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.
$9.97 $19.90 50% off
A black tropical print crop top with a plunging V-neckline and ruffled babydoll hem.
$26.90
A tan tropical print crop top featuring a strapless neckline, mesh fabric, and soft knit lining.
$29.90
A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.
$6.97 $26.90 74% off
A natural-colored crochet tube top featuring a wavy striped pattern and a sweetheart neckline.
$24.90
An airy orange crop top with a sweetheart neckline and charming open back bow design.
$36.90
A natural high-rise mini skort featuring a printed woven overlay, side tie, and stretchy knit shorts lining.
$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
A natural chevron knit midi skirt featuring a high-rise waist and bodycon silhouette.
$22.90
A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.
$32.90
A natural crochet maxi skirt featuring a high-rise waist and sultry high front slit.
$24.90
A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.
$28.90
A pink knit midi skirt featuring ruffle trim, side slit, high-rise waist, and bodycon fit.
$42.90
A sultry taupe jumpsuit with a tropical print, featuring a cutout design and wide-leg silhouette.
$34.90
A white cotton mini skort featuring a tiered ruffled overlay and hidden fitted knit shorts.
$24.90
A black tropical print maxi skirt in airy sheer mesh with a high-rise waist and sultry side slit.
$26.90
A chic ivory lace mini skirt with a high-rise waist and form-hugging fit.
$34.90
A sheer mesh maxi skirt in brown with an abstract zebra print and mid-rise waist.
$39.90
A pink floral jacquard mesh maxi skirt with a high-rise waist and flowy draped hem.
$18.97 $44.90 58% off
A natural knit midi skirt featuring a wavy striped pattern and a high center back slit.
$24.90
A vibrant yellow high-rise mini skirt featuring slinky knit fabric, side ruching, and a ruffled hem.
$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.
$32.90
A brown striped crochet bralette top featuring an open back, tie details, and ultra-cropped hem.
$42.90
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 pink floral mesh maxi skirt with a high-rise waist and flattering bodycon 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.
$29.90
A brown floral mesh crop top featuring sheer peasant sleeves and a flirty tie-front design.
$34.90
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.
Now Trending
Slay It With Style Mini Skirt in Black
$9.97 $22.90
56% 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, Free Shipping on All Orders Over $75. | Windsor Slay It With Style Mini Skirt in Black | Size: L | Leather/Satin Fabric
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
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, Free Shipping on All Orders Over $75. | Windsor Serving Style Cargo Mini Skirt in Brown | Size: XL
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
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
With this flirty midi skirt for celebrations or date night, you'll stun with the ruched detailing and high-cut side slit. Pair with the matching crop top to complete the look. Shop Matching Top: Flirty Ways Halter Lace Trim Crop TopFit & FeaturesStretchy smooth knit fabric with lining, High-rise waist, Ruching, Asymmetric high-side slit, Midi-length hem, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirty Ways Ruched High Slit Midi Skirt in Ivory | Size: L | Knit Fabric
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: L | Knit 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