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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Star-Worthy Layered Necklace
This star-worthy layered gold necklace is ready for you to style! It features three rows, showcasing beautiful and dainty star and moon charms, two of the stars adorned with cubic zirconia stones. Includes an adjustable lobster clasp closure.
Style Number/Barcode: 07002-5150
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shell It Out Choker
You don't need to scour the seashore for this beautiful gold choker! It features a row of gold shell charms, and has a lobster clasp closure.
Style Number/Barcode: 07002-5152
Category Name: Vacation Looks
Price: $4.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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3 Pack Necklace Set
Hey girl! We've got the perfect necklace set for you! It features 3 rows of varying lengths and styles.
Style Number/Barcode: 07002-5144
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Babe Script Layered Necklaces
You're such a babe, so own it with these cute layered necklaces! They feature two rows, the shorter a gold snake chain and the longer layer a dainty snake chain showcasing the script "babe."
Style Number/Barcode: 07002-5063
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Coin Necklace Set
Layer up in these coin charms to make a stylish statement! This set includes four gold necklaces that feature a snake chain and Grecian-inspired coin charm accents. Necklaces include lobster clasp closures.
Style Number/Barcode: 07002-5075
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Layered Herringbone Necklace
Layer on a touch of romance with this gold layered necklace! It features a herringbone piece, a dainty chain with a heart charm, and a third chain with a rose charm. Necklace has a lobster clasp closure.
Style Number/Barcode: 07002-5068
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Touch Choker Set
Add a touch of gold glam to your look with these trendy and chic chokers! The set includes four necklaces, one a basic chain link, one a thick metal mesh choker, one a dainty chain, and one adorned with star charms. Each includes an adjustable lobster clasp closure.
Style Number/Barcode: 07002-5066
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chill With Me Long Sleeve Square Neck Knit Romper
Perfectly chill and cute, this lounge rib knit romper was made for relaxing at home and going for a coffee run in! Crafted from stretchy rib knit fabric, this romper features cozy fitted long sleeves, a flattering square neckline, and a form-hugging short-length hem. Pair with a cozy cardigan and slippers.
Fit & Features
- Stretchy rib knit fabric
- Fitted long sleeves
- Square neckline
- Form-hugging, short-length hem
- Runs true to size
Style Number/Barcode: 06503-1271
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Star Spangled Herringbone Necklace Set
This gold necklace will be the star of your outfit! This set includes a herringbone necklace, and a dainty chain necklace with a row of small star charms. Necklaces have a post back closure.
Style Number/Barcode: 07002-5069
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake It And Rhine Necklace
Snake it and rhine with these cute necklaces! The three multi-chain necklaces feature a snake and dainty chain link design. The dainty chain is adorned with a rounded, faceted rhinestone charm. Includes lobster clasp closures.
Style Number/Barcode: 07002-5017
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Snake Chain Pendant Necklace
Layer up in style to complete your ensemble! This gold hued multi layered look features trendy snake chains and saint charms.
Style Number/Barcode: 07002-5012
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Clearance
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Long Cross Necklace
Make a dazzling statement of faith and fashion! This long simple necklace is composed of a dainty metal chain with a large rhinestone cross charm. Includes a lobster clasp closure.
Style Number/Barcode: 07002-4557
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shine In Snake Necklace Set
Add a dazzling touch to your look with a chic necklace! This set features two gold necklaces, one having a snake chain and the other having a dainty chain adorned with stationed rhinestone accents. Pack includes two necklaces.
Style Number/Barcode: 07002-0016
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Star Spangled Layered Necklace
Create fireworks in this star-studded gold layered necklace! It features six rows of snake chains adorned with rows of small star charms. Necklace has a lobster clasp closure.
Style Number/Barcode: 07002-0019
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bohemian Vibes Rhinestone Duster Earrings
Get those Boho vibes going with these chic dusters! They feature a rhinestone on post and a multi layered filigree design adorned with rhinestones. Includes a post back closure.
Style Number/Barcode: 07001-4511
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Infinity Teardrop Tassel Earrings
Have an infinitely pretty look with these gorg tassel earrings! They feature a gold infinity shaped post attached to a teardrop shape with mustard yellow tassels fanning out. Includes a post back closure.
Style Number/Barcode: 07001-4552
Category Name: Vacation Looks
Price: $9.90
Availability: Out of Stock
Product Badge:- Clearance
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Gemstone Fan Fringe Earrings
Glamorous and trendy, all in one! These gray earrings feature faceted gemstones on a gold metal post connected to half moon shaped, fanned out tassels. Includes a post back closure.
Style Number/Barcode: 07001-4538
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beaded Long Fringe Earrings
These statement earrings will be the center of attention! They feature gold hoops, long black fringes with gold beading, and an omega closure.
Style Number/Barcode: 07001-4527
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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Metal Filigree Coin Duster Earrings
Make a chic statement with these bohemian-inspired duster earrings! They feature a gold hue, a flat metal coin on post, a filigree design and Grecian-inspired coin drop detail. Includes a fish hook back
Style Number/Barcode: 07001-4519
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glimmering Gemstone Earrings
Gleam and glimmer and draw attention with these gorgeous gemstone earrings! They feature a teardrop shaped gemstone post outlined with mini rhinestones, attached to a gold filigree design adorned with numerous multi-faceted gems. Tassels cascade down the earring to sway beautifully. Includes a post back closure.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-4513
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dazzle With Rhinestone Earrings
Dazzle them all away with these colorful rhinestone earrings! The gold earrings feature a square shaped post attached to an O-ring accent detailed with varying hued rhinestones for a rainbow effect. Include a post back closure.
Style Number/Barcode: 07001-4512
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Taste So Sweet Cherry And Faux Pearl Layered Necklace
Sweeten up the vibe in this layered necklace with adorable colored rhinestone cherry charms and a luxe strand of faux pearls. Pair with a purse.
Fit & Features
- Layered necklace
- Colored rhinestone cherry charms
- Faux pearl strand
- Lobster clasp closure
Style Number/Barcode: 07002-2116
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coin Drop Hoop Earrings
Change it up.. literally.. with these fun gold earrings! They feature a metal hoop with coin drop charms. Include a post back closure.
Style Number/Barcode: 07001-4501
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ride The Wave Double Hoop Earrings
Make waves, your way! These silver earrings feature a wavy, double hoop design for an extra dazzling touch! Hoop earrings are embellished with rhinestones and made of a flexible memory wire. Includes a post back closure.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-4487
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance