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.

  • 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: In Stock

    Available Color: BROWN

    Available Size: S, M

    Product Badge:
    • Sale
  • 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