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!

  • Perf Look In Plaid Oversized Cropped Jacket

    Get a perf look for a casual everyday style in this plaid jacket! It features a collared neckline, long sleeves, a complete zip front, and a cropped, oversized fit. Pair this jacket with light wash denim and heeled booties for a trendy feel.

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Complete zip front
    • Cropped, oversized fit
    • Lined front pockets
    • Plaid print
    • Brushed woven fabric with no stretch and a smooth lining

    Style Number/Barcode: 06204-0773

    Category Name: Plaid Looks

    Price: $15.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Poised Plaid Kitten Heel Booties

    Keep it poised in plaid booties that is perf for a trendsetter like you! The booties feature an around the ankle fit, a plaid print, a pointed toe, and a stiletto kitten heel. Complete look with a bodysuit and cuffed jeans. 

    Fit & Features

    • Around the ankle fit
    • Plaid print
    • Pointed toe
    • Stiletto kitten heel
    • Back zipper closure 

    Style Number/Barcode: 07403-1222

    Category Name: Plaid Looks

    Price: $16.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Check on It Plaid Mini Skirt

    Check you out, babe! The skirt features a high rise elastic banded waist, a checkered plaid print, a mini side slit, and a mini length silhouette. The skirt is composed of lightweight knit fabric that offers a form-hugging fit. Complete the look with a bodysuit and ankle booties.

    Fit & Features

    • High rise elastic banded waist
    • Checkered plaid print
    • Mini side slit
    • Mini length silhouette
    • Form-hugging fit
    • Knit fabric with moderate stretch

    Style Number/Barcode: 06501-0354

    Category Name: Plaid Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy Plaid Tweed Mini Skirt

    Look pretty and preppy in this adorable plaid mini skirt! It features a high rise elastic banded waist, a mini length silhouette, a curve-hugging fit, and a side slit. Pair this tweed skirt with a blazer and thigh-high boots for a chic look.

    Fit & Features

    • High rise elastic banded waist
    • Short, form-hugging fit
    • Side slit
    • Tweed knit fabric
    • Moderate stretch
    • Plaid print

    Style Number/Barcode: 06501-0353

    Category Name: Plaid Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Trendsetter Glen Check Mini Skirt

    You're the major trendsetter of your squad, so you definitely need this chic mini skirt in your closet! It features a high rise waist, back zipper closure, and a mini length silhouette with a curve-hugging fit and a side slit. The skirt is composed of an unlined woven fabric with a glen check pattern. Pair this skirt with thigh-high boots for a date night.

    Fit & Features

    • High rise waist
    • Back zipper closure
    • Short, form-hugging fit
    • Side slit
    • Woven fabric with moderate stretch
    • Glen check pattern

    Style Number/Barcode: 06401-0291

    Category Name: Plaid Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Fab Plaid Lug Booties

    Keep it so fab in plaid booties that too glam to pass up! The booties feature a trendy plaid print, an around the ankle fit, goring at the back of the ankle, an almond toe, and a lug sole. Complete look with a faux leather mini skirt and crop top. 

    Fit & Features

    • Plaid print
    • Mid-calf fit
    • Lace-up front
    • Goring at the back of the ankle
    • Almond toe
    • Lug sole

    Style Number/Barcode: 07403-1221

    Category Name: Plaid Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Posh Glen Check Mini Skirt

    Look oh-so-posh in this chic mini skirt! It features a high waist, a short, curve-hugging fit, a side slit, and a gray-hued glen check pattern with a pink accent throughout. Pair this skirt with a basic long sleeve crop top and booties for an elevated everyday 'fit.

    Fit & Features

    • High waist
    • Back zipper closure
    • Mini length, form-hugging silhouette
    • Side slit
    • Glen check pattern
    • Woven fabric with no stretch

    Style Number/Barcode: 06401-0290

    Category Name: Plaid Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Checkered Ruched Mini Skirt

    Style up this adorable checkered mini skirt for a chic vibe. It features a high rise elastic banded waist, ruched side detailing with side ties, and a short, curve-hugging fit. Pair this skirt with a chunky knit sweater and booties for an elevated everyday 'fit.

    Fit & Features

    • High rise elastic banded waist
    • Ruched sides
    • Side ties at hem
    • Mini length silhouette
    • Form-hugging fit
    • Unlined knit fabric with plenty of stretch
    • Checkered print

    Style Number/Barcode: 06501-0351

    Category Name: Plaid Looks

    Price: $8.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Vibes Plaid Flannel Shacket

    Layer on the cozy vibes with this trendy plaid flannel shacket! It features a collared neckline, a complete button-down front, long sleeves with single buttons to cuff, and a relaxed, oversized fit. Style this shacket with a faux leather mini skirt and heeled booties to make your 'fit casual-chic.

    Fit & Features

    • Collared neckline
    • Complete button-down front
    • Long sleeves with single buttons to cuff
    • Buttoned chest pockets
    • Relaxed, oversized fit
    • Flannel woven fabric
    • Faux suede lining

    Style Number/Barcode: 06204-0752

    Category Name: Plaid Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bet On It Oversized Plaid Shacket

    Bet on this cute plaid shacket to keep you looking chic! The shacket features a collared neckline, a multi-button down front, long sleeves with a single-button cuff, side pockets, and a plaid print. The shacket is composed of a cozy woven fabric that offers an oversized fit. Complete your look with jeans and combat boots. 

    Fit & Features

    • Collared neckline
    • Multi-button down front
    • Long sleeves with single-button cuff
    • Side pockets
    • Plaid print
    • Oversized fit 
    • Woven fabric with no stretch

    Style Number/Barcode: 06204-0755

    Category Name: Plaid Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Plaid Lined Blazer

    Get a poised and perfect outfit by layering on this chic plaid blazer! It features a lapel collar, shoulder pads, three quarter length cuffed sleeves, and faux front pockets. Pair this blazer over a little black dress for a stylish look for happy hour.

    Fit & Features

    • Lapel collar
    • Shoulder pads
    • Three quarter length cuffed sleeves with studded strap detailing
    • Faux front pockets
    • Allover plaid print
    • Lined woven fabric with no stretch

    Style Number/Barcode: 06204-0750

    Category Name: Plaid Looks

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Plaid Sherpa Lined Shacket

    Bundle up in this adorable cozy plaid shacket! It features a collared neckline, long sleeves with single buttons to cuff, a complete button-down front, a relaxed and comfortable fit, and a soft faux fur lining. Layer this trendy shacket over a basic bodysuit and pair it with denim and combat booties for a casual everyday look.

    Fit & Features

    • Collared neckline
    • Long sleeves with single buttons to cuff
    • Complete button-down front
    • Top buttoned pockets and slanted lower pockets
    • Relaxed fit
    • Plaid woven fabric with a soft faux sherpa lining
    • No stretch

    Style Number/Barcode: 06201-0198

    Category Name: Plaid Looks

    Price: $16.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual-Chic Plaid Jacquard Joggers

    Give your everyday look a casual-chic vibe by styling up these plaid jacquard joggers! They feature a high rise elastic banded waist with a front drawstring, slanted front pockets and faux back pockets, and a tapered leg fit. Pair these pants with combat booties for the perf look for this season.

    Fit & Features

    • High rise elastic banded waist
    • Front drawstring
    • Slanted front pockets
    • Faux back pockets
    • Tapered leg fit
    • Plaid print
    • Jacquard woven fabric with minimal stretch

    Style Number/Barcode: 06402-0292

    Category Name: Plaid Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Babe Plaid Mini Skirt

    You'll for sure be the stylish babe of your squad in this adorable plaid mini skirt! It features a high rise elastic banded waist, ruched side detailing with ties at the hem, and a mini length, curve-hugging silhouette. Pair this skirt with a basic bodysuit and booties for the perfect holiday party look.

    Fit & Features

    • High rise elastic banded waist
    • Ruched side detailing
    • Ties at the hem
    • Short, form-hugging fit
    • Plaid print
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 06501-0348

    Category Name: Plaid Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Checkered A-Line Mini Skirt

    Check out this chic A-line mini skirt to add a trendy vibe to your everyday look. It features a high rise elastic banded waist, a flirty faux wrap front, and a mini length slightly flared out silhouette. Pair this skirt with a graphic tee and heeled booties.

    Fit & Features

    • High rise elastic banded waist
    • Faux wrap front
    • Short, A-line fit
    • Checkered print
    • Unlined knit fabric
    • Moderate stretch

    Style Number/Barcode: 06501-0349

    Category Name: Plaid Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Preppy In Plaid Belted Coat

    Look pretty and preppy in this adorable plaid belted coat! It features a lapel collar, double button-down detailing, and a tie front belt to cinch your waist. The allover plaid print will give you a classic-chic vibe. Wear this coat with a chunky knit beanie for a cute winter night out look.

    Fit & Features

    • Lapel collar
    • Long sleeves
    • Double button-down detailing
    • Tie front belt
    • Faux front pocket
    • Mid-length hem
    • Thick woven fabric with an allover plaid print

    Style Number/Barcode: 06201-0190

    Category Name: Plaid Looks

    Price: $18.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Plaid Pajama Leggings

    Keep it classic in plaid pajama leggings that are perfect for those chilly nights! The leggings feature an elastic high rise waist, a plaid print, and a skinny leg fit. Complete your cozy night in look with the matching crop top and fuzzy slides. 

    Shop Matching Pajama Crop Top: Classic Plaid Pajama Crop Top

    Fit & Features

    • High rise waist
    • Plaid print
    • Skinny leg fit
    • Flannel knit fabric 
    • Relaxed fit, slight stretch 
    • Matching crop top sold separately  

    Style Number/Barcode: 07103-0422

    Category Name: Plaid Looks

    Price: $15.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Play On Sleeveless Plaid Mini Dress

    Keep it playful and poised in a dress that is totally on-trend, babe! The dress features a sleeveless scoop neckline, a plaid print, and a mini length silhouette. The dress is composed of a brushed knit fabric. Complete look with ankle booties.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank-straps
    • Plaid print
    • Mini length silhouette
    • Brushed knit fabric
    • Form hugging fit
    • Moderate stretch  

    Style Number/Barcode: 05102-1067

    Category Name: Plaid Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Rise Checkered Mini Skirt

    Elevate your style in a plaid skirt that is all the rage! The skirt features a high rise waist, a checkered houndstooth print, and a side slit. Complete your look with a black long sleeve top.

    Fit & Features

    • High rise waist
    • Side slit
    • Checkered houndstooth print
    • Mini length silhouette 
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06401-0288

    Category Name: Plaid Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Waist Plaid Dress Shorts

    Give your everyday look a dressier vibe in these adorable plaid shorts! They feature a high rise waist and a figure-flattering form-hugging fit. The plaid woven fabric offers plenty of stretch. Pair these shorts with a basic crop top for a day date with bae.

    Fit & Features

    • High rise waist
    • Short, form-hugging fit
    • Plaid woven fabric
    • Plenty of stretch

    Style Number/Barcode: 06403-0139

    Category Name: Plaid Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Rise Zippered Plaid Pants

    Keep it stylish in plaid pants that are all the rage this season. The pants feature a plaid print,  high rise waist, faux zippered pockets, and a skinny leg fit. The pants are composed of a lightweight woven fabric that offers a slight stretch. Complete your look with a basic black bodysuit. 

    Fit & Features

    • High rise waist
    • Single-button and zipper closure
    • Faux zippered pockets
    • Plaid print
    • Skinny leg fit
    • Woven fabric
    • Form hugging fit, slight stretch 

    Style Number/Barcode: 06402-0290

    Category Name: Plaid Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Play On Plaid Wubby Knit Jacket

    Keep it trendy in a plaid jacket that slays your layered outfits! The jacket features a fab plaid print, a mock neck, a zippered front, long sleeves, and is composed of a cozy wubby fabric that offers a relaxed fit with slight stretch. Complete look with a mock neck midi dress and ankle booties. 

    Fit & Features

    • Mock neck
    • Plaid print
    • Zippered front
    • Long sleeves
    • Wubby knit fabric
    • Lined, Relaxed fit, minimal stretch 

    Style Number/Barcode: 06201-0186

    Category Name: Plaid Looks

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy and Poised Plaid Skinny Pants

    Keep it preppy in plaid pants that are perf for creating chic back to school outfits. The pants feature a mid-rise fit, slant pockets, a single button with zipper closure, two small zippered pockets, and a plaid print. The pants are composed of a stretchy woven fabric that offers a form hugging fit. Complete look with a faux leather jacket.

    Fit & Features

    • Mid-rise fit
    • Single-button with zipper closure
    • Slant pockets 
    • Two zippered pockets
    • Belt loops
    • Plaid print
    • Stretchy woven fabric with skinny leg fit

    Style Number/Barcode: 06402-0289

    Category Name: Plaid Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Waist Asymmetrical Hem Mini Skirt

    Let this skirt take your look to the next level! The skirt features a high rise waist, a plaid print, and an asymmetrical hem. Complete look with bodysuit and ankle booties. 

    Fit & Features

    • High rise waist
    • Plaid print 
    • Asymmetrical hem

    Style Number/Barcode: 06501-0323

    Category Name: Plaid Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free