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!

  • Always Cozy Plaid Knit Scarf

    Style up this adorable plaid knit scarf detailed with trendy frayed edge hems. Layer over a faux leather jacket for an elevated cozy vibe.

    Fit & Features

    • Plaid printed knit fabric
    • Frayed edge hems

    Style Number/Barcode: 07305-0547

    Category Name: Plaid Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Cozy Plaid Fringe Knit Scarf

    Fit & Features

    • Plaid knit fabric
    • Long design
    • Fringe hems

    Style Number/Barcode: 07305-0534

    Category Name: Plaid Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Edgy Prep Plaid Pleated Mini Skort

    Fit & Features

    • Plaid faux wool fabric
    • Mid-rise fit, belted front
    • Drop waist design
    • Mini-length pleated overlay
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06403-1115

    Category Name: Plaid Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute Icon Gingham Belted Mini Skort

    You'll be a cute icon in this gingham printed mini skort perf to pair with your cropped tees. The belted front design adds a trendy detail to the sassy silhouette.

    Fit & Features

    • Gingham printed woven fabric, stretchy knit shorts lining
    • Mid-rise waist, faux belted front design
    • Hidden side zipper with hook-eye closure
    • Pleating
    • Mini-length overlay, A-line silhouette
    • Skort in size small has a 7" front rise with a 2" inseam
    • Runs true to size

    Style Number/Barcode: 06403-1111

    Category Name: Plaid Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Preppy And Sweet Two-Pack Bow Hair Clips

    Preppy and sweet, this two-pack of bow hair clips elevates your tresses for a chic finish to every look!

    Fit & Features

    • Two-pack hair blow clips
    • One gingham bow clip
    • One ruffled satin bow clip

    Style Number/Barcode: 07006-0587

    Category Name: Plaid Looks

    Price: $2.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pattern Play Houndstooth Sling-Back Kitten Heel Pumps

    From office hours to happy hour, these houndstooth kitten heel pumps are perfect for your everyday styling.

    Fit & Features

    • Stiletto kitten heel
    • Woven material exterior, closed pointed-toe
    • Houndstooth pattern
    • Adjustable sling-back strap, buckle detail
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-5214

    Category Name: Plaid Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Polished Cozy Houndstooth Eyelash Knit Cardigan

    Fit & Features

    • Soft eyelash knit fabric with moderate stretch, ribbed hems
    • Houndstooth pattern
    • V-neckline
    • Button-down front
    • Long sleeves
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2253

    Category Name: Plaid Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Allure Checkered Knit Sleeveless Vest

    Fit & Features

    • Knit fabrication
    • V-neckline
    • Sleeveless
    • Checkered pattern
    • Ribbed hem
    • Long-sleeve top pictured not included
    • Runs true to size

    Style Number/Barcode: 06005-2251

    Category Name: Plaid Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Factor Plaid Strapless Drop Waist Romper

    Level up your style with this plaid strapless drop waist romper. Featuring a sweetheart neckline, bow trim, and pleated overlay, it's your go-to for flirty vibes and fun times!

    Fit & Features

    • Plaid knit fabric
    • Strapless sweetheart neckline
    • Bow trim accent at the bust
    • Drop waist
    • Mini-length pleated overlay, A-line silhouette
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-1260

    Category Name: Plaid Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Perfect In Plaid Drop Waist A-Line Romper

    Be the trendsetter in this plaid drop waist a-line romper. With a square neckline, cute bow, and pleated overlay, this romper is your go-to for effortless style.

    Fit & Features

    • Plaid printed knit fabric
    • Square neckline with mini bow detail
    • Tank shoulder straps, square back
    • Drop waist design
    • Mini-length pleated overlay, A-line silhouette
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-1261

    Category Name: Plaid Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Babe Gingham Print Triangle Bikini Top

    Channel that flirty babe style in this adorable gingham printed triangle bikini top with a dainty eyelet trim. Pair with the matching bikini bottoms for a sweet and sassy look.

    Shop Matching Bottoms: Flirty Babe Gingham Print Side Tie Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Gingham print
    • Triangle design, eyelet trim
    • Adjustable spaghetti straps
    • Tie-back spaghetti straps
    • Runs true to size

    Style Number/Barcode: 07104-0717

    Category Name: Plaid Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Babe Gingham Print Side Tie Bikini Bottoms

    Channel that flirty babe style in these adorable gingham printed side tie bikini bottoms with a dainty eyelet trim. Pair with one of the matching bikini tops for a sweet and sassy look.

    Shop Matching Tops: Flirty Babe Gingham Print Triangle Bikini Top, Flirty Babe Gingham Print Bandeau Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Gingham print
    • Eyelet trim
    • High-cut design, side tie closures
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-0865

    Category Name: Plaid Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Babe Gingham Print Bandeau Bikini Top

    Channel that flirty babe style in this adorable gingham printed bandeau bikini top with a ruffled trim. Pair with the matching bikini bottoms for a sweet and sassy look.

    Shop Matching Bottoms: Flirty Babe Gingham Print Side Tie Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Gingham print
    • Strapless neckline
    • Center bust cutout, tie-front detail
    • Ruffled trim
    • Thin strappy back design, hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-0718

    Category Name: Plaid Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Absolute Darling Gingham Pleated Skort

    Look and feel so darling in this gingham pleated skort for warm weather dressing!

    Fit & Features

    • Gingham print, woven fabric, stretchy knit shorts lining
    • High-rise waist, side zipper closure
    • A-line silhouette
    • Pleated mini-length skirt overlay
    • Runs true to size

    Style Number/Barcode: 06403-1097

    Category Name: Plaid Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bow Cherry Charm Keychain

    An adorable keychain with a trendy gingham print bow charm, a faux pearl bow charm, and a mini cherry charm on an O-ring metal clasp. Complete the look with a purse.

    Fit & Features

    • Gingham print bow charm
    • Faux pearl bow charm
    • Mini cherry charm
    • O-ring metal clasp

    Style Number/Barcode: 07308-0694

    Category Name: Plaid Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Two Pack Gingham Print Shoelaces

    Dress up your favorite sneakers with these two-pack gingham print shoelaces! Lace up on a pair of shoes or skates.

    Fit & Features

    • Gingham print shoelaces
    • Two pack

    Style Number/Barcode: 07308-0692

    Category Name: Plaid Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Icon Era Houndstooth Woven Mini Skirt

    Shop Matching Jacket: Icon Era Houndstooth Woven Blazer

    Fit & Features

    • Houndstooth woven fabric, stretchy knit shorts
    • High-rise waist
    • Back zipper hook-eye closure
    • Short side slit
    • Mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06401-0728

    Category Name: Plaid Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy Appeal Pleated Plaid Skort

    Fit & Features

    • Woven knit fabrication
    • High-rise waist
    • Checkered plaid pattern
    • Double buckle accent at waist
    • Pleated mini skirt overlay
    • Hidden shorts
    • Runs true to size

    Style Number/Barcode: 06503-1251

    Category Name: Plaid Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutesy Babe Gingham Bow Strap Mules

    Make any casual look all the more cutesy with these gingham-printed bow strap mules. Perf for a weekend brunch!

    Fit & Features

    • Block heel
    • Gingham printed woven material
    • Open square toe
    • Bow-accented toe strap
    • Open back, on-and-off styling
    • Luxe fit cushioned insole, faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-5238

    Category Name: Plaid Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plaid Mood Sleeveless A-Line Mini Dress

    The plaid mesh mini dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and an A-line silhouette. Complete the look with loafers for a preppy vibe.

    Fit & Features

    • Sheer mesh fabric with knit lining, plenty of stretch
    • Plaid print
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Mini-length hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5987

    Category Name: Plaid Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classically Chic Plaid High Waist Wrap Skort

    Fit & Features

    • Faux wool fabrication
    • High rise waist
    • Back zipper and hook-eye closure
    • Plaid 
    • Mini skirt overlay, hidden shorts
    • Runs true to size

     

    Shop Matching Shacket: Classically Chic Plaid Long Sleeve Oversized Shacket

    Style Number/Barcode: 06403-1067

    Category Name: Plaid Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Comfy Cozy Vibes Plaid Woven Oversized Shacket

    The comfy cozy vibes plaid woven oversized shacket is your go-to for casual chic. With a collared neckline, button-down front, and flap chest pockets, it's perfect for any laid-back adventure.

    Fit & Features

    • Plaid woven fabric with soft faux suede lining, no stretch
    • Collared neckline
    • Long sleeves with single-button detail
    • Complete button-down front
    • Buttoned flap chest pockets
    • Oversized fit

    Style Number/Barcode: 06204-1987

    Category Name: Plaid Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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

    Product Badge:
    • Ships Free