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!

  • Next Level Chic Houndstooth Woven Cropped Shacket

    Level up your look to casually chic with this trendy woven cropped shacket designed with a houndstooth pattern. It features a collared neckline, a complete button-down front, and a cropped hem with a relaxed fit.

    Fit & Features

    • Houndstooth woven fabric, no stretch
    • Collared neckline
    • Long sleeves with single-button detail
    • Button-down front, button accents down the back
    • Chest pockets
    • Cropped hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-1965

    Category Name: Plaid Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Checkered And Chic High-Waist Plaid Pants

    Fit & Features

    • Woven knit fabrication, moderate stretch 
    • High-rise waist with belt loops
    • Hook and bar closure with hidden zipper
    • Plaid pattern
    • Faux back pockets
    • Straight leg fit, flared hem
    • Runs true to size

    Style Number/Barcode: 06402-1458

    Category Name: Plaid Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

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  • 90s Trend Straight Leg Plaid Trouser Pants

    Fit & Features

    • Plaid print, woven fabric
    • High-rise waist with belt loop accents
    • Side pockets
    • Straight-leg fit
    • Runs true to size

    Style Number/Barcode: 06402-1457

    Category Name: Plaid Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute In Plaid Strapless Plaid A-Line Mini Dress

    Look and feel cute in this plaid strapless dress with a flattering A-line silhouette and a mini-length hem. Complete the look with a choker necklace.

    Fit & Features

    • Plaid print, woven fabric, woven lining
    • Strapless neckline
    • Back zipper closure
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5980

    Category Name: Plaid Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Icon Era Houndstooth Woven Blazer

    Shop Matching Bottoms: Icon Era Houndstooth Woven Mini Skirt

    Fit & Features

    • Houndstooth woven fabric, sewn-in woven lining
    • Lapel collar
    • Long sleeves
    • Double-breasted button closure
    • Front flap pockets
    • Runs true to size

    Style Number/Barcode: 06204-1955

    Category Name: Plaid Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie Vibe Gingham Print Thong Strap Sandals

    You'll love the cute vibe these thong strap sandals bring to your weekend 'fits! The adorable gingham print is a spring and summer staple.

    Fit & Features

    • Faux leather material
    • Gingham print
    • Almond-shaped toe
    • Thong strap design
    • Open back, on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1249

    Category Name: Plaid Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Comfy Trend Plaid Woven Oversized Shacket

    Throw it on and suddenly your everyday plans feel styled. This plaid woven oversized shacket layers easily over tanks and tees, giving cozy structure without trying too hard.

    Fit & Features

    • Plaid printed woven fabric with knit lining
    • Collared neckline
    • Long sleeves with single-button detail
    • Complete button-down front
    • Chest pocket
    • Oversized fit

    Style Number/Barcode: 06204-1950

    Category Name: Plaid Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • So Retro Pleated Plaid Skort

    Dare to be different in this pleated plaid skort. With a high-rise waist, mini button accents, and hidden shorts, it's the perfect blend of chic and playful for your next adventure.

    Fit & Features

    • Woven-knit fabrication
    • High-rise waist
    • Mini button accents at the waist, side zipper closure
    • Plaid print
    • Pleated mini skirt overlay
    • Hidden shorts
    • Runs true to size

    Style Number/Barcode: 06403-1080

    Category Name: Plaid Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Love's A Picnic Strapless Gingham A-Line Midi Dress

    Be loved and admired by everyone who sees you in this gingham midi dress showcasing a flattering A-line silhouette with convenient side pockets to keep your hands warm!

    Fit & Features

    • Gingham print, woven fabric, tulle and woven linings
    • Strapless neckline
    • Back zipper closure, stretch smocked panel
    • Side pockets
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3870

    Category Name: Plaid Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Casual Staple Plaid Flannel Top

    This plaid flannel top features a collared neckline with a button-down front, long sleeves you can cuff, a frayed hem, and the perfect oversized fit. Layer this casual staple over a basic top with denim!

    Fit & Features

    • Plaid cotton woven fabric, no stretch
    • Collared neckline
    • Button front
    • Long sleeves with button details
    • Single chest pocket
    • Frayed hem
    • Oversized fit

    Style Number/Barcode: 06003-2676

    Category Name: Plaid Looks

    Price: $8.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Plaid Appeal Cropped Shacket

    Fit & Features

    • Faux wool fabrication
    • Collared neckline
    • Button-down front closure
    • Dual chest pockets with button-closure
    • Long sleeves with single-button cuff
    • Cropped hem
    • Plaid pattern
    • Runs true to size

     

    Shop Matching Skort: Plaid Appeal A-Line Skort

    Style Number/Barcode: 06204-1948

    Category Name: Plaid Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Plaid Appeal A-Line Skort

    Show off your preppy side in this plaid a-line skort! With its high-rise waist, hidden shorts, and chic plaid pattern, this skort is your go-to for effortless style and comfort.

    Fit & Features

    • Wool fabrication
    • High-rise waist
    • Plaid pattern
    • Mini length, A-line skirt overlay
    • Hidden shorts
    • Runs true to size

     

    Shop Matching Shacket: Plaid Appeal Cropped Shacket

    Style Number/Barcode: 06403-1077

    Category Name: Plaid Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edgy In Plaid Scoop Neck Mesh Mini Dress

    Show your edge in this plaid mesh mini dress featuring a flattering scoop neckline and form-hugging fit with a hanky-style hem. Complete the look with a cardigan.

    Fit & Features

    • Plaid print, mesh fabric, stretchy knit lining
    • Spaghetti straps
    • Scoop neckline
    • Form-hugging fit
    • Hanky-style mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5952

    Category Name: Plaid Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Chic Choice Plaid Faux Suede Blazer

    A chic plaid faux suede blazer fit for a preppy girlie like you! Layer on this essential blazer in the perfect relaxed fit for comfort and a stylish look.

    Fit & Features

    • Plaid faux suede fabric, moderate stretch
    • Lapel collar
    • Long sleeves
    • Dual faux front pockets
    • Long-length hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-1947

    Category Name: Plaid Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Fab Icon Houndstooth Bow Bag Charm

    Fit & Features

    • Houndstooth patterned bow
    • Chunky chainlink
    • Keyring clip
    • Lobster clasp clip

    Style Number/Barcode: 07308-0672

    Category Name: Plaid Looks

    Price: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Silhouette Lace Trim Plaid Mini Dress

    Flirty and adorable, this plaid woven mini dress features a sleeveless sweetheart neckline with a dainty eyelet lace and ribbon trim and front bow detail, spaghetti straps, and a short form-hugging silhouette to highlight your curves. Style with hoop earrings and sleek mules.

    Fit & Features

    • Plaid woven-blend fabric with moderate stretch, knit lining at the bust
    • Sweetheart neckline with lace and ribbon trim, front bow detail
    • Ruched bust, underbust seam
    • Spaghetti straps
    • Mini-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5934

    Category Name: Plaid Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sophisticated Charm Houndstooth Mules

    Dazzle in these mules shoes. With a chic stiletto heel, open square toe, and mini bow accent, these mules bring luxe vibes to every step.

    Fit & Features

    • Stiletto heel
    • Open square toe
    • Wide strap over toe with mini bow accent
    • Tweed houndstooth pattern
    • Luxe fit cushioned insole 
    • Runs true to size

    Style Number/Barcode: 07401-5183

    Category Name: Plaid Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Plaid Sleeveless Knit Mini Dress

    Look and feel pretty in this plaid mini dress, which boasts a flirty V-neckline and bodycon silhouette that shows your curves! Pair with a leather jacket and flats.

    Fit & Features

    • Woven knit fabrication
    • Sleeveless v-neckline
    • Spaghetti straps
    • Plaid print 
    • Side slit
    • Mini length hem
    • Runs true to size

    Style Number/Barcode: 05102-5930

    Category Name: Plaid Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Adorable Look Plaid Print Strapless Skater Dress

    Adorably chic will be your vibe in this woven skater dress designed with a classic plaid print. It features a strapless subtle sweetheart neckline, a drop waist, and a short pleated skater silhouette for that cute flair.

    Fit & Features

    • Plaid printed woven fabric
    • Strapless sweetheart neckline
    • Back zipper closure
    • Drop waist
    • Mini-length pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5925

    Category Name: Plaid Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Plaid Passion Oversized Faux Wool Shacket

    It's the season for this plaid oversized shacket to come out and play! Keep cozy and cute in this shacket perfect for styling with boots.

    Fit & Features

    • Faux wool fabrication, faux suede lining, no stretch
    • Plaid pattern
    • Collared neckline
    • Long sleeves with single button cuff
    • Button-down front
    • Chest pockets with buttoned flap closure
    • Oversized fit

    Style Number/Barcode: 06204-1943

    Category Name: Plaid Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Cozy Plaid Woven Cropped Shacket

    Casually cozy, this plaid woven shacket features a collared neckline, long sleeves, a button-down front with buttoned chest pockets, and a cropped cinched hem with an overall relaxed fit. Layer over a basic top with a denim skirt and booties!

    Fit & Features

    • Plaid woven fabric, no stretch
    • Collared neckline
    • Long sleeves with single-button detail
    • Button-down front
    • Dual buttoned chest pockets
    • Cropped hem, elastic cinched back hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-1930

    Category Name: Plaid Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Layer Plaid Woven Shacket

    Get comfy in the cozy layer plaid woven shacket! With a relaxed fit, button-down front, and chic plaid pattern, it's perfect for casual hangouts. Total vibe!

    Fit & Features

    • Plaid woven fabric with knit lining, minimal stretch
    • Collared neckline
    • Button-down front
    • Single chest pocket
    • Long sleeves with single-button detail
    • Long-length hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-1936

    Category Name: Plaid Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Comfy Season Corduroy And Flannel Reversible Shacket

    Choose your vibe, whether you want to be cute and cozy or classic and comfy, in this reversible shacket designed with flannel and corduroy fabrics. It features a collared neckline, long sleeves, a complete button-down front, dual chest pockets on the corduroy side, and a trendy relaxed fit.

    Fit & Features

    • Reversible design, flannel woven fabric, corduroy fabric
    • Collared neckline
    • Long sleeves
    • Button-down front
    • Dual chest flap pockets on corduroy side
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-1923

    Category Name: Plaid Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic Charm Plaid Wrap Skort

    Shop Matching Jacket: Classic Charm Plaid Trench Coat

    Fit & Features

    • Faux wool fabrication
    • Mid-rise waist, back zipper and hook-eye closure
    • Mini skirt wrap overlay
    • Hidden stretchy knit shorts
    • Plaid pattern
    • Runs true to size

    Style Number/Barcode: 06403-1065

    Category Name: Plaid Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free