Plaid Looks

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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!

  • City Walk Houndstooth Plaid Blazer

    Walk down the city streets to your favorite coffee shop in this trendy blazer! It features a lapel collar, long sleeves, a long line fitted silhouette, and a plaid houndstooth pattern. The knit fabric offers a moderate stretch. Layer over a sweater dress with ankle booties.

    Fit & Features

    • Lapel collar
    • Long fitted sleeves
    • Front pockets
    • Long line fitted silhouette
    • Plaid houndstooth pattern
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0341

    Category Name: Plaid Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    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 Looks

    Price: $9.97 $22.90

    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 Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • City Girl Plaid Faux Wool Coat

    Layer on this plaid faux wool coat for a chic city girl look! It features a lapel collar, an open front, long sleeves, lined side pockets, and a mid-length hem with a fitted silhouette. The all-over plaid print will give your 'fit that classic vibe. Style over a sweater dress with knee-high boots.

    Fit & Features

    • Lapel collar, open front
    • Long sleeves
    • Side pockets, smooth lining
    • Mid-length hem, fitted silhouette, back slit accent
    • Plaid print
    • Faux wool fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0315

    Category Name: Plaid Looks

    Price: $27.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • A Polished Vibe Plaid Faux Wool Coat

    Layer on this plaid faux wool coat for a polished vibe! Featuring a lapel collar, an open front, long sleeves, side pockets, a mid-length hem, and a fitted silhouette, this coat is a definite winter staple. The all-over plaid print will keep your looks classic and chic. Style with faux leather ankle booties.

    Fit & Features

    • Lapel collar, open front
    • Long sleeves
    • Side pockets, back slit accent
    • Mid-length hem, fitted silhouette
    • Plaid print
    • Unlined faux wool fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0313

    Category Name: Plaid Looks

    Price: $27.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • City Style Plaid Long Line Blazer

    Layer on this classic plaid blazer to showcase a chic city style. It features a lapel collar, 3/4 length sleeves, front pockets, and a relaxed long-line silhouette. Style over a sweater dress with knee-high boots.

    Fit & Features

    • Lapel collar neckline
    • 3/4 length sleeves
    • Dual front pockets 
    • Open front design
    • Long line silhouette
    • Plaid print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0335

    Category Name: Plaid Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrap Me In Plaid Fringe Scarf

    Layer on this plaid scarf to brace for the cold weather ahead! It features a fringe edge design on super soft and cozy fabric. Complete the look in a cute shacket and jeans.

    Fit & Features

    • Plaid pattern
    • Fringe edge design
    • Soft and cozy fabric

    Style Number/Barcode: 07305-0432

    Category Name: Plaid Looks

    Price: $1.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Total Aesthetic Houndstooth Bucket Hat

    Match your aesthetic for the changing season in this houndstooth bucket hat! It features a classic silhouette with hints of shimmery woven lurex. Complete the look in a classic denim jacket.

    Fit & Features

    • Houndstooth pattern
    • Bucket hat silhouette
    • Woven lurex

    Style Number/Barcode: 07302-1329

    Category Name: Plaid Looks

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cuddle Weather Plaid Blanket Scarf

    Cuddle up with this adorable plaid blanket scarf! It features a soft knit fabrication with trendy fringe detailing and an all-over plaid print pattern. Style with a sweater dress and knee-high boots.

    Fit & Features

    • Large blanket design
    • Knit fabrication, no stretch
    • Fringe detailing
    • Plaid print

    Style Number/Barcode: 07305-0429

    Category Name: Plaid Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cold Babe Plaid Blanket Scarf

    You can still be a babe and brace for the cold thanks to this cozy plaid blanket scarf! It features a trendy fringe edge design on cozy and soft fabric. Complete the look in a trendy jacket for a coffee run.

    Fit & Features

    • Plaid pattern
    • Fringe edge design
    • Soft and cozy fabric

    Style Number/Barcode: 07305-0431

    Category Name: Plaid Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bundle Up Plaid Blanket Scarf

    Bundle up in this classic plaid scarf that is perfect for the fall and winter seasons! It features a large blanket design with an all-over fringe hem and a chic plaid pattern. Style with a belted trench coat and booties.

    Fit & Features

    • Large blanket design
    • Soft knit fabrication, no stretch
    • Fringe hem
    • Plaid pattern

    Style Number/Barcode: 07305-0424

    Category Name: Plaid Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Autumn Chill Buffalo Plaid Scarf

    Wrap yourself in this cozy and stylish buffalo plaid scarf! It features a frayed edge design on super soft fabric. Complete the look in a cropped jacket.

    Fit & Features

    • Buffalo plaid pattern
    • Frayed edge design
    • Super soft and cozy fabric

    Style Number/Barcode: 07305-0421

    Category Name: Plaid Looks

    Price: $4.97 $15.90

    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 Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coffee Date Chic Plaid Scarf

    This adorably chic plaid scarf is perfect for your fall coffee dates! It features a large oblong design, a soft brushed knit fabrication with fringe detailing, and an all-over plaid print pattern. Style with hoop earrings and a crossbody purse.

    Fit & Features

    • Large oblong design
    • Brushed knit fabrication, no stretch
    • Fringe detailing
    • Plaid print

    Style Number/Barcode: 07305-0422

    Category Name: Plaid Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic And Cozy Plaid Long Vest

    Layer on this plaid long vest for a classic and cozy look this season. It features a sleeveless collared neckline, a complete button-down front, dual chest pockets with flap detailing, dual side pockets, a relaxed fit, and an all-over buffalo plaid print. The faux wool fabric is soft to the touch with no stretch. Style over a long sleeve top with dark wash denim.

    Fit & Features

    • Sleeveless collared neckline
    • Button-down front
    • Dual chest pockets, flap design, button closures
    • Dual side pockets, smooth lining, side slit accents at the hem
    • Relaxed silhouette
    • Buffalo plaid print
    • Faux wool fabric, no stretch
    • Runs true to size 

    Style Number/Barcode: 06204-1499

    Category Name: Plaid Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It In Check Plaid Mini Dress

    Keep your stylish look in check with this plaid knit mini dress. It features a collared V-neckline, short sleeves, and a mini-length hem with a form-hugging, bodycon silhouette. Complete the 'fit with a dainty layered necklace and booties.

    Fit & Features

    • Collared V-neckline
    • Short fitted sleeves
    • Mini-length hem, bodycon silhouette
    • Plaid print
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4743

    Category Name: Plaid Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy Element Tweed Crop Jacket

    Add a preppy element with this tweed crop jacket to layer over your outfit. It features long sleeves, a collar neckline, snap-button down closures, two flap pockets, and an oversized silhouette. Style over a basic top and faux leather shorts for an edgy-cute look!

    Fit & Features

    • Long sleeves, collar neckline
    • Snap-button down closures
    • Two flap pockets
    • Oversized silhouette
    • Cropped hem
    • Tweed fabric
    • Runs true to size

    Style Number/Barcode: 06204-1492

    Category Name: Plaid Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Between The Lines Paper Bag Shorts

    Read between the lines...these paper bag plaid shorts are so trendy for summer! They feature a high-rise elasticized waist, belt loop accents, tie-front belt, side pockets, and a fitted short-length hem.

    Fit & Features

    • High-rise elasticized waist, paper bag style
    • Belt loop accents, tie-front belt
    • Side pockets
    • Fitted short-length hem
    • Pull-on/off styling
    • Plaid pattern, knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06403-0231

    Category Name: Plaid Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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 Looks

    Price: $6.97 $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 Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Give A Twirl Linen Skater Dress

    Have your twirl-worthy moment in this linen skater dress perfect for casual parties! It features three-quarter-length puff sleeves with ruffled hems, a square neckline, a babydoll-style seam, a flirty open-back with an elasticized lattice strap, and a short-length hem with a flared-out skater silhouette. Complete the look in this skater dress with strappy stiletto heels.

    Fit & Features

    • Three-quarter-length puff sleeves, ruffled elastic cinched hems
    • Square neckline
    • Babydoll style seam
    • Open-back, elasticized lattice strap
    • Short skater silhouette
    • Plaid linen fabric, lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4717

    Category Name: Plaid Looks

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Totally Fab Plaid Skort

    Rock a totally fab vibe with a mini skirt that channels those preppy vibes! The skort features a plaid print, a high-rise waist, a pleated body, wide leg shorts with a mini skirt overlay. The skort is composed of a lined lightweight woven fabric that offers a form hugging fit with a minimal stretch. Complete look with a crop top and lug booties! 

    Fit & Features

    • Plaid print
    • High rise waist
    • Pleated
    • Wide leg shorts, skirt overlay
    • Lined lightweight woven fabric 
    • Form hugging fit, minimal stretch, runs true to size 

    Style Number/Barcode: 06301-0142

    Category Name: Plaid Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance