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!

  • Class In Session Plaid High Slit Mini Skort

    This sassy plaid skort will earn you an A+ in style! With a high-rise waist, form-hugging fit, and mini-length hem, you'll turn heads in all the right ways - not to mention the stunning front skirt overlay and high slit. Complete the look in a cute short-sleeved top for school or casual hangs!

    Fit & Features

    • High-rise waist, elastic waistband
    • Form-hugging fit
    • Front skirt overlay, high slit
    • Mini-length hem
    • Short lining
    • Plaid print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-1100

    Category Name: Plaid Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coolness In Check Faux Sherpa Bomber Jacket

    Keep your coolness in check with this faux sherpa bomber jacket perf for casual styling! It features a collared neckline, long sleeves with tapered hems, a zip-front design, lined side pockets, and a relaxed fit. The lined cozy faux sherpa fabric features a trendy checkered print pattern. Layer this bomber jacket over a crop top with faux leather pants and combat boots!

    Fit & Features

    • Collared neckline
    • Long sleeves, tapered hems
    • Complete zip-front design
    • Dual lined side pockets
    • Relaxed fit
    • Checkered print, faux sherpa fabric, smooth woven lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06201-0409

    Category Name: Plaid Looks

    Price: $12.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love For Cozy Season Plaid Heart Print Scarf

    This adorable plaid heart print scarf will show off your love for the cozy season! Composed of a soft woven material with short fringe hems, this long scarf features a classic plaid print and the cutest all-over heart pattern with a two-tone design. Layer over a sweater dress with over-the-knee boots!

    Fit & Features

    • Soft woven material
    • No stretch
    • Short fringe hems
    • Plaid print, heart pattern
    • Two-tone design
    • Long design

    Style Number/Barcode: 07305-0483

    Category Name: Plaid Looks

    Price: $3.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shift Into Plaid Slit Mini Skirt

    Shift into this plaid mini skirt perfect for the autumn to winter seasons! It features a flattering high-rise waist, bodycon silhouette, front slit, and a mini-length hem. Complete the look in a bodysuit and heels for a sassy vibe!

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Front slit
    • Mini-length hem
    • Plaid pattern, texture knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06501-0916

    Category Name: Plaid Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make The Rules Tweed Woven Mini Skirt

    Make a bold statement in this classy tweed mini skirt!  Its form-hugging silhouette with a front slit and mini-length hem offers an irresistible look, while the tweed fabric and sewn-in woven lining give the mini skirt a posh vibe. Complete the look with the matching trench coat and corset top for a networking event or afternoon tea downtown!

    Shop Matching Jacket: Uptown Girl Tweed Belted Trench Coat

    Shop Matching Top: Uptown Girl Tweed Corset Top

    Fit & Features

    • High-rise waist
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Front slit 
    • Mini-length hem
    • Tweed fabric, sewn-in woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06401-0610

    Category Name: Plaid Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Style Plaid Knit Skort

    Bring an iconic style to your 'fits this season with this on-trend plaid knit skort. It features a high-rise waist, a mini-length overlay with a side slit, and fitted shorts. The knit fabric features a chic plaid print pattern that is perf for the fall and winter seasons. Complete the look with a long sleeve bodysuit and over-the-knee boots.

    Fit & Features

    • High-rise waist
    • Mini-length overlay, side slit
    • Fitted shorts
    • Plaid print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-1098

    Category Name: Plaid Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Preppy-Chic Plaid Envelope Skort

    This preppy-chic plaid envelope skort is the perf addition to your fall wardrobe. It features a high-rise waist, a back zipper closure, an asymmetric faux wrap-front overlay, and fitted shorts. The woven fabric features an all-over plaid print pattern. Style this skort with a basic crop top and a faux leather blazer for a cool-girl 'fit!

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Asymmetric faux wrap-front overlay
    • Fitted shorts
    • Plaid print
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06403-0355

    Category Name: Plaid Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Checkin' It Twice Plaid Mini Skort

    This plaid mini skort is so cute you'll be checking yourself out twice in the mirror! It features a flattering high-rise waist, a front skirt overlay with a slit accent, a bodycon silhouette, and shorts lining. The plaid printed woven fabric has a moderate stretch. Complete the look in a sultry corset top for day or evening plans!

    Fit & Features

    • High-rise waist, elastic waistband
    • Front skirt overlay, slit accent
    • Shorts lining, mini-length hem
    • Plaid print
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06403-0354

    Category Name: Plaid Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightfully Cute Plaid Cargo Mini Dress

    This delightfully cute plaid mini dress dares you to stand out from the crowd! It features a square neckline, spaghetti straps, trendy side cargo flap pockets, a flattering bodycon silhouette, and a mini-length hem. Layer with a cropped jacket for casual hangs or school!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side cargo flap pockets
    • Bodycon silhouette, mini-length hem
    • Plaid print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5372

    Category Name: Plaid Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Plaid Sensation Faux Wrap Mini Skort

    Be a stylish and classic sensation in this plaid mini skort! It features a high-rise waist, a trendy faux wrap front with a pleated side seam, a form-hugging fit, and a short lining on plaid print woven fabric with minimal stretch. Complete the look in a basic tee and sneakers for off-duty days!

    Fit & Features

    • High-rise waist
    • Faux wrap front, pleated side seam
    • Form-hugging fit
    • Short lining
    • Plaid print
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0353

    Category Name: Plaid Looks

    Price: $3.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Power Hour Plaid Wide-Leg Trouser Pants

    Introduce these stylish plaid trouser pants into your weekly rotation! With a high-rise smooth waistband, subtle pleating, and a wide-leg silhouette, these pants bring chic confidence to your ensemble. Complete the look in a faux leather blazer for the office or after-work cocktails!

    Fit & Features

    • Smooth high-rise waistband
    • Back zipper and hook-eye closure
    • Subtle pleating on the front
    • Wide-leg silhouette
    • Plaid print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1350

    Category Name: Plaid Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual And Chill Plaid Shacket

    Keep it casual and chill with a shacket that brings those girl-next-door vibes. The shacket features a plaid print, a multi-button down front, two chest pockets, long sleeves with a single-button cuff, and a longline length with a rounded hem. The shacket is composed of a soft faux wool fabric that offers a relaxed fit with a minimal stretch. Complete the look with thigh-high boots.

    Fit & Features

    • Plaid print
    • Collared neckline
    • Long sleeves with button cuff
    • Multi-button down front
    • Two chest pockets
    • Longline length, rounded hem
    • Faux wool fabric, relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06204-1657

    Category Name: Plaid Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Posh This Fall Faux Suede Mini Skirt

    Get posh this fall styling this faux suede mini skirt all season! It features a high-rise waist, a form-hugging fit, a mini-length hem, and a cute checkered pattern. The soft faux suede fabric offers a moderate stretch. Complete the look in knee-high boots and a sweater for autumn-to-winter fun!

    Fit & Features

    • High-rise waist, back zipper closure
    • Form-hugging fit
    • Mini-length hem
    • Checkered print
    • Faux suede fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06401-0601

    Category Name: Plaid Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Style In Check Gingham Skater Dress

    Keep your style in check in this flirty gingham skater dress! It features a sleeveless square neck, spaghetti straps, a flattering skater silhouette, and a short-length hem. The dress is designed with an adorable gingham print on brushed knit fabric with a stretchy lining. Complete your look with a statement choker necklace and heels for a party!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Skater silhouette
    • Short-length hem
    • Gingham print
    • Brushed knit fabric, stretchy lining
    • Runs true to size

      Style Number/Barcode: 05102-5349

      Category Name: Plaid Looks

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Cozy Days Faux Fur Plaid Shacket

      You'll have so many cozy days in this cute faux fur plaid shacket perfect for the chilly season! It features comfy long sleeves, a collar neckline, a button-down front, front flap pockets with button closures, and a relaxed fit. Complete the look in trendy booties for casual plans!

      Fit & Features

      • Long sleeves
      • Collar neckline
      • Button-down front
      • Front flap pockets, button closures
      • Relaxed fit
      • Plaid pattern, faux fur fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 06201-0396

      Category Name: Plaid Looks

      Price: $9.97 $59.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Poised in Plaid Belted Shacket

      Keep it poised in a plaid shacket to usher in those winter vibes. The shacket features a collared neckline, a multi-button down front, a belted waist, and a windowpane plaid print on a corduroy fabric. Style this plaid shacket with an adorable top and booties to take you to a coffee date and lunch downtown!

       Fit & Features

      • Collared neckline
      • Long sleeves, single button detail
      • Complete button-down front
      • Dual buttoned chest pockets
      • Tie-waist belt
      • Windowpane striped pattern, corduroy fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 06204-1637

      Category Name: Plaid Looks

      Price: $18.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Pop Of Style Checkered Knit Scarf

      This bright and stylish cozy knit scarf is the perfect light accessory for any outfit. Crafted with a lightweight knit material with a checkered pattern, this scarf adds a fresh splash of color and texture. Complete the look in a trendy puffer jacket for running errands!

      Fit & Features

      • Lightweight knit material
      • No stretch
      • Long design
      • Checkered pattern

      Style Number/Barcode: 07305-0462

      Category Name: Plaid Looks

      Price: $4.97 $15.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Cutie In Plaid Long Sleeve Mesh Crop Top

      You'll be a total cutie in this trendy plaid mesh crop top! Featuring a crew neckline, long fitted sleeves, a fitted cropped hem, and adorable lettuce-edge trims, this top is a casual style staple. The lightweight sheer mesh fabric features a patchwork plaid print and offers plenty of stretch. Complete the look with high-rise denim and clear mules. 

      Fit & Features

      • Crew neckline
      • Long fitted sleeves
      • Fitted cropped hem
      • Lettuce-edge trims
      • Patchwork plaid print
      • Sheer mesh fabric, plenty of stretch
      • Runs true to size

      Style Number/Barcode: 06002-1669

      Category Name: Plaid Looks

      Price: $3.97 $19.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Softest Style Plaid Frayed Scarf

      This plaid frayed scarf will be the softest style in your lineup! Perfect for wearing around your neck or shoulders, the styling possibilities are endless. Complete the look in cute boots.

      Fit & Features

      • Plaid pattern
      • Frayed edge trim
      • Ultra-soft knit material

      Style Number/Barcode: 07305-0459

      Category Name: Plaid Looks

      Price: $7.97 $16.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Ever-So-Trendy Plaid Fringe Scarf

      This ever-so-trendy plaid fringe scarf is perfect for the cold season ahead! Wrap yourself up in this comfy and ultra-soft scarf for day or night plans. Complete the look in a trendy moto jacket.

      Fit & Features

      • Plaid pattern
      • Fringe 
      • Ultra-soft knit material

      Style Number/Barcode: 07305-0458

      Category Name: Plaid Looks

      Price: $7.97 $16.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Check It Out Gingham Plaid Mini Dress

      Make a statement in this gingham plaid mini dress! The square neckline and spaghetti straps make it the perfect dress for flaunting your curves, while the bodycon silhouette and mini-length hem radiate confidence. Complete the look by layering a long sleeve top for a preppy vibe!

      Fit & Features

      • Sleeveless square neckline
      • Spaghetti straps
      • Bodycon silhouette
      • Mini-length hem
      • Gingham plaid print
      • Texture knit fabric, moderate stretch
      • Runs true to size

      Style Number/Barcode: 05102-5243

      Category Name: Plaid Looks

      Price: $9.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Perfectly Seasoned Plaid Crew Neck Mini Dress

      Fabulous and flavor-filled, step into this plaid mini dress for the new season! The mini dress features fitted long sleeves, a classic crew neckline, and a flattering bodycon silhouette on stretchy knit fabric with a trendy plaid print. Complete the look in a moto jacket for a coffee shop hang! 

      Fit & Features

      • Fitted long sleeves
      • Crew neckline
      • Bodycon silhouette
      • Mini-length hem
      • Plaid print
      • Stretchy knit fabric
      • Runs true to size

      Style Number/Barcode: 05102-5247

      Category Name: Plaid Looks

      Price: $9.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Check Me Out Plaid Bodycon Mini Dress

      You'll be the object of everyone's gaze in this trendy plaid bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a stylish lower back cutout, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The stretchy brushed knit fabric features a chic windowpane plaid print. Complete your look with clear mules!

      Fit & Features

      • Sleeveless square neckline
      • Bungee spaghetti straps
      • Lower back cutout
      • Mini-length hem, bodycon silhouette
      • Plaid print
      • Brushed knit fabric, lined bust, plenty of stretch
      • Runs true to size

      Style Number/Barcode: 05102-5230

      Category Name: Plaid Looks

      Price: $6.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Naturally A Classic Tweed Bustier

      Become an instant 90s-inspired classic in this tweed bustier to posh up your vibe! Featuring a sleeveless sweetheart neckline with non-slip grip lining, adjustable and detachable spaghetti straps so you style it strapless, a built-in padded underwire bust, a cropped hem with non-slip grip lining, and a stretchy knit back. Complete the look in a chic mini skirt and heels for a date night or party!

      Fit & Features

      • Sleeveless sweetheart neckline, non-slip grip lining
      • Adjustable and detachable spaghetti straps
      • Built-in padded and underwire bust
      • Cropped hem with non-slip grip lining
      • Tweed front design, stretchy knit back, multiple hook-eye closures
      • Runs true to size

      Style Number/Barcode: 06003-2194

      Category Name: Plaid Looks

      Price: $13.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance