Plaid
Plaid outfits bring effortless preppy chic style to your Fall looks. Think mini skirts and skorts paired with knee-high boots, or plaid dresses layered under blazers for a polished vibe. Vests add an academic twist, while trenches pull it all together with timeless flair. Tartan patterns in brown, navy, and hunter green keep it classic yet trendy. Whether you’re dressing casual or elevated, plaid is the print that makes every outfit feel effortless and iconic.
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Plaid
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Plaid Outfits: Timeless Styles for Every Winter Occasion
Discover the charm of plaid this winter with Windsor’s Plaid Outfits collection, where classic prints meet modern style. From cozy plaid dresses for family gatherings 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 winter occasion unforgettable!
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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
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
Price: $28.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Preppy Element Tweed Crop Jacket
Add a preppy element with this tweed crop jacket to layer over your outfit. It features long sleeves, a collar neckline, snap-button down closures, two flap pockets, and an oversized silhouette. Style over a basic top and faux leather shorts for an edgy-cute look!
Fit & Features
- Long sleeves, collar neckline
- Snap-button down closures
- Two flap pockets
- Oversized silhouette
- Cropped hem
- Tweed fabric
- Runs true to size
Style Number/Barcode: 06204-1492
Category Name: Plaid
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Valley Girl Faux Suede Mini Skirt
Keep fashionable wherever you go in this must-have faux suede houndstooth skirt for an effortless preppy-cute look! The skirt features a high-rise waist, hidden back zipper closure, a bodycon silhouette, and a front slit accent. Style with the matching blazer.
Shop Matching Blazer: Valley Girl Faux Suede Long Blazer
Fit & Features
- High-rise waist
- Bodycon silhouette
- Front slit accent, mini-length hem
- Hidden back zipper closure
- Houndstooth pattern
- Faux suede fabric. smooth lining. minimal stretch
- Runs true to size
Style Number/Barcode: 06401-0466
Category Name: Plaid
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Valley Girl Faux Suede Long Blazer
Keep fashionable wherever you go in this must-have faux suede houndstooth blazer for an effortless preppy-cute look! The blazer features long sleeves, a lapel collar neckline, an open-front design, hidden side pockets, a back-slit accent, and a relaxed silhouette. Style with the matching skirt.
Shop Matching Skirt: Valley Girl Faux Suede Mini Skirt
Fit & Features
- Long sleeves, lapel collar neckline
- Open-front design
- Hidden side pockets
- Back slit accent, relaxed long silhouette
- Houndstooth pattern
- Faux suede fabric. smooth lining. minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1464
Category Name: Plaid
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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City Girl Plaid Faux Wool Coat
Layer on this plaid faux wool coat for a chic city girl look! It features a lapel collar, an open front, long sleeves, lined side pockets, and a mid-length hem with a fitted silhouette. The all-over plaid print will give your 'fit that classic vibe. Style over a sweater dress with knee-high boots.
Fit & Features
- Lapel collar, open front
- Long sleeves
- Side pockets, smooth lining
- Mid-length hem, fitted silhouette, back slit accent
- Plaid print
- Faux wool fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0315
Category Name: Plaid
Price: $27.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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A Polished Vibe Plaid Faux Wool Coat
Layer on this plaid faux wool coat for a polished vibe! Featuring a lapel collar, an open front, long sleeves, side pockets, a mid-length hem, and a fitted silhouette, this coat is a definite winter staple. The all-over plaid print will keep your looks classic and chic. Style with faux leather ankle booties.
Fit & Features
- Lapel collar, open front
- Long sleeves
- Side pockets, back slit accent
- Mid-length hem, fitted silhouette
- Plaid print
- Unlined faux wool fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0313
Category Name: Plaid
Price: $27.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Best Match Plaid Slit Mini Skirt
From cool mornings to chilly afternoons, look stylish no matter the weather in this plaid mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty slit accent. Complete the look in the matching shacket and knee-high boots.
Shop The Matching Shacket: Best Match Plaid Longline Shacket
Fit & Features
- High-rise waist
- Back zipper closure
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Plaid pattern, soft woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06401-0462
Category Name: Plaid
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Best Match Plaid Longline Shacket
From cool mornings to chilly afternoons, look stylish no matter the weather in this plaid mini skirt featuring a high-rise waist, bodycon silhouette, and a flirty slit accent. Complete the look in the matching cozy skirt and knee-high boots.
Shop Matching Bottoms: Best Match Plaid Slit Mini Skirt
Fit & Features
- Long sleeves, button cuffs
- Collar neckline
- Front button-down closures
- Flap pockets, side slit accents
- Longline hem
- Plaid pattern, soft woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1459
Category Name: Plaid
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet In Tweed V-Neck Sweater
Show your sweet side! This tweed plaid sweater features long dolman sleeves, a V-neck, and a relaxed fit hem. Complete the look in faux leather pants for a dinner party!
Fit & Features
- Long dolman sleeves
- V-neck
- Relaxed fit hem
- Plaid tweed fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1600
Category Name: Plaid
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Season Brushed Plaid Scarf
Tis' the season for wearing this cozy scarf! It features a plaid pattern on the brushed knit fabric with a stitched hem. Style with knee-high boots.
Fit & Features
- Plaid pattern
- Brushed knit fabric
- Stitched hem
Style Number/Barcode: 07305-0336
Category Name: Plaid
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Neutral Plaid Scarf
The styling possibilities are endless with this neutral plaid scarf featuring a clean frayed edge design on soft and cozy fabric. Complete the look in a cute sweater dress and boots.
Fit & Features
- Plaid pattern
- Clean frayed edge design
- Soft and cozy fabric
Style Number/Barcode: 07305-0345
Category Name: Plaid
Price: $1.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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SoHo Plaid Frey Hem Scarf
Another cold day in the city? This plaid scarf will keep you cozy and stylish! Complete the look with a fuzzy sweater and knee-high boots.
Fit & Features
- Plaid pattern
- Frey hem trim
- Soft fabric
Style Number/Barcode: 07305-0350
Category Name: Plaid
Price: $1.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Aesthetic Houndstooth Bucket Hat
Match your aesthetic for the changing season in this houndstooth bucket hat! It features a classic silhouette with hints of shimmery woven lurex. Complete the look in a classic denim jacket.
Fit & Features
- Houndstooth pattern
- Bucket hat silhouette
- Woven lurex
Style Number/Barcode: 07302-1329
Category Name: Plaid
Price: $4.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Autumn Chill Buffalo Plaid Scarf
Wrap yourself in this cozy and stylish buffalo plaid scarf! It features a frayed edge design on super soft fabric. Complete the look in a cropped jacket.
Fit & Features
- Buffalo plaid pattern
- Frayed edge design
- Super soft and cozy fabric
Style Number/Barcode: 07305-0421
Category Name: Plaid
Price: $4.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cold Babe Plaid Blanket Scarf
You can still be a babe and brace for the cold thanks to this cozy plaid blanket scarf! It features a trendy fringe edge design on cozy and soft fabric. Complete the look in a trendy jacket for a coffee run.
Fit & Features
- Plaid pattern
- Fringe edge design
- Soft and cozy fabric
Style Number/Barcode: 07305-0431
Category Name: Plaid
Price: $3.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Prepped Success Plaid Mini Skirt
You'll be prepped for a successful outfit this fall by layering on this faux suede mini skirt featuring a high-rise waist, bodycon silhouette, front slit accent, and a contemporary houndstooth plaid pattern. Complete your fit with the matching blazer!
Shop Matching Blazer: Prepped Success Plaid Long Blazer
Fit & Features
- High-rise waist, hidden back zipper closure
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Houndstooth plaid pattern
- Faux suede fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06401-0465
Category Name: Plaid
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale