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.
$39.90
A rust-colored knit maxi skirt featuring bold leopard and snake prints with an O-ring waist accent.
$32.90
A sleek olive maxi skirt crafted from double-lined, stretchy knit fabric with a flattering bodycon silhouette.
$36.90
A banana yellow floral knit maxi skirt with a fluid drape, curve-hugging fit, and flared hem.
$32.90
An ivory crochet bralette top featuring a plunging V-neck, scalloped trim, and open tie-back design.
$28.90
A rust-colored knit bikini top featuring a ruched bust, charm detail, and adjustable straps for support.
$14.97 $29.90 50% off
A chartreuse ribbed knit crop jacket featuring a zip-up front, mock neckline, and fitted long sleeves.
$25.90
A taupe knit bikini bottom adorned with shimmering paillette sequins and adjustable tie-side closures.
$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.
$24.90
An ivory knit mini skirt with a flocked shell pattern and adjustable drawstring sides with seashell trims.
$29.90
An ivory mesh top with a flocked velvet floral pattern, tie-front, and bell sleeves.
$34.90
A pink mesh maxi skirt featuring an abstract floral print, ruched detailing, and a form-hugging silhouette.
$34.90
A multi-color abstract print mesh maxi skirt featuring sheer fabric, mini lining, and a form-hugging fit.
$27.90
A brown mesh tube top featuring a bold butterfly print, brushed knit lining, and dainty eyelet trim.
$39.90
A structured ivory tweed vest with metallic threading, snap button-down front, and dual faux pockets.
$24.90
A sleek rust bikini bottom featuring a high-hip silhouette, scrunch back seam, and smooth stretch fabric.
$26.90
A burgundy knit mini skort featuring tiered ruffles, a mid-rise waist, and fitted shorts underneath.
$25.90
A multi-color abstract print bikini top featuring center beaded accents and adjustable tie-back straps.
$26.90
A taupe knit bikini top with shimmering paillette sequins, triangle silhouette, and adjustable halter ties.
$26.90
A mesh tube top featuring a bold leopard and floral print with ruffle trim and a cropped hem.
$29.90
A multi-colored butterfly print mesh halter top with a cowl neckline, O-ring accents, and open back.
$39.90
A multi-colored mesh maxi skirt featuring a butterfly print, high-cut front slit, and asymmetric hem.
$32.90
A lightweight natural linen-blend cropped vest with a sleeveless V-neckline and chic button-down front.
$36.90
A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.
$54.90
A black tropical print jumpsuit featuring a plunge cowl halter neckline, open back, and wide-leg fit.
$25.90
A rust-colored triangle bikini top in smooth stretch fabric with abstract metal trim and adjustable ties.
$22.90
A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.
$49.90
A brown floral maxi dress featuring a halter neckline, front cutout, open back, and high slit.
$32.90
A rust knit crop top featuring a square halter neckline and a beaded lace-up back detail.
$42.90
A pair of natural linen-blend wide-leg trousers with pleated detailing and a high-rise waist.
$42.90
A pair of brown linen-blend wide-leg trousers with a high-rise waist and dual front pockets.
$44.90
A pair of black cotton-blend knit shorts featuring Von Dutch logo graphics and a low-rise ribbed waistband.
$29.90
A denim swim top featuring a belted strapless neckline and a front keyhole cutout.
$24.90
A lightweight ivory knit crop top featuring a tropical print, tie-front closure, and flowy short sleeves.
$26.90
An orange bikini bottom featuring adjustable side ties with statement beads and a cheeky fit.
$42.90
A gold lurex knit maxi dress featuring a crewneck, adjustable side ties, and high side slits.
$49.90
A rust-colored halter jumpsuit featuring slinky knit fabric, bold cutouts, and striking hoop details.
$32.90
An orange halter bikini top featuring adjustable beaded straps, padded cups, and knit-lined fabric.
$34.90
A brown paisley mesh skort featuring tiered ruffles, mid-rise waist, and comfortable shorts lining.
$62
A bold denim cotton-blend mini skirt featuring flame graphics and Von Dutch logo details for standout style.
