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.
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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!
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Checked Out Plaid Capri Pants
Retro called, but we’re keeping these. These plaid capri pants bring a close fit, cropped length, and a tiny bow detail that makes baby tees, fitted tanks, and kitten heels feel instantly more styled.
Fit & Features
- Plaid woven fabrication
- Low-rise waist with bow detail
- Slim fit through the hips and legs
- Cropped capri length with side hem slits
- Runs true to size
Style Number/Barcode: 06502-000127
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Prep Shift Plaid Pleated Mini Skort
This plaid mini skort brings a tailored feel to casual styling. With a mid-rise waist, drop waist seam, and mini-length pleated overlay, it also features hidden built-in shorts for added coverage. Style with the matching vest top for an easy mix of polished and cool.
Shop Matching Top: Prep Shift Plaid Cropped Button Front Vest Top
Fit & Features
- Plaid woven fabric
- Mid-rise waist
- Drop waist seam
- Side zipper closure
- Mini-length pleated overlay, A-line fit
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06303-000069
Category Name: Plaid Looks
Price: $39.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: S, M, L
Product Badge:- Part of a Set
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Prep Shift Plaid Cropped Button Front Vest Top
This cropped plaid vest top brings a tailored feel to casual styling. The halter-inspired shape and button front keep the proportions neat, while the plaid pattern does the visual work. Style it with the matching mini skort for an easy mix of polished and cool.
Shop Matching Bottoms: Prep Shift Plaid Pleated Mini Skort
Fit & Features
- Plaid-printed woven fabric
- Sleeveless V-neckline
- Halter strap, open back
- Button-front closures
- Cropped length, form-hugging fit
- Runs true to size
Style Number/Barcode: 06204-000193
Category Name: Plaid Looks
Price: $29.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Cozy Prep Plaid Fringe Scarf
Cozy up in preppy fashion. This plaid fringe scarf features a cozy, soft texture and an oversized blanket-wrap silhouette that pairs perfectly with your cold-weather fits.
Fit & Features
- Plaid pattern
- Fringe trim
- Blanket-wrap silhouette
- Soft material with fuzzy texture
Style Number/Barcode: 07305-000132
Category Name: Plaid Looks
Price: $19.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
Product Badge:- New Arrival
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Plaid Perfection Fringe Blanket Scarf
Consider your cold-weather layering officially upgraded. This cozy plaid blanket scarf features a relaxed, oversized silhouette and playful fringe ends for a chic, bundled-up look that pairs perfectly with your favorite jackets and boots.
Fit & Features
- Plaid pattern
- Fringe trim
- Blanket scarf silhouette
- Soft, fuzzy knit material
Style Number/Barcode: 07305-000131
Category Name: Plaid Looks
Price: $19.90
Availability: In Stock
Available Color: BLACK
Available Size: NS
Product Badge:- New Arrival
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Plaid Agenda Bubble Hem Bomber Jacket
Plaid just clocked in for cold weather. This brushed cropped jacket brings cozy texture, an oversized collar, and an easy boxy shape, perfect for layering with any outfit.
Fit & Features
- Plaid pattern, brushed soft fabric, sewn-in smooth woven lining
- Collared neckline with snap-button closures
- Long sleeves
- Hidden front zip-up closure
- Front open pockets
- Relaxed boxy fit
- Bubble crop hem
- Runa true to size
Style Number/Barcode: 06201-000092
Category Name: Plaid Looks
Price: $59.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Cozy Forecast Striped Blanket Scarf
Cold weather just got a whole lot cozier. This striped blanket scarf wraps you in an ultra-soft feel with a relaxed, oversized silhouette and fringe ends for that effortlessly chic layered look your winter wardrobe needs.
Fit & Features
- Neutral striped pattern
- Fringe trim ends
- Blanket scarf silhouette
- Soft cozy knit material
Style Number/Barcode: 07305-000130
Category Name: Plaid Looks
Price: $19.90
Availability: In Stock
Available Color: MOCHA
Available Size: NS
Product Badge:- New Arrival
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Cold Weather Vibe Plaid Blanket Scarf
A soft and cozy brushed finish elevates this plaid blanket scarf to your favorite cold-weather accessory. With a contemporary plaid pattern and trendy fringe trim, this scarf offers warmth and style to go with any outfit.
Fit & Features
- Plaid pattern
- Brushed soft texture
- Fringe trim
- Blanket scarf silhouette
Style Number/Barcode: 07305-000125
Category Name: Plaid Looks
Price: $19.90
Availability: In Stock
Available Color: NATURAL-2
Available Size: NS
Product Badge:- New Arrival
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Pattern Crush Floral Plaid Halter Top
Plaid with a seriously pretty plot twist. This floral flocked halter top mixes sheer mesh texture, velvet florals, and a deep V-neckline for a fitted look that feels dressed up without going overboard.
Fit & Features
- Plaid printed mesh fabric with knit lining, high stretch
- Velvet flocked floral pattern
- Sleeveless deep V-neckline, ruched bust
- Tie-back halter straps, partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000786
Category Name: Plaid Looks
Price: $29.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Study Break Plaid Halter Scoop Neck Top
Consider this your plaid era with better plans. This fitted halter top pairs a scoop neckline with a sleek cropped shape, making it the kind of throw-on piece that works with capris, denim, or a mini when you want a little prep with some attitude.
Fit & Features
- Woven plaid fabric, sewn-in knit lining
- Halter straps with scoop neckline
- Sleeveless fitted bodice
- Side zipper and hook-eye closure
- Cropped silhouette with shaped waist
- Runs true to size
Style Number/Barcode: 06003-000470
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Check Please Plaid Slit Maxi Skirt
Plaid just got a better plot twist. This slit maxi skirt pairs a flowy, A-line fit with a classic pattern for a fresher take on fall dressing. Pair it with a bodysuit or an oversized jacket, and let the skirt make a statement.
Fit & Features
- Plaid pattern, woven fabric, short woven lining
- High-rise waist, side zipper and hook-eye closure
- High front slit detail
- Flowy A-line fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-000019
Category Name: Plaid Looks
Price: $44.90
Availability: Out of Stock
Product Badge:- Ships Free
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Plaid Attitude Mid-Rise Capri Pants
Classic plaid with more attitude. These plaid capri pants offer a mid-rise waist and form-hugging fit for styling solo or matching back to the set.
Shop Matching Top: Plaid Attitude Collared Zip-Up Vest
Fit & Features
- Plaid woven fabric
- Mid-rise waist
- Knee-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06402-000050
Category Name: Plaid Looks
Price: $34.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Cozy Forecast Plaid Blanket Scarf
Consider your cold-weather layering officially upgraded. This cozy plaid blanket scarf wraps you in warmth with its oversized silhouette and classic fringe ends, bringing a polished, chic finish to your favorite coats and sweaters.
Fit & Features
- Plaid pattern
- Fringe trim
- Soft material with brushed texture
Style Number/Barcode: 07305-000121
Category Name: Plaid Looks
Price: $18.90
Availability: In Stock
Available Color: NATURAL
Available Size: NS
Product Badge:- New Arrival
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Prep Talk Plaid Pleated Mini Skort
Prep with a little plot twist. This plaid pleated mini skort brings a high-rise skater silhouette, flirty lace trim, and hidden built-in shorts for styling that looks cute without the wardrobe stress.
Fit & Features
- Plaid woven fabric
- High-rise waist
- Pleated detailing
- Mini-length overlay with skater silhouette, lace trim
- Hidden built-in shorts
- Runs true to size
How to style for Halloween: Style with a collared top, knee-high socks, heels, and clear glasses for the cutest costume.
Style Number/Barcode: 06503-000396
Category Name: Plaid Looks
Price: $39.90
Availability: In Stock
Available Color: RED
Available Size: S, M, L
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Brunch Booked Gingham Print A-Line Midi Dress
The kind of dress that gets complimented before you even sit down. This gingham print midi dress brings all the charm with a lace-trimmed sweetheart neckline, dainty tie detail, and an easy A-line fit that’s made for brunch plans.
Fit & Features
- Cotton-blend woven fabric
- Gingham print
- Sleeveless sweetheart neckline, dainty eyelash lace trim, tie detail
- Adjustable spaghetti straps
- Smocked back
- Midi-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000821
Category Name: Plaid Looks
Price: $46.00 $64.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: S, M
Product Badge:- Sale
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Plaid Attitude Collared Zip-Up Vest
Classic plaid with more attitude. This plaid zip-up vest hugs the frame in a sleek, fitted shape, with a double-zipper front for styling solo or matching back to the set.
Shop Matching Shorts: Plaid Attitude Mid-Rise Hot Shorts
Shop Matching Capris: Plaid Attitude Mid-Rise Capri PantsFit & Features
- Plaid woven fabric, minimal stretch
- Sleeveless collared neckline
- Tank straps
- Double zipper-front design
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06204-000181
Category Name: Plaid Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Plaid Behavior Low Rise Plaid Micro Shorts
Plaid micro shorts make fall styling feel instantly more interesting. Pair the low-rise fit with a fitted knit, oversized jacket, and pointed boots for a sharper seasonal look. The compact silhouette keeps the outfit balanced while still letting the plaid do the talking.
Fit & Features
- Low-rise waist
- Plaid pattern
- Button-front closure
- Belt loops
- Front pockets
- Fitted micro-short silhouette
- Runs true to size
Model Information
Model is 5'8" with a 34" bust, 24" waist, and 34" hips. She is wearing a size small.
Style Number/Barcode: 06403-000192
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Undercover Detective Four-Piece Costume Set
The clues are lining up for one very sharp detective look. This four-piece set pairs a houndstooth bodysuit with a cape, badge, and belt for a coordinated costume with a playful undercover edge. Add your own accessories and call the case closed.
Fit & Features
- Four-piece costume set includes bodysuit, cape, badge, and belt
- Houndstooth printed sleek and stretchy knit bodysuit
- Sleeveless V-neckline, patent faux leather overlay and tank straps, faux front buttons
- High-cut bodysuit silhouette, attached adjustable garter straps
- Coordinating short cape, mock neckline, faux leather tie-front design
- Decorative badge detail
- Patent faux leather adjustable belt
- Runs true to size
- Stockings not included
How to style for Halloween: Add sheer stockings, statement shoes, and sleek glasses to finish the detective look with a sharp undercover twist.
Style Number/Barcode: 06001-000718
Category Name: Plaid Looks
Price: $69.90
Availability: In Stock
Available Color: MULTI
Available Size: M/L
Product Badge:- Best Seller
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Buckle Up Plaid Hot Shorts
The prep trend is taking a bolder turn. These plaid hot shorts combine a low-rise shape with a matching wide belt and metal grommets for a more directional finish. Add a fitted tee or sleek top to keep the look current.
Fit & Features
- Plaid woven fabric
- Low-rise waist
- Wide matching grommet belt with buckle
- Hot-short silhouette
- Runs true to size
Style Number/Barcode: 06403-000178
Category Name: Plaid Looks
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Plaid Attitude Mid-Rise Hot Shorts
Classic plaid with more attitude. These plaid hot shorts offer a mid-rise waist and curve-hugging fit for styling solo or matching back to the set.
Shop Matching Top: Plaid Attitude Collared Zip-Up Vest
Fit & Features
- Plaid woven fabric
- Mid-rise waist, belt loops
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06403-000180
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: BLACK/WHITE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Picnic Plans Gingham Ruffle Mini Skort
Flirty, fun, and already on your weekend lineup. This gingham ruffle mini skort brings that effortless vibe with a comfy smocked waist and built-in shorts for the cutest plans.
Fit & Features
- Gingham printed woven fabric
- High-rise smocked waist
- Tiered ruffled overlay, eyelet trim
- Mini-length overlay with A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06303-000054
Category Name: Plaid Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tailored Mood Plaid Woven Blazer
Your “I planned this” blazer—clean, tailored, and instantly elevated. The plaid woven finish gives it that strategic, cool-girl polish that works from brunch to late-night plans without ever trying too hard.
Shop Matching Shorts: Tailored Mood Plaid Woven Shorts
Fit & Features
- Plaid printed woven fabric
- Structured tailored silhouette
- Notched lapel neckline
- Front flap pockets and multi-button closure
- Runs true to size
Style Number/Barcode: 06204-000059
Category Name: Plaid Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Polished Edit Plaid Pleated Mini Skort
For the girl who plans her power moves and her outfits. This plaid mini skort pulls any look together with a polished, pleated fit that means business (but still plays it cool). Style with the matching blazer.
Shop Matching Jacket: Polished Edit Plaid Blazer
Fit & Features
- Woven fabric, plaid print
- Mid-rise waist
- Side button accents
- Pleating
- Mini-length hem, A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06403-000082
Category Name: Plaid Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt in Motion Plaid Pleated Mini Skort
This mini skort blends preppy and playful with pleated plaid, lace trim, and built-in shorts that keep every move stress-free. Equal parts cute and cheeky—it’s the piece you reach for weekly.
Fit & Features
- Plaid printed knit fabric
- Wide mid-rise waistband
- Pleated overlay skirt with built-in shorts for coverage
- Scalloped lace trim
- Mini-length skort silhouette
- Runs true to size
Style Number/Barcode: 06503-000228
Category Name: Plaid Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free