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
A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.
$12.97 $29.90 57% off
A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$10.97 $24.90 56% off
A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.
$34.90
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$9.97 $39.90 75% off
An ivory floral mini skirt with glitter dots, ruffle trim, and a high-waist smocked style.
$13.97 $32.90 58% off
A brown striped crochet bralette top featuring an open back, tie details, and ultra-cropped hem.
$26.90
A chic ivory lace mini skirt with a high-rise waist and form-hugging fit.
$39.90
A natural woven fabric trouser with a high-rise waist and wide-leg silhouette for chic beachy vibes.
$29.90
A black floral mesh crop top featuring long sleeves, a tie-front closure, and an ultra-cropped hem.
$11.97 $28.90 59% off
A pink knit midi skirt featuring ruffle trim, side slit, high-rise waist, and bodycon fit.
$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.
$22.90
A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.
$14.97 $34.90 57% off
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$42.90
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$16.97 $39.90 57% off
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$44.90
A brown striped crochet knit midi skirt featuring a high-rise waist, thigh-high side slit, and form-hugging fit.
$29.90
A black mesh-lined crop top featuring cap sleeves, ruffled hem, and a bungee lace-up back.
$36.90
A vibrant orange floral maxi skirt in chiffon with a high-rise waist and curve-hugging silhouette.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$34.90
A white cotton mini skort featuring a tiered ruffled overlay and hidden fitted knit shorts.
$9.97 $39.90 75% off
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$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
Flirty and chic will be your vibe in this flocked floral mesh tie-front top, perf for date night. Style with the matching midi skirt and stiletto heels. Shop Matching Bottoms: Flirt Alert Flocked Floral Mesh Maxi SkirtFit & FeaturesMesh fabric with flocked velvet floral pattern, V-neckline with lace trim, Long bell sleeves, Mid-length hem with lettuce-edge trim, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt Alert Flocked Floral Mesh Tie-Front Top in Ivory | Size: L | Mesh Fabric/Mesh Fabric
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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
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
Channel that coastal chic vibe with this breezy linen maxi skirt featuring a tiered design, high-cut side slit, and flowy A-line silhouette. Fit & FeaturesLinen-blend fabric, High-rise waist, Tiered design, Thigh-high side slit, Flowy A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Coastal Breeze Linen High Slit Maxi Skirt in Natural | Size: L
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: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric
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 Ivory | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Get ready for an iconic getaway with this tie-waist wrap fringe skirt perfect for days spent under the sun or sipping on drinks poolside! Fit & FeaturesCrochet knit design, sewn-in knit lining, Wrap-tie waist, Back zipper and hook-eye closure, Cascading fringe hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Iconic Getaway Tie-Waist Wrap Fringe Skirt in Ivory | Size: M | Knit 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
Show off a breezy chic vibe in this airy lace mini skirt featuring a high-rise waist and a short form-hugging fit. Style with the matching tie-front top for a weekend getaway. Shop Matching Top: Breezy Vibes Lace Tie-Front TopFit & FeaturesSheer lace fabric with lining, High-rise waist, eyelet lace trim, Mini-length bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Breezy Vibes Lace Mini Skirt in Ivory | Size: L | Lace Fabric/Sheer Lace Fabric
One Short Day Linen High-Rise Ruffle Mini Skirt in Natural
$15.97 $36.90
57% off
Easy and effortless, this linen mini skirt boasts a playful vibe with a ruffled hem perfect for sunny-day dressing! Fit & FeaturesLinen-blend woven fabric, sewn-in knit lining, High-rise waist, Side zipper and hook-eye closure, Ruffled mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor One Short Day Linen High-Rise Ruffle Mini Skirt in Natural | Size: M | Knit Fabric/Woven Fabric