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.

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Summer Mode High-Rise Cotton Shorts in Chartreuse

$29.90

A pair of chartreuse cotton shorts featuring a high-rise elastic waist, dual front pockets, and fitted silhouette.

Windsor Flirt Alert Flocked Floral Mesh Tie-Front Top in Ivory

$29.90

An ivory mesh top with a flocked velvet floral pattern, tie-front, and bell sleeves.

Windsor Off To Paradise Tie-Front Crop Top Pant in Brown

Sale

Windsor Off To Paradise Tie-Front Crop Top Pant in Brown

$9.97 $24.90 60% off

A trendy brown abstract crop top with flowy short sleeves and a flattering tie-front design.

Summer Mode Button-Down Cotton Top in Chartreuse

$34.90

A lightweight chartreuse cotton button-down top with a collared neckline, long sleeves, and relaxed fit.

Windsor Delightful Duo Halter Polka Dot Crop Top in Black

$36.90

A black polka dot halter crop top with lace trim and padded bra cups for stylish outings.

Windsor Summer Mode Cotton Bra Top in Chartreuse

$22.90

A lightweight chartreuse cotton bra top with a sleeveless V-neckline, adjustable straps, and smocked back.

Windsor Delightful Duo Polka Dot Ruffle Skirt in Black

$36.90

A black polka dot ruffle mini skirt with a mid-rise waist and back zipper closure.

Now Trending

Windsor Beautifully Beaded Mesh Crop Top in Black

$39.90

(59)

Windsor Beautifully Beaded Mesh Crop Top in Black | Size: S | Mesh Fabric/Sheer Mesh Fabric Free Shipping on All Orders Over $75.

Hooked In Ruched Crop Top in Beige

$34.90

(57)

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 Sleeveless Halter Crop Top in Black

$19.90

(46)

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

Party Diva Cropped Rhinestone Halter Top in Brown

$32.90

(25)

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 Brown | Size: M | Knit Fabric/Rhinestone/Mesh Fabric

Feel The Vibes Halter V-Neck Crop Top in Black

$24.90

(21)

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 Black | Size: L | Cotton/Stretchy Fabric

Alluring Edge Faux Leather Lace-Up Halter Top in Burgundy

$42.90

(15)

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

Windsor Glitzy Muse Rhinestone Fishnet Crop Top in White

$39.90

(15)

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

Windsor Sheer Charm Strapless Lace Crop Top in Black

$19.90

(15)

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: L | Lace Fabric

Windsor Routinely Cute Halter Knot Crop Top in Burgundy

$26.90

(13)

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: M | Knit Fabric

Always Happy Hour Cowl Neck Crop Top in Brown

$22.90

(12)

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

Vacation Matching Sets

When it comes to packing for your next getaway, there’s a certain thrill in planning every outfit—but let’s be real, nobody wants to spend hours mixing and matching separates when you could be mapping out your beach days or scouting rooftop brunch spots. Enter vacation matching sets: the style hack that makes getting dressed on holiday almost as breezy as the ocean air. Whether you’re jetting off to a sun-soaked resort, road-tripping to a hidden gem, or just manifesting warmer days ahead in January, these coordinated looks are designed to take the guesswork out of vacation dressing. Imagine stepping out in a two piece vacation set that moves with you from poolside lounging to sunset cocktails, or a vacation skirt set that pairs perfectly with strappy sandals and a woven tote. The beauty of matching sets for vacation is in their versatility—you can wear the pieces together for a polished, put-together vibe, or mix them up with other staples in your suitcase for endless outfit options without overpacking.

Vacation sets aren’t just a win for your own wardrobe—they also make the kind of gift that says, “I know you’re already planning your next trip.” Think about it: gifting a shorts set vacation look to your best friend who’s always chasing the sun, or treating your sister to a matching set she can wear on her upcoming bachelorette weekend. There’s something universally flattering about these sets, whether you gravitate toward flowy, boho-inspired silhouettes or sleek, tailored lines. They’re made for the spontaneous—those impromptu photo ops, last-minute dinner reservations, or lazy mornings that turn into afternoons exploring local markets. And since January is all about dreaming up new adventures (or escaping the winter chill, if only in your mind), now is the perfect time to refresh your closet with pieces that promise to deliver on ease, comfort, and undeniable style. Pro tip: opt for lightweight fabrics that breathe easy in the heat, and don’t be afraid to play with prints—vacation is the ultimate excuse to have a little fun with your look.

The real magic of vacation matching sets is how they empower you to show up feeling confident and carefree, no matter where your travels take you. From the first airport selfie to that golden hour dinner by the shore, these sets are built to keep up with every mood and moment. They’re the answer to the “I have nothing to wear” panic, the secret weapon for packing light, and the shortcut to looking instantly put-together—even if you’re running on two hours of sleep and a dream. And if your itinerary includes a dip in the pool or a walk along the shore, don’t forget to explore our curated collection of Vacation Swimsuits for even more getaway-ready style. Whether you’re shopping for yourself or someone who deserves a little sunshine, vacation sets are your ticket to effortless, memorable outfits that travel as well as you do.

Reset Your Password

Email Sent

Order Status

Vacation Matching Sets

Home Vacation Matching Sets

Now Trending

Vacation Matching Sets

Related Collections