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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Play It Cute Plaid Bubble Skort
Serving cute with a little attitude—this one gets it. This mid-rise plaid bubble hem skort gives you that playful volume with built-in ease, perfect for any weekend plans.
Fit & Features
- Plaid print, woven lining, stretchy built-in knit shorts
- Mid-rise elasticized waist, belt loop accents
- Bubble mini-length hem
- Runs true to size
Style Number/Barcode: 06303-000041
Category Name: Plaid Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: S, M
Product Badge:- Sale
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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: $11.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: M, L
Product Badge:- Sale
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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, L
Product Badge:- Sale
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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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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
- Halter straps with scoop neckline
- Sleeveless fitted bodice
- 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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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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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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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: S/M, M/L, L/XL
Product Badge: -
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
- 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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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: XS, S, M, L
Product Badge: -
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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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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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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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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Ruffle Check Double Belt Plaid Mini Skort
Plaid and ruffles give this skort enough personality to carry the outfit. The mini silhouette pairs layered flounces with a double-belt waist for a playful mix of movement and edge. Keep the top fitted and let the texture do the styling.
Fit & Features
- Lightweight woven fabric, plaid print
- High-rise waist
- Double-belt waistband
- Layered ruffle design
- Mini-length overlay, A-line fit
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06403-000188
Category Name: Plaid Looks
Price: $46.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- New Arrival
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Dainty Plaid Bow-Front Mini Skort
Plaid gets a softer finish with one simple detail. This mini skort features a neat bow at the front waist, adding contrast to the structured pattern and close-to-the-body shape. The result feels polished, playful, and easy to work into your rotation.
Fit & Features
- Knit fabric
- Plaid pattern
- High-rise fit, bow detail at front waist
- Mini-length overlay, form-hugging fit
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000418
Category Name: Plaid Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Check Mate Plaid Draped Asymmetrical Skirt
Classic plaid, reworked for now. This asymmetrical skirt pairs a low-rise waist with draped construction and an uneven hem for a more fashion-forward fall look.
Shop Matching Top: Check Mate Cropped Plaid Tube Top
Fit & Features
- Plaid print, knit fabric
- Low-rise waist
- Draped asymmetric flowy silhouette
- Curve-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000202
Category Name: Plaid Looks
Price: $36.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Check Mate Cropped Plaid Tube Top
Fall plaid, but with better details. This cropped tube top uses a scarf accent to give the strapless neckline a trendy flair while the fitted silhouette flaunts your figure.
Shop Matching Bottoms: Check Mate Plaid Draped Asymmetrical Skirt
Fit & Features
- Plaid print, knit fabric
- Strapless neckline with scarf included
- Fitted crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000807
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Checks in Motion Plaid Chiffon Poncho
Plaid just got sheer. This chiffon poncho brings an airy style to bandeaus, tank tops, and denim bottoms for an effortless fall layer with a little drama.
Fit & Features
- Sheer plaid chiffon fabric
- Crew neckline with back keyhole with button closure
- Draped poncho silhouette with open sides
- Asymmetrical flowing hem
- Runs true to size
Style Number/Barcode: 06204-000199
Category Name: Plaid Looks
Price: $24.90
Availability: In Stock
Available Color: SAGE
Available Size: XS/S, M/L
Product Badge:- New Arrival
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Checked Out Plaid Slit Midi Skirt
A sleek silhouette with a sharper finish. This plaid midi skirt skims the figure before opening into a high side slit for flirty movement with each step. Style this skirt with a cute top and heels.
Fit & Features
- Plaid woven fabric
- Low-rise waist
- High front slit
- Flowy fit
- Midi-length hanky hem
- Runs true to size
Style Number/Barcode: 06401-000062
Category Name: Plaid Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Check Please Belted Plaid Mini Skort
Plaid just found its trendy flair. This belted mini skort looks like a skirt with the ease of shorts, ready for campus days, coffee runs, and last-minute plans.
Fit & Features
- Plaid print, woven fabric
- Mid-rise waist with belted accents
- Pleated flared silhouette
- Mini-length hem
- Built-in shorts lining
- Runs true to size
Style Number/Barcode: 06403-000197
Category Name: Plaid Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Plans In Plaid Knit Halter Top
Plaid just got a little flirtier. This plaid knit halter top pairs a form-hugging fit with dainty eyelet trim and a partially open back for an easy upgrade to denim, minis, and going-out plans.
Fit & Features
- Plaid knit fabric with front knit lining, moderate stretch
- Sleeveless square neckline, dainty eyelet trim
- Halter strap, dual back button closures
- Partially open back
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000829
Category Name: Plaid Looks
Price: $29.90
Availability: In Stock
Available Color: BLACK
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
Product Badge:- New Arrival
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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: XS, S, M, L
Product Badge:- Part of a Set
