Matching Sets

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

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.

  • She's A Bold Babe Woven Blazer

    Create a bold babe look in this stunning and chic woven blazer. It features long sleeves with shoulder pads, an open front with a lapel collar, front pockets, and a structured fit. Style with matching dressy shorts and clear mules.

    Shop Matching Bottoms: She's A Bold Babe Woven Shorts

    Fit & Features

    • Long sleeves with shoulder pads
    • Open front design
    • Lapel collar
    • Front pockets
    • Structured fit
    • Woven lined fabric
    • Runs true to size

    Style Number/Barcode: 06204-1532

    Category Name: Matching Sets

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's A Bold Babe Woven Shorts

    Create a bold babe look in these stunning and chic woven shorts. They feature a high-rise banded waist, hidden front side pockets, and back faux pockets along a straight-fit silhouette. Style with the matching structured blazer and clear mules.

    Shop Matching Blazer: She's A Bold Babe Woven Blazer

    Fit & Features

    • High-rise banded waist
    • Hidden front side pockets, faux back pockets
    • Straight fit silhouette
    • Pull on/off styling
    • Woven lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0247

    Category Name: Matching Sets

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oh My Pearl Bell Sleeve Crop Top

    Bring the classy glamour in this faux pearl crop top featuring eye-catching long bell sleeves, a square neckline, and a fitted bodice on texture-knit fabric with lining and minimal stretch. The all-over faux pearl embellishments add the prettiest touch! Complete the look with the matching mini skirt and trendy mules.

    Shop Matching Bottoms: Oh My Pearl Faux Wrap Mini Skirt

    Fit & Features

    • Bell long sleeves
    • Square neckline
    • Fitted bodice
    • Cropped hem
    • Faux pearl embellishments
    • Texture-knit fabric, lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4301

    Category Name: Matching Sets

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boss Babe Moves Trouser Pants

    Make major boss babe moves in these trendy trouser pants! They feature a high-rise fitted waist, vertical seams down the front, back faux pockets, and a wide-leg silhouette with a slit accent at the hem. Style with the matching cropped blazer and sleek hoop earrings.

    Shop Matching Blazer: Boss Babe Moves Cropped Blazer

    Fit & Features

    • High-rise waist, back faux pockets
    • Hidden front zipper and hook-eye closure
    • Vertical seams down the front
    • Wide-leg silhouette
    • Slit accents
    • Lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-0497

    Category Name: Matching Sets

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Boss Babe Moves Cropped Blazer

    Make major boss babe moves in this trendy cropped blazer! It features a collared deep V-neckline, long sleeves, a wrap-front design with tie-back straps, and a cropped hem with a structured fit. Style with matching trouser pants and sleek hoop earrings.

    Shop Matching Bottoms: Boss Babe Moves Trouser Pants

    Fit & Features

    • Collared V-neckline
    • Long sleeves, shoulder pads
    • Wrap-front design, tie-back straps
    • Cropped hem, structured fit
    • Lined woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1533

    Category Name: Matching Sets

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Under The Sun Tropical Tie-Front Crop Top

    Perfect for any vacation or resort escape, this tropical top boasts a sultry tie-front and a cropped silhouette for a breezy allure. Pair with the matching skirt.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Long sleeves
    • V-neckline
    • Tie-front closure
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Skirt: Under The Sun Tropical Slit Maxi Skirt

    Style Number/Barcode: 06202-000014

    Category Name: Matching Sets

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

    Product Badge:
    • Sale
  • Effortless And Elevated Cropped Blazer

    Effortless and elevated, create chic looks with this cropped blazer. It features a V-neckline with a lapel collar, long sleeves with shoulder pads, a single button-front closure, and a cropped, fitted hem. Style with the matching wide-leg pants and clear mules.

    Shop Matching Bottoms: Effortless And Elevated Wide-Leg Pants

    Fit & Features

    • V-neckline, lapel collar
    • Long sleeves with shoulder pads
    • Single button-front closure
    • Cropped, fitted hem
    • Woven lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1529

    Category Name: Matching Sets

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless And Elevated Wide-Leg Pants

    Effortless and elevated, create chic looks with these woven pants. They feature a high-rise waist, belt loops, a button-front closure, front and back pockets, and a wide-leg silhouette. Style with the matching cropped blazer and clear mules.

    Shop Matching Blazer: Effortless And Elevated Cropped Blazer

    Fit & Features

    • High-rise waist
    • Belt loops
    • Button-front closure
    • Front and back pockets
    • Wide-leg silhouette
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 06402-0494

    Category Name: Matching Sets

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Structured And Chic Wide-Leg Pants

    These structured woven pants are totally chic. They feature a high-rise waist, pleated detailing, and a wide-leg silhouette. Style with the matching cropped vest for a trendy look.

    Shop Matching Vest: Structured And Chic Cropped Vest

    Fit & Features

    • High-rise waist
    • Hidden side zipper closure
    • Pleated detailing
    • Wide-leg silhouette
    • Woven-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0688

    Category Name: Matching Sets

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Structured And Chic Cropped Vest

    This structured cropped vest is totally chic. It features a sleeveless deep V-neckline with a lapel collar, a thin strappy front with a tie-back design, and a cropped, form-hugging fit. Style with the matching wide-leg pants for a trendy look.

    Shop Matching Bottoms: Structured And Chic Wide-Leg Pants

    Fit & Features

    • Sleeveless V-neckline, lapel collar
    • Thin strappy front with a tie-back design
    • Cropped, form-hugging fit
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1530

    Category Name: Matching Sets

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Beauty Cutout Midi Skirt

    Showcase your beauty on a sunset stroll in this alluring midi skirt. It features a high-rise waist with a strappy cutout design, a midi-length, curve-hugging fit, and a chic side slit accent. Style with the matching crop top for the perfect look.

    Shop Matching Top: Sunset Beauty Halter Crop Top

    Fit & Features

    • High-rise waist, strappy cutout design
    • Midi-length hem, form-fitting silhouette
    • Side slit
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0714

    Category Name: Matching Sets

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunset Beauty Halter Crop Top

    Showcase your beauty on a sunset stroll in this alluring crop top. It features an off-the-shoulder neckline with short fitted sleeves and thin halter straps, a cinched accent at the bust, a tie-back design, and a cropped, form-hugging fit. Style with the matching midi skirt for the perfect look.

    Shop Matching Bottoms: Sunset Beauty Cutout Midi Skirt

    Fit & Features

    • Off-the-shoulder neckline
    • Short fitted sleeves, thin halter straps
    • Cinched accent at the bust
    • Tie-back design
    • Cropped, form-hugging fit
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1594

    Category Name: Matching Sets

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Fling Twist Front Crop Top

    So much for a summer fling! With this crop top, you're sure to fall for it over and over again. It features a sleeveless, sweetheart neck, criss-cross back straps, and a twisted front on lined knit fabric. Complete your look with the matching bottoms.

    Shop Matching Bottoms: Summer Fling Twist Slit Maxi Skirt

    Fit & Features

    • Sleeveless, sweetheart neck, spaghetti straps
    • Criss-cross back straps
    • Twisted front
    • Cropped hem
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4374

    Category Name: Matching Sets

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Fling Twist Slit Maxi Skirt

    So much for a summer fling! With this maxi skirt, you're sure to fall for it over and over again. It features a high-rise waist with a twist accent, a front high-cut slit, and a form-fitting silhouette on lined knit fabric. Complete your look with the matching top. 

    Shop Matching Top: Summer Fling Twist Front Crop Top

    Fit & Features

    • High-rise waist with twist accent
    • Front high-cut slit
    • Form-fitting silhouette
    • Maxi-length hem
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0673

    Category Name: Matching Sets

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fringe Dreams Faux Leather Mini Skirt

    Get ready to party in this dreamy faux leather mini skirt designed with a high-rise waist, bodycon silhouette, and an asymmetrical side cutout with fringe trim. Complete the look in a crop top and mules.

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Asymmetrical side cutout
    • Fringe trim
    • Mini-length hem
    • Faux leather fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06501-0687

    Category Name: Matching Sets

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Jazz Night Twist Front Crop Top

    Enter the room of the rhythm and blues! All eyes on you in this saucy crop top featuring a sleeveless, sweetheart neck, adjustable spaghetti straps, and a twisted bust, on pleated-lined fabric. Complete the look in the matching bottoms. 

    Shop Matching Bottoms: Jazz Night High Rise Pants

    Fit & Features

    • Sleeveless, sweetheart neck 
    • Adjustable spaghetti straps
    • Twisted bust
    • Cropped hem
    • Pleated-lined fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4527

    Category Name: Matching Sets

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Effect Abstract Wide-Leg Pants

    Printed to perfection in a flattering wide-leg silhouette, these pants boast a classic high-rise waist. Pair with the matching top.

    Fit & Features

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

    Shop The Matching Top: Sultry Effect Abstract Cowl Halter Crop Top

    Style Number/Barcode: 06502-000022

    Category Name: Matching Sets

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M

    Product Badge:
    • Sale
  • Jazz Night High Rise Pants

    Enter the room of the rhythm and blues! All eyes on you in these high-rise pants featuring a wide-leg silhouette, pull-on/off styling on pleated-lined fabric. Complete the look in the matching top.

    Shop Matching Top: Jazz Night Twist Front Crop Top

    Fit & Features

    • High-rise waistband
    • Wide-leg silhouette
    • Pull-on/off styling
    • Pleated-lined fabric
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06502-1282

    Category Name: Matching Sets

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life Of Leisure Rib Seamless Bra

    The perfect ribbed bra for living your life of leisure! It features a sleeveless, square neckline, tank-style straps, and a soft and comfortable seamless knit design. Complete the look in the matching shorts. 

    Shop Matching Shorts: Life Of Leisure Rib Seamless Shorts

    Fit & Features

    • Sleeveless, square neckline
    • Tank-style straps
    • Soft and comfortable
    • Seamless design
    • Ribbed-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 07107-0776

    Category Name: Matching Sets

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life Of Leisure Rib Seamless Shorts

    The perfect ribbed shorts for living your life of leisure! It features a smooth, high-rise waist, biker silhouette, and a soft and comfortable seamless knit design. Complete the look in the matching bra.

    Shop Matching Bra: Life Of Leisure Rib Seamless Bra

    Fit & Features

    • Smooth high-rise waist
    • Biker silhouette
    • Soft and comfortable
    • Seamless design
    • Ribbed-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 07103-0804

    Category Name: Matching Sets

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Swirls High Waist Seamless Shorts

    Slay in sleek seamless shorts that are perfect for lounging in or running errands! The shorts feature a high-rise waist, a chic swirl pattern, a mid-thigh length, and a seamless fit throughout. The shorts are composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching bralette. 

    Shop Matching Bralette: Sassy Swirls Seamless Longline Bralette

    Fit & Features

    • Swirl print
    • High rise waist
    • Mid-thigh length
    • Soft and comfortable
    • Seamless fabrication, moderate stretch
    • Runs true to size

    Style Number/Barcode: 07103-0809

    Category Name: Matching Sets

    Price: $5.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drinks On The Beach Crepe Bra Top

    Sipping on cocktails with a beach view! Sultry and chic have never looked so good as on this crepe bra top featuring a sleeveless, plunge V-neck, adjustable spaghetti straps, built-in padded bust, and an elasticized back band with hook-eye closures. Complete the look in the matching top layer. 

    Shop Matching Top: Drinks On The Beach Crepe Top

    Fit & Features

    • Sleeveless, plunge V-neck, adjustable spaghetti straps
    • Built-in padded bust
    • Elasticized back band with hook-eye closures
    • Crepe chiffon-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1912

    Category Name: Matching Sets

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hidden Gem Halter Cutout Crop Top

    You won't be able to hide this gem of a top! This halter crop top features a sleeveless, low-cut bodice, center gem insets with cutout accents on slinky knit-lined fabric with a moderate stretch. Complete the look in the matching bottoms.

    Shop The Matching Bottoms: Hidden Gem High Rise Flare Pants

    Fit & Features

    • Sleeveless, low-cut halter neck
    • Center gem insets
    • Cutout accents
    • Cropped hem
    • Slinky knit-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4357

    Category Name: Matching Sets

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hidden Gem High Rise Flare Pants

    You won't be able to hide this gem of a pant! These pants feature a sleek, high-rise waist, front gem insets, cutout accents, a form-fitting silhouette, and a flared hem on slinky knit-lined fabric with a moderate stretch. Complete the look in the matching top.

    Shop The Matching Top: Hidden Gem Halter Cutout Crop Top

    Fit & Features

    • Sleek high-rise waist
    • Front gem insets
    • Cutout accents
    • Form-fitting, flare hem
    • Slinky knit-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06502-1011

    Category Name: Matching Sets

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free