Matching sets are the easiest way to look instantly put-together while keeping it on-trend for Fall. From two-piece sets like crop tops with mini skirts to flowy fly-a-way tops paired with wide-leg pants, the options are endless. Long sleeve crop tops with maxi skirts bring a chic vibe, while jersey knits and printed mesh keep the styles fresh. Perfect for date night, brunches, or mixers, these sets take the stress out of styling and give you a ready-made outfit that always turns heads.

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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.

Holiday In The Sun Smocked Mini Skirt
If ya got it flaunt it on holiday! Sass up your look in this smocked mini skirt featuring a high-rise waist and a mini-length, curve-hugging silhouette. Complete the look with the matching crop top.

Shop Matching Top: Holiday In The Sun Smocked Crop Top

Fit & Features
- High-rise waist
- Mini-length, form-fitting silhouette
- Smocked knit-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0543

Category Name: Matching Sets

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Retro Wide-Leg Pants
Showcase a trendy retro vibe in these chic palazzo pants. They feature a high-rise smocked waist, a wide-leg silhouette, and a relaxed fit. The lightweight woven fabric features a fab all-over geometric pattern. Style with the matching bandeau top.

Shop Matching Top: So Retro Halter Bandeau Top

Fit & Features
- High-rise smocked waist
- Wide-leg silhouette
- Relaxed fit
- Geometric pattern
- Unlined woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0636

Category Name: Matching Sets

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Charming Duo Long Sleeve Bolero
A charming long sleeve bolero you'll adore for brunch or family gatherings! Pair with the matching dress for a complete look.

Fit & Features
- Soft rib knit stretchy fabric
- Fitted long sleeves
- Open front design
- Ultra-cropped hem
- Runs true to size
Shop The Matching Dress: Charming Duo Strapless Skater Mini Dress
Style Number/Barcode: 06005-2236

Category Name: Matching Sets

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Retro Halter Bandeau Top
Showcase a trendy retro vibe in this alluring bandeau top. It features a sleeveless halter neckline with spaghetti straps, a center O-ring accent at the bust, and a tie-back strap design. The lightweight woven fabric features a fab all-over geometric pattern. Style with the matching wide-leg pants.

Shop Matching Bottoms: So Retro Wide-Leg Pants

Fit & Features
- Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
- Center O-ring detail
- Tie-back strap design
- Cropped, form-hugging fit
- Geometric pattern
- Woven fabric, front knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4123

Category Name: Matching Sets

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Retro Getaway Mesh Headwrap
Make sure to pack this retro-fab headwrap for your next desert getaway! The headwrap is composed of sheer mesh fabric with an all-over paisley print pattern and has an oversized-fit wrap-around design. Style with the matching bikini and cat-eye sunglasses.

Shop Matching Bikini Top: Retro Getaway Bikini Top

Shop Matching Bikini Bottoms: Retro Getaway Bikini Bottoms

Shop Matching Skirt: Retro Getaway Mesh Mini Skirt

Shop Matching Dress: Retro Getaway Mesh Mini Dress

Shop Matching Duster: Retro Getaway Long Mesh Duster

Fit & Features
- Wrap-around design
- Paisley print
- Mesh fabric, plenty of stretch
Style Number/Barcode: 07305-0373

Category Name: Matching Sets

Price: $1.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summer Mode Cotton Bra Top
Activate summer mode with this lightweight cotton bra top featuring a sleeveless V-neckline, adjustable spaghetti straps, and a fitted ultra-cropped hem. Style with the matching button-down top and high-rise shorts for an effortlessly chic look.

Shop Matching Set: Summer Mode Button-Down Cotton Top, Summer Mode High-Rise Cotton Shorts

Fit & Features
- Textured cotton fabric
- Sleeveless V-neckline, surplice design
- Adjustable spaghetti straps
- Stretchy smocked back
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06003-000082

Category Name: Matching Sets

Price: $22.90

Availability: In Stock

Available Color: CHARTREUSE

Available Size: S, M, L
Product Badge:
- Part of a Set
Retro Getaway Bikini Bottoms
Make sure to pack these retro-fab bikini bottoms for your next desert getaway! They feature a hipster design with thin side ties and a semi-cheeky fit. The bottoms feature an all-over paisley print pattern. Style with the matching bikini top and cat-eye sunglasses.

Shop Matching Bikini Top: Retro Getaway Bikini Top

Shop Matching Headwrap: Retro Getaway Mesh Headwrap

Shop Matching Skirt: Retro Getaway Mesh Mini Skirt

Shop Matching Dress: Retro Getaway Mesh Mini Dress

Shop Matching Duster: Retro Getaway Long Mesh Duster

Fit & Features
- Hipster design
- Thin side ties
- Semi-cheeky fit
- Paisley print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07105-0788

Category Name: Matching Sets

Price: $20.90

Availability: Out of Stock
Product Badge:
- Sale
Retro Getaway Bikini Top
Make sure to pack this retro-fab bikini top for your next desert getaway! It features a basic triangle design with padded cups, halter spaghetti straps, and lower tie-back spaghetti straps. The top features an all-over paisley print pattern. Style with the matching bikini bottoms and cat-eye sunglasses.

Shop Matching Bikini Bottoms: Retro Getaway Bikini Bottoms

Shop Matching Headwrap: Retro Getaway Mesh Headwrap

Shop Matching Skirt: Retro Getaway Mesh Mini Skirt

Shop Matching Dress: Retro Getaway Mesh Mini Dress

Shop Matching Duster: Retro Getaway Long Mesh Duster

Fit & Features
- Triangle design
- Removable padding
- Halter spaghetti straps, tie at the back of the neck
- Lower tie-back spaghetti straps
- Paisley print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0641

Category Name: Matching Sets

Price: $20.90

Availability: Out of Stock
Product Badge:
- Sale
Retro Getaway Mesh Mini Skirt
Make sure to pack this retro-fab mini skirt for your next desert getaway! It features a high-rise waist, cinched detailing down one side with an adjustable drawstring, and a short, form-hugging fit. The sheer mesh fabric features an all-over paisley print pattern. Style this mini skirt over the matching bikini with cat-eye sunglasses.

Shop Matching Bikini Top: Retro Getaway Bikini Top

Shop Matching Bikini Bottoms: Retro Getaway Bikini Bottoms

Shop Matching Headwrap: Retro Getaway Mesh Headwrap

Shop Matching Dress: Retro Getaway Mesh Mini Dress

Shop Matching Duster: Retro Getaway Long Mesh Duster

Fit & Features
- High-rise elasticized waist
- Cinched detailing down one side, adjustable drawstring
- Mini-length, form-fitting silhouette
- Paisley print
- Sheer mesh fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0610

Category Name: Matching Sets

Price: $22.90

Availability: Out of Stock
Product Badge:
- Clearance
Weekend Leisure Seamless Set
You deserve some leisure time this weekend! Look cute lounging in this seamless rib-knit set featuring an asymmetrical one-shoulder crop top and matching high-rise biker shorts. Complete the look in cozy slippers.

Fit & Features
- Asymmetrical one-shoulder crop top
- High-rise biker shorts
- Seamless design for comfort
- Rib-knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0753

Category Name: Matching Sets

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Staycation High Slit Maxi Skirt
Bare it all for a saucy night out in this high-rise maxi skirt featuring a sultry front slit on a form-fitting silhouette. Complete the look in the matching bottoms.

Shop Matching Top: Staycation Twist Banded Crop Top

Fit & Features
- High-rise waist
- Front slit
- Form-fitting silhouette
- Maxi-length hem
- Sleek knit-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0597

Category Name: Matching Sets

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Staycation Twist Banded Crop Top
Bare it all for a saucy night out in this crop top featuring a sleeveless V-neckline, adjustable spaghetti straps, and a sultry twisted bodice with an elasticized band. Complete the look in the matching bottoms.

Shop Matching Bottoms: Staycation High Slit Maxi Skirt

Fit & Features
- Sleeveless, V-neck, adjustable spaghetti straps
- Twisted bodice
- Elasticized band
- Cropped hem
- Sleek knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4008

Category Name: Matching Sets

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
The Coolest Vibe Midi Skirt
Showcase the coolest vibe in this trendy midi skirt. It features a high-rise waist with a knot-front design, a midi-length asymmetrical hem with a high side slit, and an all-over marble print pattern. Complete the look with the matching crop top.

Shop Matching Top: The Coolest Vibe Cropped Tank

Fit & Features
- High-rise waist
- Knot-front design
- Midi-length, asymmetrical hem, side slit
- Curve-hugging silhouette
- Marble print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0600

Category Name: Matching Sets

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
The Coolest Vibe Cropped Tank
Showcase the coolest vibe in this trendy cropped tank. It features a sleeveless square neckline, thin tank shoulder straps, a cropped, form-hugging fit, and an all-over marble print pattern. Complete the look with the matching midi skirt.

Shop Matching Bottoms: The Coolest Vibe Midi Skirt

Fit & Features
- Sleeveless square neckline
- Thin tank shoulder straps
- Cropped, form-hugging fit
- Marble print
- Lined knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4014

Category Name: Matching Sets

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Sunset Tie-Back Crop Top
Head to a spring sunset dinner with a view in this trendy crop top! It features a square neck, elasticized tank-style straps, and an open back with tie closure on stretchy, rib-knit fabric. Complete the look in the matching skirt.

Shop Matching Skirt: Spring Sunset Slit Maxi Skirt

Fit & Features
- Sleeveless, square neck
- Elasticized tank-style straps
- Cropped hem
- Open-back, tie closure
- Stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 06001-4070

Category Name: Matching Sets

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Mode Button-Down Cotton Top
Activate summer mode with this lightweight cotton button-down top featuring a collared neckline, long sleeves, and a relaxed, long-length fit. Style with the matching bra top and high-rise shorts for an effortlessly chic look.

Shop Matching Set: Summer Mode Cotton Bra Top, Summer Mode High-Rise Cotton Shorts

Fit & Features
- Textured cotton fabric, no stretch
- Collared neckline
- Complete button-down front
- Long sleeves, single button detail
- Long-length hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06003-000081

Category Name: Matching Sets

Price: $34.90

Availability: In Stock

Available Color: CHARTREUSE

Available Size: S, M, L
Product Badge:
- Part of a Set
Spring Sunset Slit Maxi Skirt
Head to a spring sunset dinner with a view in this maxi skirt! It features a high-rise waist, bodycon silhouette, and a sultry front slit on stretchy, rib-knit fabric. Complete the look in the matching top.

Shop Matching Top: Spring Sunset Tie-Back Crop Top

Fit & Features
- High-rise waist
- Bodycon silhouette
- Front slit
- Maxi-length hem
- Stretchy, rib-knit fabric
- Runs true to size
Style Number/Barcode: 06501-0626

Category Name: Matching Sets

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Eye Of The Tiger Bandeau Crop Top
It's the eye of the tiger it's the thrill of wearing this cute bandeau crop top for your next island vacay! It features a sleeveless, strapless neckline with a flirty front knot-tie and a smocked back. Complete the look in the matching bottoms.

Shop The Matching Bottoms: Eye Of The Tiger Palazzo Pants

Fit & Features
- Sleeveless, strapless neckline
- Front knot-tie closure
- Smocked back, crop hem
- Tiger print
- Chiffon-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1742

Category Name: Matching Sets

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Tide Tropical Mini Skirt
Feel the island breeze and enter paradise in this tropical mini skirt! It features a high-rise elasticized waist, a faux-wrap front, and a bodycon silhouette. Complete the look in the matching top.

Shop Matching Top: Island Tides Tropical Tie-Front Top

Fit & Features
- High-rise elasticized waist
- Faux wrap front
- Bodycon silhouette
- Mini-length hem
- Tropical print fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0638

Category Name: Matching Sets

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Eye Of The Tiger Palazzo Pants
It's the eye of the tiger it's the thrill of wearing these cute palazzo pants for your next island vacay! It features a high-rise waist, a side hidden zipper closure, and a flowy palazzo-style leg. Complete the look in the matching top.

Shop The Matching Top: Eye Of The Tiger Bandeau Crop Top

Fit & Features
- High rise waist
- Side hidden zipper closure
- Flowy palazzo-style leg
- Tiger print
- Chiffon-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0633

Category Name: Matching Sets

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Island Tides Tropical Tie-Front Top
Feel the island breeze and enter paradise in this tropical tie-front top! It features long bishop sleeves, a plunge V-neck, and a cropped hem. Complete the look in the matching skirt.

Shop Matching Skirt: Island Tide Tropical Mini Skirt

Fit & Features
- Long bishop sleeves
- Plunge V-neck
- Tie-front closure
- Cropped hem
- Tropical print fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0308

Category Name: Matching Sets

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Made For You Tie Front Bandeau Top
This bandeau top was made for you on vacation or pretending while sipping on cocktails poolside! It features a strapless, sleeveless, neckline with a flirty tie-front and a smocked back panel. Complete the look in the matching bottoms.

Shop Matching Bottoms: Made For You High Rise Palazzo Pants

Fit & Features
- Strapless, sleeveless neckline
- Tie-front
- Smocked back
- Textured lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06001-4095

Category Name: Matching Sets

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Made For You High Rise Palazzo Pants
These palazzo pants are made for you on vacation or pretending while sipping on cocktails poolside! They feature a high-rise waist, pleat front detailing, and a wide-leg silhouette. Complete the look in the matching top.

Shop Matching Top: Made For You Tie Front Bandeau Top

Fit & Features
- High-rise waist
- Pleat front detailing
- Wide-leg silhouette
- Pull-on/off styling
- Textured lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0631

Category Name: Matching Sets

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bold Babe Tie-Dye Mini Skirt
You're a total bold babe when it comes to your style, so this mini skirt was made for you. It features a high-rise waist, side ruched detailing leading to an adjustable drawstring at the hem, a short, curve-hugging fit, and a trendy all-over tie-dye print. Style with the matching crop top and statement earrings.

Shop Matching Top: Bold Babe Tie-Dye Crop Top

Fit & Features
- High-rise waist
- Side ruching, adjustable drawstring at the hem
- Mini-length, form-fitting silhouette
- Tie-dye print
- Soft brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0599

Category Name: Matching Sets

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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