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.
$6.97 $19.90 65% off
A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.
$36.90
A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.
$6.97 $26.90 74% off
A natural-colored crochet tube top featuring a wavy striped pattern and a sweetheart neckline.
$12.97 $29.90 57% off
A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.
$9.97 $39.90 75% off
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$9.97 $24.90 60% off
An airy orange crop top with a sweetheart neckline and charming open back bow design.
$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.
$16.97 $39.90 57% off
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$17.97 $42.90 58% off
A sultry taupe jumpsuit with a tropical print, featuring a cutout design and wide-leg silhouette.
$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 white cotton mini skort featuring a tiered ruffled overlay and hidden fitted knit shorts.
$22.90
A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.
$10.97 $24.90 56% off
A black tropical print maxi skirt in airy sheer mesh with a high-rise waist and sultry side slit.
$9.97 $34.90 71% off
A pink floral mesh maxi skirt with a high-rise waist and flattering bodycon fit.
$44.90
A brown striped crochet knit midi skirt featuring a high-rise waist, thigh-high side slit, and form-hugging fit.
$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.
$13.97 $32.90 58% off
A brown striped crochet bralette top featuring an open back, tie details, and ultra-cropped hem.
$29.90
A brown floral mesh crop top featuring sheer peasant sleeves and a flirty tie-front design.
$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.
$29.90
A black floral mesh crop top featuring long sleeves, a tie-front closure, and an ultra-cropped hem.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$14.97 $34.90 57% off
A brown floral mesh midi skirt with a high-rise waist and sultry front slit.
$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.
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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
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
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: 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: S | Knit Fabric
Call Me Cutie Floral Eyelet Mini Skirt in White
$9.97 $39.90
75% 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
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
Windsor Floral Sensation High Rise Maxi Skirt in Pink
$9.97 $34.90
71% off
Everyone will adore your look in this floral mesh maxi skirt perfect for vacay or weekend plans! With a high-rise waist, it accentuates your figure while the bodycon fit flatters your curves, and the center back slit offers movement. Complete the look with the matching top. Shop The Matching Top: Floral Sensation Strapless Crop BustierFit & FeaturesFloral print, mesh fabric lined with stretchy knit, High-rise waist, Bodycon fit, Center back slit, Maxi-length, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Floral Sensation High Rise Maxi Skirt in Pink | Size: S | Mesh Fabric/Mesh Fabric
Boho Babe Lace Hanky Hem Maxi Skirt in Ivory
$13.97 $32.90
58% off
Live out your boho era in this airy sheer lace maxi skirt with a mini-length lining for a chic look. The long flowy silhouette will create that effortlessly cool vibe. Fit & FeaturesSheer lace fabric with mini-length knit lining, High-rise waist, Hip-hugging fit, Maxi-length hanky hem, Flowy silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Boho Babe Lace Hanky Hem Maxi Skirt in Ivory | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric