Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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Vacation Dresses & Outfits for Effortless Getaways
Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.
Easy, Packable Styles
Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.
Day-to-Night Versatility
Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.
Resort & Beach Essentials
Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.
Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.
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12 Multi Pack Gemstone Rings
Adorn those pretty little finger with these gold rings! This multi pack comes with 12 gold bands of varying designs including black gemstones. Sizes fit most.
Style Number/Barcode: 07004-0985
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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3 Pack Chain Link Bangles
Perfect as an everyday accessory! These gold metal bangles feature a chain link design in varying widths.Style Number/Barcode: 07003-2396
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Statement Metal Ring Variety Pack
Make a statement with silver to complete your ensemble! This variety pack includes 13 silver rings featuring geometric bands, cross charms and chevron designs. Easily wear alone or stack rings to make a chic statement!
Style Number/Barcode: 07004-0963
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cuter Than Ever Lace Ruffle Shorts
Romp around cuter than ever in these lace ruffle shorts for a flirtatious look everywhere you go!
Fit & Features
- Lace lined fabric
- Low-rise waist
- Tiered ruffled design
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06503-000019
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rainbow Infinity Ring
Keep it timelessly gorgeous with this statement making ring! It features a band a multi hued gemstones with an emerald cut.
Style Number/Barcode: 07004-0006
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shining Star Charm Anklet
Shine on like the night sky with this pretty gold anklet! It features a double row dainty ball chain, a flat metal star charm and lobster clasp closure.
Style Number/Barcode: 07003-2403
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beaded Charm Bracelet Variety Pack
Add these trendy beaded charm bracelets to your jewelry collection! The variety pack features five various charm bracelets total, three gold metal chain links with adjustable lobster clasp closures and two beaded bracelets. Rhinestones and a Hamsa hand adorn two of the bracelets.
Style Number/Barcode: 07003-2389
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Chain Link Anklet
Add a little extra touch of glam with this super cute anklet! It features a basic chain link design with a lobster clasp closure.Style Number/Barcode: 07003-2383
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rhinestone Drop Anklet
Play up that jewelry game with this silver rhinestone drop anklet! It features a single row of rhinestones with drop rhinestone accents. Closes with a lobster clasp.
Style Number/Barcode: 07003-2386
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dainty Coin Anklet
Keep it simple and chic with this dainty anklet! It features a gold dainty chain and a single row of Grecian-inspired coin charms. Includes a lobster clasp closure.
Style Number/Barcode: 07003-2379
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dainty 3 Row Chain Anklet
You'll be adorned from head to toe! This gold anklet features three rows of dainty chains, and an adjustable lobster clasp closure.
Style Number/Barcode: 07003-2375
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dazzling Dainty Rhinestone Anklet
Dazzle from head to toe with this simply chic anklet! It features a dainty gold chain adorned with a single row of mini rhinestones and a lobster clasp closure.
Style Number/Barcode: 07003-2369
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Curved Metal Cuff Bracelet
This gold cuff bracelet is minimal but adds a pretty and dainty touch to your look! It features a double curved design.
Style Number/Barcode: 07003-2378
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Herringbone Anklet
This dainty gold anklet is all you need to add some effortless chic to your look! It features a gold herringbone design with an adjustable lobster clasp closure.
Style Number/Barcode: 07003-2368
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Layered Charm Bracelets Set
Make your look trendy and chic with this gold charm bracelets set! The pack includes five bracelets, each a varying chain, three showcasing charms such as a cross, a bar accent, and a multi-faceted heart gemstone. Includes adjustable lobster clasp closures.
Style Number/Barcode: 07003-2370
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sparkle And Shine Rhinestone Anklet
Add sparkle and shine from head to toe with a cute anklet! This must have features a a two row design adorned with mini rhinestones and a lobster clasp closure.
Style Number/Barcode: 07003-2354
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Layered Chain Link Necklaces
These simple silver layered chain link necklaces are the perf addition to any outfit! They feature two rows, the shorter row a smaller daintier chain and the longer one a thicker chain link. Includes adjustable lobster clasp closures.
Style Number/Barcode: 07002-5211
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Cute Pleated Denim Mini Skirt
Keep your everyday 'fits cute and trendy with this pleated denim mini skirt. The distressed hem adds a casual flair to the adorable A-line silhouette.
Fit & Features
- Denim fabric
- Mid-rise waist, belt loops
- Front button closure
- Pleated design
- Mini-length distressed hem
- A-line fit
- Runs true to size
Style Number/Barcode: 06601-0227
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Denim fabric
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Layered Chain Link Necklaces
These simple gold layered chain link necklaces are the perf addition to any outfit! They feature two rows, the shorter row a smaller daintier chain and the longer one a thicker chain link. Includes adjustable lobster clasp closures.
Style Number/Barcode: 07002-5210
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Snake Charmer Multi Choker Pack
Charm them all with a statement necklace! This choker multi pack includes four gold hued chokers with a snake chain design and a fish bone chain. Chokers include lobster clasp closures.
Style Number/Barcode: 07002-5187
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Link Me In Necklace
Get linked up with a cute necklace to add a special touch to your look! This gold hued necklace features a two row design and a trendy cuban link pattern. Includes a lobster clasp closure.
Style Number/Barcode: 07002-5168
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Star And Moon Charm Necklace
Shine bright in this star and moon charm layered necklace! It features two rows of dainty gold chains, the shorter row featuring a ball and chain design, and the longer layer showcasing star charms and a single center moon charm. Includes an adjustable lobster clasp closure.
Style Number/Barcode: 07002-5167
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Layer On The Glam Necklace
Layer on the glam and style up your look with this gold chain link necklace! It features six rows of varying styled chain links, the top one showcasing dangling disc charms. Includes an adjustable lobster clasp closure.
Style Number/Barcode: 07002-5165
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Eye 3 Pack Necklace Set
This set of gold necklaces features three unique chain style and one rhinestone eye charm. Includes lobster clasp closures.
Style Number/Barcode: 07002-5157
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Clearance