Vacation Matching Sets
Dreaming of sun-soaked beaches and endless summer vibes? Dive into our collection of vacation matching sets that are ready to jet-set with you! These effortlessly chic combos are your ticket to turning heads from the airport lounge to sunset cocktails. Whether you're planning a tropical escape or a stylish city break, these sets have got you covered in all the right ways. Pack your bags, grab your sunnies, and get ready to slay every step of your getaway with confidence and flair. Because let's be real—every Windsor girl knows that the best adventures start with the perfect outfit.
$19.90
An ivory floral print crop top in stretchy knit fabric with a bold, chic strapless design.
$36.90
An ivory floral print maxi skirt with a high-rise waist and flowy knit fabric.
$26.90
A natural-colored crochet tube top featuring a wavy striped pattern and a sweetheart neckline.
$19.90
A natural crochet bandeau crop top with a tie-front closure, perfect for vacation or festivals.
$24.90
A trendy one-shoulder bikini top in brown lurex knit fabric with a metallic sheen.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$34.90
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$19.90
A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.
$10.97 $26.90 59% off
A pink high-rise lace mini skirt featuring adjustable side ties and a ruffled hem.
$29.90
An ivory floral ruffled skort with a high-rise smocked waistband and tiered silhouette.
$24.90
A red gingham print bandeau bikini top featuring a ruffled trim and tie-front detail.
$24.90
An airy orange woven crop top with a sweetheart neckline and charming tie-back bow design.
$24.90
A brown sweetheart bikini top with a metallic sheen, featuring lurex knit fabric and adjustable straps.
$6.97 $26.90 74% off
A stylish black and white geometric print halter crop top with a flattering O-ring bust.
$26.90
A blush bodycon midi skirt with a high-rise waist and side ruched seams in stretchy knit.
$22.90
A natural crochet crop top featuring a halter neckline and spaghetti strap tie for vacation style.
$34.90
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$24.90
A rust-colored knit tube top featuring a cutout design and beaded accents for vacation or prom.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$19.90
A chic green ribbed knit tank top featuring a sleeveless square neckline and cropped hem.
$29.90
A natural chevron knit tube top featuring a strapless neckline and fitted crop hem.
$24.90
A tropical print maxi skirt in black mesh with a high-rise waist and sultry side slit.
$29.90
An airy orange woven midi skirt with a high slit, tie detail, and flowy slim-fit silhouette.
$36.90
A chic ivory mesh maxi skirt featuring a flocked floral pattern and high-rise lace-trimmed waist.
$29.90
A pink floral mesh bustier with a strapless neckline and fitted crop hem for a flirty look.
$42.90
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$24.90
A multi-color floral tie-front bikini top with short puff sleeves and ruffled trim in knit fabric.
$54.90
A tan floral tapestry cropped jacket with a collared neckline, button-down front, and dual pockets.
$22.90
A breezy ivory lace top with a tie-front design, short sleeves, and a relaxed fit.
$39.90
An ivory floral maxi skirt with a high-rise waist and flattering bodycon fit in mesh fabric.
$26.90
A gold knit cropped halter top featuring cutouts and beaded detailing, perfect for vacations or prom.
$32.90
A natural woven fabric vest with a lapel collar and tie-front design for a chic beachy vibe.
$39.90
An ivory floral mini skirt with glitter dots, ruffle trim, and a high-waist smocked style.
$26.90
A chic ivory lace mini skirt with a high-rise waist and form-hugging fit.
$29.90
A leopard print tube top featuring a ruffled design and stretchy knit lining for festivals.
$39.90
A natural chevron knit midi skirt with a high-rise waist and bodycon silhouette.
$22.90
A chic brown bikini bottom with O-ring insets, low-rise waist, and cheeky coverage.
$18.90
A trendy brown short sarong with a metallic sheen, crafted from lurex knit fabric.
$24.90
A brown knit triangle bikini top featuring O-ring insets and a flirty knotted bust.
$22.90
A flirty white eyelet bikini bottom with dual string ties and cheeky coverage.
$22.90
A multi-colored floral bikini bottom with a low-rise waist, ruffle trim, and cheeky fit.
$29.90
An ivory mesh top with a flocked floral pattern, tie-front, and elegant bell sleeves.
$19.90
A white knit pajama top featuring a playful lemon print, short sleeves, and a fitted crop hem.
$44.90
A natural knit midi skirt featuring a wavy striped pattern and a high center back slit.
$32.90
A trendy leopard-printed mini skort with a mid-rise waist and hidden fitted shorts.
$9.97 $16.90 41% off
A stylish black mini skirt with a high-rise waist and bodycon fit in textured knit fabric.
$36.90
An ivory floral corset top with glitter dots, sweetheart neckline, and adjustable spaghetti straps.
Now Trending
Windsor Slay It With Style Mini Skirt in Black
$18 $22.90
21% off
Elevate your going-out looks in this sleek faux leather mini skirt! This high-waist mini skirt features a sexy front slit and hidden back zipper for a seamless look at every angle. Make this faux leather mini skirt your wardrobe must-have for date night or clubbing with your party squad. Pair this flirty mini skirt with a beaded bustier top or long-sleeve satin tie-front top for a sexy and fierce night-out look. Fit & FeaturesHigh-rise fit, Vertical seam details, back zipper, Front slit accent, Form-hugging fit, Mini-length hem, Unlined faux leather fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Slay It With Style Mini Skirt in Black | Size: M | Leather/Satin Fabric
Channel your western side with this trendy-chic skirt that will level up your festival look! It features a high-rise waist, an asymmetric mini-length hem with a form-hugging fit, and long fringe detailing that cascades to your ankles. The stylish fringe design will dance with you to your favorite band! Complete your 'fit with a cropped graphic tee and cowboy boots. Fit & FeaturesHigh-rise waist, Back zipper, hook and eye closure, Asymmetric mini-length hem, Form-hugging fit, Long fringe design, ankle-length hem, Faux suede fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Wild At Heart Long Fringe Skirt in Black | Size: L | Faux Suede
Serve major style in this on-trend cargo mini skirt! Featuring a high-rise waist, vertical seam detailing, cargo-style side pockets, a mini-length hem, and a form-hugging fit, this skirt will level up your basic looks. The twill fabric offers minimal stretch. Style with a halter bodysuit and strappy mules. Fit & FeaturesHigh-rise waist, Belt loops, hidden front zipper, button closure, Vertical seams, Cargo side pockets, Mini-length hem, form-hugging fit, Twill fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Serving Style Cargo Mini Skirt in Brown | Size: M
This cute and trendy cargo mini skirt will step up this season's 'fits! It features a mid-rise waist, an included removable belt with a double grommet design, cargo-style side pockets, a mini-length hem, and a fitted silhouette. The denim fabric offers a moderate stretch. Style this denim skirt with a crop top and clear mules. Fit & FeaturesMid-rise waist, hidden front buttons, zipper closure, Included removable belt, double grommet design, Dual cargo-style side pockets, Mini-length hem, Fitted silhouette, Denim fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute And Trendy Cargo Mini Skirt in Dark Denim-2 | Size: S
Fit & FeaturesStretchy smooth knit-lined fabrication, High-rise fit, Ruching, Asymmetrical high-side slit, Midi length hem, Runs true to size, Shop Matching Crop Top: Bold Staple Long Sleeve Crop Top Free Shipping on All Orders Over $75. | Windsor Bold Staple Ruched Asymmetrical Midi Skirt in Black | Size: XS
Level up your sleek status with this chic mini skirt made with smooth faux leather fabric to elevate your casual 'fits. It features a high-rise waist, a side slit accent at the hem, and a form-hugging silhouette to highlight your stunning curves. Fit & FeaturesFaux leather fabric, plenty of stretch, High-rise elasticized waist, Side slit, Mini-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Status Faux Leather Mini Skirt in Black | Size: S
Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, adjustable drawstring, High side slit, Asymmetric maxi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Breezy Boho Sheer Lace Asymmetric Maxi Skirt in Black | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Make a statement in this lace slit maxi skirt. With sheer lace, ruching, and a high slit, it's your go-to for that effortlessly chic vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, plenty of stretch, High-rise waist, Ruching, High front slit, Maxi-length hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Keep A Secret Lace Slit Maxi Skirt in Black | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Step out looking like goals in this micro mini skirt with a flirty side slit and bodycon fit that'll get you noticed! Fit & FeaturesStretchy knit fabric, High-rise waist, Side slit, Bodycon silhouette, Micro mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor First Take Micro Slit Mini Skirt in Black | Size: M | Knit Fabric
This airy woven midi skirt will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric with a mini-length lining, it features a high waist with the cutest tie detail, a high-cut side slit to showcase some leg, and a flowy slim-fit silhouette. Style with the matching crop top for a fabulous 'fit! Shop Matching Orange Top: Sunny Vibes Bow Back Woven Crop TopFit & FeaturesWoven fabric with mini-length knit lining, minimal stretch, High-rise elasticized waist, Tie detail, High side slit, Flowy slim-fit silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunny Vibes High Slit Woven Midi Skirt in Orange | Size: S | Knit Fabric/Woven Fabric
Vacation Matching Sets
Ready to make your next getaway one for the books? Matching vacation sets are here to make packing a breeze and your Insta feed pop. Think about it: you roll up to your dream destination, suitcase in hand, and every outfit is already styled to perfection. No more frantic outfit planning or mismatched vibes—just you, living your best life in coordinated looks that scream main character energy. Whether you’re jetting off for a girls’ trip, planning that romantic escape, or plotting a countryside holiday with the fam, vacation sets are the ultimate travel hack. There’s something about slipping into a 2 piece vacation set that just feels effortless—like you woke up fabulous and didn’t even have to try. The best part? These sets are basically a gift to your future self (or your BFF, because who doesn’t love a surprise that says “pack your bags, babe!”). Imagine the look on her face when she unwraps a matching vacation set that’s just *so* her. It’s the kind of present that says, “I see you, I get you, and I want you to shine.” And if you’re the one treating yourself (as you should), you’ll love how these sets make every vacay moment feel a little more put together, whether you’re exploring a new city, sipping cocktails by the pool, or dancing under the stars.
Let’s talk versatility, because that’s where matching vacation sets seriously deliver. You can mix and match tops and bottoms for endless outfit combos, or go full-on coordinated for that head-turning wow factor. Skirt sets for vacation are a total game-changer—think breezy fabrics, flirty cuts, and colors that look even better with a little sun-kissed glow. There’s a reason countryside holiday skirt sets are having a major moment; they’re perfect for twirling through flower fields, brunching on a terrace, or just vibing with your favorite playlist on a scenic drive. And when the mood calls for a little poolside glam, don’t forget to check out our curated collection of Vacation Swimsuits to complete your look. Matching vacation sets aren’t just about looking cute (though, let’s be honest, you will)—they’re about feeling confident, carefree, and totally yourself, wherever your adventures take you. Whether you’re a spontaneous road tripper, a meticulous itinerary queen, or the friend who always finds the hidden gems, these sets are your ride-or-die style companions. Pack your bags, grab your girls, and get ready to make every moment unforgettable—because your next adventure deserves an outfit (or five) that’s as bold and fun as you are.