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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.

  • Coastal Cute Linen Top And Shorts Set

    The perfect linen top and shorts set for your drive up the coast or beach cottage vacay! The oversized top features long sleeves with button cuffs, a collar neckline, a front pocket, and a button-down front. The matching shorts feature a smocked elastic high-rise waist. tie accent, side pockets, and a short-length hem. Complete the look in trendy sandals.

    Fit & Features

    • Linen top and shorts set
    • Oversized top, long sleeves, button cuffs
    • Collar neckline, front pocket
    • Button-down closures
    • Smocked elastic shorts, high-rise waist
    • Tie accent, side pockets, short hem
    • Runs true to size

    Style Number/Barcode: 06303-0227

    Category Name: Matching Sets

    Price: $21.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Crush Striped Crochet Midi Skirt

    POV: you just found your new fave beach-to-brunch vibe. This striped crochet midi skirt serves laid-back heat with a form-hugging fit and thigh-high slit made for turning heads from sunrise to sunset.

    Shop Matching Top: Summer Crush Striped Crochet Bralette Top

    Fit & Features

    • Crochet knit fabric
    • Striped pattern
    • High-rise waist
    • Thigh-high side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000027

    Category Name: Matching Sets

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

    Product Badge:
    • Sale
  • Sandy Beaches Palm Bandeau Top

    Can't you imagine strolling the beach in this palm print bandeau top? Embrace vacay in this tropical stunner featuring a sleeveless, strapless neckline, tie-front closure, and a smocked bodice. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Sandy Beaches Palm Wide-Leg Pants

    Fit & Features

    • Sleeveless, strapless neckline
    • Tie-front closure
    • Smocked bodice
    • Cropped hem
    • Palm print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1809

    Category Name: Matching Sets

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sandy Beaches Palm Wide-Leg Pants

    Can't you imagine strolling the beach in these palm print pants? Embrace vacay in this tropical stunner featuring a high-rise waist, wide-leg silhouette, and back zipper closure. Complete the look with the matching top.

    Shop Matching Top: Sandy Beaches Palm Bandeau Top

    Fit & Features

    • High rise waist
    • Wide-leg silhouette
    • Back zipper closure
    • Palm print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0655

    Category Name: Matching Sets

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Retro Swirl Print Crop Top

    Create a fab retro look for spring break with this trendy printed crop top! It features a deep V-neckline with a twist-front design, long peasant sleeves with cinched hems, a fitted cropped hem, and an all-over eye-catching swirl print pattern. The lightweight plisse woven fabric includes a front knit lining. Style with the matching shorts and clear mules.

    Shop Matching Bottoms: So Retro Swirl Print Shorts

    Fit & Features

    • V-neckline, twist-front design
    • Long peasant sleeves, elastic cinched hems
    • Fitted cropped hem
    • Swirl print pattern
    • Plisse woven fabric, front knit lining
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-2088

    Category Name: Matching Sets

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cool Girl Edge Faux Leather Tube Top

    This faux leather tube top will show off your cool-girl edge at festivals and concerts! It features a strapless straight across neckline and a fitted, ultra-cropped hem. Complete the look with the matching biker shorts and trendy cowboy boots.

    Shop Matching Bottoms: Cool Girl Edge Faux Leather Biker Shorts

    Fit & Features

    • Strapless straight across-neckline
    • Fitted, ultra-cropped hem
    • Faux leather fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 07103-0892

    Category Name: Matching Sets

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Girl Edge Faux Leather Biker Shorts

    These faux leather biker shorts will show off your cool-girl edge at festivals and concerts! They feature a flattering high-rise elastic waistband, form-hugging fit, and a mid-thigh length hem. Complete the look with the matching tube top and trendy cowboy boots.

    Shop Matching Top: Cool Girl Edge Faux Leather Tube Top

    Fit & Features

    • High-rise elastic waistband
    • Form-hugging fit
    • Biker style
    • Mid-thigh length hem
    • Faux leather fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 07103-0893

    Category Name: Matching Sets

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Marvel In Marble Mini Skirt

    You'll be such a marvel in this marble mini skirt perfect for a girl's night out! It features a high-rise waist, all-over ruching, a mini-length hem, a curve-hugging fit, and a trendy marble print pattern on a lined mesh fabric. Complete the look with the matching bustier and heels.

    Shop Matching Top: Such A Marvel In Marble Bustier

    Fit & Features

    • High-rise waist
    • Side and back ruching
    • Mini-length hem
    • Curve-hugging silhouette
    • Marble print
    • Lined mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0807

    Category Name: Matching Sets

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Story Time Printed Mesh Bustier

    Tell a story of your trendy self with this mesh bustier perfect for spring! It features a sleeveless sweetheart neck with halter straps, adjustable spaghetti straps, an underwire bust, flexible boning inserts, and a fitted crop hem. The bustier is designed with a unique tapestry print on mesh-lined fabric. Complete the look with the matching skirt.

    Shop Matching Skirt: Story Time Printed Mesh Mini Skirt

    Fit & Features

    • Sleeveless sweetheart neck, halter straps
    • Adjustable spaghetti straps
    • Underwire bust, flexible boning
    • Cropped hem
    • Tapestry print
    • Lined mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4699

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Story Time Printed Mesh Mini Skirt

    Tell a story of your trendy self with this mesh skirt perfect for spring! It features a high-rise waist, bodycon silhouette, and mini-length hem. The skirt is designed with a unique tapestry print on mesh-lined fabric. Complete the look with the matching top

    Shop Matching Top: Story Time Printed Mesh Bustier

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Mini-length hem
    • Tapestry print
    • Lined mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0789

    Category Name: Matching Sets

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Brunch 'Fit High Waist Shorts

    Elevate your weekend brunch 'fit with these chic high waist shorts! They feature an elasticized band at the back, front pockets, faux back pockets, and a fitted silhouette. Style with the matching blazer!

    Shop Matching Blazer: Chic Brunch 'Fit Oversized Blazer

    Fit & Features

    • High-rise waist, elasticized band at the back
    • Dual front pockets
    • Dual faux back pockets
    • Fitted silhouette
    • Woven fabric, lightweight woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0292

    Category Name: Matching Sets

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Brunch 'Fit Oversized Blazer

    Elevate your weekend brunch 'fit with this chic oversized blazer! It features a lapel collar, shoulder pad inserts to provide structure, long sleeves, an open front, dual front pockets, and a relaxed silhouette. Style with the matching shorts!

    Shop Matching Bottoms: Chic Brunch 'Fit High Waist Shorts

    Fit & Features

    • Lapel collar
    • Shoulder pad inserts
    • Long sleeves
    • Open front
    • Dual front pockets
    • Woven fabric, floral printed lining, no stretch
    • Relaxed, oversized fit

    Style Number/Barcode: 06204-1588

    Category Name: Matching Sets

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Resort Calling Mesh Slit Maxi Skirt

    Booked the trip? This skirt is already packed. Featuring a high-rise waist and dramatic slit skirt, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails.

    Shop The Matching Top: Resort Calling Mesh Tie Front Top

    Fit & Features

    • Floral print, attached panty knit lining
    • High-rise waist
    • High front slit
    • Flowy maxi length hem
    • Runs true to size

    Style Number/Barcode: 06501-000037

    Category Name: Matching Sets

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Sale
  • She Means Business Wide-Leg Pants

    Show them your trendsetter status in these high waist dress pants! They feature a flattering high-rise waist and a wide-leg silhouette. Style these pants with the matching blazer for a chic ensemble.

    Shop Matching Blazer: She Means Business Structured Blazer

    Fit & Features

    • High-rise waist, vertical seam detailing
    • Back zipper, hook and eye closure
    • Wide-leg fit
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-0601

    Category Name: Matching Sets

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring The Heat Printed Wide-Leg Pants

    Bring the heat to your spring break look with these trendy pants that will get everyone's attention! They feature a high-rise waist, pleating, an exaggerated wide-leg silhouette with a relaxed fit, and a sassy abstract printed design. Style with the matching crop top to be vacay-ready!

    Shop Matching Top: Bring The Heat Printed Crop Top

    Fit & Features

    • High-rise waist, back elastic band
    • Pleating
    • Wide-leg silhouette, relaxed fit
    • Abstract printed design
    • Satin woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-0536

    Category Name: Matching Sets

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring The Heat Printed Crop Top

    Bring the heat to your spring break look with this trendy crop top that will get everyone's attention! It features a sleeveless sweetheart neckline with a padded bust, thin halter straps with multiple ways to style, a stretchy smocked back, an ultra-cropped hem, and a sassy abstract printed design. Style with the matching wide-leg pants to be vacay-ready!

    Shop Matching Bottoms: Bring The Heat Printed Wide-Leg Pants

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust
    • Thin halter straps, multiple ways to style
    • Smocked back design
    • Ultra-cropped hem
    • Abstract printed design
    • Satin woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-2061

    Category Name: Matching Sets

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Marvel In Marble Bustier

    You'll be such a marvel in this marble bustier perfect for a girl's night! It features a strapless neckline, flexible boning inserts, side ruched seams, a curved cropped hem, and a trendy marble print pattern on a lined mesh fabric. Complete the look with the matching mini skirt and heels. 

    Shop The Matching BottomSuch A Marvel In Marble Mini Skirt

    Fit & Features

    • Strapless neckline
    • Flexible boning inserts, side ruched seams
    • Curved crop hem
    • Back hook and eye closures
    • Marble print
    • Lined mesh fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4704

    Category Name: Matching Sets

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • As If Moment Tweed Fitted Shorts

    Have your iconic as-if moment looking major in these 90s-inspired tweed fitted shorts featuring a high-rise waist, a back zipper closure, a form-hugging fit, and a chic plaid pattern. Style with the matching blazer to complete the look!

    Shop Matching Blazer: As If Moment Tweed Crop Blazer

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Form-hugging fit
    • Plaid pattern
    • Woven tweed fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0272

    Category Name: Matching Sets

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spring Break Vibes Wide-Leg Pants

    This trendy retro print pant radiates spring break vibes! It features a high-rise waist, wide-leg silhouette, and an all-over eye-catching marble print pattern. The pleated chiffon fabric has a full knit lining. Style with the matching tops.

    Shop Matching Tops: Spring Break Vibes Pleated Bra TopSpring Break Vibes Pleated Button-Down Top

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Wide-leg silhouette
    • Marble print pattern
    • Pleated chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-0557

    Category Name: Matching Sets

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Break Vibes Pleated Bra Top

    This trendy retro print bra top radiates spring break vibes! It features a sleeveless V-neckline, a padded bust, adjustable spaghetti straps, a fitted cropped hem, and an all-over eye-catching marble print pattern. The pleated chiffon fabric has a full knit lining. Style with the matching button-down top.

    Shop Matching Top and Pants: Spring Break Vibes Pleated Button-Down TopSpring Break Vibes Wide-Leg Pants

    Fit & Features

    • Sleeveless V-neckline, padded bust
    • Adjustable spaghetti straps
    • Back elastic strap with hook and eye closures
    • Fitted cropped hem
    • Marble print pattern
    • Pleated chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-2063

    Category Name: Matching Sets

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Break Vibes Pleated Button-Down Top

    This trendy retro print button-down top radiates spring break vibes! It features a collared neckline, long sleeves with a single button detail, a complete button-down front, a mid-length hem with a relaxed fit, and an all-over eye-catching marble print pattern. The pleated chiffon fabric is semi-sheer with a lightweight feel. Style with the matching bra top.

    Shop Matching Top And Pants: Spring Break Vibes Pleated Bra TopSpring Break Vibes Wide-Leg Pants

    Fit & Features

    • Collared neckline
    • Long sleeves, single button detail
    • Button-down front
    • Mid-length hem, relaxed fit
    • Marble print pattern
    • Pleated chiffon fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2064

    Category Name: Matching Sets

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Elevated Side Slit Skort

    Create an elevated 'fit with this chic of-the-moment skort! It features a high-rise elasticized waist, fitted shorts, and a mini-length front overlay with a side seam leading to a slit accent. The ponte knit fabric offers a moderate stretch. Style with the matching cropped bustier for a seamless look! 

    Shop Matching Top: So Elevated Ponte Crop Bustier

    Fit & Features

    • High-rise elasticized waist
    • Fitted shorts
    • Mini-length front overlay
    • Side seam leading to slit
    • Ponte knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-1030

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Resort Calling Mesh Tie Front Top

    Booked the trip? This top is already packed. Featuring a tie-front design, long sleeves and a dramatic crop hem, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails. 

    Shop The Matching Skirt: Resort Calling Mesh Slit Maxi Skirt

    Fit & Features

    • Floral print, partially lined mesh fabric
    • Long sleeves
    • Tie-front closure
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000032

    Category Name: Matching Sets

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • So Elevated Ponte Crop Bustier

    Create an elevated 'fit with this chic of-the-moment crop bustier! It features a sleeveless sweetheart neck, wide shoulder straps, bust seam detailing, and a fitted crop hem. The ponte knit fabric offers a moderate stretch. Style with the matching skort for a seamless look!

    Shop Matching BottomsSo Elevated Side Slit Skort

    Fit & Features

    • Sleeveless sweetheart neck
    • Wide shoulder straps 
    • Bust seam detailing
    • Fitted crop hem
    • Ponte knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4717

    Category Name: Matching Sets

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance