Plaid Looks

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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!

  • 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
  • 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 flannel pattern
    • High-rise fit, bow detail at front waist
    • Side zipper and hook-eye closure
    • 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: S, M, L

    Product Badge:
    • Best Seller
  • 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

  • Checked Out Plaid Low-Rise Wide-Leg Pants

    These low-rise plaid wide-leg pants make tailored styling feel a little less expected. The double-button waistband and extended tab give the waistline extra detail, while the wide-leg shape keeps the look relaxed. Pair them with a fitted baby tee or cropped knit to keep the proportions clean.

    Fit & Features

    • Plaid woven fabric
    • Low-rise waist
    • Double-button and zipper front detail
    • Extended waistband tab
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000029

    Category Name: Plaid Looks

    Price: $44.90

    Availability: In Stock

    Available Color: CHARCOAL

    Available Size: XS, S, M, L

  • 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

  • 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
  • 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
  • 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
  • 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
  • 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

  • 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
  • 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
  • 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

  • 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

  • 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
  • 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
  • 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
  • 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

  • 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
  • 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 Pants

    Fit & 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
  • 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

  • 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: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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

  • 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