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.
HomePlaid

Plaid
Product Recommendations
STYLE SPOTLIGHT
Discover Jackets, Coats, & Shackets!
Capture black skirts with trendy hardware details!
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!
-
Casually Preppy Plaid Crop Top
Step up your fall wardrobe with this casually preppy crop top! Featuring a sleeveless square neckline, thin tank shoulder straps, a cropped hem, a form-hugging fit, and an all-over plaid print, this sweater knit top is perfect for keeping it chic. Style with the matching cardigan.
Shop Matching Cardigan: Casually Preppy Plaid Cardigan
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Cropped hem, form-hugging fit
- Plaid print
- Soft sweater knit fabric, ribbed trims, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1459
Category Name: Plaid
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Casually Preppy Plaid Cardigan
Step up your fall wardrobe with this casually preppy cardigan! Featuring long sleeves, a button-down front, a mid-length hem, a relaxed fit, and an all-over plaid print, this sweater knit cardigan is perfect for keeping it chic. Style with the matching crop top.
Shop Matching Top: Casually Preppy Plaid Crop Top
Fit & Features
- Long sleeves
- Button-down front
- Mid-length hem, relaxed fit
- Plaid print
- Soft sweater knit fabric, ribbed trims, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1460
Category Name: Plaid
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Perfectly Prepped Plaid Long Blazer
Once autumn weather rolls around you'll be perfectly prepped in this plaid longline blazer featuring long sleeves, a lapel collar neckline, double-breasted button closures, and faux front pockets. Complete the look in trendy lug boots.
Fit & Features
- Long sleeves
- Lapel collar neckline
- Double-breasted button closures
- Faux front pockets
- Longline hem
- Plaid pattern, smooth knit fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06204-1342
Category Name: Plaid
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Forever In Plaid Woven Skirt
They can find you forever in this plaid woven skirt all season! It features a high-rise waist, back zipper and hook-eye closure, a bodycon fit, and a mini-length hem. Complete the look in the matching shacket.
Shop Matching Ivory Shacket: Paint The Town Plaid Flannel Shacket
Shop Matching Taupe Shacket: Forever In Plaid Woven Shacket
Fit & Features
- High-rise waist
- Back zipper and hook-eye closure
- Bodycon fit
- Mini-length hem
- Plaid pattern, non-stretch soft woven fabric
- Runs true to size
Style Number/Barcode: 06401-0635
Category Name: Plaid
Price: $6.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Forever In Plaid Woven Shacket
They can find you forever in this plaid woven shacket all season! It features cozy long sleeves with snap-button closures, a collar neckline, front snap-button closures, flap pockets, and a relaxed fit. Complete the look with the matching skirt.
Shop Matching Bottoms: Forever In Plaid Woven Skirt
Fit & Features
- Long sleeves with snap-button closures
- Collar neckline
- Front snap-button closures
- Flap pockets
- Relaxed fit
- Plaid pattern, non-stretch soft woven fabric
- Runs true to size
Style Number/Barcode: 06204-1452
Category Name: Plaid
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Pretty And Posh Plaid Coat
You'll look pretty and posh this winter season with your new fave faux wool coat! It features a lapel collar, long sleeves, faux front pockets, and a chic plaid pattern. Layer this coat over a basic bodysuit with a faux leather mini skirt.
Fit & Features
- Lapel collar
- Long sleeves
- Faux front pockets
- Faux wool fabric, no stretch
- Plaid pattern
- Runs true to size
Style Number/Barcode: 06201-0279
Category Name: Plaid
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
-
Chill Temps Plaid Crop Shacket
When the temps are starting to chill you'll be reaching for this plaid crop shacket to keep cozy and cute! The shacket features long sleeves with button cuffs, a collared neckline, front button-down closures, flap pockets, and a relaxed fit. Complete the look in a basic bodysuit and jeans for a casual hang.
Fit & Features
- Long sleeves with button cuffs
- Collared neckline
- Front button-down closures
- Flap pockets
- Cropped hem, relaxed fit
- Plaid pattern, non-stretch woven fabric
- Fits true to size
Style Number/Barcode: 06204-1436
Category Name: Plaid
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Good To Be Plaid Woven Crop Top
What can we say? It feels good to be in this plaid crop top for fall! It features long sleeves with button cuffs, a collar neckline, button-up front closures, and a relaxed fit on lightweight woven fabric. Complete your trendy look in a mini skirt for the perf ootd!
Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button-up front closures
- Relaxed crop hem
- Plaid pattern
- Lightweight non-stretch woven fabric
- Fits true to size
Style Number/Barcode: 06003-1774
Category Name: Plaid
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Keep It On Check Plaid Crop Jacket
Keep your fall look in check in this plaid crop jacket perf for the cozy season! It features long sleeves, a collar neckline, snap-button front closures, flap pockets, and a pull tab hem with button closure. Complete the look in trendy boots.
Fit & Features
- Long sleeves, collar neckline
- Snap-button front closures
- Flap pockets
- Pull tab hem with button closure
- Cropped length
- Plaid pattern, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1421
Category Name: Plaid
Price: $18.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Season Of Flannel Plaid Corset
Behold, it's the season for this flannel plaid corset! Keep your looks casual and chic with this top featuring a sleeveless V-neckline, adjustable spaghetti straps, hidden front hook and eye closures, and a curved, cropped hem. Complete the look with the matching shacket and leggings.
Shop Matching Shacket: Season Of Flannel Plaid Shacket
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Hidden front hook and eye closures
- Back zipper, hook and eye closure
- Curved, cropped hem
- Plaid flannel woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1967
Category Name: Plaid
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
All The Trendy Vibes Bra Top
Showcase all the trendy vibes with this fitted bra top. It features a sleeveless V-neckline, adjustable spaghetti straps, a cropped, form-hugging fit, and an all-over square windowpane pattern. Style with the matching button-up top and dark wash denim.
Shop Matching Top: All The Trendy Vibes Button-Up Top
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Smocked back design
- Cropped, form-hugging fit
- Square windowpane pattern
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1873
Category Name: Plaid
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
All The Trendy Vibes Button-Up Top
Showcase all the trendy vibes with this chic collared top. It features a complete button-up front, long sleeves with dual button details, a chest pocket, and an all-over square windowpane pattern. Style with the matching bra top and dark wash denim.
Shop Matching Top: All The Trendy Vibes Bra Top
Fit & Features
- Collared neckline
- Snap button-up front
- Long sleeves, dual button details at the hems
- Chest pocket
- Relaxed fit
- Square windowpane pattern
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1872
Category Name: Plaid
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sassy Plaid Skater Skirt
School's in session in this perfect plaid skater skirt for a cute look for class! The short skirt features a high-rise waist, back zipper closure, and a flirty pleated hem on soft woven flannel fabric. Complete your look in a collared shirt.
Fit & Features
- High-rise waist
- Back zipper closure
- Pleated hem
- Short-length
- Plaid pattern
- Flannel woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06401-0470
Category Name: Plaid
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Season Of Flannel Plaid Shacket
Behold, it's the season for this flannel plaid shacket! Cozy up on those brisk walks crunching leaves in this so-soft shacket featuring long sleeves with button cuffs, a collar neckline, a front pocket, button-down closures, and a relaxed curved hem. Complete the look with the matching corset and leggings.
Shop Matching Top: Season Of Flannel Plaid Corset
Fit & Features
- Long sleeves, button cuffs
- Collar neckline
- Front pocket
- Button-down closures
- Relaxed curved hem
- Plaid flannel woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1489
Category Name: Plaid
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Big Apple Corduroy Plaid Trench Coat
Big apple energy whether or not you're in the city! Layer on this plaid trench coat to elevate your outfit. It features long sleeves with button cuffs, a collar neckline, front flap pockets, a button-down front, and a tie-waist belt. Complete the look in a mini sweater dress and booties.
Fit & Features
- Long sleeves, button cuffs
- Collar neckline
- Front flap pockets
- Button-down front
- Tie-waist belt
- Plaid pattern, corduroy fabric
- Fits true to size
Style Number/Barcode: 06204-1413
Category Name: Plaid
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Plaid Princess Tweed Mini Skirt
Everyone knows you're the princess of plaid! This 90's-inspired tweed skirt features a high-rise waist, back zipper closure and lower slit accent, and a mini-length hem. Complete the look in the matching top.
Shop Matching Top: Plaid Princess Tweed Tube Top
Fit & Features
- High-rise waist
- Back zipper closure
- Lower back slit accent
- Mini-length hem
- Plaid pattern
- Lined tweed woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06401-0468
Category Name: Plaid
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Seasonal Plaid Crepe Mini Skirt
It's feeling like the season of plaid! Create a cute and casual outfit with this crepe mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty slit accent. Complete the look with a denim jacket.
Fit & Features
- High-rise waist
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Plaid pattern
- Crepe knit fabric
- Fits true to size
Style Number/Barcode: 06501-0699
Category Name: Plaid
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Plaid Haven Casual Woven Blazer
Get your closet ready for fall with this plaid woven blazer perfect for layering over your chic workwear fits! It features long sleeves with shoulder pads, a lapel collar neckline, single front button closure, faux pockets, and a hip-length hem. Complete the look in booties.
Fit & Features
- Long sleeves, shoulder pads
- Lapel collar neckline
- Single front button closure
- Faux pockets
- Hip-length hem
- Plaid pattern, lined woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1438
Category Name: Plaid
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Gone Off The Grid Plaid Joggers
Take your fashion to new heights in these grid plaid joggers featuring a high-rise waist, eye-catching suspenders along the sides, a relaxed fit, and elasticized hem. Complete the look in a basic crop tee and sneakers.
Fit & Features
- High-rise waist
- Front button and hidden zipper closure
- Belt loop accents, side pockets
- Suspenders along the sides
- Relaxed fit, elasticized hem
- Grid plaid, woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06302-0690
Category Name: Plaid
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Cool And Classic Plaid Twist Top
A cool take on a forever classic! This plaid woven top brings effortless styling for back-to-school, fall festivals, and PSL runs. It features long sleeves with buttoned cuffs, a collar neckline, a three-button front closure, and a twisted crop hem. Complete the look in skinny jeans and sneakers.
Fit & Features
- Long sleeves, buttoned cuffs
- Collar neckline
- Three-button down front closures
- Twisted crop hem
- Plaid print
- Woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1842
Category Name: Plaid
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Preppy Fall Vibes Knit Mini Skirt
This adorable knit mini skirt will bring the preppy fall vibes to your looks! It features a high-rise waist, a short, curve-hugging fit, a chic side slit, and an all-over jacquard houndstooth print. Style with a corset top, a cropped cardigan, and mules.
Fit & Features
- High-rise elasticized waist
- Mini-length hem, form-fitting silhouette
- Side slit
- Jacquard houndstooth print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0718
Category Name: Plaid
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Plaid Crush Slit Mini Skirt
Got a seasonal crush on plaid? This mini skirt is perfect for adding to the collection! It features a high-rise waist, bodycon silhouette, and front slit accent on stretchy knit fabric. Complete the look in a cutout crop top and boots.
Fit & Features
- High-rise waist
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Plaid print
- Knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0701
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Plaid Me Up Flocked Mini Skirt
Shift into the season of plaid! This mini skirt features a high-rise waist, bodycon silhouette, and a front slit accent on flocked knit fabric. Complete the look in a flirty crop top for lunch with friends.
Fit & Features
- High-rise waist
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Plaid pattern
- Flocked knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0700
Category Name: Plaid
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Casual Fall Days Flannel Shacket
Layer on this trendy flannel shacket for those casual fall days! It features a collared neckline, long sleeves, a button-down front, buttoned chest pockets, a relaxed fit, and an all-over plaid print. Style with a basic bodysuit, denim, and combat boots.
Fit & Features
- Collared neckline
- Long sleeves, buttons to cuff
- Button-down front
- Buttoned chest pockets
- Relaxed fit
- Plaid print, woven flannel fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1444
Category Name: Plaid
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale