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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STYLE SPOTLIGHT
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Capture black skirts with trendy hardware details!
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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              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
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
 
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              Check Me Out Mid-Rise Gingham Shorts
              
              
              
              
                With these mid-rise gingham shorts, you'll be checking yourself out in every mirror you pass!
Fit & Features
- Gingham print, woven fabric
 - Mid-rise waist
 - Ruffled trim hem
 - Runs true to size
 
Style Number/Barcode: 06303-000025
Category Name: Plaid
Price: $9.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: BLK/WHT
Available Size: L
Product Badge:- Sale
 
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              Girly Gingham Print Ruffled Mini Dress
              
              
              
              
                You love all things girly, so this adorable gingham print mini dress is perfect for you. The all-over smocked design adds stretch, while the ruffled neck and hem bring the cutesy vibe.
Fit & Features
- Smocked cotton fabric, high stretch
 - Gingham print
 - Sleeveless sweetheart neckline, ruffled trim, small bow detail
 - Adjustable spaghetti straps
 - Mini-length ruffled hem
 - Form-hugging fit
 - Runs true to size
 
Style Number/Barcode: 05102-000163
Category Name: Plaid
Price: $14.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: GREEN
Available Size: S, M, L
Product Badge:- Sale
 
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              So Sweet Floral And Plaid Patchwork Mini Dress
              
              
              
              
                Create the perfect weekend look in this oh-so-sweet mini dress designed with a floral and plaid patchwork pattern. The crochet bust trim and tie-front detail are dainty details you'll adore.
Fit & Features
- Woven fabric, no stretch
 - Ditsy floral and plaid patchwork pattern
 - Sleeveless sweetheart neckline, crochet trim and tie-front detail, ruched bust
 - Adjustable spaghetti straps
 - Hidden back zipper, hook-eye closure
 - Mini-length hem, fitted A-line silhouette
 - Runs true to size
 
Style Number/Barcode: 05101-000178
Category Name: Plaid
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
 
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              Vintage Charm Gingham Slit Peasant Maxi Skirt
              
              
              
              
                Vintage charm is yours with this gingham peasant maxi skirt showcasing a modern high front slit for effortless movement!
Fit & Features
- Gingham print, woven fabric
 - High-rise elasticized waist
 - High front slit
 - Flowy ruffled maxi-length silhouette
 - Runs true to size
 
Style Number/Barcode: 06301-000002
Category Name: Plaid
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
 
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              Flirtatious Vibe Gingham Ruffled Mini Skort
              
              
              
              
                This adorable gingham printed mini skort will give off flirty vibes with its drop waist design and ruffled mini-length overlay. Features hidden fitted shorts for coverage.
Fit & Features
- Cotton-blend woven fabric
 - Gingham print
 - Stretchy smocked drop waist
 - Tiered ruffled mini-length overlay, eyelet trim
 - Hidden fitted knit shorts
 - Runs true to size
 
Style Number/Barcode: 06303-000005
Category Name: Plaid
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
 
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              Sweet And Trendy Gingham Print Crop Top
              
              
              
              
                Sweet and trendy, this gingham printed crop top is the cutest style for casual summer 'fits. It features a square neckline with mini bow accents and a cropped, curved hanky hem perf for pairing with denim shorts.
Fit & Features
- Woven fabric, gingham print, sewn-in knit lining
 - Sleeveless square neckline, mini bow accents
 - Adjustable spaghetti straps, side zipper with hook-eye closure
 - Back strap accent, smocked back design
 - Cropped curved hanky hem
 - Form-hugging fit
 - Runs true to size
 
Style Number/Barcode: 06003-000089
Category Name: Plaid
Price: $6.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: L
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              Short But Sweet Gingham Bow Shorts
              
              
              
              
                Short but super sweet! These gingham shorts are the cherry on top of a perfect sunny day look featuring a flattering high-rise waist and side bow ties.
Fit & Features
- Gingham print, cotton woven fabric
 - High-rise elasticized waist
 - Hidden side pockets
 - Side bow ties
 - Fitted hem
 - Runs true to size
 
Style Number/Barcode: 06303-000017
Category Name: Plaid
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
 
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              Summer Pick Gingham Halter Crop Top
              
              
              
              
                The cutest gingham crop top for any summer day! Look and feel so cute in this top with a pretty open back with tie-back details and a ruffled crop hem to show off your figure.
Fit & Features
- Gingham print, woven fabric
 - Plunge halter neckline, spaghetti strap tie
 - Ruffled crop hem
 - Open back, tie-back details
 - Runs true to size
 
Style Number/Barcode: 06003-000072
Category Name: Plaid
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
 
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              Sweet Like Sugar Gingham Print Skater Dress
              
              
              
              
                This gingham skater dress is all flounce and flirt, from the dainty bow detail to the ruffled puff sleeves—perfect for farmers' market strolls, daydreams, and twirling through your soft girl era.
Fit & Features
- Cotton-blend woven fabric
 - Gingham print
 - V-neckline with small bow detail, short puff sleeves, ruffled trim
 - Stretchy smocked bodice
 - High-rise waist seam
 - Short pleated skater silhouette
 - Runs true to size
 
Style Number/Barcode: 05102-000139
Category Name: Plaid
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
 
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              Prep It Up Ruffled Plaid Mid-Rise Skort
              
              
              
              
                This ruffled plaid mini is here to play. With a flattering mid-rise waist and adjustable drawstring, it's giving effortless style with a flirty ruffled short silhouette.
Fit & Features
- Plaid print, cotton woven fabric, stretchy short knit lining
 - Mid-rise waist with an adjustable drawstring tie
 - Tiered ruffle silhouette
 - Short hem
 - Runs true to size
 
Style Number/Barcode: 06303-000016
Category Name: Plaid
Price: $34.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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              Flirt Alert Plaid Lace-Up Mini Skirt
              
              
              
              
                Serving school-girl energy but make it cool girl approved. The lace-up waist and flouncy fit make this the ultimate skirt for brunch dates or casual hangs!
Fit & Features
- Plaid print, cotton woven fabric, stretchy knit shorts lining
 - High-rise waist
 - Front lace-up detail
 - Flouncy mini-length hem
 - Runs true to size
 
Style Number/Barcode: 06303-000033
Category Name: Plaid
Price: $39.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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              Plaid Cutie Halter Crop Top
              
              
              
              
                This halter crop serves major summer energy with its open front design, flirty strappy back, and breezy plaid vibes—perfect for concerts, farmers markets, or coffee dates.
Fit & Features
- Plaid print, cotton-blend woven fabric
 - Halter plunge neckline, bust lining
 - Open back with dual spaghetti strap ties
 - Open front design
 - Cropped hem
 - Runs true to size
 
Style Number/Barcode: 06003-000111
Category Name: Plaid
Price: $26.90
Availability: In Stock
Available Color: TAN
Available Size: S, M, L
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              Catch Feelings Plaid Pleated Skort
              
              
              
              
                She’s sweet, but she’s not subtle. This skort knows how to turn a hallway into a runway—with flirty pleats and lace-up sides that do all the flirting for you.
Fit & Features
- Plaid print, woven fabric
 - Mid rise waist
 - Dual side tie accents
 - Pleated mini skirt overlay, shorts lining
 - Runs true to size
 
Style Number/Barcode: 06303-000031
Category Name: Plaid
Price: $36.90
Availability: In Stock
Available Color: TAUPE
Available Size: S, M, L
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              Gingham Goals Hair Bow Clip Set
              
              
              
              
                Giving coquette-core with a picnic twist. This gingham hair bow clip set adds that effortlessly sweet finish to braids, half-up styles, or a low pony.
Fit & Features
- Two-pack hair bow clip set
 - Woven material, gingham print
 - Long design
 - Alligator clip closures
 
Style Number/Barcode: 07006-000056
Category Name: Plaid
Price: $9.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
Product Badge: - 
              
                
              
              Prepped For Style Pleated Plaid Skort
              
              
              
              
                This plaid pleated mini skort is flirty, playful, and perfect for styling with baby tees or oversized layered this fall season!
Fit & Features
- Plaid print, woven fabric, shorts lining
 - Low-rise waist
 - Pleated mini-length skirt overlay
 - Runs true to size
 
Style Number/Barcode: 06403-000041
Category Name: Plaid
Price: $34.90
Availability: In Stock
Available Color: TAUPE
Available Size: S, M, L
Product Badge:- Best Seller
 
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              Prep School Crush Plaid Mini Skort
              
              
              
              
                Plaid but make it flirty—this pleated mini skort has side bow ties and a preppy vibe that’s giving major cool-girl energy. Perfect with tees and chunky knits or crop tops and heels for a cute evening look.
Fit & Features
- Mid-rise waist
 - Side bow accents
 - Pleated mini skirt overlay
 - Shorts lining
 - Runs true to size
 
Style Number/Barcode: 06403-000035
Category Name: Plaid
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Best Seller
 
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              Ace The Look Plaid Pleated Romper
              
              
              
              
                Plaid but make it playful—this strapless romper brings preppy vibes with a fitted bodice and flirty pleated hem. Perfect for when you want to keep it cute but still cool-girl.
Fit & Features
- Plaid print, knit fabric
 - Strapless neckline
 - Fitted bodice, hidden side zipper and hook-eye closure
 - Pleated skirt overlay, shorts lining
 - Runs true to size
 
Style Number/Barcode: 06503-000123
Category Name: Plaid
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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              Checkmate Vibes Plaid Hot Shorts
              
              
              
              
                Preppy, but make it spicy. These plaid hot shorts hug your curves with a comfy stretch fit that’s made for coffee runs, party nights, and everything in between.
Fit & Features
- Knit fabric, high stretch
 - Plaid print
 - Low-rise waist
 - Cheeky form-hugging fit
 - Runs true to size
 
Style Number/Barcode: 06503-000126
Category Name: Plaid
Price: $29.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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              Plaid About You Vest Top
              
              
              
              
                A little preppy, a little flirty—this plaid vest top does both. Perfect for dressing up or keeping it casual, it’s your go-to for effortless styling.
Shop Matching Bottoms: Plaid About You Mini Skort
Fit & Features
- Woven fabric with knit lining, moderate stretch
 - Plaid print
 - Sleeveless scoop neckline
 - Tank shoulder straps
 - Button-down front
 - Fitted mid-length hem
 - Runs true to size
 
Style Number/Barcode: 06202-000048
Category Name: Plaid
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
 
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              Plaid About You Mini Skort
              
              
              
              
                A little preppy, a little flirty—this plaid mini skort does both. Perfect for dressing up or keeping it casual, it’s your go-to for effortless styling.
Shop Matching Top: Plaid About You Vest Top
Fit & Features
- Woven fabric, moderate stretch
 - Plaid print
 - Mid-rise waist, mini bow detail
 - Side zipper with hook-eye closure
 - Mini-length overlay, fitted silhouette
 - Hidden knit fitted shorts
 - Runs true to size
 
Style Number/Barcode: 06503-000128
Category Name: Plaid
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Part of a Set
 
 - Woven fabric, moderate stretch
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              Plaid Attitude Pleated Mini Skort
              
              
              
              
                Prep, but make it playful. This plaid pleated mini skort features a buckle belt detail that gives school-girl energy with a cool-girl twist. Perfect for pairing with the matching cropped vest.
Shop Matching Top: Plaid Attitude Cropped Vest Top
Fit & Features
- Plaid woven fabric
 - Mid-rise waist with belt detail
 - Pleated mini-length skirt overlay
 - Shorts lining
 - Runs true to size
 
Style Number/Barcode: 06403-000040
Category Name: Plaid
Price: $34.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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              Checkmate Plaid Trench Vest
              
              
              
              
                Plaid, but polished. This faux wool trench vest comes belted at the waist for a cinched fit, making it the perfect pairing with the matching skort.
Shop Matching Bottoms: Checkmate Plaid Mini Skort
Fit & Features
- Plaid pattern, faux wool-lined fabric
 - Sleeveless design
 - Lapel collar neckline
 - Double-breasted button front closures
 - Tie-waist belt, belt loop accents
 - Longline hem
 - Runs true to size
 
Style Number/Barcode: 06201-000024
Category Name: Plaid
Price: $59.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
 
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              Preppy Play Plaid Bloomer Shorts
              
              
              
              
                These plaid bloomer shorts give lounge-meets-street vibes with their relaxed fit and gathered hem—perfect for pairing with an oversized tee, chunky sweater, or your “just rolled out but still cute” mood.
Fit & Features
- Plaid print, chiffon fabric, sewn-in woven lining
 - Mid-rise waist with bow accent
 - Smocked form-hugging silhouette
 - Ruffled trim hem
 - Runs true to size
 
Style Number/Barcode: 06503-000162
Category Name: Plaid
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
 
