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.
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RECOMMENDED
$24.90
An airy orange crop top with a sweetheart neckline and charming open back bow design.
$29.90
An airy orange woven midi skirt with a high slit and tie detail for sunny vibes.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$19.90
A natural crochet bandeau crop top with a tie-front closure, perfect for vacations and festivals.
$6.97 $26.90 74% off
A stylish black and white geometric print halter crop top with a flattering O-ring bust.
$36.90
An ivory floral print maxi skirt with a high-rise waist and flowy knit fabric.
$33.90
A chic brown strapless midi dress with a bodycon silhouette in soft, stretchy rib knit fabric.
$26.90
A stretchy green midi skirt featuring ruching and an asymmetrical high-side slit for stylish occasions.
$9.97 $32.90 70% off
An ivory lace mini skirt with a high-rise waist and adjustable drawstring for a flattering fit.
$22.90
A natural crochet crop top featuring a halter neckline and spaghetti strap tie for vacation style.
$54.90
A tan floral tapestry cropped jacket with a collared neckline, button-down front, and dual pockets.
$6.97 $18.90 63% off
A vibrant red crop top with a smocked knit fabric, sweetheart neckline, and tie-front detail.
$9.97 $36.90 73% off
A mauve high-rise denim skort with zipper detailing and pleated hem for versatile style.
$39.90
An ivory floral maxi skirt with a high-rise waist and flattering bodycon fit in mesh fabric.
$6.97 $22.90 70% off
A brown strapless tube crop top with a smocked back and cinched front for a flirty look.
$25.90
An olive bikini top with textured triangle cups, O-ring detail, and adjustable back ties.
$26.90
A natural-colored crochet tube top featuring a wavy striped pattern and a keyhole cutout.
$24.90
An olive high-rise bikini bottom with a V-cut waist and adjustable side ties for a custom fit.
$9.97 $29.90 67% off
A vibrant red smocked knit flare pant with a flattering V-waist, perfect for vacations or nights out.
$26.90
A pink high-rise lace mini skirt with adjustable side ties and a ruffled mini-length hem.
$34.90
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$22.90
A brown nylon-blend bikini bottom with a V-cut design and ruched side detailing.
$22.90
A vibrant yellow bikini bottom with ribbed knit fabric, V-cut design, and scrunched sides.
$24.90
A brown polka-dot one-shoulder bikini top in stretchy nylon with a form-hugging fit.
$29.90
An ivory mesh top with a flocked velvet floral pattern, tie-front, and elegant bell sleeves.
$24.90
A brown high V-cut bikini bottom with adjustable side ties and cheeky coverage in textured fabric.
$9.97 $22.90 56% off
A black and white tropical tie front crop top with fluttery sleeves and palm print knit fabric.
$9.97 $16.90 41% off
A stylish black mini skirt featuring a high rise waist and bodycon fit in textured knit fabric.
$9.97 $32.90 70% off
A taupe crochet crop sweater with dual tie-front closures and trendy flare cuffs.
$26.90
A brown textured bandeau bikini top with removable padded cups and secure hook closures.
$9.97 $42.90 77% off
A multi-colored leopard print midi skirt with lined mesh fabric and a back center slit.
$29.90
A brown floral mesh crop top featuring sheer peasant sleeves and a flirty tie-front design.
$25.90
A yellow ribbed knit bikini top featuring an off-the-shoulder ruffled design with structured underwire support.
$24.90
A brown triangle bikini top with adjustable straps and knotted detail, made from stretchy nylon-blend fabric.
$29.90
A pink floral mesh bustier with a strapless neckline and fitted crop hem for a flirty look.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$26.90
A gold knit cropped halter top featuring cutouts and beaded detailing, perfect for vacations or prom.
$44.90
A natural knit midi skirt featuring a wavy striped pattern and a high center back slit.
$34.90
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$19.90
An ivory floral print crop top in stretchy knit fabric with a bold, chic strapless design.
$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 corset top with flexible boning and a form-hugging fit.
$36.90
A chic ivory mesh maxi skirt featuring a flocked floral pattern and high-rise lace-trimmed waist.
$29.90
A pair of rust-colored knit wide-leg pants with a mid-rise waist and flared hem.
$34.90
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$29.90
A floral ivory skort with a ruffled tiered silhouette and high-rise smocked waistband.
Now Trending
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, | Windsor Slay It With Style Mini Skirt in Black | Size: S | Leather/Satin Fabric Free Shipping on All Orders Over $75.
Windsor Bring On The Glam Mini Skirt in Ivory
$9.97
$39.90
75% off
Bring on the glamour with a mini skirt that is part sultry, part glitz! The skirt features a high-rise waist, an asymmetrical high side slit, a rhinestone fringe, and a mini-length hem. The skirt is composed of a lined faux leather fabric that offers a form-hugging fit with a moderate stretch. Complete the look with a bodysuit and mules. Fit & FeaturesHigh rise waist, Asymmetrical high side slit, Rhinestone fringe, Mini length hem, Faux leather fabric, Form-hugging fit, moderate stretch , Runs true to size, | Windsor Bring On The Glam Mini Skirt in Ivory | Size: S | Leather/Rhinestone Free Shipping on All Orders Over $75.
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, | Windsor Wild At Heart Long Fringe Skirt in Tan | Size: S | Faux Suede Free Shipping on All Orders Over $75.
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, | Windsor Serving Style Cargo Mini Skirt in Brown | Size: M Free Shipping on All Orders Over $75.
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, | Windsor Cute And Trendy Cargo Mini Skirt in Black | Size: S Free Shipping on All Orders Over $75.
Capture bold style with this faux leather slit mini skirt in a sleek bodycon silhouette. Pair with knee-high boots. Fit & FeaturesFaux leather fabrication, Mid-rise fit, High side slit, Mini length hem, Runs true to size, | Windsor Bold Allure Faux Leather Mini Skirt in Wine | Size: L Free Shipping on All Orders Over $75.
Boho Allure Ruffled Lace Midi Skirt in Black
$9.97
$29.90
67% off
Bring the bohemian western allure to your summer 'fits with this breezy ruffled lace midi skirt! Designed with sheer floral lace fabric, it includes a built-in knit shorts lining for coverage. The skirt features a high-rise elasticized waist for added stretch, an asymmetric midi-length hem creating a high-cut side slit accented with a ruffled trim, and a form-hugging silhouette. Style with a crop top and sandals. Fit & FeaturesSheer floral lace fabric with knit shorts lining, Moderate stretch, High waist, Asymmetric midi-length hem, Ruffled trim, Form-hugging fit, Runs true to size, | Windsor Boho Allure Ruffled Lace Midi Skirt in Black | Size: M | Lace Fabric/Knit Fabric Free Shipping on All Orders Over $75.
Sculpted Sultry Bandage Mini Skirt in Chartreuse
$9.97
$34.90
71% off
This flirty and sultry bandage mini skirt has everything you need to stand out! Featuring a high-rise waist, a bodycon silhouette, and a mini-length hem, it flatters your curves with every move. Crafted from a seamless bandage knit fabric designed to fit like a glove. Complete the look with the matching top. Shop Matching Top: Sculpted Sultry Bandage Halter Crop TopFit & FeaturesSleeveless halter neckline with strap, Open back, Flexible boning, front hook and eye closures, Cropped hem, Seamless bandage knit fabric, Minimal stretch, Runs true to size, | Windsor Sculpted Sultry Bandage Mini Skirt in Chartreuse | Size: XS | Knit Fabric Free Shipping on All Orders Over $75.
A pleated mini skirt perfect for downtown girlies! Pair with a crop sweater and boots. Fit & FeaturesWoven fabric, Faux leather belted mid-rise waist, Pleated silhouette, Short-length hem, Runs true to size, | Windsor Downtown Girl Belted Pleated Mini Skirt in Plum | Size: S | Leather/Woven Fabric Free Shipping on All Orders Over $75.
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, | Windsor Sunny Vibes High Slit Woven Midi Skirt in Orange | Size: M | Knit Fabric/Woven Fabric Free Shipping on All Orders Over $75.