Matching Sets
Matching sets are the easiest way to look instantly put-together while keeping it on-trend for Fall. From two-piece sets like crop tops with mini skirts to flowy fly-a-way tops paired with wide-leg pants, the options are endless. Long sleeve crop tops with maxi skirts bring a chic vibe, while jersey knits and printed mesh keep the styles fresh. Perfect for date night, brunches, or mixers, these sets take the stress out of styling and give you a ready-made outfit that always turns heads.
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Matching Sets
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Matching Sets That Serve Style in Every Fall Scene
From rooftop dinners to weekend getaways, Windsor’s matching sets deliver effortless coordination and head-turning style. Whether you’re dressing for a seasonal soirée, a night out, or a casual hang, these outfits take the guesswork out of getting ready.
Everyday Ease & Polished Pairings
Slip into two-piece skirt sets or wide-leg pant sets with matching crop tops for daytime polish. Cozy ribbed knits, soft sweater fabrics, and sleek satins keep things comfortable and put-together. Style with ankle boots and layered jewelry for casual glam that moves with you.
Night-Out Energy & Elevated Looks
Dial it up with sleek two-piece matching sets paired with a tailored blazer or curve-hugging silhouettes. Faux leather finishes, halter details, and tie-front designs bring the heat—just add strappy heels or heeled boots and a mini bag for your next night out.
Mix, Match & Layer
Wear the full look or break it up—pair your top with jeans or faux leather pants, or swap in a fitted bodysuit for your skirt. Finish with a cropped jacket or a longline duster coat for extra dimension.
Explore Windsor’s full collection of matching sets online, in-app, or in-store to level up your fall wardrobe.
What are matching sets?
Matching sets are coordinated outfits that include two or more pieces, such as a blouse and pants or a crop top and skirt. Windsor’s matching sets go beyond the basics, featuring stylish combos like blazer and skirt sets, lounge tops with joggers, and trendy T-shirts with biker shorts. Some sets even include matching accessories or jackets for a fully styled look. Whether you’re dressing for a casual day, a vacation, or a night out, matching sets make putting together an outfit effortless and stylish.
Are matching sets a trend?
Absolutely! Matching sets are a must-have trend that Windsor carries all year long. These coordinated outfits take the guesswork out of styling while delivering an effortlessly put-together look. Whether you’re keeping it casual or dressing up for an event, Windsor’s curated selection ensures you’re always on-trend.
What do you call a two-piece outfit?
A two-piece outfit is often called a matching set or co-ords (short for coordinates). These stylish separates are designed to be worn together, but they’re also perfect for mixing and matching to create fresh, new looks.
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Glam Up And Go Wrap Mini Skirt
This sexy wrap mini skirt will bring the effortless glamour to your party look! It features a high-rise elastic banded waist for comfortable wear, a faux wrap-front design creating a chic side slit, a mini-length hem, and a form-hugging silhouette. The stretchy knit fabric features a subtle sheen that will look stunning under the lights Style this mini skirt with the matching crop top for a complete outfit for your next club night out.
Shop Matching Top: Glam Up And Go Cropped Tank Top
Fit & Features
- High-rise elastic banded waist
- Faux wrap-front design, side slit
- Mini-length hem
- Form-hugging silhouette
- Knit fabric, sheen, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0945
Category Name: Matching Sets
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glam Up And Go Cropped Tank Top
This sexy cropped tank top will bring the effortless glamour to your party look! It features a sleeveless V-neckline with a trendy triangle bust seam outline, adjustable spaghetti straps, and a fitted cropped hem. The stretchy knit fabric features a subtle sheen that will look stunning under the lights. Style this crop top with the matching mini skirt for a complete outfit for your next club night out.
Shop Matching Bottoms: Glam Up And Go Wrap Mini Skirt
Fit & Features
- Sleeveless V-neckline
- Triangle bust seam outline
- Adjustable spaghetti straps
- Fitted cropped hem
- Knit fabric, sheen, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-5035
Category Name: Matching Sets
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fashion Boot Camp Denim Cargo Joggers
Step up as a stylish cadet in these denim cargo joggers! The pants feature a flattering high-rise waist, side pockets, and lower cargo flap pockets with dual button closures, a jogger-style leg, and a pull strap along the cuff. Complete the look with the matching jacket for casual hangs or school!
Shop Matching Jacket: Fashion Boot Camp Denim Bomber Jacket
Fit & Features
- High-rise waist
- Front button and hidden zipper closure, belt loop accents
- Side pockets, lower cargo flap pockets, dual button closures
- Jogger-style leg
- Pull tab straps along the cuff
- Denim woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06302-0780
Category Name: Matching Sets
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fashion Boot Camp Denim Bomber Jacket
Step up as a stylish cadet in this denim bomber jacket! The jacket features a high neckline, long sleeves with elasticized cuffs, front zipper closure, dual flap pockets with snap button closures, and an elasticized cinch crop hem. Complete the look with the matching bottoms for casual hangs or school!
Shop Matching Bottoms: Fashion Boot Camp Denim Cargo Joggers
Fit & Features
- Long sleeves, elasticized cuffs
- High neckline
- Front zipper closure
- Dual flap pockets with snap buttons
- Elasticised cinch crop hem
- Denim woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06204-1622
Category Name: Matching Sets
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Iconic Vibes Pinstripe Trouser Pants
Create an iconic look and have a major it-girl moment in these pinstripe trouser pants! They feature a high-rise waist, dual front pockets, dual faux back pockets, a wide-leg silhouette, and a relaxed fit. The woven fabric features a pinstripe pattern for a chic flair. Complete your look with the matching vest or blazer to wear from the office to dinner!
Shop Matching Tops: Iconic Vibes Pinstripe Cropped Vest, Iconic Vibes Pinstripe Blazer
Fit & Features
- High-rise waist, back elastic waistband, pleating
- Hidden front zipper, hook and bar closure
- Dual front pockets, dual faux back pocket slits
- Wide-leg silhouette, relaxed fit
- Pinstripe pattern
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-1334
Category Name: Matching Sets
Price: $3.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Korrie Formal Woven Crop Blazer
Special Occasion
It's double the fun with the Korrie formal blazer to showcase your fashionista at Homecoming! She features long sleeves, a lapel collar neckline, a single front button closure, and a cropped hem. The blazer jacket is composed of a smooth woven fabric with a sewn-in knit lining. Style with the matching skirt and platform heels for a school dance or red carpet event!
Shop Matching Bottom: Korrie Formal High-Rise Tulle Slit Maxi Skirt
Fit & Features
- Long sleeves
- Lapel collar neckline
- Single front button closure
- Cropped hem
- Smooth woven fabric, sewn-in knit lining
- Runs true to size
Style Number/Barcode: 06204-1618
Category Name: Matching Sets
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Korrie Formal High-Rise Tulle Slit Maxi Skirt
Special Occasion
It's double the fun with the Korrie formal maxi skirt to showcase your fashionista at Homecoming! She features a high-rise waist, a voluminous tiered ruffle maxi-length silhouette, a sultry high front slit to show some leg, and a floor-length hem. The long skirt is composed of a tulle mesh fabric with a stretchy knit short lining. Style with the matching blazer and platform heels for a school dance or red carpet event!
Shop Matching Blazer: Korrie Formal Woven Crop Blazer
Fit & Features
- High-rise waist
- Back zipper and hook-eye closure
- Voluminous tiered ruffle maxi-length silhouette
- High front slit
- Floor-length hem
- Tulle mesh fabric, short stretchy knit lining
- Runs true to size
Style Number/Barcode: 06501-0871
Category Name: Matching Sets
Price: $29.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tied In Cozy Chenille Tie-Waist Robe
Tie yourself up in this cozy chenille robe perfect for lounging around! The robe features long sleeves, an open-front design, a tie-waist belt, front pockets for keeping your hands warm, and a mid-length hem on ultra-soft chenille knit fabric. Complete the look in the matching pajama top and bottoms for a chill night!
Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top
Shop Matching Pajama Bottoms: Fuzzy Feels Chenille High-Rise Jogger Pajamas
Fit & Features
- Long sleeves
- Open-front design
- Tie-waist belt, front pockets
- Mid-length hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0942
Category Name: Matching Sets
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hello Cutie Chenille Crop Pajama Top
Look and feel like a cutie in this chenille pajama top! The tank top features a sleeveless square neckline, tank-style straps, and a cropped hem on ultra-soft and cozy knit chenille fabric. Complete the look in the matching pajama bottoms and robe for the perfect lounge sesh!
Shop Matching Pajama Bottoms: Fuzzy Feels Chenille High-Rise Jogger Pajamas
Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe
Fit & Features
- Sleeveless square neckline
- Tank-style straps
- Cropped hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0938
Category Name: Matching Sets
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fuzzy Feels Chenille High-Rise Jogger Pajamas
Get cozy lounging in these chenille jogger pajamas! They feature a high-rise elasticized waistband, a skinny jogger-leg silhouette, and ribbed cuffs on ultra-soft and cozy chenille knit fabric. Complete the look in the matching pajama top and robe for a chill night in!
Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top
Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe
Fit & Features
- High-rise elasticized waistband
- Skinny jogger-leg silhouette
- Ribbed cuffs
- Ultra-soft chenille knit fabric
- Minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0940
Category Name: Matching Sets
Price: $13.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cell Block Cutie Inmate Tie-Front Top
Serving “too hot for lockdown” vibes—this costume top is a total scene-stealer. The cropped tie-front design and cheeky "Inmate" lettering are your ticket to an unforgettable entrance.
Shop Matching Bottoms: Cell Block Cutie Inmate Belted Hot Shorts
Fit & Features
- Smooth stretch knit fabric
- Collared neckline
- Front tie closure
- Short sleeves
- Inmate lettering at back
- Ultra cropped hem
- Runs true to size
Style Number/Barcode: 06202-000039
Category Name: Matching Sets
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cuddle Time Chenille Crop Cardigan
Wrap yourself in this chenille crop cardigan for a cute and cuddly vibe! The sweater features long sleeves, a ribbed open-front design, and a cropped hem on ultra-soft and cozy chenille knit fabric. Complete the look in the matching cozy pajama top and bottoms for a chill night in!
Shop Matching Pajama Top: Chill Night Chenille Crop Tank Top
Shop Matching Pajama Bottoms: Feeling The Vibe High-Rise Chenille Joggers
Fit & Features
- Long sleeves
- Ribbed open-front design
- Cropped hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0946
Category Name: Matching Sets
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling The Vibe High-Rise Chenille Joggers
Feel the cozy vibes in these chenille joggers perfect for lounging on the weekend! The jogger pants feature a high-rise elastic drawstring waist, a skinny jogger-style leg, and are crafted from ultra-soft and stretchy chenille rib knit fabric. Complete the look in the matching pajama top and cardigan for the perfect lounge sesh!
Shop Matching Pajama Top: Chill Night Chenille Crop Tank Top
Shop Matching Cardigan: Cuddle Time Chenille Crop Cardigan
Fit & Features
- High-rise elastic drawstring waist
- Skinny jogger-style leg
- Ultra-soft chenille rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0947
Category Name: Matching Sets
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chill Night Chenille Crop Tank Top
Settle in for a cozy night in this chenille crop top! With its ultra-soft ribbed chenille knit fabric, sleeveless design, spaghetti straps, and square neckline, you'll feel comfortable and stylish all night long. Complete the look in the matching pajama bottoms and cardigan for the perfect lounge sesh!
Shop Matching Pajama Bottoms: Feeling The Vibe High-Rise Chenille Joggers
Shop Matching Cardigan: Cuddle Time Chenille Crop Cardigan
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cropped hem
- Ultra-soft and cozy
- Ribbed chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0945
Category Name: Matching Sets
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Play Date High Rise Straight-Leg Pants
Play up a cute and comfy style with these knit pants for all of your casual plans! The pants feature a flattering high-rise banded waist and a straight-leg silhouette on stretchy rib knit fabric. Complete the look with the matching cardigan.
Shop Matching Top: Play Date Sweater Knit Cardigan
Fit & Features
- High-rise banded waist
- Straight leg silhouette
- Stretchy sweater rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-2391
Category Name: Matching Sets
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Play Date Sweater Knit Cardigan
Play up a cute and comfy style with this sweater knit cardigan for all of your casual plans! The cardigan features fitted long sleeves, a V-neckline, button-down front closures, and a flirty center slit along the hem on stretchy rib knit fabric. Complete the look with the matching bottoms.
Shop Matching Bottoms: Play Date High Rise Straight Leg Pants
Fit & Features
- Fitted long sleeves
- V-neckline
- Button-down front closures
- Center slit along the hem
- Stretchy sweater rib knit fabric
- Runs true to size
Style Number/Barcode: 06005-1759
Category Name: Matching Sets
Price: $3.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Iconic Vibes Pinstripe Blazer
Create an iconic look and have a major it-girl moment in this pinstripe blazer! It features a lapel collar, shoulder pad inserts to provide structure, long sleeves, a single front button closure, dual front faux flap pockets, and a fitted silhouette for a streamlined look. The lined woven fabric features a pinstripe pattern for a chic flair. Complete your look with the matching shorts or pants to wear from meetings to happy hour!
Shop Matching Bottoms: Iconic Vibes Pinstripe Trouser Shorts, Iconic Vibes Pinstripe Trouser Pants
Fit & Features
- Lapel collar, shoulder pad inserts, long sleeves
- Single front button closure
- Dual front faux flap pockets
- Fitted silhouette
- Pinstripe pattern
- Woven fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06204-1638
Category Name: Matching Sets
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Iconic Vibes Pinstripe Trouser Shorts
Create an iconic look and have a major it-girl moment in these pinstripe trouser shorts! They feature a high-rise waist, a front button and hidden zipper closure, dual front pockets, and a relaxed fit. The woven fabric features a pinstripe pattern for a chic flair. Complete your look with the matching vest or blazer for weeknight happy hours!
Shop Matching Tops: Iconic Vibes Pinstripe Cropped Vest, Iconic Vibes Pinstripe Blazer
Fit & Features
- High-rise waist
- Front button and hidden zipper closure
- Dual front pockets
- Relaxed fit
- Pinstripe pattern
- Woven fabric, lining, no stretch
- Runs true to size
Style Number/Barcode: 06403-0346
Category Name: Matching Sets
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Iconic Vibes Pinstripe Cropped Vest
Create an iconic look and have a major it-girl moment in this pinstripe cropped vest! It features a sleeveless V-neckline, wide tank shoulder straps, three front button closures, two front faux pockets, an angled cropped hem, and a fitted silhouette. The lined woven fabric features a pinstripe pattern for a chic flair. Complete your look with the matching shorts or pants for weeknights after the office or weekend plans with your friends!
Shop Matching Bottoms: Iconic Vibes Pinstripe Trouser Shorts, Iconic Vibes Pinstripe Trouser Pants
Fit & Features
- Sleeveless bodice, V-neckline, wide tank shoulder straps
- Vertical curved seams down the bust and front
- Three front button closures, two front faux pocket slits
- Angled cropped hem, fitted silhouette
- Pinstripe pattern
- Woven fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06204-1639
Category Name: Matching Sets
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Ahead One-Shoulder Tunic Top
You'll always be ahead of the trends in this one-shoulder tunic top perfect for elevating your everyday look! It features a fitted long sleeve, a side ruched adjustable drawstring atop a flirty slit, and a long hem on stretchy rib knit fabric. Style with the matching bottoms.
Shop Matching Bottoms: Always Ahead High Rise Flare Pants
Fit & Features
- One shoulder neckline
- Fitted long sleeve
- Side ruched adjustable drawstring
- Side slit, long hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 06001-4978
Category Name: Matching Sets
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cell Block Cutie Inmate Belted Hot Shorts
Serving “too hot for lockdown” vibes—these costume shorts are a total scene-stealer. The belted low-rise waist and cheeky hem are your ticket to an unforgettable entrance.
Shop Matching Top: Cell Block Cutie Inmate Tie-Front Top
Fit & Features
- Smooth stretch knit fabric
- Low-rise belted waist
- Form-hugging fit
- Cheeky hem
- Runs true to size
Style Number/Barcode: 06503-000101
Category Name: Matching Sets
Price: $12.97 $29.90
On Sale: Yes
Availability: In Stock
Available Color: ORANGE
Available Size: L
Product Badge:- Sale
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Always Ahead High-Rise Flare Pants
You'll always be ahead of the trends in these flare pants perfect for elevating your everyday look! The pants feature a flattering high-rise waist, hip-hugging fit, and flared hem on stretchy rib knit fabric. Style with the matching top.
Shop Matching Top: Always Ahead One-Shoulder Tunic Top
Fit & Features
- High-rise elastic banded waist
- Hip-hugging fit
- Flared hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 06502-2398
Category Name: Matching Sets
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fall Back In Love Cable Knit Topper
Fall back in love with all things cozy and cute! This cable knit topper is essential for shifting into the new season. It features a ribbed mock neckline and long sleeves with ribbed cuffs on soft and stretchy fabric. Complete the look with the matching top.
Shop Matching Top: Fall Back In Love Cable Knit Crop Top
Fit & Features
- Ribbed mock neckline
- Long sleeves, ribbed cuffs
- Cable knit design
- Soft and stretchy fabric
- Runs true to size
Style Number/Barcode: 06005-1729
Category Name: Matching Sets
Price: $3.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall Back In Love Cable Knit Crop Top
Fall back in love with all things cozy and cute! This cable knit crop top is essential for shifting into the new season. It features a scoop neck, tank shoulder straps, and a ribbed hem on soft and stretchy fabric. Complete the look with the matching topper.
Shop Matching Topper: Fall Back In Love Cable Knit Topper
Fit & Features
- Sleeveless scoop neck
- Tank shoulder straps
- Ribbed crop hem
- Cable knit design
- Soft and stretchy fabric
- Runs true to size
Style Number/Barcode: 06005-1730
Category Name: Matching Sets
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale