Holiday Midi Skirts

Get ready to sleigh the holiday season with our fabulous collection of holiday midi skirts! Perfect for every festivity under the twinkling lights, these skirts are your go-to for adding that extra dash of glam to your wardrobe. Whether you're sipping cocoa by the fire or tearing up the dance floor at the annual office party, our midi skirts have got you covered. From velvet textures to shimmering sequins, you'll have all eyes on you as you make your grand entrance. So go ahead, strut your stuff and let those holiday vibes shine through with every step!

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Chic Allure High-Slit Midi Skirt in Burgundy

$29.90

A burgundy knit midi skirt featuring a high-rise waist, front ruching, and an asymmetric high side slit.

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Sweet Stroll Ruched Midi Skirt in Black

$7.97 $39.90 80% off

A black cotton-blend midi skirt featuring adjustable side ruching and a relaxed, mid-rise silhouette.

Windsor Daydream Flow Plaid Chiffon Skirt in Brown

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Windsor Daydream Flow Plaid Chiffon Skirt in Brown

$9.97 $39.90 75% off

A brown plaid chiffon skirt featuring a flowy A-line silhouette and an asymmetrical handkerchief hem.

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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

Holiday Midi Skirts

There’s just something about a midi holiday skirt that makes every winter gathering feel a little more magical. Maybe it’s the way the hem hits just below the knee—long enough to keep the January chill at bay, but short enough to show off your favorite boots or that perfect pair of sparkly heels you’ve been waiting to wear. Holiday midi skirts are the unsung heroes of festive style, delivering a sweet spot between elegance and ease. Whether you’re headed to a family brunch, a low-key office celebration, or a last-minute dinner with friends, these skirts make getting dressed feel like less of a puzzle and more of a party. Think of the midi as your go-to for those “I want to look put together, but not like I tried too hard” moments. Pair a pleated metallic number with a cozy knit and you’re instantly the best-dressed guest at the table—no extra effort required. Or, if you’re feeling bold, reach for a velvet or lace option and let the texture do the talking. The beauty of a midi holiday skirt is its versatility: it can be dressed up with a silky cami and statement earrings or toned down with a tucked-in tee and chunky cardigan. For anyone who’s ever stressed about repeating an outfit, here’s the secret—the right skirt makes every top in your closet feel brand new.

Choosing the perfect holiday midi skirt comes down to a few personal details—your mood, your plans, and, of course, your own signature style. If you’re shopping for yourself, look for details that make you feel special, whether that’s a shimmering sequin finish, a classic plaid, or a playful tulle overlay. The midi length is universally flattering, but don’t be afraid to experiment with silhouettes: A-line skirts are a classic for a reason, offering a gentle flare that flatters every figure, while wrap styles can highlight your waist and pencil midis bring a little extra polish. Petite? Aim for a hem that lands at the lower calf to elongate your frame. Love a little drama? A high-waisted fit with a belted accent can define your shape and add a touch of vintage glam. And if you’re gifting—a midi holiday skirt is actually a thoughtful, unexpected choice for sisters, best friends, or anyone who loves to have a few “wow” pieces in their wardrobe. It’s a gift that says, “I know you’ll find a million ways to wear this,” and trust us, she will. Holiday skirts aren’t just for December—they’re the kind of versatile staple that transitions seamlessly into January and beyond, layered up with tights and boots or paired with lighter pieces as winter gives way to spring.

When it comes to styling, the real fun begins. The key is balance: tuck in your top or opt for a fitted sweater to keep your silhouette sleek and avoid that dreaded frumpy feeling. Don’t be shy about mixing textures—satin with chunky knits, velvet with crisp cotton, or lace with a touch of leather. If you’re feeling adventurous, add a belt to define your waist or throw on a cropped jacket for a little edge. And if you’re still searching for inspiration, you can always browse our curated selection of Holiday Skirts to discover new ways to make the midi work for you. Every piece is chosen with real life in mind—designed to bring a little extra joy to your everyday routine, whether you’re headed out or staying in. The right holiday midi skirt doesn’t just complete your outfit—it sets the tone for your whole season, giving you the confidence to show up exactly as you want to be seen.

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