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.
$22.90
A brown cowl neck crop top crafted from double-lined, stretchy knit fabric with adjustable spaghetti straps.
$32.90
An abstract animal print burgundy mini skort featuring tiered ruffles, sheer mesh, and hidden knit shorts.
$34.90
A pair of ivory knit wide-leg pants featuring a tropical print, high-rise waist, and relaxed fit.
$42.90
A black bouclé lurex mini skort featuring a sparkly woven texture, gold buttons, and a ruffle hem.
$32.90
An olive green maxi skirt crafted from double-lined, slinky knit fabric with a flattering bodycon fit.
$36.90
A light blue floral mesh maxi skirt featuring a high-rise waist, ruching, and a high-cut side slit.
$32.90
A grey mesh mini skirt featuring rhinestone floral embellishments and an abstract print for modern shine.
$32.90
An ivory crochet bralette top featuring a plunging V-neck, scalloped trim, and open tie-back design.
$29.90
A light blue floral mesh halter top featuring a plunging V-neckline, tie-back straps, and open back.
$24.90
An olive green crop tank top crafted from double-lined, slinky knit fabric with a square neckline.
$39.90
A rust-colored knit maxi skirt featuring bold leopard and snake prints with an O-ring waist accent.
$36.90
A banana yellow floral knit maxi skirt with a fluid drape, curve-hugging fit, and flared hem.
$29.90
A chartreuse ribbed knit crop jacket featuring a zip-up front, mock neckline, and fitted long sleeves.
$29.90
A black mesh-lined hot short featuring a low-rise waist and playful ruffled detailing for a flirty look.
$29.90
A grey mesh halter top featuring rhinestone floral embellishments and an abstract print for modern shine.
$25.90
A rust-colored knit bikini bottom featuring cheeky coverage, adjustable beaded side ties, and a low-rise waist.
$24.90
A sheer mesh zebra print crop top with a crew neckline and short sleeves for bold style.
$34.90
A black pinstripe knit vest featuring a V-neckline, button-up front, and cropped hem for chic style.
$36.90
A rust-colored mesh maxi skirt featuring an abstract animal print, high-rise waist, and back slit.
$28.90
A rust-colored knit bikini top featuring a ruched bust, charm detail, and adjustable straps for support.
$25.90
A multicolor crochet knit swim short featuring a wavy texture and low-rise waist for a flirty vibe.
$29.90
An ivory mesh top with a flocked floral pattern, tie-front, and elegant bell sleeves.
$34.90
A multi-color abstract print mesh maxi skirt featuring sheer fabric, mini lining, and a form-hugging fit.
$24.90
A sleek rust bikini bottom featuring a high-hip silhouette, scrunch back seam, and smooth stretch fabric.
$34.90
A pink mesh maxi skirt featuring an abstract floral print, ruched detailing, and a form-hugging silhouette.
$25.90
A sleek pink bikini bottom with a high V-cut design, perfect for stylish, sun-soaked days.
$29.90
A rust mesh halter top featuring an abstract animal print, plunging cowl neckline, and open back.
$25.90
A taupe knit bikini bottom adorned with shimmering paillette sequins and adjustable tie-side closures.
$25.90
A multi-color abstract print bikini top featuring center beaded accents and adjustable tie-back straps.
$39.90
A charcoal faux leather vest featuring a double zip-front, studded trim, and a form-hugging fit.
$26.90
A rust knit halter top featuring a draped cowl neckline, O-ring accents, and bold animal print.
$29.90
A rust-colored, high-stretch snake print tank featuring a plunging V-neckline and beaded strappy back.
$27.90
A brown mesh tube top featuring a bold butterfly print, brushed knit lining, and dainty eyelet trim.
$32.90
A taupe cropped tank top featuring sheer floral lace, knit lining, and a heart-accented back strap.
$24.90
An ivory knit mini skirt with a flocked shell pattern and adjustable drawstring sides with seashell trims.
$26.90
A burgundy knit mini skort featuring tiered ruffles, a mid-rise waist, and fitted shorts underneath.
$39.90
A light blue mesh crop top featuring shimmering sequins and a strappy lace-up open back.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$26.90
A vibrant orange halter bikini top crafted from smooth, stretchy swim fabric with adjustable string ties.
$25.90
A rust-colored triangle bikini top in smooth stretch fabric with abstract metal trim and adjustable ties.
$36.90
A black polka dot halter crop top with lace trim and padded bra cups for stylish outings.
$22.90
A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.
$26.90
A pink bandeau halter bikini top featuring a sleek knit-lined fabric and trendy metal hoop accent.
$25.90
A blue gingham triangle bikini top featuring adjustable spaghetti straps and a comfortable lined fabric.
$32.90
A rust knit crop top featuring a square halter neckline and a beaded lace-up back detail.
$24.90
A high-cut bikini bottom featuring a bold multi-color abstract print and a cheeky, stylish fit.
$26.90
A brown knit bikini top featuring hoop inserts, wraparound tie details, and adjustable spaghetti straps.
$39.90
A structured ivory tweed vest with metallic threading, snap button-down front, and dual faux pockets.
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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: M | 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: S
Step out looking like goals in this micro mini skirt with a flirty side slit and bodycon fit that'll get you noticed! Fit & FeaturesStretchy knit fabric, High-rise waist, Side slit, Bodycon silhouette, Micro mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor First Take Micro Slit Mini Skirt in Black | Size: S | Knit 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: XS
A maxi skirt that feels like slipping into vacation mode without even trying. The soft floral print mesh hugs just right, giving you that effortless “I’m ready for whatever” confidence—day plans or date nights included. Shop Matching Top: Vacay Bloom Floral Mesh Halter TopFit & FeaturesSheer mesh fabric with knit lining, high stretch, Large floral print, High-rise waist, Ruching, High-cut side slit, Maxi-length hem, form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Vacay Bloom Floral Mesh Maxi Skirt in Light Blue | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Low-rise nostalgia meets modern street style—this denim cargo mini skirt is made for layering with baby tees, tanks, or oversized fits. The pocket detail gives it that effortless “just stepped out of an early 2000s music video” energy. Fit & FeaturesDenim fabric with color fade effect, Mid-rise waist, Cargo-style front and side pockets, Fitted mini-length hem, Front button closure, belt loop accents, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Throwback Cool Denim Cargo Mini Skirt | Size: XL
When subtle isn’t the move, this mesh midi skirt delivers. With a thigh-high slit and ruched waist, it’s the kind of style that owns the night and brings the confidence. Fit & FeaturesSheer mesh fabric with knit lining, high stretch, High-rise waist, ruching, Ultra-high front slit, Asymmetric midi-length hem, Flowy fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Confidence High Slit Mesh Midi Skirt in Black | Size: S | Knit Fabric/Mesh Fabric/Sheer Mesh 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: M | Leather
Sleek with a little edge, this mini skirt is made for plans that don’t end early. The smooth knit finish and subtle butterfly detail bring just enough intrigue, while the side slit keeps things flirty without trying too hard. Fit & FeaturesSmooth knit fabric with stretch, Low-rise waist, High front slit with subtle butterfly detailing, Form-hugging fit, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor After Dark Flutter Mini Skirt in Black | Size: M | Knit Fabric
Easy yes, zero hesitation. This mini skirt brings a clean fit with just enough drama—perfect for spontaneous plans and outfits that don’t need a backup. Shop Matching Top: Check In Chic Polka Dot Halter CorsetFit & FeaturesWoven knit fabrication, Ruched mid-rise waist, Polka dot pattern, Ruffled high side slit, Mini length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Check In Chic Polka Dot Mini Skirt in Ivory | Size: S | Knit Fabric