Evening Skirts

Ready to steal the spotlight, Windsor girl? Evening skirts are your ticket to turning any night into a runway-worthy moment. Whether you're sashaying into a gala or dancing under the stars, these skirts are designed to make you feel like the star of every show. From flirty minis that flirt with the dance floor to elegant maxis that sweep across the room, our collection is all about embracing your unique style and letting your confidence shine. So, slip into an evening skirt and let your fabulous self do the talking—because when it comes to making an entrance, you've got it down to an art!

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Wild At Heart Long Fringe Skirt in Tan

$29.90

A tan faux suede skirt with a high-rise waist and long fringe detailing for a festival-ready look.

Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

A black stretchy knit midi skirt with high-rise fit, ruching, and an asymmetrical high-side slit.

Windsor Chasing The Night Bodycon Dress Mini Skort in Black

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Windsor Chasing The Night Bodycon Dress Mini Skort in Black

$22.90

A sleek black faux leather bodycon mini skort with a high-rise waist and stretchy knit lining.

Windsor Dance The Night Away Sequin Mini Skirt in Black

Windsor Dance The Night Away Sequin Mini Skirt in Black

$39.90

A black sequin mini skirt with a high-rise waist and form-hugging fit for nights out.

Windsor Fringe Attitude Faux Suede Mini Skirt in Black

$29.90

A black faux suede mini skirt with flirty side fringe and a flattering bodycon fit.

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.

Windsor Fabulous Fit Side Slit Knit Mini Skirt in Black

$19.90

A chic black knit mini skirt with a high-rise elastic waist and sultry side slit.

She's Irresistible Faux Leather A-Line Mini Skirt in Black

$39.90

An edgy black faux leather mini skirt with side button details and a flirty A-line silhouette.

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 City Chic Faux Leather Belted Mini Skirt in Black

$32.90

A chic black faux leather mini skirt featuring a belted waist and side flap pockets.

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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

Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black

$26.90

(14)

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: L

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

City Chic Faux Leather Belted Mini Skirt in Black

$32.90

(2)

Dare to dazzle in this faux leather belted mini skirt. With a mid-rise waist, metal grommets, and side pockets, it's your go-to for a fierce and fabulous look. Fit & FeaturesCoated faux leather fabrication, Mid-rise waist, Belted waist with metal grommets, Side pockets with flap closure, Mini length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor City Chic Faux Leather Belted Mini Skirt in Black | Size: S

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

Sultry Eye Candy Floral Velvet Mesh Mini Skirt in Black

$29.90

(2)

Be the sultry eye candy in this floral velvet mesh mini skirt! The high-rise waist and bodycon fit add a touch of allure and a flattering fit. Pair with the matching top. Fit & FeaturesFlocked floral velvet pattern, mesh-lined fabric, High-rise waist, Bodycon silhouette, Mini-length hem, Runs true to size, Shop The Matching Top: Sultry Eye Candy Floral Velvet Mesh Bustier Free Shipping on All Orders Over $75. | Windsor Sultry Eye Candy Floral Velvet Mesh Mini Skirt in Black | Size: S | Mesh Fabric

She's Irresistible Faux Leather A-Line Mini Skirt in Black

$39.90

(2)

A faux leather mini skirt like this will make you simply irresistible! This high-rise skirt flaunts side button details for an edgy vibe and a flirty a-line silhouette perfect for pairing with heels or boots. Fit & FeaturesSleek faux leather fabric, High-rise waist, Side snap-button and zipper closures, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor She's Irresistible Faux Leather A-Line Mini Skirt in Black | Size: M

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

Evening Skirts

When evening plans pop up—whether it’s a black-tie gala, an intimate dinner, or that first big night out of the new year—there’s something about slipping into a statement skirt that just feels right. Evening skirts are the secret weapon in any wardrobe, built for those moments when you want to show up and show off, but still keep a little mystery. Think sweeping silhouettes that flirt with the dance floor, luxe fabrics that catch the light just so, and details that make you feel like every entrance is a main event. In January, when the world is still shaking off the holiday sparkle but you’re not quite ready to let go of the glam, a great evening skirt is the perfect bridge—elevated enough for winter’s most festive invites, but versatile enough to style again as the seasons shift. You can layer up with cozy knits and tall boots or lean into the drama with a sleek bodysuit and strappy heels. The beauty is in the options: one skirt, endless ways to spin it.

Choosing the right evening skirt comes down to a mix of mood, occasion, and that gut feeling you get when you know you’ve found “the one.” Maybe you’re shopping for yourself, ready to refresh your closet with a piece that feels both classic and current. Or maybe you’re hunting for the perfect gift for your best friend—the one who’s always RSVPing “yes” and never repeats an outfit in her camera roll. Evening skirts make a thoughtful present for anyone who loves to dress up, experiment with new looks, or just have a little fun with fashion. They’re also a lifesaver for last-minute invites: pair with a tucked-in blouse for instant polish, or throw on an oversized blazer for a modern edge that says “I just threw this together” (even if you totally didn’t). And if the invite calls for something extra-special, you can always explore our curated collection of Evening Formal Dresses for even more inspiration.

No matter your style, evening skirts are designed to work with you—not against you. High-waisted fits that flatter every curve, slinky satins that move with you, and bold prints that stand out in a sea of LBDs. It’s about feeling like the most confident version of yourself, whether you’re heading out for cocktails, celebrating a milestone, or just treating a random Tuesday like an occasion (because why not?). The right skirt lets you set the tone—elegant, edgy, romantic, or somewhere in between—without having to overthink it. And isn’t that the goal? Getting dressed should be a celebration, not a chore. So go ahead, find the skirt that speaks to you, and let your night unfold from there.

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