Casual Plaid Dresses
Hey there, trendsetter! Get ready to slay the day with casual plaid dresses that are as versatile as they are chic. Perfect for everything from a coffee date with your besties to a spontaneous road trip, these dresses are your ultimate go-to for effortlessly cool vibes. Whether you're channeling grunge goddess or laid-back luxe, we've got the styles that'll make you feel like the main character in every scene. Embrace those classic checks and let your personality shine through because you were born to stand out, not blend in!
$9.97 $59.90 83% off
A charming red gingham skater dress featuring an open back, ruffled hem, and lace-trimmed neckline.
$21 $29.90 30% off
An adorable charcoal plaid mini dress with sheer lace trims and a chic center bow detail.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a bodycon silhouette.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$35.90
A burgundy plaid mini dress with lace trim, spaghetti straps, and a form-hugging silhouette.
$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
Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Yellow
$19.97 $32.90
39% off
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 Yellow | Size: L | Knit Fabric
Casual Plaid Dresses
Plaid dresses are that one closet staple you’ll reach for again and again, whether you’re vibing with a classic checkered dress or feeling the flirty energy of a windsor gingham dress. There’s just something about those bold lines and playful patterns that make every outfit feel a little more put-together without even trying. Imagine rolling out of bed, tossing on a plaid dress, and instantly looking like you spent hours planning your look—yeah, that’s the magic of plaid. It’s the ultimate go-to for coffee runs with your girls, lazy afternoons at the park, or those spontaneous road trips that start with “let’s just see where we end up.” And if you’re the friend who’s always on the hunt for the perfect gift, a plaid dress is basically a love letter in clothing form. It’s thoughtful, versatile, and guaranteed to make your bestie feel like the main character, whether she’s snapping pics for the ‘gram or just living her best life.
When it comes to picking out the perfect windsor plaid dress, it’s all about finding your vibe. Maybe you’re into those oversized silhouettes that give off major borrowed-from-my-crush energy, or you want something fitted and flirty that’s ready for brunch dates and rooftop hangs. Don’t forget to play with details—think ruffled hems, cute tie belts, or a sweet button-down neckline that lets you layer with your favorite tee or rock solo for that effortless “I woke up like this” look. And let’s be real: plaid dresses are basically the chameleons of your wardrobe. Dress them down with sneakers and a messy bun for errands, or throw on some chunky boots and a denim jacket when you’re feeling a little extra. For anyone who loves mixing it up, plaid is the print that plays nice with everything—leather jackets, cozy cardigans, even your wildest accessories. It’s made for the girl who’s always on the move, who wants to look cute without the stress, and who knows that confidence is the best accessory she can wear.
Plaid isn’t just a pattern; it’s a whole mood. Whether you’re channeling retro picnic vibes in a gingham mini or keeping it low-key with a checkered dress that’s perfect for every day, these pieces are made to move with you—no matter what’s on your calendar. They’re the kind of dresses that work for study sessions, first dates, family dinners, and everything in between. If you’re thinking about treating yourself (or someone you love) to a wardrobe upgrade, plaid dresses are the definition of timeless-meets-trendy. You’ll find yourself reaching for them whenever you want to look cute without overthinking it. Want to see all the ways you can style this iconic print? Check out the full collection on our Women's Plaid Dresses page and get ready to make every day your runway.