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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.

  • Brushed Ribbed Knit Pajama Leggings

    Keep it basic with cozy pajama leggings to lounge in. The leggings feature high rise waist with drawstring, a skinny leg fit, and composed of a brushed ribbed fabric that offers a relaxed fit with a moderate stretch. Complete look with the matching crop top.

    Shop Matching Crop Top: Brushed Ribbed Knit Pajama Crop Top

    Fit & Features

    • High rise waist
    • Drawstring waist
    • Skinny leg fit
    • Brushed ribbed fabric
    • Relaxed fit
    • Moderate stretch
    • Matching crop top sold separately

    Style Number/Barcode: 07103-0499

    Category Name: Matching Sets

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brushed Ribbed Knit Pajama Crop Top

    Keep it casual in a cozy pajama crop top! The top features a scoop neckline, long sleeves, and a cropped hem. The top is composed of a brushed ribbed fabric that offers a relaxed fit with a moderate stretch. Complete look with the matching leggings. 

    Shop Matching Pajama LeggingsBrushed Ribbed Knit Pajama Leggings

    Fit & Features

    • Scoop neckline
    • Long sleeves
    • Cropped hem
    • Brushed ribbed fabric
    • Relaxed fit
    • Moderate stretch 
    • Matching leggings sold separately 

    Style Number/Barcode: 07103-0498

    Category Name: Matching Sets

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Star Cheerleader Costume Set

    Serving spirit squad glam with a sultry twist—this star cheerleader costume set brings a cropped vest, tie-front top, and belted cheeky shorts together for a look that’s made to hype the crowd. Perfect for Halloween costume parties!

    Fit & Features

    • Smooth knit top with collared V-neckline, tie-front design, long sleeves with tapered hems, and fitted ultra-cropped hem
    • Smooth knit vest with embroidered star patches, fringe trim, and cropped hem
    • Smooth knit hot shorts with low-rise waist, belt loops, and cheeky, form-hugging fit
    • Woven belt with embroidered star patches, buckle, and grommet details
    • Runs true to size
    • Please note the pom-poms and boots are not included

     

    How To Style For Spooky Season:

    Pair with the metallic pom-poms and knee-high cowboy boots for a look that slays.

    Style Number/Barcode: 06503-000068

    Category Name: Matching Sets

    Price: $29.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Chic Sweater Knit Cardigan

    Get a cute and chic everyday look in this sweater knit cardigan! It features long blouson sleeves with tapered hems, a V neckline, a partial button-down front, and a cropped, relaxed fit. Pair this cardigan with the matching crop top and high waist jeans for the perf outfit.

    Shop Matching Top: Cute And Chic Sweater Knit Crop Top

    Fit & Features

    • Long blouson sleeves
    • V neckline
    • Partial button-down front
    • Cropped
    • Relaxed fit
    • Sweater knit fabric

    Style Number/Barcode: 06005-0887

    Category Name: Matching Sets

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Chic Sweater Knit Crop Top

    Get a cute and chic everyday look in this sweater knit crop top! It features a sleeveless bodice, tank-like shoulder straps, a square neck and back, and a cropped, form-hugging fit. Pair this top with the matching cardigan and high waist jeans for the perf outfit.

    Shop Matching Cardigan: Cute And Chic Sweater Knit Cardigan

    Fit & Features

    • Tank-like shoulder straps
    • Square neck and back
    • Cropped
    • Form-fitting style
    • Sweater knit fabric

    Style Number/Barcode: 06005-0886

    Category Name: Matching Sets

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreaming of Luxe Satin Pajama Bralette

    Keep it dreamy in a satin pajama bralette that brings the luxe! The bralette features triangle cups, sleek spaghetti straps, and an elastic band. Complete your look with the matching pajama shorts and fuzzy slippers.

    Shop Matching Bottoms: Dreaming of Luxe Satin Pajama Shorts

    Fit & Features

    • Triangle cups
    • Sleek spaghetti straps 
    • Elastic band
    • Satin-like fabric with minimal stretch
    • Relaxed fit
    • Matching shorts sold separately
    • Runs true to size

    Style Number/Barcode: 07107-0528

    Category Name: Matching Sets

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreaming of Luxe Satin Pajama Shorts

    Keep it dreamy in satin pajama shorts that bring the luxe! The pajama shorts feature an elastic high-rise waist, a cheeky fit, and are composed of a satin-like fabric. Complete your look with the matching bralette and fuzzy slippers.

    Shop Matching Bralette: Dreaming of Luxe Satin Pajama Bralette

    Fit & Features

    • Elastic high-rise waist
    • Cheeky fit
    • Satin-like fabric with minimal stretch
    • Relaxed fit
    • Matching bralette sold separately
    • Runs true to size

    Style Number/Barcode: 07103-0486

    Category Name: Matching Sets

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cherry Charm Tank With Shorts And Scrunchie Set

    Keep it charming in this cute pajama set! It features a cute scoop neck tank that has a cherry graphic design on the bodice. The matching high waist pajama shorts feature cherry graphics adorned with "sweet dreams" in a cute script, a frilly ruffled hem, and a cheeky fit. The pajama set also includes a matching scrunchie to style tresses with. Finish your look with fuzzy slippers for the perfect lounge look. 

    Fit & Features

    • Sleeveless scoop-neck tank with adjustable spaghetti straps
    • Cherry graphic design on the bodice
    • High waist shorts with a cherry graphic
    • "Sweet dreams" written throughout shorts in a script font
    • Frilly ruffled hem, cheeky fit
    • Relaxed fit, moderate stretch 
    • Matching scrunchie

    Style Number/Barcode: 07103-0443

    Category Name: Matching Sets

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rose Darling Ravishing Ruched Mini Skirt

    Let this romantic skirt showcase your affinity for the sweet life! Get dolled up for date night with bae when you style the skirt with the matching smocked top dainty heart charm necklaces and mules. The skirt features a gorge ditsy rose print, a high-rise waist, ruched drawstrings at the side seam, and a mini-length silhouette.

    Shop Matching Top: Rose Darling Ravishing Ruffled Smocked Top

    Fit & Features

    • High rise waist
    • Ruched drawstrings
    • Ditsy floral print
    • Mini length silhouette
    • Form hugging fit
    • Matching top sold separately

    Style Number/Barcode: 06501-0339

    Category Name: Matching Sets

    Price: $14.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rose Darling Ravishing Ruffled Smocked Top

    Let this romantic top showcase your affinity for the sweet life! Get dolled up for date night with bae when you style the top with the matching skirt, dainty heart charm necklaces, and mules. The top features a gorge ditsy floral print, V-neckline, a smocked bodice, short sleeves with a ruffled hem, and a cropped hem. 

    Shop Matching Skirt: Rose Darling Ravishing Ruched Mini Skirt

    Fit & Features

    • V-neckline
    • Short sleeves with ruffled hem
    • Cropped hem
    • Smocked bodice
    • Disty floral print
    • Form hugging fit, moderate stretch 
    • Matching skirt sold separately 

    Style Number/Barcode: 06001-3032

    Category Name: Matching Sets

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart Of Glam High Waist Mini Skirt

    Yes, babe, you have a heart of glam and a chic and sultry style! Showcase your romantic side in this adorable mini skirt. It features a high rise waist and a short, curve-hugging fit. The skirt is composed of a knit fabric with a velvet burnout heart pattern. Pair this skirt with the matching top and layer on a faux leather jacket for date night.

    Shop Matching Top: Heart Of Glam Cowl Neck Crop Top

    Fit & Features

    • High rise waist
    • Mini length silhouette
    • Form-hugging fit
    • Knit fabric
    • Velvet burnout heart pattern

    SHOP ALL HEART OF GLAM COLLECTION

    Style Number/Barcode: 06501-0359

    Category Name: Matching Sets

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart Of Glam Cowl Neck Crop Top

    Yes, babe, you have a heart of glam and a chic and sultry style! Showcase your romantic side in this adorable crop top. It features spaghetti straps, a cowl neckline, a square back, and a cropped, form-hugging fit. The top is composed of a knit fabric with an all-over velvet burnout heart pattern. Pair this top with the matching skirt and layer on a faux leather jacket for date night.

    Shop Matching Bottoms: Heart Of Glam High Waist Mini Skirt

    Fit & Features

    • Spaghetti straps
    • Cowl neckline
    • Square back
    • Cropped
    • Form-fitting style
    • Knit fabric
    • Velvet burnout heart pattern

     

    SHOP ALL HEART OF GLAM COLLECTION

    Style Number/Barcode: 06001-3121

    Category Name: Matching Sets

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back To Basics High Waist Joggers

    Bring it back to basics in high waist joggers that keep it chill! The joggers feature a high rise waist, drawstring, side pockets, and a straight leg fit with elastic tapered hem. Complete look with the matching crop top hoodie and chunky sneakers to nail those casual vibes. 

    Shop Matching Cropped Hoodie: Back To Basics Cropped Drawstring Hoodie

    Fit & Features

    • High rise waist
    • Drawstring
    • Side pockets
    • Straight leg
    • Tapered elastic hem
    • Relaxed fit, moderate stretch 
    • Matching cropped hoodie sold separately 

    Style Number/Barcode: 06502-0492

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spellbinding Beauty Witch Costume Set

    Serve spellbinding vibes in this fierce witch costume set that’s equal parts sultry and iconic. From the curve-hugging fit of the catsuit and bodysuit to the statement accessories, it’s your ticket to casting looks all night long.

    Fit & Features

    • Sheer green mesh catsuit with mock neckline, long fitted sleeves, and form-hugging fit
    • Faux leather sleeveless bodysuit with sweetheart neckline, structured underwire, lace-up front, spaghetti straps, back zipper closure, and a cheeky, form-hugging fit
    • Faux leather short cape with collared neckline and button-front closure
    • Woven witch hat with tall pointed top and wide brim
    • Runs true to size

     

    How To Style For Spooky Season:

    Style with thigh-high boots and you’ll cast a Halloween look that’s bold, bewitching, and totally unforgettable.

    Style Number/Barcode: 06001-000194

    Category Name: Matching Sets

    Price: $24.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Trendsetter Cropped Cardigan

    Showcase your chic trendsetter status when you layer on this cropped cardigan! It features long fitted sleeves, a V-neckline, a button-down front, and a cropped, form-fitting style. Complete your look with the matching crop top, a plaid mini skirt, and chunky sneaks.

    Shop Matching Top: Chic Trendsetter Crop Top

    Fit & Features

    • Long fitted sleeves
    • V-neckline
    • Button-down front
    • Cropped
    • Form-hugging fit
    • Faux angora knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-0916

    Category Name: Matching Sets

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Trendsetter Crop Top

    Showcase your chic trendsetter status in this adorable crop top! It features a sleeveless bodice with spaghetti straps that cross in the back, a V-neckline, and a cropped, form-fitting style. Complete your look with the matching cardigan, a plaid mini skirt, and chunky sneaks.

    Shop Matching Cardigan: Chic Trendsetter Cropped Cardigan

    Fit & Features

    • Spaghetti straps
    • Cross-back design
    • V-neckline
    • Cropped
    • Form-hugging fit
    • Faux angora knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-0915

    Category Name: Matching Sets

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catching Cozy Vibes Cropped Pajama Tank

    Catch cozy vibes, not feelings in this cute pajama tank! The tank features a sleeveless scoop neckline, adjustable spaghetti straps, and a cropped hem. The top is composed of a soft to the touch blended knit fabric that offers a relaxed fit with plenty of stretch. Complete your look with the matching pajama shorts! 

    Shop Matching Shorts: Catching Cozy Vibes Pajama Shorts 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Cropped hem
    • Knit fabric
    • Relaxed fit 
    • Plenty of stretch
    • Matching shorts sold separately 

    Style Number/Barcode: 07103-0489

    Category Name: Matching Sets

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catching Cozy Vibes Pajama Shorts

    Catch cozy vibes, not feelings in these cute pajama shorts. The shorts feature an elastic high rise waist and a cheeky fit. The shorts are composed of a soft to the touch blended knit fabric that offers a relaxed fit with plenty of stretch. Complete your look with the matching pajama tank.

    Shop Matching Tank: Catching Cozy Vibes Cropped Pajama Tank

    Fit & Features

    • Elastic high rise waist
    • Cheeky fit
    • Knit fabric
    • Relaxed fit
    • Plenty of stretch
    • Matching tank sold separately

    Style Number/Barcode: 07103-0490

    Category Name: Matching Sets

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Peachy Pajama Tank With Shorts And Scrunchie Set

    Keep it peachy keen in this cute pajama set! It features a cute scoop neck tank that has the graphic: "Just Peachy" on it in a girly font. The matching high waist pajama shorts feature peach graphics, a frilly ruffled hem, and a cheeky fit. The pajama set also includes a matching scrunchie to style tresses with. Finish your look with fuzzy slippers for the perfect lounge look. 

    Fit & Features

    • Sleeveless scoop neck tank
    • Adjustable spaghetti straps
    • "Just Peachy" graphic in a girly font
    • High waist shorts with peach graphic
    • Frilly ruffled hem, cheeky fit
    • Matching scrunchie

    Style Number/Barcode: 07103-0440

    Category Name: Matching Sets

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bad Babes Club Tank With Shorts And Scrunchie Set

    Go off, baddie! Shows off your style in this pajama set that tells it like it is! It features a cute scoop neck tank that has the graphic: "Bad Babes Club" on it in a retro font. The matching high waist pajama shorts feature mini heart graphics and a cheeky bottom. The pajama set also includes a matching scrunchie to style tresses with. Finish your look with fuzzy slippers for the perfect lounge look.

    Fit & Features

    • Sleeveless scoop-neck tank
    • Adjustable spaghetti straps
    • "Bad Babes Club" graphic in a retro font
    • High waist shorts with a heart graphic
    • Cheeky fit
    • Matching scrunchie

    Style Number/Barcode: 07103-0442

    Category Name: Matching Sets

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pastel Leopard Print Pajama Tank and Shorts Set

    Keep it sweet and fierce in this cute pajama set! The set includes a tank and shorts combination that features a chic leopard print with pastel hues. The tank features a sleeveless scoop neckline, adjustable spaghetti straps, and a cropped hem. The matching shorts feature a mid-rise waist, a cheeky fit, and a ruffled hem. Complete your lounge outfit with fuzzy slippers

    Fit & Features

    • Set includes tank and shorts
    • Pastel hued leopard print
    • Sleeveless scoop neckline, adjustable spaghetti straps
    • Cropped hem
    • Mid-rise waist with ruffled hem
    • Cheeky fit
    • Relax fit, moderate stretch 

    Style Number/Barcode: 07103-0441

    Category Name: Matching Sets

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Comfy And Casual Triangle Bralette

    Get a comfy and casual look, perf for lounging at home, in this adorable bralette! It features a triangle design with adjustable spaghetti straps, a wrap front V neckline, and a banded hem. Pair this bralette with the matching pajama shorts and fuzzy slippers.

    Shop Matching Bottoms: Comfy And Casual Pajama Shorts

    Fit & Features

    • Triangle design
    • Adjustable spaghetti straps
    • Wrap front V neckline
    • Banded hem
    • Soft to the touch brushed knit fabric

    Style Number/Barcode: 07107-0529

    Category Name: Matching Sets

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Comfy And Casual Pajama Shorts

    Get a comfy and casual look, perf for lounging at home, in these adorable pajama shorts! They feature a high rise banded waist with a tulip short design. Pair these shorts with the matching bralette and fuzzy slippers.

    Shop Matching Top: Comfy And Casual Triangle Bralette

    Fit & Features

    • High rise banded waist
    • Tulip short design
    • Soft to the touch brushed knit fabric 

    Style Number/Barcode: 07103-0488

    Category Name: Matching Sets

    Price: $9.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • FavEx Delivery Driver Costume Set

    Signed, sealed, and delivered—you’re the hottest drop of the night. This FavEX top, shorts, and accessories Halloween costume set brings a playful twist that’s cheeky, confident, and party-perfect.

    Fit & Features

    • Knit top with collared V-neckline, short sleeves, color-blocked shoulders, "FavEx" embroidered script, and a fitted, ultra-cropped hem
    • Knit shorts with a high-rise elasticized waist, belt loops, color-blocked sides, and a cheeky, form-hugging fit
    • Knit belt with front buckle and grommet detail, buttoned side pouch with belt loops
    • Faux leather fingerless gloves with adjustable strap
    • Baseball cap with "FavEx" embroidered script and adjustable back strap
    • Sheer nylon thigh-high stockings
    • Runs true to size

    Style Number/Barcode: 06001-000192

    Category Name: Matching Sets

    Price: $24.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: L/XL

    Product Badge:
    • Halloween Badge