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.
$19.90
A natural crochet bandeau crop top with a tie-front closure, perfect for vacations and festivals.
$44.90
A natural knit midi skirt featuring a wavy striped pattern and a high center back slit.
$34.90
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$36.90
A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.
$19.90
A vibrant yellow knit crop top featuring a tropical floral print and a strapless neckline.
$29.90
A floral ivory skort with a ruffled tiered silhouette and high-rise smocked waistband.
$24.90
A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.
$39.90
A natural-colored woven fabric trouser with a high-rise waist and wide-leg silhouette.
$32.90
A lime yellow halter crop top featuring clear sequin embroidery, tie-back straps, and a fitted hem.
$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.
$19.90
A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.
$12.97 $29.90 57% off
A natural chevron knit tube top featuring a strapless neckline and fitted crop hem.
$46.90
A black and white striped midi skirt with a bodycon silhouette and mid-rise waist in stretchy knit.
$22.90
A blush knit crop top featuring a ruffled V-neckline and tie-front closure for a chic look.
$26.90
A gold knit cropped halter top featuring cutouts, beaded detailing, and halter neck ties.
$19.90
A vibrant yellow halter crop top crafted from stretchy knit fabric with a cowl neckline and ruched sides.
$39.90
An ivory floral mini skirt with glitter dots, ruffle trim, and a high-waist smocked style.
$36.90
A vibrant orange floral maxi skirt in chiffon with a high-rise waist and curve-hugging silhouette.
$24.90
A brown knit triangle bikini top featuring O-ring insets and a flirty knotted bust.
$24.90
A black tropical print maxi skirt in airy sheer mesh with a high-rise waist and sultry side slit.
$26.90
A natural-colored crochet tube top featuring a wavy striped pattern and a sweetheart neckline.
$24.90
A vibrant yellow high-rise mini skirt featuring slinky knit fabric, side ruching, and a ruffled hem.
$24.90
A rust-colored knit tube top featuring a cutout design and beaded accents for vacation or prom.
$28.90
A pink knit midi skirt featuring ruffle trim, side slit, high-rise waist, and bodycon fit.
$32.90
A natural crochet maxi skirt with a high-rise waist and sultry front slit, perfect for vacations.
$42.90
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$26.90
A chic ivory lace mini skirt with a high-rise waist and form-hugging fit.
$22.90
A breezy ivory lace top with a tie-front design, short sleeves, and a relaxed fit.
$34.90
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$13.97 $32.90 58% off
A leopard-printed woven mini skort with a mid-rise waist and side zipper closure.
$29.90
A black mesh-lined crop top featuring cap sleeves, ruffled hem, and a bungee lace-up back.
$39.90
A black floral mesh maxi skirt featuring a high-rise waist, dramatic front slit, and attached panty lining.
$32.90
A natural woven fabric vest with a tie-front design and lapel collar for a chic beachy vibe.
$29.90
A pink mesh-lined hot short featuring a low-rise waist and playful ruffled detailing for a flirty look.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$39.90
A black tropical print maxi skirt in stretchy knit fabric with a high front slit and flowy silhouette.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$9.97 $22.90 56% off
A black and white tropical tie front crop top with fluttery sleeves and palm print knit fabric.
$29.90
A rust-colored knit pant with a mid-rise waist and flared wide-leg hem.
$32.90
A brown striped crochet bralette top featuring an open back, tie details, and ultra-cropped hem.
$24.90
A brown one-shoulder bikini top with a metallic sheen and sweetheart padded bust.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$42.90
A pair of multi-color woven palazzo pants featuring a tropical print, high-rise waist, and wide-leg silhouette.
$29.90
A brown floral mesh crop top featuring sheer peasant sleeves and a flirty tie-front design.
$36.90
A black polka dot halter crop top with lace trim and padded bra cups for stylish outings.
$42.90
A sultry taupe jumpsuit with a tropical print, featuring a cutout design and wide-leg silhouette.
Now Trending
Windsor Beautifully Beaded Mesh Crop Top in Black | Size: S | Mesh Fabric/Sheer Mesh Fabric Free Shipping on All Orders Over $75.
Embrace sultry charm and chic style with this ruched corset crop top. The flattering off-the-shoulder neckline exudes elegance, while the gathered hook and eye bodice accentuate your hourglass figure. Its cropped length offers a fresh, modern edge—perfect with high-waisted denim or skirts. The tie sleeves introduce a playful touch to this versatile top, ideal for amplifying a night-out ensemble or a casual brunch look with friends. Fit & FeaturesOff-the-shoulder neckline, ruched short sleeves, Sweetheart bust with lace trim, Padded cups, built-in non-slip strip , Hidden front hook-eye closures, Cropped hem, Lined mesh fabric, minimal stretch, Runs true to size , Free Shipping on All Orders Over $75. | Windsor Hooked In Ruched Crop Top in Beige | Size: L | Mesh Fabric/Mesh Fabric
Take the plunge and dare to show skin in this sleeveless halter crop top for a night out! Featuring a halter cowl neckline with bar trim, an open back, and a stylish crop hem, this top is perfect for standing out and making a statement. Complete the look in sleek faux leather pants. Fit & FeaturesSlinky knit fabric, plenty of stretch, Bar trim, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Take The Plunge Sleeveless Halter Crop Top in Pink-2 | Size: L | Leather/Knit Fabric
Bring the heat in this fab crop top! It features a round neckline, long sleeves, and a cropped hem. The all-over heat stones give this top all the dazzling shine you need! The crop top is composed of a sheer unlined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with a high waist mini skirt and heels for a stunning night out look. Fit & FeaturesCrew neckline, Long fitted sleeves, Heat stones, Cropped hem, Unlined mesh fabric, Form-hugging fit, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Feel The Heat Stone Crop Top in Black | Size: L | Mesh Fabric/Mesh Fabric
Windsor Casual Must-Have Crew Neck Crop Top in Black | Size: S Free Shipping on All Orders Over $75.
You'll be easy and breezy in this strapless lace crop top perfect for concerts or festivals! This flirty top features a strapless neckline, a front slit with a drawstring tie, and an asymmetrical cropped hem on lace-lined fabric. Complete the look in a denim mini skirt. Fit & FeaturesLace fabric lined with stretchy knit, Strapless neckline, Front slit, drawstring tie, Asymmetrical cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sheer Charm Strapless Lace Crop Top in Black | Size: S | Lace Fabric
Everyone will want your style secrets after seeing you in this glitzy rhinestone crop top! It features a crew neckline, long fitted sleeves, a fitted cropped hem, and is composed of a sultry sheer fishnet fabric with all-over mini rhinestone embellishments. Style over a lacy bralette with faux leather pants for a night out. Fit & FeaturesCrew neckline, Long fitted sleeves, Fitted cropped hem, Sheer fishnet fabric, Mini rhinestone embellishments, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glitzy Muse Rhinestone Fishnet Crop Top in White | Size: S | Leather/Rhinestone
Give off edgy glam girl energy in this sultry rhinestone fishnet top! It features a crew neckline, long fitted sleeves, a fitted, cropped hem, and all-over mini rhinestone embellishments for an alluring shine. The sheer fishnet fabric offers a moderate stretch. Style over a bralette with faux leather shorts for festival season! Fit & FeaturesCrew neckline, Long fitted sleeves, Fitted, cropped hem, Mini rhinestone embellishments, Sheer fishnet fabric, Moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Edgy Glam Girl Rhinestone Fishnet Top in Black | Size: M | Leather/Rhinestone
You'll be such a trendy cutie in this lace-up ribbed smooth knit crop top! Made with the iconic ribbed smooth knit fabric, it offers plenty of stretch for ultra-comfortable wear. The top features a crew neckline, short sleeves, an open lower back with a lace-up strappy design to add some allure, and a cropped hem with a form-hugging fit for a snatched look. Style with a denim skirt and lace-up heels! Fit & FeaturesRibbed smooth knit fabric, plenty of stretch, Crew neckline, Short sleeves, Open lower back, lace-up straps, tie closure, Cropped, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Trendy Cutie Lace-Up Ribbed Smooth Knit Crop Top in Black | Size: XS | Knit Fabric
A cropped rhinestone halter top that'll inspire your next going-out look! It features a sultry plunge cowl neckline and a partially open back that turns heads. Pair with jeans. Fit & FeaturesSheer mesh fabric with knit lining, moderate stretch, Studded rhinestones, Plunging halter neckline, cowl bust, Mini bar strap at bust, Halter neck ties, partially open back , Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Party Diva Cropped Rhinestone Halter Top in Beige | Size: S | Knit Fabric/Rhinestone/Mesh 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.