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!
$36.90
A grey plaid skort with a pleated drop waist and hidden shorts in knit fabric.
$39.90
A navy blue plaid mini skirt featuring a lace-up high waist and flouncy woven fabric hem.
$36.90
A black and white gingham mini skirt featuring a high-rise waist and bodycon silhouette in woven fabric.
$26.90
A gingham printed mini skort with a trendy belted front and stretchy knit shorts lining.
$46.90
An adorably chic taupe skater dress featuring a plaid print and strapless sweetheart neckline.
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This adorable strapless A-line mini dress is so your vibe! Designed with a stretchy lined knit fabric, it features a strapless straight-across neckline, chic pleated detailing at the bust, and a flirty flowy A-line silhouette on the mini-length hem. Style for a girl's night with statement earrings and strappy mules. Fit & FeaturesStretchy knit fabric with knit lining, Strapless straight neckline, no-slip strip, Pleated bust, A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Your Vibe Strapless A-line Mini Dress in Light Blue | Size: L | Knit Fabric
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
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XS | Knit Fabric
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 Pink | Size: S | Knit Fabric/Satin Fabric
A true showstopper of a mini dress perfect for adding a touch of sparkle to any occasion. The short-length rhinestone dress features a square neckline and adjustable spaghetti straps, while the A-line silhouette flatters your figure down to the uneven-cut hem. Complete the look in platform sandals for a dressy night out! Fit & FeaturesSleeveless square neckline, Adjustable spaghetti straps, Back zipper and hook-eye closure, A-line silhouette, Mini-length hem, uneven cut design, Rhinestone-embellished, mesh fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sparkling Perfection Rhinestone A-Line Mini Dress in Pink | Size: XS | Knit Fabric/Rhinestone/Mesh Fabric
Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Light Blue | Size: M | Knit Fabric/Rhinestone
This chic side slit knit mini skirt will give you a fabulous fit and become a favorite in your closet! The ponte knit fabric offers a structured fit with moderate stretch. The high waist features an elasticized waistband for comfortable wear, while the mini-length hem and side slit accent will give that sultry flair. The bodycon silhouette will hug your gorgeous curves. Style this mini skirt with a basic bodysuit and ankle booties for happy hour. Fit & FeaturesPonte knit fabric, moderate stretch, High-rise elasticized waist, Mini-length hem, Asymmetric seam, side slit, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fabulous Fit Side Slit Knit Mini Skirt in Black | Size: L | Knit Fabric
Windsor Brenda Low Back Bow Taffeta Skater Dress in Black
$19.97 $64.90
69% off
Chat, dance, and twirl the night away in the Brenda taffeta skater dress! The short dress is ready to party with a voluminous silhouette and a stunning low-cut back with a statement bow. Fit & FeaturesTaffeta fabric lined with tulle, stretchy knit fabric, Tank shoulder straps, Low back with bow, Skater silhouette, Short-length hem, Runs true to size, Where to Wear:Prom, brides, weddings, bridesmaids, fancy date nights, dinner parties, cocktail events Free Shipping on All Orders Over $75. | Windsor Brenda Low Back Bow Taffeta Skater Dress in Black | Size: XS | Knit Fabric
A sassy mini dress to slip on when the sun goes down and the beat is calling you to the dancefloor! This dress is featured in a sultry bodycon silhouette with a halter neckline accented with hoop inserts. Fit & FeaturesAbstract print, stretchy knit fabric, Cowl halter neckline, hoop accents, Bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sun Goes Down Halter Abstract Bodycon Mini Dress in Brown | Size: S | Knit Fabric
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette. Fit & FeaturesDouble-lined brushed knit fabric, moderate stretch, Strapless straight neckline, Ruched side seams, Bodycon silhouette, Mini-length tiered ruffled hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Brown | Size: S | Knit Fabric
Plaid Skirts
When it comes to plaid skirts, you already know you’re about to serve a look that’s equal parts classic and rebellious—think Cher Horowitz meets your favorite pop-punk icon with a dash of modern It-girl energy. Whether you’re all in for the iconic plaid mini skirt or vibing with a flirty plaid pink skirt, there’s a Windsor plaid skirt out there with your name on it, ready to turn sidewalks into runways and group hangouts into full-on fashion moments. These skirts are the ultimate wardrobe chameleons: dress them up with a crisp button-down and knee-high boots for a little academic edge, or go full-on fun with a graphic tee and chunky sneakers. Plaid isn’t just a print—it’s a whole mood, and no matter your style, there’s a pattern and color combo that’ll have you feeling like the main character. And honestly, if you’re on the hunt for a gift that’ll make your bestie’s jaw drop, a pink and brown plaid skirt wrapped up with a note that says “for your next adventure” is basically a friendship bracelet in clothing form.
Let’s talk details, because the right plaid skirt is all about nailing the fit, the vibe, and the possibilities. If you’re all about showing off those legs, a plaid mini skirt is your ride-or-die—pair it with a slouchy sweater or a fitted crop top and you’ve got instant cool-girl status. Or maybe you’re feeling that preppy-cute energy? Go for a pleated plaid skirt and throw on a blazer, then watch as everyone suddenly wants you on their study team (or their party guest list). The beauty of plaid is that it works for literally everyone, from the trendsetter who’s always first to post her OOTD, to the low-key babe who loves a closet staple she can wear a million ways. And let’s be real, plaid skirts are basically made for making memories—think spontaneous road trips, late-night concerts, or just twirling around your room with your BFFs. They’re also the ultimate “treat yourself” buy, because nothing says confidence like stepping out in a skirt that makes you feel unstoppable. Don’t forget, if you want to level up your whole vibe, check out our curated Plaid Outfits page for inspo that’ll have your followers double-tapping in seconds.
Plaid skirts are for the girls who love to stand out and the ones who want to blend a little tradition with a lot of personality. Whether you’re shopping for yourself or searching for that perfect gift, these skirts deliver on every front: comfort, style, and major main-character energy. Picture yourself strutting into brunch, coffee dates, or your next big event—heads turn, compliments fly, and you’re living your best life with zero apologies. From the sweet charm of a plaid pink skirt to the edgy flair of a darker check, the options are endless and the compliments are guaranteed. So go ahead, pick the plaid that feels like you, and get ready to own every room you walk into. Windsor’s got your back, your style, and your next iconic look—because you deserve nothing less than legendary.