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Booked the trip just to wear this. These bikini bottoms serve sculpted support with cheeky coverage and beaded detail, plus adjustable side ties that let you customize the fit before you hit the pool. Style with the matching bikini top. Shop Matching Top: Hotter Than Summer Bikini TopFit & FeaturesSmooth stretch knit fabric, Low-rise waist, Adjustable side ties with beaded accents, Cheeky fit, Returns are not accepted without the hygienic liner, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Hotter Than Summer Bikini Bottoms in Rust | Size: L | Knit Fabric
Meet the bikini bottom that nails that effortless, flirty vibe without overthinking it. The sharp V-cut sculpts your shape and serves up that confident, beach-dream vibe you’ll want in every sun-soaked moment. Shop Matching Top: Flirty Vibe Tie-Front Bandeau Bikini TopFit & FeaturesV-cut front waist, High-cut sides for a sleek, minimal look, Cheeky back coverage, Smooth stretch knit fabric, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Flirty Vibe V-Cut Bikini Bottoms in Ivory | Size: L | Knit Fabric
Shimmer that catches the light and refuses to be subtle. These paillette sequin bikini bottoms feature tie-side closures that keep the fit adjustable for beach days, poolside lounging, or sunset photos. Style with the matching bikini top and cover-up. Shop Matching Set: Sunlit Muse Paillette Sequin Bikini Top, Sunlit Muse Paillette Sequin Mini Cover-UpFit & FeaturesKnit fabric, moderate stretch, Front paillette sequin embroidery, Tie-side closures, Ruched cheeky fit, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Sunlit Muse Paillette Sequin Bikini Bottoms in Taupe | Size: S
Make a splash in this dreamy triangle bikini top, featuring a soft flocked texture that gives effortless coastal-cool energy. Finished with a delicate shell charm at the center, it’s the prettiest little detail for your next sun-kissed moment. Shop The Matching Top: Seaside Whisper Shell Charm Bikini TopShop The Matching Cover Up: Seaside Whisper Cover Up SkirtFit & FeaturesFlocked texture-lined fabric, Low-rise V-cut waist, Adjustable side ties, Cheeky bottom, Shell charm accent, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Seaside Whisper Shell Charm Bikini Bottoms in Ivory | Size: L
This is the layer that turns a simple bikini into a full look. This ruffled mesh sarong hugs in all the right places with a flirty tie-waist and sheer finish that was made for beach clubs, pool parties, and spontaneous golden hour plans. Fit & FeaturesSheer mesh fabric with high stretch, Tie-waist design, Long ruffled accents, Mini-length ruffled hem, form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sheer Confidence Ruffled Mesh Sarong Swimwear in Black | Size: S/M | Mesh Fabric/Sheer Mesh Fabric
These bikini bottoms brings that effortless “I woke up glowing” energy with its sleek high-hip silhouette. Easy to slip on, easy to style, and perfect for that sun-kissed moment you know is happening the second you hit the beach. Shop the matching top. Shop The Matching Top: Sand And Shine Triangle Bikini TopFit & FeaturesHigh hip bikini bottom silhouette, Scrunch back seam for shaping, Smooth stretch swim fabrication, Minimal coverage for a bold finish, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Sand And Shine Bikini Bottoms in Rust | Size: L
Sun out, confidence on. These bikini bottoms keep it clean and flattering with a barely there fit that feels effortless from shoreline walks to all-day lounging. Shop The Matching Bikini Top: Hot Weather Favorite String Bikini TopFit & FeaturesSmooth swim fabric with a soft stretch feel, Hoop inserts, Minimal coverage, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Hot Weather Favorite Bikini Bottoms in Orange | Size: M
These bikini bottoms are serving effortless allure with attitude. The classic bikini bottoms get an upgrade with hoop insets and a sleek back ruched seam that highlights your shape from every angle. Shop the matching bikini bottom. Shop Matching Top: Golden Coast Hoop Detail Bikini TopFit & FeaturesSleek knit fabric, Mid-rise fit, Hoop side inserts, Back ruched seam, Cheeky bottom, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Golden Coast Hoop Detail Bikini Bottoms in Brown | Size: L | Knit Fabric
This one hits before you even hit the water. These bikini bottoms feature a clean high V-cut accent for a trendy vibe made for sun-soaked plans. Pair with the matching top. Shop The Matching Top: Poolside Proof Hoop Detail Bandeau Bikini TopFit & FeaturesSleek knit-lined fabric, Bandeau halter-style neckline with ties, Removable padding, Hoop insert, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Poolside Proof High-Cut Bikini Bottoms in Pink | Size: S
It's looking like a hot girl summer with these denim bikini bottoms. From the belted low-rise waist to the cheeky bottom, these swim bottoms will be sizzling by the water! Shop Matching Top: Hot Girl Summer Denim Bikini TopFit & FeaturesDenim swim fabric, Belted low-rise waist, Cheeky bottom, Runs true to size, Returns are not accepted without the hygienic liner, Free Shipping on All Orders Over $75. | Windsor Hot Girl Summer Denim Bikini Bottom | Size: M