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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.

  • Sweet Flirt High Waist Ditsy Floral Ruched Mini Skirt

    Sweet and flirty, this floral ruched mini skirt will capture the soft girl trend! The lightweight knit fabric is detailed with an adorable ditsy floral print for the cutest vibes. The skirt features a high-rise elasticized waist, a ruched seam with an adjustable drawstring for a customized fit, a short front slit, and a bodycon silhouette. Style with the matching tie-front top for a day date!

    Shop Matching Top: Sweet Flirt Flutter-Sleeve Ditsy Floral Tie-Front Top

    Fit & Features

    • Ditsy floral printed knit fabric, moderate stretch
    • High-rise elasticized waist
    • Ruched seam with adjustable drawstring
    • Short slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1005

    Category Name: Matching Sets

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance For Two High Rise Slit Maxi Skirt

    You'll be sure to fall in love with this flowy maxi skirt for a dreamy summer wardrobe! With its elasticized high-rise waist, flowy tiered silhouette, and front slit, you'll feel effortlessly elegant. Complete the look with the matching top.

    Shop Matching Top: Romance For Two Sleeveless Crop Top

    Fit & Features

    • Gauze woven fabric, short woven lining
    • High-rise elasticized waist
    • Front slit
    • Flowy tiered silhouette
    • Runs true to size

    Style Number/Barcode: 06301-0189

    Category Name: Matching Sets

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Duo High-Rise Buckle Pleated Denim Mini Skirt

    The flirtiest duo around town includes you and this denim mini skirt!  Featuring a high-rise waist with buckle detailing, an a-line silhouette, and a side slit, while the pleated mini-length hem adds a touch of playfulness. Complete the look with the matching top.

    Shop Matching Top: Flirty Duo Strapless Sweetheart Denim Crop Top

    Fit & Features

    • Medium wash denim fabric, no stretch
    • High-rise waist with buckle detailing
    • Back zipper closure
    • A-Line silhouette
    • Side slit
    • Pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 06601-0205

    Category Name: Matching Sets

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Moves Snake Print Wide-Leg Jeans

    Laidback fit, untamed edge. These snake print wide leg jeans bring a bold twist to your denim rotation, perfect for pairing with crop tops, corsets, or oversized knits when you’re in the mood to stand out.

    Fit & Features

    • Snake print, denim cotton fabric
    • Mid-rise waist
    • Wide-leg silhouette
    • Front button and hidden zipper closure, belt loop accents
    • Front and back pockets
    • Runs true to size

    Style Number/Barcode: 06602-000074

    Category Name: Matching Sets

    Price: $54.90

    Availability: In Stock

    Available Color: SNAKE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Floral Sensation High Waist Pants

    Keep it sensational in floral pants this season! The pants feature a high-rise waist, a ditsy floral print, and a wide leg hem. Complete look with the matching crop top.

    Shop Matching Crop Top: Floral Sensation Off The Shoulder Top

    Fit & Features

    • High rise waist
    • Wide leg hem
    • Ditsy floral print
    • Form hugging fit
    • Runs true to size 

    Style Number/Barcode: 06502-0608

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Good V-Waist Smocked Flare Pants

    Looking good will be effortless in these flare pants perfect for vacation or a hot night out! Made of smocked stretchy knit fabric, these pants offer comfort and a flattering silhouette. The cinched mid-rise V-waist and hip-hugging fit will accentuate your curves, while the flared hem adds a touch of flare to your outfit. Complete the look with the matching top.

    Shop Matching Top: Looking Good Sweetheart Tie Front Crop Top

    Fit & Features

    • Stretchy smocked knit fabric
    • Mid-rise V-waist with cinch
    • Hip-hugging fit
    • Flare hem
    • Runs true to size

    Style Number/Barcode: 06502-2495

    Category Name: Matching Sets

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Retreat Sweetheart Tropical Crop Top

    Getaway in this tropical crop top for the sweetest vacay vibe! This crop top features wide shoulder straps, a sweetheart neckline for a flattering look, padded bra cups for support, and a stretchy smocked back and cropped hem to flaunt your figure. Complete the look with the matching bottoms.

    Shop The Matching Bottoms: Getaway Retreat High Rise Tropical Pants

    Fit & Features

    • Tropical print, woven fabric, sewn-in lining
    • Wide shoulder straps
    • Sweetheart neckline
    • Padded bra cups
    • Stretchy smocked back
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2504

    Category Name: Matching Sets

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Chic Blazer With Linen

    You'll be looking chic for the season in this lightweight linen-blend blazer with a cinched long-sleeve design. Style with the matching trouser shorts for an elevated weekend vibe!

    Shop Matching Bottoms: Looking Chic Belted Trouser Shorts With Linen

    Fit & Features

    • Linen-blend woven fabric, smooth woven lining, no stretch
    • Lapel collar
    • Three-quarter-length sleeves, cinched design
    • Dual front faux pockets
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-2123

    Category Name: Matching Sets

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming And Chic Snake Print Crop Top

    Shake up your warm-weather wardrobe with this charming and chic snake print crop top! It features short flutter sleeves, a sweetheart neckline with a tie front closure, and a cropped, form-hugging fit. The lightweight brushed knit fabric offers plenty of stretch. Pair this top with the matching pants and some chic new accessories.

    Shop Matching Bottoms: Charming And Chic Snake Print Flared Pants

    Fit & Features

    • Short flutter sleeves
    • Sweetheart neckline
    • Tie front closure
    • Cropped, form-fitting style
    • Brushed knit fabric with plenty of stretch
    • Snake print
    • Runs true to size

    Style Number/Barcode: 06001-3076

    Category Name: Matching Sets

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Good Sweetheart Tie Front Crop Top

    Looking good will be effortless in this crop top perfect for vacation or a hot night out! Made of smocked stretchy knit fabric, this top offers comfort and a flattering silhouette. The sweetheart neckline and cropped hem will flatter your figure, while the tie-front adds a touch of flare to your outfit. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Looking Good V-Waist Smocked Flare Pants

    Fit & Features

    • Stretchy smocked knit fabric
    • Spaghetti straps
    • Sweetheart neckline
    • Tie-front 
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5225

    Category Name: Matching Sets

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Two Cute High Rise Floral Mini Skirt

    Look darling in this floral mini skirt all summer long! The ultra-stretchy brushed knit fabric showcases an adorable dainty floral print for the prettiest vibe. The high-rise waist and bodycon fit add a touch of femininity, while the ruched side seams and mini-length hem flaunt your figure. Complete the look with the matching top.

    Shop Matching Top: Two Cute Lace-Up Floral Crop Top

    Fit & Features

    • Floral print
    • Stretchy brushed knit fabric
    • High-rise waist
    • Ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1032

    Category Name: Matching Sets

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fierce And Flirty Snake Print Halter Top

    This snake print crop top shows off a halter neckline and zip-up front that make it the ultimate going-out piece—perfect for pairing with matching bottoms or styling solo for that wild-card edge.

    Fit & Features

    • Snake print, denim cotton fabric
    • Plunge halter neckline
    • Zip-up front closure
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000189

    Category Name: Matching Sets

    Price: $36.90

    Availability: In Stock

    Available Color: SNAKE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Classically Chic Brushed Knit Duster

    Keep it classically chic with a duster that is part comfy and part chic. The duster features an open draped front, long sleeves, and a flowy long length. The duster is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching jumpsuit. 

    Shop Matching Jumpsuit: Classically Chic Brushed Knit Jumpsuit

    Fit & Features

    • Draped open front
    • Long sleeves
    • Long length 
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06202-0210

    Category Name: Matching Sets

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Me Pretty Satin Abstract Wide-Leg Pants

    Color you pretty in these satin pants to brighten up this new season! They feature a flattering high-rise waist, an elasticized back band, front pleating, and a wide-leg silhouette on smooth satin with an abstract print. Complete the look with the matching top for a vacation!

    Shop Matching Top: Color Me Pretty Satin Abstract Crop Top

    Fit & Features

    • High-rise waist, elasticized back band
    • Front pleating
    • Wide-leg silhouette
    • Abstract print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1371

    Category Name: Matching Sets

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Vibes Denim Halter Top

    Perfect for any occasion, this denim halter top will look so chic paired with jeans! The plunging V-neck is accented with a buckle strap under the bust, leading to a front flyaway design. Pair with the matching jeans.

    Shop Matching Bottoms: Fresh Vibes Mid-Rise Wide Leg Denim Jeans

    Fit & Features

    • Denim fabric
    • Sleeveless plunging halter V-neckline
    • Buckle strap under the bust
    • Partially open back, lower smocked back
    • Front flyaway design
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06003-2754

    Category Name: Matching Sets

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made For The Glamour Sequin Blazer

    This gorgeously glam sequin blazer is a major must-have for a girl's night out! It features a lapel collar, long sleeves, a button-front closure, dual front pockets, a relaxed silhouette, and all-over sequin embroidery for a stunning shine. Style with the matching shorts and platform heels.

    Shop Matching Bottoms: Made For The Glamour Sequin Shorts

    Fit & Features

    • Lapel collar, long sleeves, shoulder pads
    • Button-front closure, dual front pockets
    • Relaxed silhouette
    • All-over sequin embroidery
    • Mesh fabric, sewn-in woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1625

    Category Name: Matching Sets

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Allure Chiffon Palazzo Pants

    Radiate your gorgeous allure in these chic chiffon palazzo pants! Designed with an airy sheer chiffon fabric with a lightweight woven lining for coverage, these pants are perfect for the summer season. They feature a high-rise fit with a stretchy elastic waistband and a relaxed wide-leg silhouette for style and comfort. Complete the look with the matching bra top!

    Shop Matching Top: Gorgeous Allure Ruched Chiffon Bra Top

    Fit & Features

    • Sheer chiffon fabric, woven lining, no stretch
    • High waist, elastic waistband
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06402-1413

    Category Name: Matching Sets

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Fun High Rise Striped Knit Midi Skirt

    Give your vacay style a dynamic upgrade in this flirty knit midi skirt perfect for a getaway or weekend fun! The skirt boasts a high-rise waist, a bodycon fit, a center back slit for movement, and a midi-length hem on pointelle knit fabric showcasing a trendy striped pattern. Complete the look with the matching top.

    Shop Matching Top: Flirty Fun V-Neck Tie Striped Knit Crop Top

    Fit & Features

    • Pointelle knit fabric, striped pattern
    • High-rise waist
    • Center back slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1013

    Category Name: Matching Sets

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Duo Strapless Sweetheart Denim Crop Top

    The flirtiest duo around town includes you and this denim crop top! Featuring a strapless sweetheart neckline with a mini rosette detail, a fitted silhouette, and a cropped hem that adds a touch of playfulness. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Flirty Duo High-Rise Buckle Pleated Denim Mini Skirt

    Fit & Features

    • Medium wash denim fabric, no stretch
    • Strapless sweetheart neckline with mini rosette detail
    • Back zipper closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2456

    Category Name: Matching Sets

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Studded and Snatched Straight Leg Denim Jeans

    Western goes rockstar in these denim jeans. The mid-rise waist and studded trim bring all the attitude—pair it with the matching denim top for max impact.  

    Shop The Matching Top: Studded and Snatched Denim Crop Top

    Fit & Features

    • Denim fabric, vintage-inspired color fading, slight stretch
    • Mid-rise waist
    • Studded side trim
    • Straight-leg silhouette
    • Front button closure, pockets, belt loop accents
    • Runs true to size

    Style Number/Barcode: 06602-000046

    Category Name: Matching Sets

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Gorgeous Allure Ruched Chiffon Bra Top

    Radiate your gorgeous allure in this sultry ruched chiffon bra top! Designed with an airy sheer chiffon fabric with a front knit lining for coverage, this bra top is perfect for looking sunkissed this season. It features a sleeveless subtle sweetheart neckline, ruching at the bust with padding for support, and adjustable spaghetti straps for a customized fit. The smocked back design offers added stretch, while the ultra-cropped fitted hem creates a snatched silhouette. Complete the look with the matching palazzo pants!

    Shop Matching Bottoms: Gorgeous Allure Chiffon Palazzo Pants

    Fit & Features

    • Sheer chiffon fabric, front knit lining
    • Sweetheart neckline
    • Ruched bust, padding
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Ultra-cropped hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2537

    Category Name: Matching Sets

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Vacay Spaghetti Strap Tie-Back Crop Top

    The perfect tropical floral crop top to look stylish on your vacay! With its sleeveless V-cut neckline with ruching at the bust, spaghetti straps, and a tie-back design, this top offers a trendy silhouette. The fitted ultra-cropped hem and eye-catching tropical floral print add a touch of boldness to your look. Pair with the matching midi skirt and espadrille wedges! 

    Shop Matching Bottoms: Tropical Vacay High-Rise Slit Midi Skirt

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric
    • V-wired neckline, ruched bust
    • Spaghetti straps
    • Tie-back design
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5221

    Category Name: Matching Sets

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Livin' High Rise Palazzo Crochet Pants

    These crochet palazzo pants were meant for living under the sun! Whether you're heading to a festival or a getaway, these pants will keep you boho-cute. They feature an elasticized high-rise waist and a flattering relaxed silhouette. Complete the look with the matching top.

    Shop Matching Top: Sunshine Livin' Halter Crochet Crop Top

    Fit & Features

    • Crochet fabric lined with stretchy knit
    • High-rise elasticized waist
    • Relaxed silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0823

    Category Name: Matching Sets

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Arrival Floral Trim Knit Mini Skirt

    Bring the flirtatious vibes when you arrive at the party in this sweet floral trim mini skirt! The stretchy knit fabric showcases a stunning sheen to catch everyone's eye. The skirt is shaped with a high-rise elasticized waist for added strap, a ruched seam with a dainty floral embroidered applique trim, and a short front slit. The bodycon fit on the mini-length silhouette will create a snatched look. Complete your fab look with the matching crop top!

    Shop Matching Top: Flirty Arrival Floral Trim Knit Crop Top

    Fit & Features

    • Stretchy knit fabric with sheen
    • High-rise elasticized waist
    • Ruched seam, floral embroidered applique trim
    • Short front slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1027

    Category Name: Matching Sets

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale