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 $29.90 67% off
A black tropical print crop top in stretchy knit fabric with long sleeves and a sultry tie-front.
$39.90
A natural-colored woven fabric trouser with a high-rise waist and wide-leg silhouette.
$29.90
A pair of chartreuse cotton shorts featuring a high-rise elastic waist, dual front pockets, and fitted silhouette.
$9.97 $29.90 67% off
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.
$29.90
A black mesh-lined crop top featuring cap sleeves, ruffled hem, and a bungee lace-up back.
$9.97 $39.90 75% off
A natural chevron knit midi skirt with a high-rise waist and bodycon silhouette.
$29.90
An ivory mesh top with a flocked velvet floral pattern, tie-front, and bell sleeves.
$9.97 $24.90 60% off
A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.
$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.
$36.90
A black polka dot halter crop top with lace trim and padded bra cups for stylish outings.
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Windsor Beautifully Beaded Mesh Crop Top in Black | Size: S | Mesh Fabric/Sheer Mesh Fabric Free Shipping on All Orders Over $75.
Embrace sultry charm and chic style with this ruched corset crop top. The flattering off-the-shoulder neckline exudes elegance, while the gathered hook and eye bodice accentuate your hourglass figure. Its cropped length offers a fresh, modern edge—perfect with high-waisted denim or skirts. The tie sleeves introduce a playful touch to this versatile top, ideal for amplifying a night-out ensemble or a casual brunch look with friends. Fit & FeaturesOff-the-shoulder neckline, ruched short sleeves, Sweetheart bust with lace trim, Padded cups, built-in non-slip strip , Hidden front hook-eye closures, Cropped hem, Lined mesh fabric, minimal stretch, Runs true to size , Free Shipping on All Orders Over $75. | Windsor Hooked In Ruched Crop Top in Beige | Size: L | Mesh Fabric/Mesh Fabric
Take the plunge and dare to show skin in this sleeveless halter crop top for a night out! Featuring a halter cowl neckline with bar trim, an open back, and a stylish crop hem, this top is perfect for standing out and making a statement. Complete the look in sleek faux leather pants. Fit & FeaturesSlinky knit fabric, plenty of stretch, Bar trim, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Take The Plunge Sleeveless Halter Crop Top in Black | Size: S | Leather/Knit Fabric
Get ready to feel the vibes of this elevated basic halter V-neck crop top! It's perfect for styling with any bottoms. Fit & FeaturesSmooth knit, cotton-blend, stretchy fabric, Halter V-neck, Crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Feel The Vibes Halter V-Neck Crop Top in Green | Size: XS | Cotton/Stretchy Fabric
A cropped rhinestone halter top that'll inspire your next going-out look! It features a sultry plunge cowl neckline and a partially open back that turns heads. Pair with jeans. Fit & FeaturesSheer mesh fabric with knit lining, moderate stretch, Studded rhinestones, Plunging halter neckline, cowl bust, Mini bar strap at bust, Halter neck ties, partially open back , Fitted cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Party Diva Cropped Rhinestone Halter Top in Beige | Size: M | Knit Fabric/Rhinestone/Mesh Fabric
Everyone will want your style secrets after seeing you in this glitzy rhinestone crop top! It features a crew neckline, long fitted sleeves, a fitted cropped hem, and is composed of a sultry sheer fishnet fabric with all-over mini rhinestone embellishments. Style over a lacy bralette with faux leather pants for a night out. Fit & FeaturesCrew neckline, Long fitted sleeves, Fitted cropped hem, Sheer fishnet fabric, Mini rhinestone embellishments, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glitzy Muse Rhinestone Fishnet Crop Top in White | Size: L | Leather/Rhinestone
You'll be easy and breezy in this strapless lace crop top perfect for concerts or festivals! This flirty top features a strapless neckline, a front slit with a drawstring tie, and an asymmetrical cropped hem on lace-lined fabric. Complete the look in a denim mini skirt. Fit & FeaturesLace fabric lined with stretchy knit, Strapless neckline, Front slit, drawstring tie, Asymmetrical cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sheer Charm Strapless Lace Crop Top in Black | Size: S | Lace Fabric
Add that alluring edge to your 'fits with this sleek faux leather halter top featuring a plunging V-neck, lace-up front and back for a snatched look, and a form-hugging silhouette. Fit & FeaturesFaux leather fabric, knit lining, minimal stretch, Sleeveless plunging V-neckline, Halter straps, snap button closures, Lace-up front with grommet design, Partially open back, lace-up back, Fitted mid-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Alluring Edge Faux Leather Lace-Up Halter Top in Burgundy | Size: L | Leather/Knit Fabric
Embrace the sultry vibes of this cowl neck crop top for your next happy hour spree! Pair with the matching skirt to complete the vibe. Shop Matching Bottoms: Always Happy Hour High-Rise Slit Midi Skirt, Catch The Curve High Slit Midi SkirtFit & FeaturesDouble-lined slinky knit stretchy fabric, Cowl neckline, Adjustable spaghetti straps, Side ruched seams, Fitted crop hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Always Happy Hour Cowl Neck Crop Top in Brown | Size: S | Knit Fabric/Stretchy Fabric
Always cute, this halter knot crop top will elevate any pair of jeans! Fit & FeaturesSmooth stretchy knit fabric, Halter V-neckline, tie straps, Knotted bust, Center split design, Cropped hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Routinely Cute Halter Knot Crop Top in Burgundy | Size: L | Knit Fabric