Plaid Skirts

Plaid skirts are the ultimate blend of classic charm and modern flair, ready to elevate your wardrobe game with a wink and a nod. Whether you're channeling preppy vibes or edgy chic, these skirts are your ticket to turning heads and making memories. Pair them with your fave graphic tee for a laid-back look or dress them up with a sleek blouse for those nights when you're feeling extra. No matter the occasion, plaid skirts are here to remind you that fashion is all about having fun and expressing your fearless self. So go ahead, strut your stuff and let the world know you're unstoppable!

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Windsor Plaid Charm Pleated Drop Waist Skort in Grey

$36.90

A grey plaid skort with a pleated drop waist and hidden shorts in knit fabric.

Flirt Alert Plaid Lace-Up Mini Skirt in Navy Blue

$39.90

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

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Cute Icon Gingham Belted Mini Skort in Black/white

$10.97 $26.90 59% off

A gingham printed mini skort in black and white with a trendy faux belted front design.

Adorable Look Plaid Print Strapless Skater Dress in Taupe

$46.90

An adorably chic taupe skater dress featuring a plaid print and strapless sweetheart neckline.

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Windsor Senorita Mesh Strappy Mini Dress in Pink

$32.90

(91)

Look and feel like a sultry senorita in this mesh mini dress perfect for an chic night on the town! It features a sleeveless cowl neckline, dual adjustable spaghetti straps with a tie-neck closure, and side and back ruched seams designed to flaunt your curves along the bodycon silhouette. Complete the look with hoop earrings. Fit & FeaturesSleeveless cowl neckline, Dual adjustable spaghetti straps, tie-neck closure, Side and back ruched seams, Back zipper and hook-eye closure, Bodycon silhouette, mini-length hem, Mesh fabric, brushed soft knit stretchy lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Senorita Mesh Strappy Mini Dress in Pink | Size: M | Knit Fabric/Mesh Fabric/Mesh Fabric

Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Sage

$32.90

(80)

This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Sage | Size: L | Knit Fabric/Satin Fabric

Windsor Lucy Taffeta Bow Mini Party Dress in White

$79.90

(70)

The Lucy mini party dress is sleek and simple from the front and stunning from the back. Turn heads as you stun from the back with a flirty big bow tie with a dramatic train that glides against the floor! Fit & FeaturesTaffeta structured woven-lined fabric, slight stretch, Strapless, square neckline, non-slip grip, Hidden side zipper, hook and eye closure, Front and back pleating and ruching, Form-hugging, mini-length hem, Detachable back bow with train, Runs true to size, Where to Wear:Homecoming, weddings, brides, bachelorettes, big birthday events, fancy date nights, gorgeous dinner parties, cocktail soirees, rehearsal dinners, engagement photoshoots and parties Free Shipping on All Orders Over $75. | Windsor Lucy Taffeta Bow Mini Party Dress in White | Size: XS

Windsor Cute Attitude Ponte Slit Mini Skort in Black

$27.90

(67)

Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: L | Knit Fabric

Lena Strapless Bodycon Beaded Mesh Mini Dress in Pink

$84.90

(59)

Express your devotion to romance in the Lena mesh mini dress perfect for modern brides, birthday girls, or graduates! The strapless cowl neckline adds a touch of elegance, while the bodycon fit accentuates your figure. Fit & FeaturesBeaded mesh fabric, stretchy knit lining, Strapless cowl neckline, Back zipper and hook-eye closure, Bodycon fit, mini-length hem, Runs true to size, Where to Wear:Prom, date nights, bachelorettes, girl's night out, birthdays Free Shipping on All Orders Over $75. | Windsor Lena Strapless Bodycon Beaded Mesh Mini Dress in Pink | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric

Get Down With Basic Slit Mini Skirt in Black

$16.90

(53)

Minimal, but never boring. This sleek mini skirt brings the heat with a flirty slit and body-hugging fit made for going out or dressing up your everyday looks. Fit & FeaturesStretchy and smooth knit fabric, High-rise elasticized waistband, Mini-length hem, short front slit, Bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: M | Knit Fabric

Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Navy Blue

$35.90

(47)

Show off a flawless allure in this figure-flaunting mini dress! Designed with a sleek knit fabric with a fab sheen, this mini-length dress offers plenty of stretch so you can dance all night. The sleeveless bodice is shaped with a pleated cowl neckline for a chic draped effect and spaghetti straps. The pleating across the bodycon silhouette will accentuate your stunning curves. Style with metallic heels for a club night out.Fit & FeaturesStretchy sleek knit fabric, Sleeveless pleated cowl neckline, Spaghetti straps, Pleating, Bodycon fit, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flawless Allure Cowl Neck Bodycon Mini Dress in Navy Blue | Size: L | Knit Fabric

Catalina Rhinestone And Pearl Formal Mini Dress in White

$69.90

(42)

Bling on the sultry glamour with the sparkling details of the stunning Catalina formal mini dress with a bodycon silhouette that will flaunt your gorgeous figure! Fit & FeaturesSheer mesh fabric, full-length knit lining, plenty of stretch, Mini iridescent rhinestones, faux pearl embellishments, Sleeveless cowl neckline, Adjustable spaghetti straps, Mini-length hem, bodycon silhouette, Runs true to size, Where to Wear:Prom, bachelorettes, birthdays, girl's night out, date nights Free Shipping on All Orders Over $75. | Windsor Catalina Rhinestone And Pearl Formal Mini Dress in White | Size: S | Knit Fabric/Rhinestone/Mesh Fabric

Stunning Sophistication Rhinestone Mini Dress in Wine

$42.90

(38)

Keep it sophisticated with a satin mini dress that radiates luxe. The dress features a sleeveless square neckline, detachable rhinestone embellished spaghetti straps, ruched side and back seams, and a form-hugging silhouette and mini-length hem. Complete look with rhinestone heels and a satin clutch. Fit & FeaturesSleeveless square neckline, Detachable rhinestone spaghetti straps, Ruched side and back seams, Form-hugging silhouette, Mini-length hem, Lined sleek satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Stunning Sophistication Rhinestone Mini Dress in Wine | Size: M | Rhinestone/Satin Fabric

Windsor Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Navy Blue

$39.90

(29)

You'll have that perfect glow in this satin mini dress at the party! This stunning mini-length dress features a strapless neckline for a classic style, and a side pleated seam adds a touch of sophistication and creates a flattering A-line silhouette. Complete the look with stiletto heels. Fit & FeaturesSatin fabric lined with stretchy knit, Strapless neckline, Side pleated seam, A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Navy Blue | Size: L | Satin Fabric

Plaid Skirts

Plaid skirts are having a moment, but let’s be honest—they never really left. There’s something about the crisp lines and bold checks that just works, season after season. Whether you’re channeling classic schoolgirl vibes or leaning into a more grown-up, grunge-inspired look, a plaid skirt is the ultimate closet chameleon. October is the perfect time to bring them out, too—think cozy knits, knee-high boots, and a hint of that back-to-campus energy (even if you’re years past your last homeroom bell). If you’re eyeing a plaid skirt for yourself or considering one as a gift, you’re tapping into a piece that’s both timeless and totally on-trend. These skirts aren’t just for fall, but there’s something about chilly mornings, crunchy leaves, and a navy blue plaid mini skirt that just feels right. They’re a go-to for anyone who wants to look put-together without trying too hard, and the styling possibilities are endless. Pair one with a chunky sweater for weekend coffee runs or dress it up with a fitted blazer for a night out—either way, you’re winning.

When it comes to choosing the right plaid skirt, it’s all about balancing personality and practicality. Mini, midi, or something in between, there’s a length and pattern for every mood. If you’re not sure how to style plaid skirt options for different occasions, start by thinking about your favorite pieces already in your closet. A crisp white tee makes any plaid skirt Windsor-worthy, and if you’re feeling bold, try mixing patterns with a striped top or layering with a leather jacket for a little edge. The beauty of the Windsor plaid skirt collection is that it’s designed to keep up with your ever-changing plans—day-to-night, desk-to-dinner, or even that last-minute invite you just can’t pass up. These skirts also make a thoughtful gift for anyone who loves a dash of nostalgia with their modern wardrobe. Picture your best friend opening up a plaid skirt dress she’s been eyeing, or your sister styling her new plaid skirt Windsor style for her next big event. It’s a gift that feels personal, but still leaves plenty of room for her to make it her own.

Plaid is more versatile than you might think. Sure, it’s a fall staple, but it works year-round with the right pairings. Swap out boots for sneakers in the spring, or add tights and a turtleneck when the temperature drops. And if you’re ready to go all-in on the trend, don’t stop at the skirt—mix and match with Plaid Tops for a coordinated look that’s equal parts playful and polished. At the end of the day, plaid skirts are about celebrating your style, your way. They’re not just a throwback—they’re a blank canvas for whatever vibe you’re feeling. From the subtle sophistication of a navy blue plaid mini skirt to the bold statement of a full plaid skirt dress, these pieces are made for living in, not just looking at. So go ahead—twirl, layer, and make it yours. The best outfits are the ones that feel like you, and with plaid, you’re always in good company.

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