Casual Wrap Skirts

Looking for a wardrobe staple that’s as versatile as your social calendar? Say hello to casual wrap skirts, the ultimate go-to for effortlessly chic vibes. Whether you're brunching with the squad or strolling through the city, these skirts are your trusty sidekick, ready to elevate any look with a twist of playful elegance. With a dash of sass and a sprinkle of charm, casual wrap skirts are here to make sure you strut your stuff with confidence and flair. Get ready to wrap yourself in style and turn every sidewalk into your personal runway!

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Cool-Girl Vibes Faux Leather Wrap Skort in Black

$22.90

A sleek black faux leather wrap skort with a high-rise waist and pleated detailing.

Windsor Radiant Sweetie Floral Polka Dot Ruffle Skirt in Black

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Windsor Radiant Sweetie Floral Polka Dot Ruffle Skirt in Black

$9.97 $26.90 63% off

A black woven skort with a floral polka dot print and ruffled mini-length skirt overlay.

Windsor Delightful Duo Polka Dot Ruffle Skirt in Black

$36.90

A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.

Flirt Alert Plaid Lace-Up Mini Skirt in Navy Blue

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Flirt Alert Plaid Lace-Up Mini Skirt in Navy Blue

$16.97 $39.90 57% off

A navy blue plaid mini skirt featuring a lace-up front, high-rise waist, and flouncy woven fabric.

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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

Casual Wrap Skirts

There’s something about a casual wrap skirt that just gets it—effortless, adaptable, and endlessly wearable, no matter how full your calendar is. If you’ve ever stood in front of your closet, coffee in hand, debating between looking put-together and actually being comfortable, you already know the magic of a wrap skirt. These pieces are the ultimate chameleons: they move with you from lazy Sunday brunches to spontaneous city strolls, from workday commutes to last-minute dinner plans. The beauty is in the wrap—literally. The adjustable fit means you’re never boxed in, whether you’re layering up with tights and boots in December or keeping it breezy with sneakers and a tee when spring rolls around. And let’s not forget the styling potential. Cinch the tie for a more defined waist, or let it sit low for that relaxed, off-duty vibe. Add a chunky sweater and a scarf for winter warmth, or switch to a simple tank when the forecast finally lets up. The casual wrap skirt is the piece you reach for when you want to look like you tried—without actually trying.

Gifting a casual wrap skirt? Genius move. It’s the kind of present that says, “I see your style, and I totally get you.” Perfect for your sister who’s always on the go, your best friend who’s building her capsule wardrobe, or even your mom who’s rediscovering her love of fashion. The adjustable fit takes the guesswork out of sizing, and the easy silhouette suits just about every body type. It’s also a win for anyone who loves pieces that multitask—think quick changes between Zoom meetings and coffee runs, or packing light for a weekend getaway. And if you’re shopping for yourself (as you should), consider it a little act of self-care. Because let’s be honest: we all deserve a wardrobe that keeps up with real life, not just highlight reels. Wrap skirts are also a lifesaver during those in-between seasons when the weather can’t make up its mind. Layer up with tights and boots now, then swap for sandals when the sun comes out. It’s the year-round staple you didn’t know you needed, until you realize you’re reaching for it on repeat.

If your style leans classic, boho, or somewhere in between, there’s a wrap skirt for that. Look for soft, flowy fabrics that drape just right, or opt for a structured cotton for a crisp, tailored feel. Prints and solids both have their moment—florals for a touch of romance, stripes for a dash of preppy, or solid neutrals that go with literally everything. And don’t underestimate the power of a well-placed ruffle or an asymmetrical hem to elevate your everyday look. The best part? You don’t have to sacrifice comfort for style. The wrap design lets you adjust the fit to your mood (and your menu—holiday dinners, anyone?), while the silhouette flatters without feeling fussy. If you’re ready to expand your rotation or want more inspiration, check out the full collection of Casual Skirts for even more ways to keep your looks fresh, easy, and totally you.

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