Women's Plaid Dresses

Get ready to turn heads and make waves with our collection of women's plaid dresses that scream style and confidence. Whether you're channeling your inner 90s grunge queen or embracing a chic, preppy vibe, these dresses are here to elevate your wardrobe game. Perfect for any occasion, from casual brunches to spontaneous adventures, our plaid dresses are the ultimate go-to for those who love to mix timeless patterns with modern flair. So, Windsor girl, it's time to strut your stuff and show the world that plaid is anything but plain!

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Windsor Find Me In Plaid A-Line Mini Dress in Charcoal

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Windsor Find Me In Plaid A-Line Mini Dress in Charcoal

$19.97 $35.90 44% off

A charcoal plaid mini dress featuring a strapless folded neckline and flattering A-line silhouette in soft knit.

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Windsor Heat Check Halter Mini Dress

$9.97 $39.90 75% off

A multi-colored plaid halter mini dress featuring a deep plunge neckline and ruched mesh-lined fabric.

Adorable Look Plaid Print Strapless Skater Dress in Taupe

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Adorable Look Plaid Print Strapless Skater Dress in Taupe

$20.97 $46.90 55% off

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

Edgy In Plaid Scoop Neck Mesh Mini Dress in Burgundy

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Edgy In Plaid Scoop Neck Mesh Mini Dress in Burgundy

$19.97 $26.90 26% off

A burgundy plaid mesh mini dress featuring a scoop neckline, spaghetti straps, and a hanky-style hem.

Windsor Attitude Check Velvet Cutout Mini Dress in Black

$39.90

A black velvet mini dress featuring bold cutouts, metallic ring accents, and a lace-up open back.

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Senorita Mesh Strappy Mini Dress in Pink

$19.97 $32.90
39% off

(92)

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: L | Knit Fabric/Mesh Fabric/Mesh Fabric

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

$32.90

(88)

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 Red | Size: L | Knit Fabric/Satin Fabric

Windsor Lucy Taffeta Bow Mini Party Dress in White

$79.90

(73)

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

(69)

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 White

$84.90

(62)

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 White | Size: XL | Knit Fabric/Mesh Fabric/Mesh Fabric

Get Down With Basic Slit Mini Skirt in Black

$16.90

(56)

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: XS | Knit Fabric

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Flawless Allure Cowl Neck Bodycon Mini Dress in Light Blue

$19.97 $35.90
44% off

(48)

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 Light Blue | Size: L | Knit Fabric

Catalina Rhinestone And Pearl Formal Mini Dress in Yellow

$69.90

(44)

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 Yellow | Size: M | Knit Fabric/Rhinestone/Mesh Fabric

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Stunning Sophistication Rhinestone Mini Dress in Wine

$19.97 $42.90
53% off

(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

Perfect Glow Strapless Pleat A-Line Satin Mini Dress in Gold

$39.90

(31)

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 Gold | Size: L | Satin Fabric

Women's Plaid Dresses

Plaid dresses have a way of bridging the gap between classic charm and modern versatility, making them a wardrobe staple that never really leaves the style conversation. Whether you’re reaching for a crisp A-line silhouette that flatters every curve, a sleek fitted design for that effortlessly put-together vibe, or the always-cool shirt dress (hello, borrowed-from-the-boys energy), there’s a plaid dress for every mood and moment. In January, when the weather calls for layers and cozy textures, a plaid dress becomes your secret weapon—think of it as the perfect canvas for chunky knits, knee-high boots, and your favorite wool coat. There’s something about the pattern itself—those intersecting lines in rich, earthy tones or bold pops of color—that feels both nostalgic and fresh, like a nod to vintage prep but with all the attitude of right now. If you’re building a brown plaid outfit for chilly mornings or eyeing a windsor plaid dress for that brunch you almost forgot about, you’re in good company. The beauty of plaid is how easily it adapts: belt it, layer it, dress it up or down, and it always looks intentional. And let’s be honest, a plaid dress is the answer when you want to look like you tried (without actually trying that hard).

Shopping for plaid dresses is as much about expressing your personal style as it is about practical, real-life dressing. Maybe you’re hunting for a plaid dress near me because you need something that transitions seamlessly from work to weekend, or maybe you’re on the lookout for a gift that feels thoughtful but not overdone—plaid always delivers. These dresses make fantastic presents for friends who love a touch of retro flair, sisters who live in boots and tights all winter, or anyone who appreciates a pattern that stands out in a sea of solids. Plaid is also a favorite for those “I have nothing to wear” mornings, when you need a one-and-done outfit that feels both comfortable and camera-ready. If you’re leaning into the season, pair a midi or maxi plaid dress with a turtleneck underneath and a statement belt for extra polish, or keep it casual with sneakers and a denim jacket for those rare sunny afternoons. And don’t forget the details—belts, scarves, hats, and layered jewelry can all transform your look, letting you play with proportions and textures. The best part? Plaid dresses come in a spectrum of lengths and fits, from flirty minis to sophisticated midis, so you can find the perfect match for your body type and your calendar. If you’re craving even more inspiration or want to browse a curated selection, check out our Casual Plaid Dresses for ideas that fit every occasion and every mood.

When it comes to styling, plaid dresses offer endless possibilities. Picture yourself in a classic plaid shirt dress, buttons undone just enough, layered with a chunky cardigan and finished with combat boots—equal parts cozy and cool. Or maybe you’re feeling a fitted plaid dress with sleek heels and a bold lip for that dinner date you’ve been looking forward to all week. Plaid dresses invite you to play, to experiment, and to make the look entirely your own. They’re the kind of pieces that handle repeat wears with ease (just switch up your accessories and no one will notice), and they’re built for those moments when you want to feel both comfortable and completely on point. Whether you’re shopping for yourself or picking out a gift, plaid dresses deliver that rare mix of practicality, personality, and polish. They’re timeless, yes, but never boring—always ready to help you show up as your best-dressed self, no matter where you’re headed.

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Women's Plaid Dresses

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Women's Plaid Dresses

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