Plaid Looks
Plaid is back, but not in the way you remember. This trending edit plays with plaid in unexpected ways, with blue and brown colorways giving the checkered pattern a fresh update. Find going out tops, halters, and off-the-shoulder shapes in flowy cotton gauze and chiffon, plus midi skirts, maxis, two-piece matching sets, and mini skorts. Funnel neck jackets and bombers add a cool-weather edge, making these looks easy for coffee runs, off-duty 'fits for winter, and plans that need a little more personality.
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Plaid Outfits: Timeless Styles for Every Winter Occasion
Discover the charm of plaid this season with Windsor’s Plaid Outfits collection, where classic prints meet modern style. From cozy plaid dresses for Frinedsgiving dinner to stylish plaid jackets that add warmth and flair, this collection has everything you need to stay chic this season. Embrace the holidays with matching plaid sets or layer up with plaid shackets and scarves that bring a festive touch to any look. Try a plaid skirt set with ankle boots for a holiday party or add a plaid cardigan to your favorite jeans for a cozy weekend style. Complete your outfit with plaid print heels or a plaid scarf for the ultimate winter vibe. Shop Windsor’s Plaid Outfits collection for more ideas and make every look unforgettable!
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High Waist Plaid Joggers With Chain
Impress with a look that's off the chain, boo! The joggers feature a plaid pattern, a high-rise waist, a single-button with hidden zipper closure, slant pockets, cargo pockets, a skinny leg fit with elastic hem, and a removable swag chain accent. The joggers are composed of a brushed twill knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with a bodysuit and ankle booties.
Fit & Features
- Plaid pattern, removable swag chain
- High-rise waist
- Single-button with hidden zipper closure
- Slant pockets, cargo pockets
- Skinny leg fit, elastic hem
- Brushed twill knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06302-0244
Category Name: Plaid Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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S'more Plaid Faux Fur Woven Shacket
Looking for some more plaid to add to your closet? This shacket makes a perfect addition! It features button-cuffed long sleeves, a collared neckline with button-down closures, flap pockets with button closures, and two side pockets, and faux fur woven-lined fabric with no stretch. Style with distressed jeans and booties.
Fit & Features
- Button-cuff long sleeves
- Collared neckline, button-down
- Flap button pockets, side pockets
- Plaid pattern, oversized fit
- Faux fur woven-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1094
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cuddle Weather Plaid Sherpa Reversible Jacket
Cuddle up in this cute jacket that is uber cozy and chic! The jacket features a reversible design, a plaid pattern, long sleeves, hidden side pockets, and a hood. The jacket is composed of a faux sherpa knit fabric that offers a relaxed fit with minimal stretch. Complete look with a beanie and ankle booties to head to the pumpkin patch.
Fit & Features
- Reversible design
- Draped open front
- Plaid pattern
- Long sleeves, hidden side pockets
- Hood
- Faux sherpa knit
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06201-0270
Category Name: Plaid Looks
Price: $14.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Trendy Reversible Shacket
Keep it trendy in this adorable cozy shacket! It has a reversible design, with a corduroy fabric on the exterior and a soft woven flannel fabric on the interior. The jacket features a collared neckline, long sleeves, a complete button-down front, top buttoned pockets on the exterior, and lower front pockets on the interior. Layer this relaxed-fitting shacket over a knit mini dress and pair it with knee-high boots.
Fit & Features
- Reversible style
- Collared neckline
- Long sleeves with single buttons to cuff
- Complete button-down front
- Top buttoned pockets on the exterior
- Lower front pockets on the interior
- Corduroy and woven flannel fabrics, no stretch
- Runs true to size
Style Number/Barcode: 06204-1093
Category Name: Plaid Looks
Price: $15.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get A Clue Plaid Blazer Dress
Showcase a trendy look with this effortlessly fab dress that will give you an all-in-one outfit! It features a blazer-designed top with a V-neckline and a lapel collar, shoulder pads, long sleeves, a dual snap-button front, a waist cutout, and a short fitted skirt with a high waist and a faux button-down design. The plaid woven fabric has a smooth lining and no stretch. Pair this dress with strappy mules.
Fit & Features
- Blazer-designed top
- V-neckline, lapel collar
- Shoulder pads, long sleeves
- Dual snap-button front
- Waist cutout, hidden side zipper closure
- Short fitted skirt, high waist, faux button-down design
- Woven fabric, smooth lining, no stretch, plaid print
- Runs true to size
Style Number/Barcode: 05102-4209
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Casual Plaid Wool Shacket
Layer on the cozy casual vibes with this adorable plaid shacket! It features a collared neckline, long sleeves, a complete button-down front, and a relaxed fit. The wool fabric offers comfortable wear. Style this shacket with leggings and combat boots.
Fit & Features
- Collared neckline
- Long sleeves, single-button details
- Complete button-down front
- Buttoned chest pockets
- Wool fabric, no stretch
- Plaid print
- Runs true to size
Style Number/Barcode: 06204-1089
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Stunner Plaid Mini Dress
You'll be a total trendy stunner in this sultry sleeveless plaid mini dress! It features a square neckline, spaghetti straps, an open back with a strappy design, and a short, curve-hugging silhouette. Complete the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, strappy design
- Mini-length, form-hugging fit
- Plaid print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4205
Category Name: Plaid Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Check It Plaid Button Shacket
Check out how cute this plaid shacket is! It features long sleeves with button cuffs, a collared neckline, a button-down front, flap pockets, and a relaxed fit. Complete the look in knee-high boots for the perf daytime 'fit.
Fit & Features
- Long sleeves, button cuffs
- Collared neckline, flap pockets
- Button-down front
- Plaid pattern
- Soft woven fabric, no stretch
- Relaxed silhouette
- Runs true to size
Style Number/Barcode: 06204-1088
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Plaid Mood Cropped Blazer
Channel a plaid mood with a cute blazer! The blazer features a collared neckline, long sleeves, a double-breast button design, and a semi-cropped hem. The blazer is composed of Ponte-like woven fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching mini skirt.
Shop Matching Mini Skirt: Plaid Mood High Slit Mini Skirt
Fit & Features
- Collared neckline, lapel accent
- Long sleeves
- Double-breasted button design
- Semi-cropped hem
- Ponte-like knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-1080
Category Name: Plaid Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plaid Mood High Slit Mini Skirt
Channel a plaid mood with a cute mini skirt! The skirt features a plaid print, a high-rise waist, a mini side slit, and a mini-length silhouette. The skirt is composed of a ponte knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching blazer and a blouse.
Shop Matching Blazer: Plaid Mood Cropped Blazer
Fit & Features
- Plaid print
- High rise waist
- Mini side slit
- Ponte knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06401-0339
Category Name: Plaid Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Preppy And Pleated Plaid Skater Skirt
Showcase your trendy status in this preppy plaid skater skirt! It features a high waist, pleated detailing, and an adorable fit and flare skater silhouette. Style this skirt with a collared crop top and cute sneakers.
Fit & Features
- High-rise waist
- Back zipper closure
- Pleated
- Short skater silhouette
- Plaid print
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06401-0334
Category Name: Plaid Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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First In Class Plaid Mini Skirt
Keep it classy with a mini skirt that hits the style mark! The skirt features a plaid print, pleats, and a skater silhouette. Complete look with a cardigan and combat boots for a look that's on-trend!
Fit & Features
- Plaid print
- Pleats
- Skater hem
- Brushed knit fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06401-0335
Category Name: Plaid Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Preppy Chic Plaid Cropped Blazer
Keep it preppy with a plaid blazer that elevates your look! The blazer features a plaid print, a collared neckline with lapel accents, a single button closure, long sleeves, and a cropped hem. The blazer is composed of a lightweight woven fabric that offers a form-hugging fit with minimal stretch. Complete look with the matching mini skirt.
Shop Matching Mini Skirt: Preppy Chic Plaid Mini Skirt
Fit & Features
- Plaid print
- Collared neckline, lapels
- Single-button closure
- Long sleeves
- Cropped hem
- Lightweight woven fabric
- Form-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1077
Category Name: Plaid Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Preppy Chic Plaid Mini Skirt
Keep it preppy with a plaid mini skirt that elevates your look! The skirt features a plaid print, a high-rise waist, a mini side slit, and a mini-length silhouette. The skirt is composed of a lightweight woven fabric that offers a form-hugging fit with minimal stretch. Complete look with the matching cropped blazer.
Shop Matching Blazer: Preppy Chic Plaid Cropped Blazer
Fit & Features
- Plaid print
- High-rise waist
- Mini side slit
- Mini-length
- Lightweight woven fabric
- Form-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06401-0331
Category Name: Plaid Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring The Flare Plaid Pants
Bring the flare with pants that are oh so stylish! The pants feature a plaid print, a high-rise waist, and a straight leg with a flared hem. Complete look with a crop top and sling-back heels.
Fit & Features
- High rise waist
- Plaid print
- Straight leg, flared hem
- Side zipper closure
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0239
Category Name: Plaid Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Plaid Suspender Mini Skirt
This on-trend suspender mini skirt will give your look a casually chic vibe! It features a plaid print, spaghetti straps, a high waist, a back zipper closure, a stylish side slit, and a mini-length curve-hugging silhouette. Pair this skirt with a cute top and sneakers.
Fit & Features
- Plaid print
- Spaghetti straps
- High waist
- Back zipper closure
- Side slit
- Short, form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-0451
Category Name: Plaid Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breaking The Rules Plaid Mini Dress
Break the rules with a mini dress that doesn't play it safe! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with thigh-high boots.
Fit & Features
- Plaid print
- Sleeveless square neckline
- Spaghetti straps
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4168
Category Name: Plaid Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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First In Class Plaid Mini Dress
Keep it classy with a plaid dress that is perf for making a stylish first impression. The dress features a sleeveless square neckline, spaghetti straps, a plaid print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4169
Category Name: Plaid Looks
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfectly Posh Tweed Plaid Blazer
Give your style a posh feel in this tweed plaid blazer. Featuring long sleeves, a lapel collar neckline, and cropped hem. Complete the look with the matching skirt.
Shop Matching Skirt: Perfectly Posh Tweed Plaid Skirt
Fit & Features
- Long sleeves
- Lapel collar neckline
- Tweed plaid pattern
- Cropped hem
- Cotton blend, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0217
Category Name: Plaid Looks
Price: $25.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plaid Daze Cropped Tank
Get on-trend for fall in this plaid cropped tank. It features a sleeveless design with wide straps, a scoop neckline, and a cropped form-hugging fit. The lightweight knit fabric offers a moderate stretch. Complete the look with the matching cardigan.
Shop Matching Cardigan: Plaid Daze Cropped Cardigan
Fit & Features
- Sleeveless, wide straps
- Scoop neckline
- Cropped, form-hugging fit
- Lightweight fabric, moderate stretch
- Plaid print
- Runs true to size
Style Number/Barcode: 06005-1098
Category Name: Plaid Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plaid Mood Button Up Flannel Top
Throw on a cute plaid top to go with your PSL this season, babe! The top features a plaid print, a collared neckline, a button-down front, a large chest pocket, long sleeves, and a frayed cropped hem. The top is composed of a flannel knit fabric that offers a relaxed fit. Complete the look with high waist jeans and booties.
Fit & Features
- Plaid print
- Collared neckline
- Button-down front, large chest pocket
- Long sleeves, single button detail
- Frayed cropped hem
- Flannel knit fabric, no stretch
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06003-1411
Category Name: Plaid Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keeping It Classy High Rise Plaid Jogger
Keep it classy with joggers that can be dressed up as a cute WFH outfit! The joggers feature a plaid print, a high-rise elastic waist, a single button with zipper closure, slant pockets, faux back pockets, and a skinny leg fit. Complete look with a bodysuit and blazer.
Fit & Features
- High rise elastic waist
- Plaid print
- Single-button with zipper closure
- Slant pockets, faux back pockets
- Skinny leg fit
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06302-0222
Category Name: Plaid Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Poised Ponte Plaid Crop Top
Keep it so poised with a crop top that elevates your style! The top features a plaid print, a sleeveless square neckline, bungee spaghetti straps, and a cropped hem. The top is composed of a ponte knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching mini skirt.
Shop Matching Mini Skirt: So Poised Ponte Plaid Mini Skirt
Fit & Features
- Plaid print
- Sleeveless square neckline
- Cropped hem
- Bungee spaghetti straps
- Ponte knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3465
Category Name: Plaid Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Poised Ponte Plaid Mini Skirt
Keep it so poised with a mini skirt that elevates your style! The skirt features a plaid print, a high-rise waist, and a mini-length silhouette. The skirt is composed of a ponte knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching crop top.
Shop Matching Crop Top: So Poised Ponte Plaid Crop Top
Fit & Features
- Plaid print
- High rise waist
- Mini length silhouette
- Ponte knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0439
Category Name: Plaid Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free