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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.

  • Cancun Vacay Tropical Slit Maxi Skirt

    Cancun isn't ready for this one! Jet set on vacay in this tropical maxi skirt featuring a high-rise elasticized waistband, a front high slit, floral and leaf pattern, and a maxi-length hem on gauze woven fabric. Style with the matching tropical top.

    Shop Matching Top: Cancun Vacay Tropical Multi-Wear Top

    Fit & Features

    • High-rise elasticized waistband
    • Front high slit
    • Floral and leaf pattern
    • Maxi-length hem
    • Relaxed silhouette
    • Gauze woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0078

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cancun Vacay Tropical Multi-Wear Top

    Cancun isn't ready for this one! Jet set on vacay in this tropical halter top featuring multi-wear straps so you can style it as a halter or tube top, floral and leaf pattern, and a cropped hem. Style with the matching tropical maxi skirt. 

    Shop Matching Skirt: Cancun Vacay Tropical Slit Maxi Skirt

    Fit & Features

    • Multi-wear straps
    • Cropped hem
    • Back smocked panel
    • Floral and leaf pattern
    • Gauze woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1297

    Category Name: Matching Sets

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Effect Abstract Cowl Halter Crop Top

    Printed to perfection in a flattering halter silhouette, this crop top boasts a sultry cowl neckline and an open back to show some skin! Pair with the matching pants.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • Cowl halter neckline, tie straps
    • Open back
    • Fitted crop hem
    • Runs true to size

    Shop The Matching Pants: Sultry Effect Abstract Wide-Leg Pants

    Style Number/Barcode: 06001-000107

    Category Name: Matching Sets

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Making Headlines Satin Tunic Top

    This newspaper print tunic top is sure to make headlines! It features long sleeves with button cuffs, a collared neckline, a button-down front, side slit accents, and a flowy silhouette on satin fabric with no stretch. Complete the look with the matching bralette.

    Shop Matching Bralette: Making Headlines Satin Bralette Top

    Fit & Features

    • Long sleeves, button cuffs
    • Collared neckline
    • Button-down front
    • Side slit accents
    • Flowy silhouette
    • Newspaper print, satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1663

    Category Name: Matching Sets

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Making Headlines Satin Bralette Top

    This newspaper print bralette top is sure to make headlines! It features a V-neck, adjustable spaghetti straps, a front knot accent, and an elasticized back strap. Composed of satin-lined fabric with no stretch. Style with the matching tunic top.

    Shop Matching Tunic Top: Making Headlines Satin Tunic Top

    Fit & Features

    • V-neck
    • Front knot accent
    • Adjustable spaghetti straps
    • Elasticized back strap
    • Newspaper print
    • Satin-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1662

    Category Name: Matching Sets

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Elevated Woven Blazer

    Refresh your wardrobe with this chic and elevated blazer! It features a lapel collar, shoulder pads, long sleeves, a single-button closure, and a fitted silhouette. The smooth crepe fabric includes a woven lining. Style with the matching trouser shorts or pants for a seamless look.

    Shop Matching Shorts: Chic And Elevated Woven Trouser Shorts

    Shop Matching Pants: Chic And Elevated Woven Trouser Pants

    Fit & Features

    • Lapel collar
    • Shoulder pads, long sleeves
    • Single-button front closure
    • Dual front pockets
    • Fitted silhouette
    • Crepe fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1652

    Category Name: Matching Sets

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Art Satin Wide Leg Pants

    Abstract art you can wear! Slay an art gallery opening in these fierce satin pants featuring a high-rise elasticized waistband, front pleating, and a wide-leg silhouette. Complete the look in the matching top.

    Shop Matching Top: Abstract Art Satin Convertible Top

    Fit & Features

    • High-rise elasticized waistband
    • Front pleating
    • Wide-leg silhouette
    • Abstract print, satin fabric
    • Runs true to size

    Style Number/Barcode: 06402-0414

    Category Name: Matching Sets

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Paradise Cove Cowl Neck Crop Top

    Enter paradise cove in true vacay style! This tropical tank top features a sleeveless, cowl neck, sleek bungee spaghetti straps, cropped hem, and a trendy palm print on stretchy lined fabric. Complete the look in the matching bottoms and sunglasses.

    Shop Matching Bottoms: Paradise Cove Slit Maxi Skirt

    Fit & Features

    • Sleeveless, cowl neck, bungee spaghetti straps
    • Cropped hem
    • Tropical palm-print
    • Stretchy lined knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4262

    Category Name: Matching Sets

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Move Linen Woven Blazer

    On the move and looking stylish! Slay the day in this linen woven blazer featuring long sleeves with button accents, a lapel collared neckline, dual button front closure, and a three-pocket styling. Complete the look in the matching top and bottoms.

    Shop Matching Top: On The Move Linen Crop Top

    Shop Matching Bottoms: On The Move Linen Wide Leg Pants

    Fit & Features

    • Long sleeves, button accents
    • Lapel collar neckline
    • Three-pocket styling
    • Relaxed silhouette
    • Linen woven lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1297

    Category Name: Matching Sets

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Move Linen Crop Top

    On the move and looking stylish! Slay the day in this linen woven blazer featuring long sleeves with button accents, a lapel collared neckline, dual button front closure, and a three-pocket styling. Complete the look in the matching top and bottoms.

    Shop Matching Blazer: On The Move Linen Woven Blazer

    Shop Matching Bottoms: On The Move Linen Wide Leg Pants

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Smocked back
    • Cropped hem
    • Linen woven lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1696

    Category Name: Matching Sets

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On The Move Linen Wide Leg Pants

    On the move and looking stylish! Slay the day in this linen woven blazer featuring long sleeves with button accents, a lapel collared neckline, dual button front closure, and a three-pocket styling. Complete the look in the matching top and bottoms.

    Shop Matching Top: On The Move Linen Crop Top

    Shop Matching Blazer: On The Move Linen Woven Blazer

    Fit & Features

    • High-rise waist, clip-closure, hidden zipper
    • Belt loop accents
    • Hidden side pockets
    • Pleat front detailing
    • Wide-leg silhouette
    • Linen woven lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0627

    Category Name: Matching Sets

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knit Happens Halter Sweater Top

    This sweater knit top happens to be a perfect match for your closet! It features a sleeveless, halter v-neck, partial open-back, and a cropped hem. Complete the look in the matching cardigan.

    Shop Matching Cardigan: Knit Happens Crop Knit Cardigan

    Fit & Features

    • Sleeveless, halter v-neck
    • Partial open-back
    • Cropped hem
    • Rib-knit sweater fabric
    • Runs true to size

    Style Number/Barcode: 06005-1045

    Category Name: Matching Sets

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For The Weekend Flowy Pants

    You'll be ready for a relaxing weekend getaway with these cute flowy pants. They feature a high-rise waist, a wide-leg silhouette with a chic front split hem design, and a woven short lining. Complete the look with the matching tube top and strappy sandals.

    Shop Matching Top: Ready For The Weekend Tube Top

    Fit & Features

    • High-rise waist, elasticized back
    • Hidden side zipper, hook and eye closure
    • Wide-leg silhouette, front split hem design
    • Woven short lining
    • Textured woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-0465

    Category Name: Matching Sets

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mornings In Tulum Tropical Tie-Front Crop Top

    Waking up in paradise got sweeter with this tropical crop top in your luggage! It boasts flowy short sleeves and a tie-front design perfect for styling over a bikini. Pair with the matching pants.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Short sleeves
    • Tie-front design
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Pants: Mornings In Tulum Tropical Wide-Leg Pants

    Style Number/Barcode: 06202-000015

    Category Name: Matching Sets

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Knit Happens Crop Knit Cardigan

    This sweater knit cardigan happens to be a perfect match for your closet! It features long sleeves, a three-button down front closure, and a cropped hem. Complete the look in the matching top.

    Shop Matching Top: Knit Happens Halter Sweater Top

    Fit & Features

    • Long sleeves
    • Three-button down front
    • Cropped hem
    • Rib-knit sweater fabric
    • Runs true to size

    Style Number/Barcode: 06005-1046

    Category Name: Matching Sets

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Kaleidoscope Boho Tie-Front Top

    Escape the city life for paradise with this boho crop top featuring a sleeveless, sweetheart neck, adjustable spaghetti straps, a tie-front detail, back smocked design, and a kaleidoscope print. Complete the look in the matching skirt. 

    Shop Matching Skirt: Kaleidoscope Boho Slit Maxi Skirt

    Fit & Features

    • Sleeveless, sweetheart neck
    • Adjustable spaghetti straps
    • Tie-front detail
    • Back smocked design
    • Kaleidoscope boho print
    • Runs true to size

    Style Number/Barcode: 06003-1556

    Category Name: Matching Sets

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Stunning Ruched Tube Top

    Keep it so stunning with a stylish tube top! The top features a sleeveless sweetheart neckline with a ruched center and an asymmetrical cropped hem. The top is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching maxi skirt.

    Shop Matching Skirt: So Stunning Asymmetrical Maxi Skirt

    Fit & Features

    • Sleeveless sweetheart neckline
    • Ruched center 
    • Asymmetrical cropped hem 
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06001-4031

    Category Name: Matching Sets

    Price: $6.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kaleidoscope Boho Slit Maxi Skirt

    Escape the city life for paradise with this boho maxi skirt featuring a high-rise waist, front high-cut slit, and a kaleidoscope print. Complete the look in the matching top.

    Shop Matching Top: Kaleidoscope Boho Tie-Front Top

    Fit & Features

    • High-rise waist
    • Front high-cut slit
    • Maxi-length hem
    • Kaleidoscope boho print
    • Runs true to size

    Style Number/Barcode: 06301-0103

    Category Name: Matching Sets

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For The Weekend Tube Top

    You'll be ready for a relaxing weekend getaway with this cute cropped tube top. It features a strapless sweetheart neckline, a front lace-up design, and a majorly cropped hem. Complete the look with the matching flowy pants and strappy sandals.

    Shop Matching Bottoms: Ready For The Weekend Flowy Pants

    Fit & Features

    • Strapless sweetheart neckline, no-slip strip
    • Front lace-up design, tie closure
    • Cropped, form-hugging fit
    • Textured woven fabric, front lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1880

    Category Name: Matching Sets

    Price: $21.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • At Your Leisure Seamless Shorts

    All you need is this seamless biker short for the perfect lounge sesh! It features a supportive high-rise waistband, side contouring panels, and a biker-length hem composed of a buttery soft knit fabric. Complete the look in the matching bralette with your favorite slippers. 

    Shop Matching Bralette: At Your Leisure Seamless Bralette

    Fit & Features

    • High-rise supportive waistband
    • Side contouring panels
    • Form-fitting 
    • Biker-length hem
    • Buttery soft and comfortable
    • Seamless knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 07103-0796

    Category Name: Matching Sets

    Price: $9.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • At Your Leisure Seamless Bralette

    All you need is this seamless bralette for the perfect lounge sesh! It features a scoop neck, tank-style straps, a longline hem, and a racerback design composed of a buttery soft knit fabric. Complete the look in the matching bottoms with your favorite slippers. 

    Shop Matching Bottoms: At Your Leisure Seamless Shorts

    Fit & Features

    • Scoop neck
    • Tank-style straps
    • Longline hem
    • Racerback design
    • Buttery soft and comfortable
    • Seamless knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 07107-0769

    Category Name: Matching Sets

    Price: $9.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Chill Seamless Bralette

    Have yourself the perfect chill sesh in this seamless bralette featuring a sleeveless V-neck, dual spaghetti straps, and a partial open-back, on a soft and comfortable ribbed knit fabric. Complete the look in the matching shorts.

    Shop Matching Shorts: Perfectly Chill Seamless Shorts

    Fit & Features

    • Sleeveless,V-neck
    • Dual spaghetti straps
    • Partial open-back design
    • Soft and comfortable
    • Seamless, rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 07107-0768

    Category Name: Matching Sets

    Price: $6.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed Florals Twist Crop Top

    Let the sunshine on this flirty floral crop top perf for a brunch with the girls! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, twist accent bodice, and a back smocked panel with zipper closure. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Sunkissed Florals A-Line Skirt

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Twist accent bodice
    • Cropped hem
    • Back smocked panel, zipper closure
    • Floral print, lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1824

    Category Name: Matching Sets

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mornings In Tulum Tropical Wide-Leg Pants

    Waking up in paradise got sweeter with these tropical pants in your luggage! It boasts a flattering high-rise waist and a flowy wide-leg design perfect for styling over a swimsuit Pair with the matching top.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • High-rise waist
    • Flowy wide-leg silhouette
    • Runs true to size

     

    Shop The Matching Top: Mornings In Tulum Tropical Tie-Front Crop Top

    Style Number/Barcode: 06502-000021

    Category Name: Matching Sets

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free