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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.

  • All Day Darling Sleeveless Lace Crop Top

    You'll be darling all day in this lace crop top at parties and brunch! Made of soft knit floral lace fabric, it's both stylish and comfortable.  It features a square neckline, bungee spaghetti straps, and a ruched bust for a flattering fit. Complete the look with the matching mini skirt.

    Shop Matching Bottoms: All Day Darling High Rise Lace Mini Skirt

    Fit & Features

    • Floral lace knit fabric, sewn-in lining, moderate stretch
    • Square neckline
    • Bungee spaghetti straps
    • Ruched bust
    • Cropped length 
    • Runs true to size

    Style Number/Barcode: 06001-5185

    Category Name: Matching Sets

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Enticing Sparkle Sequin Midi Skirt

    Look absolutely enticing in this sequin midi skirt for endless sparkle! The midi skirt is designed with a flattering high-rise waist and bodycon silhouette on sequin-embellished fabric that shimmers under the light. Complete the look in the matching top for a dressy occasion!

    Shop Matching Top: Enticing Sparkle Sequin Crop Top

    Fit & Features

    • Fitted long sleeves
    • Square neckline
    • Form-hugging
    • Cropped hem
    • Sequin-embellished knit fabric, sewn-in knit lining
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06501-0882

    Category Name: Matching Sets

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Boho High Waist Crinkle Knit Flare Pants

    These crinkle knit flare pants will give you those trendy boho vibes you've been lusting after! Designed with a crinkle-textured knit fabric, these pants feature a high elasticized waist, a hip-hugging fit that continues through the leg, and a flared hem to add some stylish allure. Complete your bohemian-chic look with the matching top and sandals!

    Shop Matching Top: So Boho Lace-Up Crinkle Knit Top

    Fit & Features

    • Stretchy crinkle-textured knit fabric
    • High elasticized waist
    • Hip-hugging fit, form-hugging fit through the leg
    • Flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2434

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Vibes Woven Wide-Leg Pants

    These airy woven wide-leg pants will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric, they feature a flattering high-rise elasticized waist, front pockets, and a flowy wide-leg silhouette. Style with the matching crop top for a fabulous 'fit!

    Shop Matching Top: Sunny Vibes Bow Back Woven Crop Top

    Fit & Features

    • Woven fabric with minimal stretch
    • High-rise elasticized waistband
    • Wide-leg fit
    • Dual front pockets
    • Runs true to size

    Style Number/Barcode: 06402-1365

    Category Name: Matching Sets

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out For The Night High Rise Mesh Mini Skirt

    Get ready to turn heads in this high-rise mesh mini skirt! With its high-rise waist and bodycon fit, this skirt will accentuate your curves and give you a confident, daring look. The mini-length hem and texture mesh-lined fabric add a touch of edginess to your outfit. Complete the look with the matching top. 

    Shop Matching Top: Out For The Night Strapless Strappy Crop Top

    Fit & Features

    • Texture mesh lined fabric, moderate stretch
    • High rise waist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-0961

    Category Name: Matching Sets

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Downtown Meetings Pinstripe Linen Skort

    The perfect pinstripe linen skort for your meetings downtown - whether it's for business or pleasure! Featuring a high-rise waist and faux button front closures, this skort exudes chic while the faux wrap front skirt overlay and mini-length hem add a touch of modern flair. Complete the look with the matching vest.

    Shop The Matching Vest: Downtown Meetings Pinstripe Linen Vest

    Fit & Features

    • Pinstripe print, linen blend fabric lined with knit
    • High-rise waist
    • Back zipper and hook-eye closure
    • Faux wrap front skirt overlay, faux buttons
    • Mini-length
    • Runs true to size

    Style Number/Barcode: 06303-0254

    Category Name: Matching Sets

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Cutie Bell Sleeve Crochet Crop Top

    Show off the cutest boho vibe in this breezy crochet crop top! Designed with an airy sheer crochet knit fabric, this top is perfect for summer days spent by the coast. It features a wide scoop neckline, long bell sleeves with a stylish flare, a tie-back design at the neck, and a cropped hem with a form-hugging fit. Complete your look with the matching wide-leg pants and a pair of strappy sandals!

    Shop Matching Bottoms: Boho Cutie Crochet Wide-Leg Pants

    Fit & Features

    • Sheer crochet knit fabric, minimal stretch
    • Scoop neckline
    • Long bell sleeves
    • Tie-back design
    • Fitted cropped hem
    • Bra lining not included
    • Runs true to size

    Style Number/Barcode: 06005-1951

    Category Name: Matching Sets

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glittery Vibes High Slit Maxi Skirt

    Bring on the glittery vibes for your next girl's night in this high slit maxi skirt! Designed with a glitzy glitter knit fabric that has a mini-length lining, this long skirt is glam perfection. It features a high waist, a hip-hugging fit to flaunt your figure, a maxi-length hem with a high-cut back slit for an alluring detail, and an overall form-fitting silhouette for a sultry slay. Complete your going-out look with the matching crop top and clear heels!

    Shop Matching Top: Glittery Vibes Ruched Spaghetti Strap Crop Top

    Fit & Features

    • Textured glitter knit fabric with mini-length knit lining
    • Plenty of stretch
    • High waist
    • Maxi-length hem
    • Back slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-0932

    Category Name: Matching Sets

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Prowl High Rise Zebra Maxi Skirt

    On the prowl and ready to unleash fierceness in this zebra print maxi skirt! It features a flattering high-rise waist with an elastic banded back for added stretch, a high front slit to show some leg, and a flowy maxi silhouette. Complete the look with the matching top.

    Shop Matching Top: On The Prowl Strapless Zebra Crop Top

    Fit & Features

    • Zebra print, woven fabric
    • High-rise waist with elastic banded back
    • High front slit
    • Flowy maxi silhouette
    • Runs true to size

    Style Number/Barcode: 06301-0191

    Category Name: Matching Sets

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's The Main Rib Knit Slouchy Bolero

    Flaunt your look with ease and chicness layering this bolero sweater this season! The bolero features slouchy long sleeves, an open front design, and an ultra-cropped hem on soft and stretchy rib knit fabric. Style with the matching dress and heels for weekend plans!

    Shop Matching Dress: She's The Main Rib Knit Strapless Midi Dress

    Fit & Features

    • Slouchy long sleeves
    • Open front design
    • Ultra-cropped hem
    • Soft and stretchy
    • Rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06202-0496

    Category Name: Matching Sets

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Match High-Rise Palazzo Pants

    Flirt up your style in these palazzo pants on vacation or weekend fun! The high-rise waist and wide-leg silhouette provide a flattering fit, while the flowy design adds a touch of playful charm. Complete the look with the matching top.

    Shop Matching Top: Flirty Match Short Sleeve Tie-Front Top

    Fit & Features

    • Woven fabric, no stretch
    • High-rise elasticized waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1396

    Category Name: Matching Sets

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Cutie Crochet Wide-Leg Pants

    Show off the cutest boho vibe in these breezy crochet wide-leg pants! Designed with an airy sheer crochet knit fabric, these pants are perfect for summer days spent by the coast. They feature a high waist, a hip-hugging fit, and a wide-leg silhouette for that effortlessly chic vibe. Complete your look with the matching crop top and a pair of strappy sandals!

    Shop Matching Top: Boho Cutie Bell Sleeve Crochet Crop Top

    Fit & Features

    • Sheer crochet knit fabric, moderate stretch
    • High-rise elastic banded waist
    • Hip-hugging fit
    • Wide-leg silhouette
    • Panty lining not included
    • Runs true to size

    Style Number/Barcode: 06502-2488

    Category Name: Matching Sets

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Tropical Knit Wide-Leg Pants

    These alluring tropical wide-leg pants will have you ready for a dreamy vacay! The stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The pants are shaped with a high-rise elasticized waistband for comfortable wear and a relaxed wide-leg silhouette for a trendy look. Style with the matching crop top and hoop earrings.

    Shop Matching Top: Vacay Ready Tropical Knit Halter Crop Top

    Fit & Features

    • Abstract tropical print
    • Stretchy knit
    • High elasticized waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2481

    Category Name: Matching Sets

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Prettiest Vibe High Waist Floral Woven Skort

    Give off the prettiest vibe in this floral woven mini skort perfect for the season. Designed with a lightweight woven fabric, it features a subtle rose print pattern for a sweet feminine flair. The skort is shaped with a high-rise waist, a mini-length overlay with hidden stretchy knit shorts, a short side slit for a chic detail, and a slim-fit silhouette. Style with the matching crop top for a cute brunch look!

    Shop Matching Top: Prettiest Vibe Puff Sleeve Floral Woven Crop Top

    Fit & Features

    • Floral print
    • Non-stretch woven fabric
    • High waist
    • Mini-length overlay, hidden stretchy knit shorts
    • Back zipper with hook and eye closure, side slit
    • Slim-fit
    • Runs true to size

    Style Number/Barcode: 06303-0255

    Category Name: Matching Sets

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Tropical Knit Halter Crop Top

    This alluring tropical halter crop top will have you ready for a dreamy vacay! The lined stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The crop top is shaped with a sleeveless halter neckline with a sultry V-shaped cutout, tie-back halter straps, ruched side seams to accentuate your curves, and a form-hugging fit for a snatched look. Style with the matching wide-leg pants and hoop earrings.

    Shop Matching Bottoms: Vacay Ready Tropical Knit Wide-Leg Pants

    Fit & Features

    • Abstract tropical print
    • Stretchy lined knit
    • Halter neckline, V-shaped cutout
    • Tie-back spaghetti straps
    • Ruched side seams
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5210

    Category Name: Matching Sets

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Perfection Ruffled Floral Chiffon Maxi Skirt

    Be gorgeous and perfect all season in this floral chiffon maxi skirt at formal soirees! Made with floral and leaf print chiffon fabric, this skirt is a must-have for any fashion-forward girlie. Its high-rise waist and tiered ruffled silhouette create a flattering fit, while the maxi-length hem adds a chic touch. Complete the look with the matching top.

    Shop The Matching Top: Gorgeous Perfection Halter Floral Chiffon Crop Top

    Fit & Features

    • Floral and leaf print, chiffon fabric lined with stretchy knit
    • High-rise waist
    • Back zipper and hook-eye closure
    • Tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 06401-0685

    Category Name: Matching Sets

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Mood Crochet Cropped Sweater

    This cropped sweater is designed with a breezy open crochet knit fabric, creating a bold sheer look perf for weekend getaways. It features a wide boat neckline and long bell sleeves to give off those effortlessly chic vibes. Style with the matching maxi skirt.

    Shop Matching Bottoms: Weekend Mood Crochet Maxi Skirt

    Fit & Features

    • Open crochet knit fabric, minimal stretch
    • Boat neckline
    • Long bell sleeves
    • Cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-2113

    Category Name: Matching Sets

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Downtown Meetings Pinstripe Linen Vest

    The perfect pinstripe linen vest for your meetings downtown - whether it's for business or pleasure! Featuring a sleeveless V-neckline and button front closures, this vest exudes chic while the faux pockets and curved crop hem add a touch of modern flair. Complete the look with the matching skort.

    Shop The Matching Skort: Downtown Meetings Pinstripe Linen Skort

    Fit & Features

    • Pinstripe print, linen blend fabric lined with knit
    • V-Neckline
    • Button front closures
    • Faux pockets
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1739

    Category Name: Matching Sets

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daily Vibe Cross Belted Denim Mini Skirt

    For a cute look that's always a vibe, this denim mini skirt elevates your cool status! Featuring a figure-flattering V-cut high-rise waist with a cross-belted design, and a bodycon fit that flaunts your curves along the mini-length hem. Complete the look with the matching top.

    Shop Matching Top: Daily Vibe Strapless Belted Denim Crop Top

    Fit & Features

    • Denim fabric, moderate stretch
    • V-Cut high-rise waist
    • Cross belted design
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06601-0200

    Category Name: Matching Sets

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Match High Rise Slit Denim Maxi Skirt

    You and this denim maxi skirt will be a trendy match! This denim skirt features a flattering high-rise waist and form-hugging fit, while the high front slit adds a touch of boldness to the maxi-length hem. Complete the look with the matching top.

    Shop Matching Top: Trendy Match Sleeveless Denim Crop Top

    Fit & Features

    • Dark wash denim fabric, slight stretch
    • High-rise waist
    • Back zipper and hook-eye closure
    • High front slit design
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06601-0207

    Category Name: Matching Sets

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sophisticated Posh Zip Up Tweed Plaid Skort

    A tweed plaid skort is perfect for adding a touch of sophistication and posh for afternoon tea or a dressy brunch! The high-rise waist has side pockets for keeping your hands warm and a-line silhouette create a flattering fit, while the pleated skirt overlay adds a touch of playfulness. Crafted from tweed plaid woven fabric, this skort exudes posh style and with shorts lining, you'll stay comfortable all day long.

    Shop Matching Shacket: Sophisticated Posh Zip Up Tweed Plaid Shacket

    Fit & Features

    • Tweed plaid woven fabric lined with shorts
    • Back zipper and hook-eye closure
    • High-rise waist
    • Side pockets
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 06403-0369

    Category Name: Matching Sets

    Price: $20.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Alluring Dream High-Rise Lace Rosette Maxi Skirt

    You'll captivate everyone in this alluring lace maxi skirt for an effortless dreamy look at dinner!  With a flattering high-rise waist and delicate rosette flower, this lace skirt features a high side slit and form-hugging fit. Complete the look with the matching top.

    Shop Matching Top: Alluring Dream V-Neck Lace Rosette Crop Top

    Fit & Features

    • Lace fabric, sewn-in knit lining, stretchy
    • High-rise waist with trim
    • Rosette flower
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-1033

    Category Name: Matching Sets

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serenade Me V-Neck Crop Top

    A dreamy look awaits in this sleeveless top with a flattering V-neckline and fitted crop hem that flaunts your figure. Pair with the matching skirt to complete the look!

    Fit & Features

    • Double-lined smooth knit stretchy fabric
    • V-neckline
    • Wide shoulder straps
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Skirt: Serenade Me Bodycon Midi Skirt

    Style Number/Barcode: 06001-000041

    Category Name: Matching Sets

    Price: $19.90

    Availability: In Stock

    Available Color: MOCHA

    Available Size: S

    Product Badge:
    • Part of a Set
  • Preppy Perfection Gingham Twill Cropped Blazer

    Style up a look of preppy perfection with this gingham twill cropped blazer! This structured blazer is designed with a fine twill fabric and a chic gingham pattern to step up your everyday 'fits. It features a classic lapel collar, open front design, long sleeves with button accents and shoulder pads, and a cropped hem with an all-over fitted silhouette. Pair with the matching mini skort for a seamlessly fab look!

    Shop Matching Bottoms: Preppy Perfection Gingham Twill Skater Skort

    Fit & Features

    • Fine twill fabric, sewn-in woven lining
    • Gingham pattern
    • Lapel collar, open front design
    • Long sleeves with buttons, shoulder pads
    • Cropped hem
    • Fitted
    • Runs true to size

    Style Number/Barcode: 06204-1725

    Category Name: Matching Sets

    Price: $10.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale