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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.

  • Chill Mood Ribbed Knit Crop Top

    Keep it chill and relax in this comfy ribbed knit crop top. It features a sleeveless crew neckline, tank shoulder straps, a cropped hem with a lettuce-edge trim, and a form-hugging fit. The ribbed knit fabric features a cool mineral wash design. Style with the matching flare-leg pants.

    Shop Matching Bottoms: Chill Mood Ribbed Knit Flare-Leg Pants

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Cropped hem, lettuce-edge trim
    • Form-hugging fit
    • Ribbed knit fabric, mineral wash design
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 07103-0905

    Category Name: Matching Sets

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Sensation Strapless Crop Bustier

    Everyone will adore your look in this floral mesh bustier perfect for vacay or weekend plans! This top is made from a mesh lined fabric boasting a fun and flirty floral print. With a strapless neckline, it accentuates your figure while the fitted crop hem flatters your curves. Complete the look with the matching maxi skirt.

    Shop Matching Bottoms: Floral Sensation High Rise Maxi Skirt

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Fitted crop hem
    • Back zipper and hook-eye closure
    • Runs true to size

    Style Number/Barcode: 06001-5288

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Match Chevron Knit Tube Top

    Trend right with this chevron knit tube top for weekend fun or vacation! Pair with the matching skirt to complete the look.

    Fit & Features

    • Chevron pattern, stretchy knit lined fabric
    • Strapless neckline
    • Fitted crop hem
    • Runs true to size

    Shop The Matching Skirt: Trendy Match Chevron Knit Midi Skirt

    Style Number/Barcode: 06005-2254

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Allure High-Slit Midi Skirt

    Effortlessly chic with a sultry twist. This high-slit midi skirt hugs in all the right places with a sleek, stretchy fit made for nights that call for a little extra allure.

    Shop Matching Top: Chic Allure Cowl Neck Crop Top

    Fit & Features

    • Smooth knit fabric, high stretch
    • High-rise waist
    • Front ruching
    • Asymmetric high-cut side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000074

    Category Name: Matching Sets

    Price: $29.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sensational Match Bodycon Midi Skirt

    Make a sensational impression in this bodycon midi skirt on vacay or brunch! Pair with the matching top to complete the cute look.

    Shop Matching Top: Sensational Match Tie-Front Ruffle Crop Top

    Fit & Features

    • Smooth stretchy double-lined knit fabric
    • High-rise waist
    • Side ruched seams
    • Center back slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000021

    Category Name: Matching Sets

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All That Shines Rhinestone Fishnet Maxi Skirt

    Fit & Features

    • Partially lined fishnet fabrication
    • High-rise waist
    • Rhinestone and gemstone accents
    • Mini skirt-length knit lining
    • Sheer maxi length hem
    • Runs true to size


    Shop Matching Top: All That Shines Rhinestone Crop Top

    Style Number/Barcode: 06501-1097

    Category Name: Matching Sets

    Price: $89.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Looking Chic Belted Trouser Shorts With Linen

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

    Shop Matching Blazer: Looking Chic Blazer With Linen

    Fit & Features

    • Linen-blend woven fabric, smooth woven lining, no stretch
    • High-rise waist, belted design
    • Dual front pockets
    • Pleating
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06303-0299

    Category Name: Matching Sets

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Babe Eyelet Lace Blazer

    Elevate your weekend looks with this chic eyelet lace blazer with a double-breasted design and relaxed fit. Style with the matching shorts and your fave heels.

    Shop Matching Bottoms: Chic Babe Eyelet Lace Shorts

    Fit & Features

    • Floral eyelet lace fabric, woven lining, no stretch
    • Lapel collar
    • Long sleeves
    • Double-breasted design
    • Dual front pockets, back slit
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-000001

    Category Name: Matching Sets

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Maldives Please Tropical Mesh Mini Skirt

    Pack your bags with this stunning tropical mesh mini skirt on your way to the Maldives! Enjoy fun in the sun in this sultry mini skirt featuring a high-rise waist, flattering ruching, and a bodycon silhouette. Style with the matching top and duster to complete the look!

    Shop Matching Top And Duster: Maldives Please Tropical Mesh Bustier, Maldives Please Tropical Mesh Duster

    Fit & Features

    • High-rise elastic banded waist
    • Dual front vertical seams, ruched detailing
    • Back zipper, hook and eye closure
    • Bodycon silhouette
    • Tropical print
    • Sheer lightweight mesh fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0933

    Category Name: Matching Sets

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Purrfectly On Trend Leopard Mini Skort

    You'll be purrfectly on trend in this leopard-printed mini skort with a short overlay hiding fitted shorts. Style with the matching tie-front vest for a chic vibe.

    Shop Matching Top: Purrfectly On Trend Leopard Tie-Front Vest

    Fit & Features

    • Leopard-printed woven fabric
    • Mid-rise waist
    • Side zipper closure
    • Mini-length overlay
    • Fitted shorts
    • Runs true to size

    Style Number/Barcode: 06303-0298

    Category Name: Matching Sets

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Sophistication Satin Trouser Shorts

    Show off a major sleek and sophisticated style in these woven satin trouser shorts. They feature a high-rise waist, a back zipper closure, and a chic, fitted silhouette. The smooth satin fabric will give your 'fit that luxe look. Pair with the matching blazer and platform heels.

    Shop Matching Blazer: Sleek Sophistication Satin Blazer

    Fit & Features

    • High-rise waist
    • Hidden back zipper closure
    • Fitted silhouette
    • Woven satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0293

    Category Name: Matching Sets

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Duo Strapless Skater Mini Dress

    A charming strapless skater dress you'll adore for brunch or family gatherings! Pair with the matching bolero for a complete look.

    Fit & Features

    • Soft rib knit stretchy fabric
    • Strapless neckline, non-slip grip lining
    • Skater silhouette
    • Flair mini-length hem
    • Runs true to size

     

    Shop The Matching Bolero: Charming Duo Long Sleeve Bolero

    Style Number/Barcode: 06005-2235

    Category Name: Matching Sets

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romance In Bloom Floral Tie-Front Top

    A top that’s equal parts sweet and sultry. With a tie-front and ruffle trim, this floral top is your go-to for brunch, concerts, or just serving soft-girl vibes all season.

    Shop Matching Bottoms: Romance In Bloom Floral Ruffle Skort

    Fit & Features

    • Floral print lace-lined fabric
    • Cap sleeves
    • Open front design with tie closure
    • Ruffled trim
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000051

    Category Name: Matching Sets

    Price: $29.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Special Moment Floral Glitter Dot Corset Top

    Your spotlight will shine in this floral corset top with sparkly glitter dots that'll glisten under the sun! Pair with the matching skirt.

    Fit & Features

    • Floral print, glitter dot, mesh-lined fabric
    • Sweetheart neckline, ruffle trim, padded bra cups
    • Adjustable spaghetti straps, lace trim
    • Lace trim fitted bodice
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Skirt: Special Moment Floral Glitter Dot Mini Skirt

    Style Number/Barcode: 06003-2734

    Category Name: Matching Sets

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Color Me Pretty Satin Abstract Crop Top

    Color you pretty in this satin crop top to brighten up this new season! It features a sleeveless plunge halter neckline, a center hardware insert, and an ultra-cropped hem on smooth satin with an abstract print. Complete the look with the matching bottoms for a vacation!

    Shop Matching Bottoms: Color Me Pretty Satin Abstract Wide-Leg Pants

    Fit & Features

    • Sleeveless plunge halter neckline
    • Front hardware insert
    • Ultra-cropped hem
    • Abstract print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2286

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Impression Faux Suede Mini Skirt

    Make a stylish impression with this of-the-moment mini skirt. Designed with smooth faux suede fabric, it is shaped with a high-rise waist and a short fitted silhouette, accented with a sleek button-down design. Pair with the matching moto jacket for an elevated everyday look.

    Shop Matching Jacket: Stylish Impression Faux Suede Moto Jacket

    Fit & Features

    • Faux suede fabric, minimal stretch
    • High-rise waist
    • Button-down design
    • Back zipper hook-eye closure
    • Mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06401-0737

    Category Name: Matching Sets

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romance In Bloom Floral Ruffle Skort

    A skort that’s equal parts sweet and sultry. With a high-rise waist and ruffled hem, this floral skort is your go-to for brunch, concerts, or just serving soft-girl vibes all season.

    Shop Matching Bottoms: Romance In Bloom Floral Tie-Front Top

    Fit & Features

    • Floral print lace-lined fabric
    • High-rise waist
    • Form-hugging fit
    • Tiered ruffled mini-length hem
    • Stretchy knit shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000109

    Category Name: Matching Sets

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Call Me Cutie Lace-Up Floral Eyelet Corset Top

    Get ready for everyone to call you cute in this floral corset top designed with a flirty lace-up back that captures attention and a cropped hem that lets you flaunt your figure. Pair with the matching bottoms.

    Shop Matching Bottoms: Call Me Cutie Floral Eyelet Mini Skirt

    Fit & Features

    • Floral print, eyelet woven lined fabric
    • Strapless neckline
    • Front hidden hook and eye fasteners
    • Flexible boning
    • Lace-up back
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2726

    Category Name: Matching Sets

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blooming Bliss Lace-Up Floral Mesh Bustier

    Bloom this season in this floral mesh bustier on every occasion! This playful piece features a square neckline, shoulder straps, and a lace-up back for a flirty touch. Flexible boning provides support and a cropped hem flaunts your figure. Complete the look with the matching bottoms and block heels.

    Shop Matching Bottoms: Blooming Bliss High-Rise Bodycon Floral Maxi Skirt

    Fit & Features

    • Blooming floral print, stretchy mesh fabric, sewn-in knit lining
    • Square neckline, shoulder straps
    • Flexible boning
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5289

    Category Name: Matching Sets

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Covetable Cutie High-Rise Denim Mini Skirt

    This cute denim mini skirt features a classic high-rise waist, front pockets for stylish convenience, and a form-hugging fit. Perfect for everyday styling.

    Shop Matching Jacket: Covetable Cutie Contrast Stitch Denim Jacket

    Fit & Features

    • Dark wash denim, minimal stretch
    • High-rise waist
    • Form-hugging mini-length fit
    • Front button and hidden zipper closure
    • Front pockets
    • Runs true to size

    Style Number/Barcode: 06601-0216

    Category Name: Matching Sets

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fly By Satin Butterfly Crop Top

    Whimsical and sleek, this satin crop top will inspire you to spread your wings! It features peasant long sleeves, a sweetheart neck, a stretchy smocked back, and a twisted cropped hem. The top is composed of an abstract butterfly print on non-stretch satin fabric. Style with the matching bottoms.

    Shop Matching Bottoms: Fly By Satin Butterfly Midi Skirt

    Fit & Features

    • Peasant long sleeves
    • Sweetheart neck
    • Stretchy smocked back
    • Twisted cropped hem
    • Abstract butterfly print
    • Non-stretch satin fabric
    • Runs true to size

    Style Number/Barcode: 06003-2136

    Category Name: Matching Sets

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set For Good High Rise Texture Mini Skirt

    You'll be set for good in this stylish mini skirt all season! Featuring a flattering high rise waist and bodycon silhouette, this mini-length skirt offers the perfect fit. Complete the look with the matching top.

    Shop Matching Top: Set For Good Cap Sleeve Slit Texture Crop Top

    Fit & Features

    • Texture sheer fabric, knit lining, minimal stretch
    • High rise waist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1034

    Category Name: Matching Sets

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blooming Bliss High-Rise Bodycon Floral Maxi Skirt

    All of your loveliest looks will include this floral maxi skirt! Featuring a flattering high-rise waist and side ruched seams, this bodycon silhouette hugs your curves for a stunning look down to the fitted maxi-length hem. Complete the look with the matching top and heels for any dressy occasion.

    Shop Matching Top: Blooming Bliss Lace-Up Floral Mesh Bustier

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining, moderate stretch
    • High-rise waist
    • Back zipper and hook-eye closure
    • Side ruched seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1038

    Category Name: Matching Sets

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Unmatched Boldness Leopard Print Crop Top

    Channel your wild side in this leopard print crop top. With a cowl neckline and asymmetrical hem, this mesh beauty is perfect for making a fierce statement.

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Leopard print
    • Asymmetrical cropped hem
    • Runs true to size


    Shop Matching Midi Skirt: Unmatched Boldness Leopard Print Midi Skirt

    Style Number/Barcode: 06001-5559

    Category Name: Matching Sets

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free