Plaid Looks
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.
Now Trending
STYLE SPOTLIGHT
Discover Jackets, Coats, & Shackets!
Capture black skirts with trendy hardware details!
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!
-
Plaid Charm Pleated Drop Waist Skort
Have fun in the plaid charm pleated drop waist skort! With a playful plaid pattern, hidden shorts, and dual tab accents, this skort is your go-to for a cheeky, carefree vibe.
Fit & Features
- Woven knit fabrication
- Drop waist
- Dual tab accent at waist
- Pleated
- Plaid pattern
- Mini skirt overlay
- Hidden shorts
- Runs true to size
Style Number/Barcode: 06403-1059
Category Name: Plaid Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Major Sweetheart Smocked Gingham Cotton Skater Dress
This short skater dress features an adorable gingham print on lightweight lined cotton fabric. The smocked waist offers added stretch, while the fit-and-flare silhouette gives that flirty touch, perfect for a day date.
Fit & Features
- Gingham printed cotton fabric with woven lining, no stretch
- Scoop neckline with keyhole cutout and tie-front
- Adjustable spaghetti straps
- Stretchy smocked waist
- Short tiered skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5891
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Find Me In Plaid A-Line Mini Dress
Tried and trendy, this plaid mini dress boasts a strapless folded neckline and a flattering A-line silhouette. Pair with boots.
Fit & Features
- Plaid pattern, soft knit fabric
- Strapless folded neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5884
Category Name: Plaid Looks
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Effortless Cutie Long Sleeve Plaid Shacket
Layer on this effortlessly cute long sleeve plaid shacket perfect for pairing with a fitted top and denim jeans for everyday styling.
Fit & Features
- Plaid printed faux wool fabric, no stretch
- Collared neckline
- Button down front
- Long sleeves with single-button detail
- Dual chest pockets
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-1914
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
So Sweet Bow And Plaid Mini Skirt
Bring the charm with a plaid mini skirt featuring a mid-rise drop waist and dual bow accents. Complete your look with a cardigan and sneakers.
Fit & Features
- Woven fabrication, moderate stretch
- Plaid pattern
- Mid-rise drop waist
- Double bow accent
- Hidden back zipper closure
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 06401-0702
Category Name: Plaid Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Adorable Flair Plaid Pleated Drop Waist Mini Skort
This adorable plaid woven mini skort features a mid-rise fit, a trendy drop waist design, and a short pleated A-line silhouette layered over fitted shorts. Style with a cozy sweater and knee-high boots.
Fit & Features
- Plaid woven fabric
- Mid-rise fit
- Drop waist design, side zipper closure
- Mini-length pleated overlay, A-line fit
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-0754
Category Name: Plaid Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cozy Season Plaid Button-Down Shacket
Layer on this trendy plaid shacket perfect for cozy season featuring a collared neckline, long sleeves with buttons to cuff, a complete button-down front, chest pockets, and a casually chic relaxed fit. Style with jeans and booties.
Fit & Features
- Woven fabric with buffalo plaid print, no stretch
- Collared neckline
- Long sleeves with single-button detail
- Button-down front
- Dual flap chest pockets
- Long-length hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06204-1915
Category Name: Plaid Looks
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Fall Flair Plaid Woven Bubble Hem Skater Dress
Add some flair to your fall 'fits in this chic skater dress designed with a plaid printed cotton woven fabric. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a trendy V-shaped waist, and a short skater silhouette with the cutest bubble hem.
Fit & Features
- Plaid cotton woven fabric with knit lining, minimal stretch
- Square neckline
- Adjustable spaghetti straps
- Back zipper with hook-eye closure
- V-shaped waist
- Short skater silhouette, bubble hem
- Runs true to size
Style Number/Barcode: 05102-5870
Category Name: Plaid Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Preppy Glam Strapless Pleated Plaid Romper
A strapless plaid romper that flaunts your preppy glam flair! It features a trendy sweetheart neckline with a velvet bow and a pleated mini skirt overlay. Pair with loafers.
Fit & Features
- Woven knit fabric with moderate stretch
- Checkered plaid print
- Strapless sweetheart neckline, velvet mini bow accented trim at bust
- Drop waist seam
- Pleated mini skirt overlay, hidden shorts
- Romper in size small is 24" top hem to bottom hem with an 8.5" front rise and a 1.5" inseam
- Runs true to size
Style Number/Barcode: 06503-1220
Category Name: Plaid Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Fab Icon Houndstooth Tweed Heart Bag
Fit & Features
- Tweed knit fabrication
- Faux leather trim
- Faux pearl top handle
- Houndstooth pattern
- All-around zipper closure
- Detachable chain shoulder strap
Style Number/Barcode: 07203-2060
Category Name: Plaid Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Perfectly Plaid Woven Oversized Cropped Shacket
Perfectly plaid woven oversized cropped shacket is your go-to for laid-back vibes. With a collared neckline, button-down front, and flap pockets, it's perfect for any chill hangout or meet-up.
Fit & Features
- Plaid woven fabric with smooth woven lining, no stretch
- Collared neckline
- Long sleeves with single-button detail
- Complete button-down front
- Flap chest pockets
- Cropped hem
- Oversized fit
Style Number/Barcode: 06204-1900
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Classic Mood Glen Plaid Woven Oversized Blazer
This classic glen plaid woven blazer features a lapel collar, long sleeves, an open front with a double-breasted button design, and a chic oversized fit perfect for layering. Style with a mini dress and knee-high boots.
Fit & Features
- Glen plaid woven fabric with smooth woven lining, no stretch
- Lapel collar
- Long sleeves
- Dual front faux flap pockets
- Open front, double-breasted button design
- Oversized fit
Style Number/Barcode: 06204-1903
Category Name: Plaid Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Classically Chic Plaid Long Sleeve Oversized Shacket
Your new favorite plaid long sleeve oversized shacket for cozy and trendy vibes. Complete the look with the matching skort.
Shop Matching Bottoms: Classically Chic Plaid High Waist Wrap Skort
Fit & Features
- Plaid faux wool fabric, no stretch
- Collared neckline
- Button down front
- Dual chest pockets with snap-button closures
- Long sleeves with dual snap-button details
- Runs true to size
Style Number/Barcode: 06204-1898
Category Name: Plaid Looks
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Basic Vibes Cropped Plaid Shacket
Every girl needs this plaid shacket to create cute cold-weather fits'! The shacket features a classic plaid pattern on cozy faux wool fabric that helps keep you warm. Complete the look with boots.
Fit & Features
- Faux wool fabrication, no stretch
- Collared neckline
- Button-down front
- Dual buttoned chest pockets
- Long sleeves with single-button detail
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1896
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Cutest Agenda Buckle Plaid Mini Skort
A plaid mini skort features a high-rise waist with trendy dual side faux leather buckle accents and a faux wrap skirt design that shapes the form-hugging fit. Perfect with boots for back-to-school styling.
Fit & Features
- Plaid pattern, woven fabric, slight stretch
- High-rise waist with dual side faux leather buckle accents
- Faux wrap skirt design
- Form-hugging mini-length silhouette
- Runs true to size
Style Number/Barcode: 06403-0631
Category Name: Plaid Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Plaid Moment Sleeveless Knit Romper
Fit & Features
- Plaid printed woven knit fabrication with minimal stretch
- Strapless straight neckline, no-slip strip
- Flexible boning, back zipper with hook-eye closure
- Mini skirt length front overlay, dual side slits
- Cheeky shorts
- Romper in size small is 23" top hem to bottom hem with a 12" front rise and a 3" inseam
- Runs true to size
Style Number/Barcode: 06403-0627
Category Name: Plaid Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Plaid printed woven knit fabrication with minimal stretch
-
Memorable Vibe Strapless Plaid Pleated Mini Dress
A strapless plaid mini dress features a form-hugging fit with a sassy pleated hem. Perfect for back-to-school styling.
Fit & Features
- Plaid print, woven fabric, slight stretch
- Strapless folded neckline
- Back zipper closure
- Form-hugging fit
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5862
Category Name: Plaid Looks
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Charming Direction Sleeveless Plaid Romper
A sleeveless plaid romper features a square neckline adorned with a velvet bow and a flattering form-hugging fit that leads to the flared short-length hem. Perfect for back-to-school styling.
Fit & Features
- Plaid print, knit fabric, minimal stretch
- Square neckline, velvet bow, shoulder straps
- Form-hugging fit
- Flared short-length hem
- Shorts lining
-
Romper in size small is 29" shoulder to hem with an 8" front rise and a 1.5" inseam
- Runs true to size
Style Number/Barcode: 06503-1214
Category Name: Plaid Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Autumn Attitude Strapless Pleated Plaid Mini Dress
Embrace the new season in this plaid mini dress featuring a strapless neckline, form-hugging silhouette, and a flirty pleated mini-length hem. Perfect for back-to-school and styling with flats.
Fit & Features
- Plaid pattern, knit fabric, moderate stretch
- Strapless folded neckline
- Form-hugging silhouette
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5863
Category Name: Plaid Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
On-Point Plaid Faux Wool Shacket
Fit & Features
- Faux wool fabrication with knit lining
- Plaid pattern
- Collared neckline
- Button-down front
- Chest pockets with flap closure
- Long sleeves with single button cuff
- Oversized fit
Style Number/Barcode: 06204-1876
Category Name: Plaid Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Rodeo Cowgirl Gingham Tie-Front Romper
Channel the cutest western vibe as a rodeo cowgirl this Halloween in this adorable romper! It features a gingham-printed top with a collared V-neckline and tie-front design, a bold waist cutout, and high-rise shorts with a cheeky form-hugging fit. Complete your costume with the cowgirl hat, hair bow set, and the perfect pair of cowboy boots!
Fit & Features
- Stretchy knit fabric
- Gingham-printed top, denim-printed shorts
- Collared V-neckline, tie-front design
- Long fitted sleeves
- Front waist cutout, high-rise waist, cheeky form-hugging fit
- Romper in size small is 28" shoulder to hem with a 12" front rise and a 1" inseam
- Runs true to size
Style Number/Barcode: 06503-1213
Category Name: Plaid Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Classic Charm Plaid Trench Coat
Shop Matching Bottoms: Classic Charm Plaid Wrap Skort
Fit & Features
- Faux wool fabrication with smooth woven lining, no stretch
- Plaid pattern
- Collared neckline, double-breasted button closure
- Long sleeves with buttoned straps
- Lined slant pockets
- Long length hem
- Runs true to size
Style Number/Barcode: 06201-0507
Category Name: Plaid Looks
Price: $9.97 $74.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Sweet Perception Strapless Plaid Pleated Romper
A strapless plaid romper features a velvet bow, form-hugging fit, and a trendy pleated short-length hem. Style with cute flats for back-to-school or casual occasions.
Fit & Features
- Plaid print, knit fabric, minimal stretch
- Strapless neckline, velvet bow
- Form-hugging fit
- Pleated short-length hem
- Shorts lining
- Romper in size small is 22" shoulder to hem with an 8" front rise and a 1.5" inseam
- Runs true to size
Style Number/Barcode: 06503-1210
Category Name: Plaid Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Adorable Pose High-Rise Plaid Mini Skort
A plaid mini skort features a flattering high-rise waist and bodycon silhouette. Perfect for back-to-school styling.
Fit & Features
- Plaid print, smooth knit stretchy fabric, shorts lining
- High-rise waist
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06503-1207
Category Name: Plaid Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale