Matching Sets
Two-piece sets are the ultimate answer to “what am I wearing?” Shop casual to dressy coordinating pieces made for effortless dressing, from a crop top and midi skirt to a dressy top and mini skirt or a long sleeve top and maxi. Printed mesh and lace bring the going-out energy, while boucle, sweater knits, and denim sets keep daytime looks polished. Choose black, brown, or burgundy for a fall-ready finish that moves easily from weekend brunch to night out plans, concerts and festivals. Matching never looked this low-effort.
Now Trending
Matching Sets That Serve Style in Every Scene
From rooftop dinners to weekend getaways, Windsor’s matching sets deliver effortless coordination and standout style. Whether you're dressing for a night out, a vacation, or a casual day, these sets make getting ready feel easy and elevated.
Everyday Ease & Polished Pairings
Slip into two-piece skirt sets or wide-leg pant sets with matching crop tops for a clean, polished look. Lightweight knits, breathable fabrics, and smooth satins keep things comfortable while still feeling styled. Pair with sandals or heels and layered jewelry for an effortless finish.
Night-Out Energy & Elevated Looks
Turn up the look with sleek two-piece matching sets featuring curve-hugging fits, halter necklines, and tie-front details. Satin finishes and bold silhouettes bring the statement—just add strappy heels and a mini bag for your next night out.
Mix, Match & Layer
Wear the full set or style each piece your way. Pair your top with jeans or tailored shorts, or switch in a bodysuit with your skirt. Add a lightweight jacket or blazer for an extra layer that keeps your look refined.
Explore Windsor’s full collection of matching sets online, in-app, or in-store to refresh your wardrobe with easy, on-trend outfits.
What Are Matching Sets?
Matching sets are coordinated outfits made up of two or more pieces, like a crop top and skirt or a blouse and pants. Designed to be worn together, they create a complete, styled look with minimal effort. Windsor’s sets range from casual lounge styles to elevated options for nights out and special plans.
Are Matching Sets a Trend?
Yes, matching sets are a go-to style that stays on trend. They offer a simple way to look put-together while still feeling comfortable. Whether you're dressing up or keeping it casual, these sets make styling quick and easy.
What Do You Call a Two-Piece Outfit?
A two-piece outfit is often called a matching set or co-ord. These pieces are designed to be worn together, but they can also be mixed and matched with other items to create fresh, versatile looks.
-
Like It Or Dot High Rise Shorts
Like it or not, these polka dot shorts will surely be your fav! It features a high-rise waist and a flowy silhouette. The shorts are composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete the look in the matching top.
Shop Matching Top: Like It Or Dot Puff Sleeve Crop Top
Fit & Features
- High-rise waist
- Flowy silhouette
- Polka dot pattern
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06503-0961
Category Name: Matching Sets
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Darling Ditsy Floral Tie-Front Top
Keep your everyday look darling and sweet with this adorable top! It features short flutter cap sleeves, a V-neckline with a tie-front design, a cropped fit, and an all-over ditsy floral print. Style with the matching mini skirt and espadrille wedges.
Shop Matching Bottoms: Darling Ditsy Floral Mini Skirt
Fit & Features
- Short flutter cap sleeves
- V-neckline
- Tie-front
- Cropped
- Ditsy floral print
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06202-0272
Category Name: Matching Sets
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Darling Ditsy Floral Mini Skirt
Keep your everyday look darling and sweet with this adorable skirt! It features a high-rise waist, ruched detailing leading to a front slit, a short, curve-hugging fit, and an all-over ditsy floral print. Style with the matching crop top and espadrille wedges.
Shop Matching Top: Darling Ditsy Floral Tie-Front Top
Fit & Features
- High-rise waist
- Ruching
- Front slit
- Mini-length, form-fitting silhouette
- Ditsy floral print
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06501-0567
Category Name: Matching Sets
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Trendy Pleated And Striped Shorts
Keep it trendy with shorts that are all the rage! The shorts feature a trendy striped pattern, a high-rise waist, and a cheeky bottom. Complete the look with the matching tube top.
Shop Matching Top: Trendy Pleated And Striped Tube Top
Fit & Features
- High-rise waist
- Striped pattern
- Cheeky bottom
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06503-0477
Category Name: Matching Sets
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
All Night Wrap Maxi Skirt
Look sexy in this maxi skirt for your next all-nighter! It features a high-rise waist, wrap-twist front, and sultry slit. Composed of sleek knit fabric with a moderate stretch. Style with the matching top.
Shop The Matching Top: All Night Plunge Halter Top
Fit & Features
- High-rise waist
- Wrap twist
- Front slit
- Maxi length hem
- Sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0587
Category Name: Matching Sets
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Off To Paradise Wide-Leg Abstract Pants
A trending abstract pants designed with a flattering high-rise waist and a wide-leg design that flaunts your figure on vacay! Pair with the matching top to complete the look.
Fit & Features
- Abstract print, stretchy knit fabric
- High-rise waist
- Wide-leg silhouette
- Runs true to size
Shop The Matching Top: Off To Paradise Tie-Front Crop Top
Style Number/Barcode: 06502-000010
Category Name: Matching Sets
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
All Night Plunge Halter Top
Look sexy in this halter top for your next all-nighter! It features a halter plunge neckline with dual button closure and an ultra-cropped hem. Composed of sleek knit fabric with a moderate stretch. Style with the matching bottoms.
Shop The Matching Skirt: All Night Wrap Maxi Skirt
Fit & Features
- Halter plunge neckline
- Dual button closure
- Ultra cropped hem
- Sleek knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06001-3970
Category Name: Matching Sets
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Cabana High-Rise Wide Leg Pants
These wide-leg pants are made for the cabana life! It features a high-rise elasticized waist, a wide-leg silhouette, and a pull-on/off styling. Composed of hacci smooth knit fabric with a moderate stretch. Style with the matching top.
Shop Matching Top: Cabana Long Sleeve O-Ring Crop Top
Fit & Features
- High-rise elasticized waistband
- Wide leg silhouette
- Pull-on/off styling
- Hacci smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0840
Category Name: Matching Sets
Price: $26.90
Availability: Out of Stock
Product Badge:- Clearance
-
Cabana Long Sleeve O-Ring Crop Top
A crop top like this was made for the cabana life! It features long peasant sleeves, a collared plunge V-neck with an eye-catching o-ring center, and an open-back with tie-back closure. Composed of hacci smooth knit fabric with a moderate stretch. Style with the matching bottoms.
Shop Matching Bottoms: Cabana High-Rise Wide Leg Pants
Fit & Features
- Long peasant sleeves, elasticized hems
- Collared plunge V-neck
- O-ring center
- Cropped hem
- Open-back, tie closure
- Hacci smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4086
Category Name: Matching Sets
Price: $29.90
Availability: Out of Stock
Product Badge:- Sale
-
Seal The Deal Mini Skirt
Stun in a mini skirt that will have you business ready to take on the day! The skirt features a high-rise waist, a mini-length hem, and a back zipper closure. Complete your boss babe look with the matching blazer and mules.
Shop Matching Blazer: Seal The Deal Blazer
Fit & Features
- High-rise waist
- Mini length hem
- Back zipper closure
- Lined woven fabric
- Form-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06401-0429
Category Name: Matching Sets
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Seal The Deal Blazer
Stun in a blazer that will have you business ready to take on the day! The blazer features a collared neckline, lightly padded shoulders, a multi-button down front, a faux chest pocket, long sleeves, front pockets, and a mid-length hem. The blazer is composed of a lined woven fabric that offers a relaxed fit with minimal stretch. Complete look with the matching mini skirt and mules.
Shop Matching Mini Skirt: Seal The Deal Mini Skirt
Fit & Features
- Collared neckline
- Lightly padded shoulders
- Multi-button down front
- Faux chest pocket
- Long sleeves
- Front pockets
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1319
Category Name: Matching Sets
Price: $15.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Casual Trendsetter Fleece Shorts
Keep it cute and casual in these trendy fleece shorts that will step up your loungewear! They feature a high-rise elasticized waist, side pockets, and a relaxed fit. The shorts are composed of a cozy knit fabric with a soft fleece lining and offer a moderate stretch. Complete the look with the matching cropped hoodie.
Shop Matching Hoodie: Basic Cropped Fleece Hoodie
Fit & Features
- High-rise elasticized waist
- Side pockets
- Relaxed fit
- Knit fabric, fleece lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0959
Category Name: Matching Sets
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
See Ya Later Snake Twist Midi Skirt
Tell em' boy bye! You'll be looking so fab in this snake midi skirt featuring a high-rise waist, bodycon silhouette, and a twist front accent on brushed, stretchy knit fabric. Complete the look in the matching top.
Shop Matching Top: See Ya Later Snake Twist Crop Top
Fit & Features
- High-rise waist
- Bodycon silhouette
- Twist front accent
- Midi-length hem
- Stretchy brushed knit fabric
- Runs true to size
Style Number/Barcode: 06501-0627
Category Name: Matching Sets
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
See Ya Later Snake Twist Crop Top
Tell em' boy bye! You'll be looking so fab in this snake crop top featuring long sleeves, a plunge v-neck, and a twisted bodice on brushed, stretchy knit fabric. Complete the look in sultry faux leather pants and heels.
Shop Matching Skirt: See Ya Later Snake Twist Midi Skirt
Fit & Features
- Long sleeves
- Plunge v-neckline
- Twisted bodice
- Cropped hem
- Stretchy brushed knit fabric
- Runs true to size
Style Number/Barcode: 06001-4071
Category Name: Matching Sets
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
That Preppy Vibe Houndstooth Blazer
Haven't you heard? That preppy vibe is so trendy this season! Create a cute look in this houndstooth plaid blazer featuring long sleeves, a collared neckline, an open-front with dual button closure, and flap pockets. Complete the look in the matching shorts.
Shop Matching Shorts: That Preppy Vibe Houndstooth Shorts
Fit & Features
- Long sleeves
- Collared neckline
- Open-front, dual button closure
- Flap pockets
- Cropped hem
- Houndstooth plaid pattern
- Woven-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1316
Category Name: Matching Sets
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Off To Paradise Tie-Front Crop Top
A trending abstract crop top designed with flowy short sleeves and a tie-front design that flaunts your figure on vacay! Pair with the matching pants.
Fit & Features
- Abstract print, stretchy knit fabric
- Short sleeves
- V-neckline
- Tie-front design
- Cropped hem
- Runs true to size
Shop The Matching Pants: Off To Paradise Wide-Leg Abstract Pants
Style Number/Barcode: 06202-000002
Category Name: Matching Sets
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
That Preppy Vibe Houndstooth Shorts
Haven't you heard? That preppy vibe is so trendy this season! Create a cute look in this houndstooth plaid blazer featuring long sleeves, a collared neckline, an open-front with dual button closure, and flap pockets. Complete the look in the matching shorts.
Shop Matching Blazer: That Preppy Vibe Houndstooth Blazer
Fit & Features
- High-rise waist
- Front button closure, belt loop accents
- Pleat detailing
- Form-fitting silhouette
- Houndstooth plaid pattern
- Woven-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06403-0221
Category Name: Matching Sets
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
So Sassy Snake Print Wide-Leg Pants
Give off major sassy vibes in these snake print pants! They feature a high-rise elasticized waist, a form-hugging fit throughout the leg, and a wide-leg hem. The lightweight snake-printed knit fabric features all-over lurex thread detailing for a cool metallic look. Style these pants with chic sunglasses.
Shop Matching Top: So Sassy Snake Print Cropped Tank
Fit & Features
- High-rise elasticized waist
- Form-hugging fit throughout the leg
- Wide-leg hem
- Snake print
- Lurex knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0798
Category Name: Matching Sets
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
So Sassy Snake Print Cropped Tank
Give off major sassy vibes in this trendy snake print cropped tank! It features a sleeveless V-neckline with a halter strap, a sultry lace-up front, and a cropped, form-hugging fit. The lightweight snake-printed knit fabric features all-over lurex thread detailing for a cool metallic look. Style this tank with chic sunglasses.
Shop Matching Bottoms: So Sassy Snake Print Wide-Leg Pants
Fit & Features
- Sleeveless V-neckline
- Halter strap
- Lace-up front, tie closure
- Cropped, form-hugging fit
- Snake print
- Lurex knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4016
Category Name: Matching Sets
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Forever Cozy Chenille Pajama Shorts
Snuggle up in these adorable and cozy chenille pajama shorts! They feature a high-rise elasticized waist with ribbed detailing, a form-hugging fit, and are composed of a super soft chenille fabric. Pair with the matching pajama tank.
Shop Matching Top: Forever Cozy Chenille Pajama Tank
Fit & Features
- High-rise elasticized waist, ribbed detailing
- Form-hugging fit
- Chenille knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0755
Category Name: Matching Sets
Price: $8.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Forever Cozy Chenille Pajama Tank
Snuggle up in this adorable and cozy chenille pajama tank! It features a sleeveless V-neckline, thin shoulder straps, a cropped, ribbed hem, and is composed of a super soft chenille fabric. Pair with the matching pajama shorts.
Shop Matching Bottoms: Forever Cozy Chenille Pajama Shorts
Fit & Features
- Sleeveless V-neckline
- Thin shoulder straps
- Cropped, ribbed hem
- Form-hugging fit
- Chenille knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0761
Category Name: Matching Sets
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bohemian Flair Halter Crop Top
Bring the bohemian flair to your festival 'fit with this trendy halter top. It features a sleeveless plunging V-neckline, halter straps, dual tie-front details, a cropped form-hugging fit, and an all-over bohemian-inspired print. Style with the matching flare pants.
Shop Matching Bottoms: Bohemian Flair Printed Pants
Fit & Features
- Sleeveless deep V-neckline
- Halter straps
- Double tie-front design
- Cropped fit
- Bohemian-inspired print
- Brushed knit fabric
- Runs true to size
Style Number/Barcode: 06001-3895
Category Name: Matching Sets
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Bohemian Flair Printed Pants
Bring the bohemian flair to your festival 'fit with these trendy pants. They feature a high-rise waist, a form-hugging fit throughout the leg, a fab flared hem, and an all-over bohemian-inspired print. Style with the matching crop top.
Shop Matching Top: Bohemian Flair Halter Crop Top
Fit & Features
- High-rise waist
- Fitted silhouette throughout the leg, flared hem
- Bohemian-inspired print
- Brushed knit fabric
- Runs true to size
Style Number/Barcode: 06502-0747
Category Name: Matching Sets
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Tropical Getaway Mesh Crop Top
Escape to a tropical paradise with a cute crop top that brings those island vibes. The top features a sleeveless square neckline, bungee spaghetti straps, a tropical palm leaf print, and a cropped hem. The top is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching mini skirt.
Shop Matching Skirt: Tropical Getaway Mesh Mini Skirt
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Cropped hem
- Palm leaf print
- Lined mesh fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3751
Category Name: Matching Sets
Price: $5.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale