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!

  • 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
  • Preppy Girl Plaid V-Neck Mini Dress

    This plaid mini dress is for all the preppy girls! It features a sleeveless V-neckline, spaghetti straps, a bodycon fit, and a flirty front slit accent on stretchy knit fabric. Style with a cropped blazer and booties to complete the look!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Bodycon fit
    • Front slit accent
    • Mini-length hem
    • Plaid print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5161

    Category Name: Plaid Looks

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Match Plaid Lace-Up Mini Dress

    Find your perfect match in this casual-chic plaid mini dress! Featuring a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, a mini-length hem, a form-hugging fit, and a classic plaid windowpane print, this dress is a stylish must-have. Pair with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, cross-back lace-up straps, tie closure
    • Mini-length hem, form-hugging fit
    • Plaid windowpane print
    • Lined soft knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5159

    Category Name: Plaid Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty And Posh Tweed Bustier Top

    Pretty and posh, create an iconic look with this tweed bustier top! It features a sleeveless sweetheart neckline with a bustier-style bodice, a built-in padded bust, thin tank shoulder straps, and a fitted cropped hem. The plaid pattern on the tweed knit fabric gives it that chic factor. Style with the matching mini skirt!

    Shop Matching Bottoms: Pretty And Posh Tweed Mini Skirt

    Fit & Features

    • Sleeveless sweetheart neckline, bustier-style bodice
    • Built-in padded bust
    • Tank shoulder straps, back zipper closure
    • Fitted cropped hem
    • Plaid pattern, tweed knit fabric, smooth knit front lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4858

    Category Name: Plaid Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty And Posh Tweed Mini Skirt

    Pretty and posh, create an iconic look with this tweed mini skirt! It features a high-rise waist with a back zipper closure, a mini-length hem, and a form-hugging fit. The plaid pattern on the tweed knit fabric gives it that chic factor. Style with the matching bustier top!

    Shop Matching Top: Pretty And Posh Tweed Bustier Top

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Mini-length hem
    • Form-hugging fit
    • Plaid pattern, tweed knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0834

    Category Name: Plaid Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect In Plaid Crepe Slit Mini Skirt

    This crepe skirt is perfection in plaid! Be a trendsetter in this mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty front slit along the hem. Style with a cool crop moto jacket and a basic top to complete the look!

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Front slit
    • Mini-length hem
    • Plaid print
    • Crepe fabric
    • Runs true to size

    Style Number/Barcode: 06501-0826

    Category Name: Plaid Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life's A Prize Tweed Strapless Bow Dress

    Poised and polished, this tweed mini dress is a prize-worthy option for afternoon tea parties, a dressy brunch, or meeting the parents! Features a strapless neckline with non-slip grip lining, a statement bow on the front with a lovely faux pearl centerpiece, and a curve-hugging silhouette. The dress is composed of a tweed plaid material with a smooth woven lining. Style with chic stiletto pumps and a mini tote bag.

    Fit & Features

    • Strapless neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Front statement bow, faux pearl centerpiece
    • Curve-hugging silhouette
    • Mini-length hem
    • Tweed plaid fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2342

    Category Name: Plaid Looks

    Price: $28.97 $62.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On Another Level Checkered Print Flare Pants

    These retro fab checkered print flare pants will have your festival 'fit on another level! They feature a high-rise waist, a hip-hugging fit, a flared hem, and a bold checkered print pattern that will have all eyes on you. The ribbed knit fabric offers plenty of stretch. Style with a basic crop top and strappy sandals.

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Flared hem
    • Checkered print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2252

    Category Name: Plaid Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • As If Moment Tweed Fitted Shorts

    Have your iconic as-if moment looking major in these 90s-inspired tweed fitted shorts featuring a high-rise waist, a back zipper closure, a form-hugging fit, and a chic plaid pattern. Style with the matching blazer to complete the look!

    Shop Matching Blazer: As If Moment Tweed Crop Blazer

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Form-hugging fit
    • Plaid pattern
    • Woven tweed fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0272

    Category Name: Plaid Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Girl Next Door Gingham Mini Skirt

    You'll be the trendy girl next door in this gingham mini skirt that is perf for the season! It features a high-rise waist, a short, curve-hugging fit, a chic side slit, and an all-over gingham plaid print. The woven fabric offers a moderate stretch. Style with a cropped sweater and knee-high boots.

    Fit & Features

    • High-rise elasticized waist
    • Mini-length hem, side slit
    • Fitted bodycon silhouette
    • Gingham plaid print
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06401-0534

    Category Name: Plaid Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Gingham Plaid Mini Skirt

    This chic gingham plaid mini skirt will give you that cool-girl vibe! It features a high-rise waist, side pockets, a short, fitted silhouette, and an all-over trendy gingham print. Style with a basic bodysuit and over-the-knee boots.

    Fit & Features

    • High-rise waist
    • Side pockets
    • Form-hugging, mini-length hem
    • Hidden side zipper closure
    • Gingham plaid print, woven fabric. minimal stretch
    • Runs true to size

    Style Number/Barcode: 06401-0525

    Category Name: Plaid Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • City Chic Checkered Mini Skirt

    Show off a city chic look perf for a stroll downtown in this woven checkered mini skirt. It features a high-rise fit with a belted waist, a short, form-hugging silhouette, and a classic checkered window pane pattern. Style with a basic bodysuit and an oversized blazer.

    Fit & Features

    • High-rise fit, hidden size zipper closure
    • Belted waist, rectangular buckle
    • Mini-length hem
    • Form-hugging fit
    • Checkered window pane pattern
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06401-0522

    Category Name: Plaid Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plaid For You Belted Mini Skirt

    Fall for this trendy plaid mini skirt this autumn! It features a high-rise, belted waist with buckle closure and belt loops, hidden side zipper closure, and a form-hugging silhouette. Complete the look in knee-high boots.

    Fit & Features

    • High-rise
    • Belted waist, belt loops
    • Hidden side zipper closure
    • Form-hugging
    • Mini-length hem
    • Plaid pattern, smooth woven fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06401-0523

    Category Name: Plaid Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Social Scene Plaid Tweed Blazer

    With so much on your calendar, this plaid tweed blazer will have you looking posh and poised! It features long sleeves, a lapel collar neckline, front button closures, and a cropped hem. Complete the look in matching bottoms and mules.

    Shop Matching Bottoms: Social Scene Plaid Tweed Skirt

    Fit & Features

    • Long sleeves
    • Lapel collar neckline
    • Front button closures
    • Cropped hem
    • Plaid pattern
    • Tweed woven fabric, lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1552

    Category Name: Plaid Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Social Scene Plaid Tweed Skirt

    With so much on your calendar, this plaid tweed mini skirt will have you looking posh and poised! It features a high-rise waist, faux flap pockets, and button-down closures. Complete the look in the matching blazer and mules.

    Shop Matching Blazer: Social Scene Plaid Tweed Blazer

    Fit & Features

    • High-rise waist
    • Faux flap pockets
    • Button-down closures
    • Plaid pattern 
    • Mini-length hem
    • Tweed woven fabric, lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06401-0516

    Category Name: Plaid Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall Mood Plaid Mini Skirt

    Get in the fall mood with this posh plaid mini skirt! It features a high-rise waist, side pockets, a short, fitted silhouette, and an all-over chic plaid print. Style with a cropped sweater and ankle booties.

    Fit & Features

    • High-rise waist
    • Side pockets
    • Hidden side zipper and hook-eye closure
    • Form-hugging, mini-length hem
    • Plaid print, woven fabric
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06401-0515

    Category Name: Plaid Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cargo Without Plaid Short Dress

    You can't go without this plaid short dress perfect for autumn days and layering for winter nights! The dress features a sleeveless square neck, spaghetti straps, side flap pockets, and a bodycon silhouette. Complete the look in a basic long sleeve top and lug booties.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Side flap pockets
    • Bodycon silhouette
    • Short-length hem
    • Plaid pattern, knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05102-4898

    Category Name: Plaid Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • As If Moment Tweed Mini Skirt

    Have your iconic as-if moment looking major in this 90s-inspired tweed mini skirt featuring a high-rise waist, a back zipper with a hook-eye closure, a bodycon silhouette, a flirty front slit, and a chic plaid pattern. Style with the matching blazer to complete the look!

    Shop Matching Blazer: As If Moment Tweed Crop Blazer

    Fit & Features

    • High-rise waist
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Front slit accent, mini-length hem
    • Plaid pattern
    • Tweed fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06401-0510

    Category Name: Plaid Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • As If Moment Tweed Crop Blazer

    Have your iconic as-if moment looking major in this 90s-inspired tweed crop blazer featuring long sleeves, shoulder pads for structure, a lapel collar neckline, a front button closure, and a chic plaid pattern. Style with the matching bottoms to complete the look!

    Shop Matching Skirt: As If Moment Tweed Mini Skirt

    Shop Matching Shorts: As If Moment Tweed Fitted Shorts

    Fit & Features

    • Long sleeves, shoulder pads
    • Lapel collar neckline
    • Front button closure
    • Cropped hem
    • Plaid pattern
    • Tweed fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1566

    Category Name: Plaid Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gone Off The Grid Plaid Joggers

    Take your fashion to new heights in these grid plaid joggers featuring a high-rise waist, eye-catching suspenders along the sides, a relaxed fit, and elasticized hem. Complete the look in a basic crop tee and sneakers.

    Fit & Features

    • High-rise waist
    • Front button and hidden zipper closure
    • Belt loop accents, side pockets
    • Suspenders along the sides
    • Relaxed fit, elasticized hem
    • Grid plaid, woven fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06302-0690

    Category Name: Plaid Looks

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • She's All That Tweed Plaid Blazer

    Show up as that IT girl in this tweed plaid blazer for the perfect posh style! It features long sleeves, a lapel collar neckline, double-breasted button closures, flap pockets, and a slightly oversized silhouette. Complete the look in thigh-high boots.

    Fit & Features

    • Long sleeves, lapel collar neckline
    • Double-breasted button closures
    • Flap pockets
    • Slight oversized silhouette
    • Plaid pattern
    • Tweed lurex woven fabric
    • Fits true to size

    Style Number/Barcode: 06204-1535

    Category Name: Plaid Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale