Plaid
Plaid outfits bring effortless preppy chic style to your Fall looks. Think mini skirts and skorts paired with knee-high boots, or plaid dresses layered under blazers for a polished vibe. Vests add an academic twist, while trenches pull it all together with timeless flair. Tartan patterns in brown, navy, and hunter green keep it classic yet trendy. Whether you’re dressing casual or elevated, plaid is the print that makes every outfit feel effortless and iconic.
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Plaid Outfits: Timeless Styles for Every Winter Occasion
Discover the charm of plaid this winter with Windsor’s Plaid Outfits collection, where classic prints meet modern style. From cozy plaid dresses for family gatherings 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 winter occasion unforgettable!
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High Waist Snap Front Plaid Skinny Pants
Keep your style in check with these trendy plaid skinny pants! They feature a flattering high waist with snap button front closures and a tapered leg fit. Pair these pants with a curve-hugging bodysuit and strappy heels for a casual date night look.
Fit & Features
- High rise waist
- Snap button front closures
- Two zippered front pockets
- Tapered leg fit
- Plaid print
- Woven fabric
Style Number/Barcode: 06402-0281
Category Name: Plaid
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Plaid Crop Top
Keep it pretty and chic in a plaid crop top! The top features a plunging wrap V-neckline, quarter-length flutter sleeves, a chic plaid print, and a lower back keyhole with back ties. Complete look with high waist jeans.
Fit & Features
- Wrap V-neckline
- 3/4 flutter sleeves
- Plaid print
- Lower back keyhole with back ties
- Cropped hem
Style Number/Barcode: 06003-1037
Category Name: Plaid
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fashionably Chic Plaid Skinny Pants
Get a fashionably chic vibe, perf for the office, in these plaid skinny pants! They feature a flattering high rise waist with a front V cut and a tie front detail. Pair these pants with a form-hugging bodysuit for an adorable look.
Fit & Features
- High rise waist with front V cut
- Tie front accent
- Back zipper closure
- Tapered pant legs
- Allover plaid print
- Woven fabric
Style Number/Barcode: 06402-0266
Category Name: Plaid
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tied To Style Plaid Skinny Pants
Make sure your stylish look is on point in these plaid skinny pants! They feature a high rise waist with a front V cut and an adorable tie front detail. Pair these pants with heeled booties for an office-ready look.
Fit & Features
- High rise waist with front V cut
- Tie front accent
- Back zipper closure
- Tapered pant legs
- Allover plaid print
- Woven fabric
Style Number/Barcode: 06402-0267
Category Name: Plaid
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glen Check Faux-Wrap Front Skirt
Stylish and chic, this glen check mini skirt is a fall staple for sure! It features a faux-wrap front and a curve-hugging silhouette. Pair this skirt with a crop top and chunky sneakers for an adorable everyday 'fit.
Fit & Features
- High rise waist
- Faux-wrap front
- Short, form-hugging fit
- Allover plaid print
- Knit fabric
Style Number/Barcode: 06501-0316
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic In Plaid Knit Mini Skirt
Get a chic look in pretty plaid in this must-have mini skirt for fall! It features a curve-hugging silhouette with a trendy side slit. Pair this skirt with a bodysuit and strappy heels for a go-to casual date night look.
Fit & Features
- High rise waist
- Short, form-hugging fit
- Side slit
- Allover plaid print
- Knit fabric
Style Number/Barcode: 06501-0311
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Playful Plaid Tie Waist Romper
Keep it playful in a chic plaid romper for your next date night. The romper features a sleeveless V-neckline with spaghetti straps, a chic tie-waist belt, and fitted cheeky shorts. Complete your look with chunky sneakers.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Plaid print
- Tie waist belt
- Cheeky shorts
- Lightweight woven fabric
- Form hugging fit
Style Number/Barcode: 06403-0132
Category Name: Plaid
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Plaid Woven Mini Dress
Keep it pretty in a plaid dress that is so on trend this season! The dress features a sleeveless square neckline, a plaid print, and a mini length silhouette. Complete your cute date night look with black mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Woven fabric
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 05102-0891
Category Name: Plaid
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Waist Plaid Cargo Skinny Pants
Keep it poised in plaid pants to create a preppy look! The pants feature a high rise waist, a plaid print, cargo-styled pockets, and a skinny leg fit. Complete your look with a cute crop top and ankle booties.
Fit & Features
- High rise fit
- Plaid print
- Cargo-styled pockets
- Skinny leg fit
- Front zipper closure
Style Number/Barcode: 06402-0282
Category Name: Plaid
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Babe Belted Plaid Mini Skirt
Look like such a babe in this chic belted plaid mini skirt! Featuring an overall form-hugging fit and an of the moment plaid print, this skirt is a season staple. Pair it with a cute crop top and mules for an adorable day date look.
Fit & Features
- High rise waist
- Belted waist
- Short, form-hugging fit
- Allover plaid print
- Woven fabric
Style Number/Barcode: 06401-0268
Category Name: Plaid
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet And Chic Plaid Mini Skirt
Showcase your sweet and chic side in this adorable plaid mini skirt! Featuring a flattering high rise waist and trendy side slit, this skirt would pair perfectly with some heeled booties. A definite must-have for a cute daytime date look.
Fit & Features
- High rise waist
- Back zipper closure
- Small side slit
- Allover plaid print
- Woven fabric
Style Number/Barcode: 06401-0267
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruched Plaid Mini Skirt
Keep it stylish in a plaid skirt that keeps you, on-trend girl! The skirt features a high rise waist, a plaid pattern, and ruched drawstrings at each side. Complete your look with a graphic tee shirt and booties.
Fit & Features
- High rise waist
- Plaid print
- Mini length silhouette
- Ruched drawstring at each side
- Form hugging fit
Style Number/Barcode: 06501-0302
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Waist Plaid Perfection Skinny Pants
Keep it posied in plaid pants that bring the chic factor to your outfits! The pants feature a high waist, a tie waist belt, a trendy plaid print, and a skinny leg fit with a tapered hem. Complete your look with a black top and mules.
Fit & Features
- High rise waist
- Tie waist belt
- Plaid print
- Skinny leg fit
- Tapered cuff
Style Number/Barcode: 06402-0265
Category Name: Plaid
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Tie Front Plaid Skinny Pants
Get a chic office-ready look in these adorable plaid skinny pants! They feature a flattering high rise waist with a V cut out in the front, a tie front detail, and a flattering, tapered fit. Pair these pants with strappy heels and you'll be a major boss babe.
Fit & Features
- High rise waist with front V cut out
- Tie front
- Skinny leg fit
- Allover plaid print
- Woven fabric
Style Number/Barcode: 06402-0264
Category Name: Plaid
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Houndstooth Plaid Mini Skirt
Keep it preppy in a plaid skirt that keeps your look on point! The skirt features a trendy houndstooth plaid pattern and a mini side slit. Complete your outfit with a tie waist crop top and sneakers to nail that casual look.
Fit & Features
- High rise waist
- Houndstooth plaid pattern
- Mini length silhouette
- Mini side slit
Model is 5'9" with 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06501-0299
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Preppy In Plaid Double Slit Mini Skirt
Get a preppy, pretty look in this trendy plaid mini skirt! Featuring a form-hugging fit and double front slits, this skirt is perf for your next party. Simply add on an adorable crop top and strappy heels for a go-to look.
Fit & Features
- High rise waist
- Short, form-hugging fit
- Double front slits
- Plaid woven fabric
Style Number/Barcode: 06401-0254
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Check Me Out Plaid Skort Romper
Check you out in this adorable plaid skort romper! Featuring a chic plaid print and an overall fitted silhouette, this romper is a must to add to your fall wardrobe. Paired with some chunky sneakers, you'll be ready for a night out with the girls.
Fit & Features
- Spaghetti straps
- V neckline
- Small front slit on skirt overlay
- Fitted shorts
- Allover plaid print
- Knit fabric
Style Number/Barcode: 06503-0160
Category Name: Plaid
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Waist Pleated Plaid Mini Skirt
Keep it preppy in a classic plaid skirt that hits the mark. The skirt features a flattering high rise waist, a classic plaid pattern, and a pleated body. Complete your preppy-inspired outfit with a crop top and boots.
Fit & Features
- High rise waist
- Classic plaid pattern
- Pleated detail
- Mini length silhouette
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06401-0250
Category Name: Plaid
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Poised in Plaid Tie Back Romper
Keep it poised in a plaid romper that is perfect for this season. The romper features a trendy plaid pattern, a sleeveless square neckline, a mid-drift cutout, and an open back with a tie back detail. Complete your look with block heels and a chic cuff.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mid-drift cutout
- Plaid pattern
- Wide leg shorts with skirt overlay
- Partially open back with tie back accent
- Lightweight woven fabric
Style Number/Barcode: 06503-0155
Category Name: Plaid
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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High Rise Glen Check Woven Mini Skirt
Chic and of the moment, this glen check woven mini skirt is a must for your fall wardrobe. It features a flattering high rise waist and a trendy double slit front detail. Wear with an off the shoulder bodysuit and some chunky sneakers for that casual cute fall look.
Fit & Features
- High rise waist
- Back zipper closure
- Double front slit detail
- Short, curve-hugging fit
- Glen check print
- Woven fabric
Model is 5'8" with a 30" bust, 23" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06401-0252
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Plaid Woven Mini Skirt
Get an effortlessly pretty look in this trendy plaid woven mini skirt! With its flattering high rise waist and chic side slit, this skirt is a must for a casual date night out. Pair with a cute top and layer on a leather jacket.
Fit & Features
- High rise waist
- Hidden back zipper closure
- Small side slit
- Short, curve-hugging fit
- Plaid print
- Woven fabric
Style Number/Barcode: 06401-0251
Category Name: Plaid
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfectly Plaid High Waist Joggers
These plaid high waist joggers couldn't get any more perfect for fall! They feature large cargo pocket detailing and a trendy jogger hem. Pair with a basic cami and classic block heels to a coffee shop with bae!
Fit & Features
- High rise waist
- Front button closure
- Slanted front pockets
- Large cargo side pockets
- Cinched jogger hem
- Plaid print
- Woven fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06302-0165
Category Name: Plaid
Price: $11.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Poised In Plaid Tie Waist Skinny Pants
Look posh and poised in these chic plaid tie waist skinny pants! They feature a high rise waist with a tie front detail and a flattering skinny leg fit. Wear them to the office and you can easily transition them for happy hour afterward. Pair with a cute blouse and classic block heels.
Fit & Features
- High rise waist
- Tie front accent
- Back zipper closure
- Skinny leg fit
- Plaid print
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06402-0269
Category Name: Plaid
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glen Check Mini Skirt
Preppy and chic, this glen check mini skirt needs to be in your closet. It features a high rise waist, a back zipper closure, a front slit, and a short, form hugging fit. The skirt is composed of a knit fabric with moderate stretch.Style Number/Barcode: 06401-0107
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance