black

$19.90

(8)

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: XS

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: S | Knit Fabric

Windsor Trendy Moves Long Fringe Skirt in Black

$36.90

(4)

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

Life Of The Party Lace-Up Mini Skirt in Brown

$42.90

(2)

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: M | Leather

Shake It Up Fringe Maxi Skirt in Tan

$29.90

(2)

Shake and shimmy at concerts and festivals in this showstopping fringe maxi skirt with your fave cowboy boots! Fit & FeaturesFaux suede fabric, High-rise waist, back zipper and hook-eye closure, Fringe silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Shake It Up Fringe Maxi Skirt in Tan | Size: S | Faux Suede

Cue The Sparkle Rhinestone Fishnet Maxi Skirt in Silver

$89.90

(2)

Cue the sparkle—this rhinestone fishnet maxi skirt was made to own the night. With a thigh-skimming slit and trendy shine, it'll give off effortless cool-girl glam. Shop Matching Top: Cue The Sparkle Rhinestone Fishnet Halter TopFit & FeaturesRhinestone-embellished, mesh-lined fabric, High-rise fit with subtle stretch, High side slit design, Form-hugging silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cue The Sparkle Rhinestone Fishnet Maxi Skirt in Silver | Size: S

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Windsor Check Please Plaid Mini Skort Skirt in Ivory

$17.97 $39.90
55% off

(2)

Prep but make it playful. This plaid mini skort gives you that flirty skirt look with the hidden comfort of shorts—aka your new go-to for coffee runs, brunch plans, or anything that needs a little “effortless but put-together” look. Shop the matching trench coat. Shop The Matching Trench Coat: Check Please Plaid Trench CoatFit & FeaturesPlaid pattern, wool-blend fabric, stretchy knit shorts lining, Mid-rise waist, Back zipper and hook-eye closure, Front faux wrap skirt overlay, Shorts bottom, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Check Please Plaid Mini Skort Skirt in Ivory | Size: XS | Knit Fabric

Sale

Windsor So Perfect Mid-Rise Pleated Denim Mini Skirt

$7.97 $36.90
78% off

(2)

The perfect denim mini skirt will elevate your everyday style with a trendy pleated silhouette and a flattering mid-rise waist. Complete the look with a graphic tee. Fit & FeaturesDenim fabric, minimal stretch, Mid-rise waist with seam detailing, Front button and hidden zipper closure, Pleated silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Perfect Mid-Rise Pleated Denim Mini Skirt | Size: L

Chic Confidence High Slit Mesh Midi Skirt in Black

$26.90

(2)

When subtle isn’t the move, this mesh midi skirt delivers. With a thigh-high slit and ruched waist, it’s the kind of style that owns the night and brings the confidence. Fit & FeaturesSheer mesh fabric with knit lining, high stretch, High-rise waist, ruching, Ultra-high front slit, Asymmetric midi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Confidence High Slit Mesh Midi Skirt in Black | Size: L | Knit Fabric/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.

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