Plaid Looks
Plaid is back, but not in the way you remember. This trending edit plays with plaid in unexpected ways, with blue and brown colorways giving the checkered pattern a fresh update. Find going out tops, halters, and off-the-shoulder shapes in flowy cotton gauze and chiffon, plus midi skirts, maxis, two-piece matching sets, and mini skorts. Funnel neck jackets and bombers add a cool-weather edge, making these looks easy for coffee runs, off-duty 'fits for winter, and plans that need a little more personality.
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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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Check Mate Plaid Cabby Hat
Prep just got a little more interesting. This plaid cabby hat brings textured charm and a vintage-inspired shape to denim, mini skirts, and layered fall looks that could use something extra.
Fit & Features
- Cabby hat structure
- Short curved brim
- Textured plaid woven fabric
Style Number/Barcode: 07302-000447
Category Name: Plaid Looks
Price: $16.90
Availability: In Stock
Available Color: NATURAL
Available Size: NS
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Pattern Play Gingham Plaid A-Line Maxi Skirt
Longer lines are having their fall moment. This A-line maxi skirt pairs a clean drop waist seam with a gingham plaid pattern for a silhouette that feels polished, current, and easy to layer into autumn looks. The shape gives boots and fitted knits plenty of room to do their thing.
Fit & Features
- Gingham plaid pattern, airy woven fabric
- Drop waist seam, mid-rise design
- Back zipper and hook-eye closure
- A-line silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06301-000022
Category Name: Plaid Looks
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
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Check Point Plaid Side Slit Capri Pants
A little plaid goes a long way when the styling gets creative. These fitted capri pants bring a tailored-looking touch to oversized knits, sleek bodysuits, and cropped jackets. Finish with kitten heels for a chic outfit with a playful edge.
Fit & Features
- Plaid pattern, soft knit fabric with stretch
- Mid-rise waist
- Skinny-leg capri silhouette
- Side slit accents
- Runs true to size
Style Number/Barcode: 06502-000162
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Plaid Crush Asymmetric Midi Skirt
The plaid obsession continues, with a playful new twist. This flowy mesh midi skirt pairs flattering waist ruching with an asymmetric handkerchief hem that moves with every step. Style with the matching halter top.
Shop Matching Top: Plaid Crush Lace-Trim Halter Cami Top
Fit & Features
- Plaid-printed mesh fabric, knit lining, high stretch
- Mid-rise waist
- Ruched detailing, drop waist seam
- Asymmetric midi-length hem
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 06501-000218
Category Name: Plaid Looks
Price: $36.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Plaid Crush Lace-Trim Halter Cami Top
A little plaid, a little lace, and plenty of flirt. This halter cami top pairs a plunging, lace-trimmed neckline with curve-hugging ruching and a flirty open back for a cute, on-trend look. Style with the matching midi skirt.
Shop Matching Bottoms: Plaid Crush Asymmetric Midi Skirt
Fit & Features
- Plaid-printed mesh fabric with knit lining, high stretch
- Sleeveless V-neckline, lace trim
- Halter tie-back spaghetti straps, open back
- Ruched side seams
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000862
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Pattern Play Plaid Wide Leg Trouser Jorts
Who says tailored has to play by the rules? These plaid jorts bring a fresh perspective with crisp front pleats and a relaxed, wide-leg shape. The result is a polished look with just the right amount of attitude.
Fit & Features
- Plaid pattern, woven fabric
- Mid-rise waist
- Side pockets
- Wide-leg fit
- Below-the-knee length hem
- Runs true to size
Style Number/Barcode: 06403-000204
Category Name: Plaid Looks
Price: $49.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Pleat Scene Belted Plaid Mini Skort
Fall dressing just found its pleated favorite. A checked pattern, crisp mini shape, and wide buckle belt give this skort a trend-forward feel with just enough structure. Pair it with a cropped sweater and boots for an easy seasonal refresh.
Fit & Features
- Plaid pattern, woven fabric, built-in shorts lining
- Mid-rise belted waist, belt loop accents
- Pleated A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 06403-000202
Category Name: Plaid Looks
Price: $44.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Check Please Plaid Ruffle Mini Skort
The details are doing the most here. This plaid knit mini skort layers ruffles with a ruched waistband and lace trim for a textured finish that feels more dimensional from every angle. Built-in shorts keep the layered shape grounded underneath.
Fit & Features
- Plaid-printed knit fabric, moderate stretch
- Mid-rise waist with dainty lace trim
- Drop waist seam, ruched detailing
- Mini-length tiered ruffled overlay, A-line fit
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06503-000451
Category Name: Plaid Looks
Price: $36.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Line Up Plaid Wrap Mini Skort
Classic plaid gets a more tailored angle. This wrap mini skort uses a fitted shape and structured front overlay to sharpen the silhouette without overworking the look. It’s the kind of detail that makes fall outfits feel instantly more intentional.
Shop The Matching Coat: Line Up Longline Plaid Trench Coat
Fit & Features
- Mini-length hem
- Plaid pattern, faux wool fabric, sewn-in woven lining
- Structured form-hugging fit
- Wrap-front skirt overlay, high-rise waist
- Shorts bottom
- Runs true to size
Style Number/Barcode: 06403-000199
Category Name: Plaid Looks
Price: $44.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Preppy Attitude Plaid Knit Mock Neck Mini Dress
A little prep, a little attitude, and plenty of reasons to wear it on repeat. This plaid knit mini dress keeps things chic with a sleek mock neckline, curve-skimming bodycon fit, and a back keyhole cutout that's anything but predictable.
Fit & Features
- Plaid knit fabric
- Sleeveless mock neckline
- Tank shoulder straps
- Back keyhole cutout
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000875
Category Name: Plaid Looks
Price: $45.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Line Up Longline Plaid Trench Coat
Tailoring meets plaid with just the right amount of attitude. This longline trench coat uses notched lapels and a double-breasted front to give the patterned design a clean, structured edge. It’s the layer that makes the rest of the outfit look more intentional.
Shop The Matching Skort: Line Up Plaid Wrap Mini Skort
Fit & Features
- Longline length with front pockets
- Plaid pattern, faux wool fabric, sewn-in woven lining
- Notched lapels
- Double-breasted front button closures
- Long sleeves with button strap cuffs
- Runs true to size
Style Number/Barcode: 06201-000138
Category Name: Plaid Looks
Price: $79.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Prep Play Plaid Mesh Halter Ruffle Mini Dress
The plaid mesh gives this mini dress a fresh, flirty edge, while the ruched bodice adds extra texture through the waist. The halter neckline keeps the shape sleek up top, and the tiered ruffle skirt brings playful movement below. Style it with knee-high boots and simple gold jewelry for a look that feels cute, current, and a little cheeky.
Fit & Features
- Plaid mesh fabric with knit lining, high stretch
- Halter V-neckline
- Ruched bodice detailing
- Tiered ruffle hem
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000850
Category Name: Plaid Looks
Price: $39.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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90s Prep Girl Plaid Ruffle Mini Dress
Lock in the 90s prep girl look with a mini dress that makes the costume instantly recognizable. The fitted strapless bodice, yellow plaid pattern, sheer black lace inset, and ruffled skirt keep the look polished and playful. Style it with knee-high socks and classic accessories for Halloween.
Fit & Features
- Plaid printed woven fabric, knit lining
- Strapless sweetheart neckline, eyelash lace trim, rhinestone buckle detail, no-slip strip
- Sheer lace inset
- V-shaped drop waist seam
- Smocked back, hidden zipper with hook-eye closure
- Tiered ruffled design, mini-length A-line fit, hidden built-in knit panty lining
- Runs true to size
How to style for Halloween: Complete the 90s prep girl costume with knee-high socks, heels, and a sleek handbag.
Style Number/Barcode: 05103-001299
Category Name: Plaid Looks
Price: $64.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Prep Talk Plaid Halter Pleated Romper
The details are giving this romper its extra charm. Lace trim frames the halter neckline and hem, while the fitted bodice and crisp pleats keep the shape polished. The open back and hidden shorts add a playful finish without taking away from the plaid.
Fit & Features
- Plaid knit fabric, moderate stretch
- Halter V-neckline, tie-back straps, open back
- Lace-trimmed neckline and hem
- Fitted bodice, drop waist seam
- Pleated mini-length overlay, A-line fit
- Hidden built-in knit shorts
- Runs true to size
Style Number/Barcode: 06503-000429
Category Name: Plaid Looks
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Check Please Plaid Halter Top
Plaid just found its trendy flair. This halter top features a deep V-neckline, open back, and fitted silhouette perfect for campus days, coffee runs, and last-minute plans. Style with the matching mini skort.
Shop Matching Bottoms: Check Please Plaid Belted Mini Skort
Fit & Features
- Plaid-printed woven fabric
- Sleeveless plunging V-neckline
- Halter strap with elastic detail
- Open back, lower stretchy smocked design
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06003-000483
Category Name: Plaid Looks
Price: $32.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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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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Check Please Plaid Belted 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. Style with the matching halter top.
Shop Matching Top: Check Please Plaid Halter Top
Fit & Features
- Plaid-printed woven fabric
- Mid-rise waist with belted accents
- Side zipper closure
- Pleated, flared, A-line silhouette
- Mini-length hem
- Built-in knit 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: S, M, L
Product Badge:- Part of a Set
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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 lightweight woven fabric with smooth woven lining, no stretch
- Mid-rise waist
- Drop waist seam
- 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
Product Badge:- Best Seller
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Flirty In Plaid Mesh Ruffle Mini Skort
Plaid just got a little more flirtatious. This mesh mini skort hugs the waist with ruched detailing and features a mini-length overlay with a ruffled side accent that makes the matching halter top feel instantly more styled.
Shop Matching Top: Flirty In Plaid Mesh Halter Top
Fit & Features
- Plaid-printed mesh fabric with knit lining, high stretch
- Mid-rise waist, ruched detailing
- Drop waist seam
- Mini-length ruffled overlay, A-line fit
- Ruffled side cascading accent
- Hidden built-in shorts
- Runs true to size
Style Number/Barcode: 06503-000423
Category Name: Plaid Looks
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Flirty In Plaid Mesh Halter Top
Plaid just got a little more flirtatious. This mesh halter top hugs the figure with ruched sides, a plunging V-neckline, and an open back that makes the matching mini skort feel instantly more styled.
Shop Matching Bottoms: Flirty In Plaid Mesh Ruffle Mini Skort
Fit & Features
- Plaid-printed mesh fabric with knit lining, high stretch
- Sleeveless V-neckline
- Tie-back halter straps, open back
- Ruched side seams
- Mid-length hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-000814
Category Name: Plaid Looks
Price: $29.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Checked In Plaid Funnel Neck Bomber Jacket
Plaid just found its cooler weather upgrade. This cropped bomber jacket mixes an oversized fit with a high funnel neck and relaxed sleeves for an easy throw-on layer that makes mini skirts, denim, and boots instantly styled.
Fit & Features
- Plaid pattern, woven fabric, sewn-in woven lining
- High funnel neckline with snap-button closures
- Relaxed long sleeves with snap-button cuffs
- Front zip-up closure
- Oversized fit
- Cropped bubble hem
- Runs true to size
Style Number/Barcode: 06202-000143
Category Name: Plaid Looks
Price: $59.90
Availability: Out of Stock
Product Badge:- Ships Free
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Autumn Edit Plaid Cabby Cap
A little vintage, very fall ready. This plaid cabby cap mixes a softly structured crown with a contrast faux suede brim and buckle detail for the kind of finishing touch that makes denim, knits, and trench coats feel instantly more styled.
Fit & Features
- Plaid cabby cap silhouette
- Contrast faux suede brim
- Side buckle accent
- Paneled crown with top button
- Structured visor
Style Number/Barcode: 07302-000401
Category Name: Plaid Looks
Price: $18.90
Availability: Out of Stock
Product Badge:- Ships Free
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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
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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