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.
$14.97 $36.90 59% off
A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.
$6.97 $32.90 79% off
A brown striped crochet bralette top featuring an open back, tie details, and ultra-cropped hem.
$13.97 $32.90 58% off
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$9.97 $24.90 60% off
A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.
$9.97 $39.90 75% off
An ivory floral mini skirt with glitter dots, ruffle trim, and a high-waist smocked style.
$22.90
A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.
$39.90
A natural woven fabric trouser with a high-rise waist and wide-leg silhouette for chic beachy vibes.
$9.97 $29.90 67% off
A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.
$10.97 $26.90 59% off
A chic ivory lace mini skirt with a high-rise waist and form-hugging fit.
$9.97 $39.90 75% off
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$29.90
A black mesh-lined crop top featuring cap sleeves, ruffled hem, and a bungee lace-up back.
$18.97 $44.90 58% off
A brown striped crochet knit midi skirt featuring a high-rise waist, thigh-high side slit, and form-hugging fit.
$9.97 $34.90 71% off
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$29.90
An ivory mesh top with a flocked velvet floral pattern, tie-front, and bell sleeves.
$29.90
A pair of chartreuse cotton shorts featuring a high-rise elastic waist, dual front pockets, and fitted silhouette.
$17.97 $42.90 58% off
An ivory knit wrap skirt with a tie-waist and cascading fringe hem for a chic getaway look.
$14.97 $34.90 57% off
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$12.97 $29.90 57% off
A black floral mesh crop top featuring long sleeves, a tie-front closure, and an ultra-cropped hem.
$9.97 $39.90 75% off
A natural chevron knit midi skirt with a high-rise waist and bodycon silhouette.
$34.90
A lightweight chartreuse cotton button-down top with a collared neckline, long sleeves, and relaxed fit.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$12.97 $29.90 57% off
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.
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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
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
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
Windsor Iconic Getaway Tie-Waist Wrap Fringe Skirt in Ivory
$17.97 $42.90
58% off
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
Windsor Vacay Ready High Rise Crochet Maxi Skirt in Natural
$13.97 $32.90
58% off
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
This faux leather skirt gives life to the party vibes! It has lace-up sides that demand attention, a high-rise waist, and a flattering form-hugging fit that shows off your figure. Fit & FeaturesFaux leather fabric, High-rise waist, Back zipper closure, Side lace-ups , Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Life Of The Party Lace-Up Mini Skirt in Brown | Size: S | Leather
Blissful View Crochet Knit Midi Skirt in Light Blue
$9.97 $39.90
75% off
Enjoy stylish bliss in this crochet midi skirt on your next getaway or weekend outing! The skirt offers a flattering high-rise waist, a bodycon fit, and a midi-length hem. Complete the look with the matching halter top. Shop Matching Top: Blissful View Halter Crochet Crop TopFit & FeaturesCrochet knit fabric, geometric pattern, knit lining, High-rise waist, ribbed detail, Midi-length hem, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Blissful View Crochet Knit Midi Skirt in Light Blue | Size: L | Knit Fabric
Breezy Vibes Lace Mini Skirt in Ivory
$10.97 $26.90
59% off
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