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.
$9.97 $19.90 50% off
A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.
$6.97 $26.90 74% off
A natural-colored crochet tube top featuring a wavy striped pattern and a sweetheart neckline.
$44.90
A brown striped crochet knit midi skirt featuring a high-rise waist, thigh-high side slit, and form-hugging fit.
$24.90
An airy orange crop top with a sweetheart neckline and charming open back bow design.
$18.97 $44.90 58% off
A natural knit midi skirt featuring a wavy striped pattern and a high center back slit.
$9.97 $39.90 75% off
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$29.90
A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.
$34.90
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$28.90
A pink knit midi skirt featuring ruffle trim, side slit, high-rise waist, and bodycon fit.
$26.90
A tan tropical print crop top featuring a strapless neckline, mesh fabric, and soft knit lining.
$24.90
A black tropical print maxi skirt in airy sheer mesh with a high-rise waist and sultry side slit.
$36.90
A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.
$26.90
A chic ivory lace mini skirt with a high-rise waist and form-hugging fit.
$24.90
A vibrant yellow high-rise mini skirt featuring slinky knit fabric, side ruching, and a ruffled hem.
$24.90
A brown one-shoulder bikini top with a metallic sheen and sweetheart padded bust.
$42.90
A sultry taupe jumpsuit with a tropical print, featuring a cutout design and wide-leg silhouette.
$22.90
A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.
$34.90
A white cotton mini skort featuring a tiered ruffled overlay and hidden fitted knit shorts.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$24.90
A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.
$14.97 $34.90 57% off
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$42.90
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$29.90
A pink mesh-lined hot short featuring a low-rise waist and playful ruffled detailing for a flirty look.
$9.97 $39.90 75% off
An ivory floral mini skirt with glitter dots, ruffle trim, and a high-waist smocked style.
$34.90
A lightweight chartreuse cotton button-down top with a collared neckline, long sleeves, and relaxed fit.
$29.90
A brown floral mesh crop top featuring sheer peasant sleeves and a flirty tie-front design.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$32.90
A brown striped crochet bralette top featuring an open back, tie details, and ultra-cropped hem.
$36.90
A black polka dot halter crop top with lace trim and padded bra cups for stylish outings.
$29.90
A pair of chartreuse cotton shorts featuring a high-rise elastic waist, dual front pockets, and fitted silhouette.
$29.90
A black floral mesh crop top featuring long sleeves, a tie-front closure, and an ultra-cropped hem.
Now Trending
Slay It With Style Mini Skirt in Black
$9.97 $22.90
56% 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: L | 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 Tan | Size: XS | Faux Suede
Windsor Cute And Trendy Cargo Mini Skirt in Dark Denim-2
$13.97 $34.90
60% off
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
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: L | Knit 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
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 Ivory | Size: M | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades! Fit & FeaturesCrochet fabric, stretchy knit lining, High-rise elasticized waist, High front slit, Flowy maxi-length silhouette, Runs true to size , Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top Free Shipping on All Orders Over $75. | Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural | Size: L | Knit Fabric
Call Me Cutie Floral Eyelet Mini Skirt in White
$16.97 $39.90
57% off
Get ready for everyone to call you cute in this floral mini skirt designed with a flirty layered ruffle that captures attention and a mini-length hem that lets you flaunt your figure. Pair with the matching top. Shop Matching Top: Call Me Cutie Lace-Up Floral Eyelet Corset TopFit & FeaturesFloral print, eyelet woven lined fabric, Stretchy smocked high-rise waist, Layered ruffle , Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Call Me Cutie Floral Eyelet Mini Skirt in White | Size: L
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.