Fashion Plaid Skirts

Fashion plaid skirts are your ticket to effortlessly chic vibes, blending timeless patterns with modern flair. Whether you're channeling your inner punk rock queen or embracing preppy elegance, these skirts are a versatile must-have for every wardrobe. Pair them with a sleek turtleneck for a sophisticated look or throw on a graphic tee for that cool-girl edge. From brunch dates to boardroom meetings, fashion plaid skirts have got your back, turning every sidewalk into your personal runway. Get ready to strut your stuff and make a statement that's as bold as you are!

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Sweet And Scandalous Plaid Lace Mini Skort in Red

$39.90

A red plaid knit mini skort with pleated flare, lace-trim hem, and low-rise waist.

Polished Edit Plaid Pleated Mini Skort in Brown

Best Seller

Polished Edit Plaid Pleated Mini Skort in Brown

$42.90

A brown plaid woven mini skort featuring pleats, side button accents, and hidden fitted shorts.

Checkmate Plaid Mini Skort in Brown

$39.90

A brown plaid mini skort crafted from faux wool with front button details and a high-rise waist.

Check Me Out Ruffle Mini Skort in Black

$36.90

A black plaid knit mini skort featuring tiered ruffles, built-in shorts, and a playful silhouette.

Plaid Attitude Pleated Mini Skort in Navy Blue

$34.90

A navy blue plaid pleated mini skort in woven fabric with a buckle belt and shorts lining.

Plaid About You Mini Skort in Brown

$34.90

A brown plaid mini skort featuring a mid-rise waist, mini bow detail, and hidden fitted shorts.

Windsor Sweet On Repeat Plaid Skort in Navy Blue

Best Seller

Windsor Sweet On Repeat Plaid Skort in Navy Blue

$34.90

A navy blue plaid pleated skort with front bow ties, featuring woven fabric and a stretchy knit lining.

Prep It Up Ruffled Plaid Mid-Rise Skort in Blue

Sale

Prep It Up Ruffled Plaid Mid-Rise Skort in Blue

$7.97 $34.90 77% off

A blue plaid cotton skort featuring a mid-rise waist, adjustable drawstring, and flirty ruffled tiers.

Daydream Flow Plaid Chiffon Skirt in Brown

Sale

Daydream Flow Plaid Chiffon Skirt in Brown

$16.97 $39.90 57% off

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

Windsor Flirt Alert Plaid Lace-Up Mini Skirt in Navy Blue

$39.90

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

Now Trending

Keep It Cool Mid-Rise Acid-Wash Denim Skort in Black

$34.90

(17)

Capture cool vibes in this on-trend acid-wash denim skort! Designed with a cotton-blend denim fabric, the skort offers a moderate stretch. The flattering mid-rise waist leads to a mini-length overlay over hidden fitted shorts for coverage. The skort features a classic five-pocket and belt loop design and a hidden front zipper and button closure. Style with a graphic tee and combat boots for an edgy-chic concert look. Fit & FeaturesAcid wash cotton-blend denim fabric, moderate stretch, Mid-rise waist, Five-pocket and belt loop design, hidden front zipper, button closure, Mini-length overlay, hidden fitted shorts, Form-hugging fit, Skort in size small has a 10" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep It Cool Mid-Rise Acid-Wash Denim Skort in Black | Size: XS | Cotton

It-Girl Sparkle Rhinestone Denim Skort in Black

$44.90

(9)

Built for the spotlight, this rhinestone denim skort gives it-girl after-hours energy. With its high-rise waist and body-hugging fit, it’s your go-to when you want all eyes on you. Shop Matching Top: It-Girl Sparkle Rhinestone Denim Halter TopFit & FeaturesDenim fabrication with rhinestone embellishments, Mid-rise waist, Mini-length skort design with back shorts lining, Front zipper and button closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor It-Girl Sparkle Rhinestone Denim Skort in Black | Size: S

Charming Allure Drop Waist Tiered Lace Skort in Ivory

$29.90

(8)

Look and feel charming in this lace skort designed with flirty ruffles and knit-fitted shorts for coverage. Pair with a jean jacket. Fit & FeaturesMesh floral lace fabrication, moderate stretch, Drop waist, Tiered-ruffles, Mini skirt-like overlay, Knit fitted shorts, Skort in size small has an 8" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Charming Allure Drop Waist Tiered Lace Skort in Ivory | Size: L | Lace Fabric

Buckle Down Denim Mini Skort in Brown

$39.90

(7)

This isn’t just a skort—it’s a serve. Buckle straps + a form-hugging fit = instant upgrade to your “I just threw this on”.Fit & FeaturesDenim fabric, stretchy shorts lining, Mid-rise waist, dual side buckle straps, Back zipper and hook-eye closure, Form-hugging fit, Skirt overlay with hidden snap-button closure, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Buckle Down Denim Mini Skort in Brown | Size: XL

Admirable Style High-Rise Ponte Mini Skort in Black

$24.90

(6)

Bring on the compliments in this high-rise skort featuring a flattering A-line silhouette and mini-length hem. The smooth ponte knit fabric offers a polished look and plenty of stretch. Fit & FeaturesPonte knit fabric, shorts lining, moderate stretch, High-rise waist, A-line silhouette, Mini-length hem, Skort has a 11.5” front rise with a 1.5” inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Admirable Style High-Rise Ponte Mini Skort in Black | Size: S | Knit Fabric

School's Out High-Rise Pleated Ponte Skort in Black

$29.90

(6)

Achieve a preppy look with this pleated ponte skort in a flattering high-rise waist and mini-length perfect for showing off boots or flats! Fit & FeaturesPonte knit fabric, shorts lining, High-rise waist, Pleated skirt overlay, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor School's Out High-Rise Pleated Ponte Skort in Black | Size: XS | Knit Fabric

Perfection High-Rise Ruffled Mini Skort in Black

$34.90

(5)

The perfect ruffled skort that will turn heads with every wear! Fit & FeaturesKnit fabric, High-rise waist, Ruffled mini-length skirt overlay, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfection High-Rise Ruffled Mini Skort in Black | Size: S

Style Game High-Rise Buckle Pleated Mini Skort in Black

$32.90

(4)

Level up your style game in this ponte mini skort this weekend! This skort features a high-rise waist with faux leather buckle accents, adding a touch of chic edginess. The pleated mini-length hem adds flirty movement, while the shorts lining ensures comfort and coverage. Complete the look in a cute graphic tee and sneakers. Fit & FeaturesPonte knit fabric, stretchy knit shorts lining, High-rise waist with faux leather buckle accents, Pleated mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Style Game High-Rise Buckle Pleated Mini Skort in Black | Size: L | Leather/Knit Fabric

Sale

Fierce And Trendy Mid-Rise Leopard Mini Skort

$14.97 $36.90
59% off

(4)

Unleash your fierce and trendy side in this leopard mini skort! The belted waist and pleated skirt overlay create a trendy look while the mini hem shows off your legs. Fit & FeaturesLeopard print, denim fabric, Mid-rise belted waist, belt loop accents, Pleated skirt overlay, side zipper closure, Shorts lining, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fierce And Trendy Mid-Rise Leopard Mini Skort | Size: M

Windsor Polished Edge Ruffle Bouclé Skort in Black

$42.90

(4)

This bouclé lurex mini skort serves polished-but-playful energy — sparkly woven texture, gold button details, and a flirty ruffle hem that ties the whole “effortlessly chic” vibe together. It’s giving a holiday party, a gallery opening, and any night you want to look expensive without even trying. Shop The Matching Jacket: Polished Edge Crop Bouclé JacketFit & FeaturesBouclé lurex woven fabrication, sewn-in lining, Mini skort silhouette with flounce ruffle hem, Decorative button and pocket detailing, Hidden shorts for comfort, Back zipper and hook-eye closure, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Polished Edge Ruffle Bouclé Skort in Black | Size: M | Woven Fabric

Fashion Plaid Skirts

Plaid skirts have a way of stepping into your wardrobe and instantly making everything feel a little more considered, a little more intentional—without ever looking like you tried too hard. There’s a reason they’ve earned icon status, cycling through decades and trends with a wink and a twirl. Right now, that energy feels especially right for January: the start of a new year, the promise of a fresh semester, and the kind of crisp, chilly air that calls for layers and clever styling. Whether you’re building a blue plaid skirt outfit with knee-high boots and a chunky knit, or reaching for a pink plaid skirt to brighten up a grey day, there’s something about plaid that just works. It’s playful but polished, classic but never stuffy. The real magic is in the versatility—dress it up for a dinner date with a fitted turtleneck and statement earrings, or keep it casual with tights, sneakers, and a slouchy cardigan for coffee runs or campus hangs. If you’re gifting, plaid skirts are a thoughtful pick for anyone who loves to mix preppy with a little bit of edge, or for that friend who’s always hunting for the next “it” piece to break up her rotation of jeans and leggings.

When you’re shopping for a plaid skirt, consider the mood you want to serve: a plaid mini skirt sexy enough for a night out pairs perfectly with over-the-knee boots and a sharp blazer, while a longer, pleated style leans into that effortless academic vibe. Color is everything—classic reds and greens channel tradition, but don’t sleep on a blue plaid skirt for a cool, unexpected twist or a pink plaid skirt for a softer, more playful take. Fit is key, too. High-waisted options cinch you in and elongate your silhouette, while a mid-rise sits comfortably for all-day wear. Look for details like subtle pleats, raw hems, or a touch of stretch that make a windsor plaid skirt feel like it was made for you. And don’t underestimate the power of layering: tights, tall socks, and oversized knits let you keep your favorite skirts in rotation long after the holiday lights come down. Whether you’re styling for the classroom, brunch, or a spontaneous night out, plaid skirts are the kind of piece that moves with you—easy to dress up, down, or somewhere in between, depending on your mood (and your calendar).

If you’re ready to refresh your rotation or just want to see how many ways you can work plaid into your everyday looks, the possibilities are endless. Plaid skirts make a strong case for outfit repeating, especially when you start mixing textures, colors, and accessories to suit the season. They’re an easy way to experiment with trends—think moto jackets, cropped sweaters, or even a graphic tee layered underneath for a bit of attitude—without ever feeling overdone. And if you’re still building your collection, or just need a little inspiration, our curated selection is here to help you find that perfect fit. For more options and style ideas beyond the classics, check out our full range of Fashion Skirts to keep your wardrobe feeling fresh all year long.

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