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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Shape Up Rhinestone Earrings
Shape up your jewelry collection with these gold earrings. They feature a round and large rectangle outline adorned with mini rhinestones. Include post back closure.
Style Number/Barcode: 07001-4473
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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O Ring Textured Earrings
Bring the glam with a little texture with these silver earrings! They feature a textured disc on post and a large O ring. Includes a post back closure.
Style Number/Barcode: 07001-4480
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Two-Tone Tassel Fan Earrings
These tribal-inspired tassel fan earrings are beautiful statement pieces for festival and summer! They feature a round beaded stud, a round tassel fan design with a beaded center, and a post back closure.
Style Number/Barcode: 07001-4471
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropic Tassel Fanned Earrings
Go for an exotic glam look with these fab gold and mustard earrings! They feature a metal leaf design with fanned out fringe. Include a post back closure.
Style Number/Barcode: 07001-4481
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam It Up O-Ring Earrings
Glam up your look and give off confidence with these bold earrings! They feature a gold hue with a large textured round post and a textured O-ring attached. Include a post back closure.
Style Number/Barcode: 07001-4479
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Twisted Double Hoop Earrings
Give your look a pretty twist with these gold hoop earrings! They feature two interlocked twisted hoops that bring plenty of glam and a post back closure.
Style Number/Barcode: 07001-4454
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tiered Diamond Tassel Earrings
Draw extra attention to that pretty little face with these super cute earrings! They feature a tiered tassel design, gold metal accents and a hook closure.
Style Number/Barcode: 07001-4446
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Cross Duster Earrings
These dainty gold earrings will be your new favorite pair! They feature a cross design with a hook closure.
Style Number/Barcode: 07001-4392
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cross Charm Hoops
Pair these cross charm hoops with your festival 'fits for the cutest looks! They feature thin gold hoops with studded engraved cross pendants. Includes omega closures.
Style Number/Barcode: 07001-4421
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Square Frame Stud Earrings
These unique earrings feature a round rhinestone stud between a double square gold frame.
Style Number/Barcode: 07001-4420
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Luxe Dainty Braided Dusters
Make an elegant statement with these graceful dusters! They feature a gold hue, a multi row braided design and a post back closure.
Style Number/Barcode: 07001-4418
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Spirit Short Sleeve Knot Tie Mini Dress
This short sleeve mini dress is the cutest for casual outings! Made from soft and stretchy rib knit fabric, this dress will keep you comfy and stylish all day long. With a flattering bodycon fit and a unique front knot tie detail, this dress exudes charm. The asymmetrical mini-length hem adds a touch of playfulness, making this a must-have. Complete the look in platform sneakers.
Fit & Features
- Rib knit fabric, moderate stretch
- Crew neckline
- Bodycon fit
- Front knot tie detail
- Runs true to size
Style Number/Barcode: 05102-5762
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fanned Out Tassel Earrings
You'll be a major fan of these festive fanned out tassel earrings! They feature a hammered gold metal post connected to a half moon shape with fanned out emerald green tassels. Includes a post back closure.
Style Number/Barcode: 07001-4390
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beaded Fan Tassel Earrings
Have some fun with your accessories today! This bold set feature a beaded round frame with mustard colored fringe in a fan tassel design.
Style Number/Barcode: 07001-4411
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Clearance
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4 Pack Metal Ear Cuffs
These will soon become your favorite go to look! This four pack of earrings feature gold metal ear cuffs in two styles.
Style Number/Barcode: 07001-4414
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Tiered Tassel Earrings
Draw extra attention to that pretty little face with these super cute neon yellow earrings! They feature a tiered tassel design, gold metal accents and a post closure.
Style Number/Barcode: 07001-4408
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Statement Making Long Fringe Earrings
Make a statement in these fun magenta earrings! They feature a gold hammered post with long fringe.
Style Number/Barcode: 07001-4409
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wow Factor Fan Tassle Earrings
Total WOW factor kinda earrings. They feature a large round tortoise print disk with mustard fan fringe. Include a post back closure.
Style Number/Barcode: 07001-4410
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Double Hoop Earrings
These gold double hoop earrings are larger than life! They feature a large hoop with a small hoop inside. They are composed of a gold textured metal and have a post back closure.
Style Number/Barcode: 07001-4407
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Coin Hoop Earrings Set
These gold hoop earrings will give you a major glam factor! The set features three pairs, the first a pair of mini hoops with coin accents with engraved details, and the second a bigger pair of thinner hoops with larger coins hanging down with Grecian inspired details. The last pair are basic large thin hoops. Each feature an omega closure.
Style Number/Barcode: 07001-4400
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tiered Diamond Tassel Earrings
Draw extra attention to that pretty little face with these super cute earrings! They feature a tiered tassel design, gold metal accents and a hook closure.
Style Number/Barcode: 07001-4396
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Shine In Rhinestone Hoops
Shine so fine in these rhinestone hoops! They feature a full gold hoop adorned with glimmering rhinestones so you can sparkle the night away.
Style Number/Barcode: 07001-4321
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bloom In Rhinestones Tassel Earrings
Let your beauty bloom in these gorgeous black earrings! They feature a floral design on post with mini rhinestones and a gold outline. The draping tassles feature a luxe mauve hue to make a chic statement.
Style Number/Barcode: 07001-4298
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glam Alert Hoops
Glam alert! These bold hoops will for sure step up your glam game! The earrings feature large flat sleek gold hoops with omega closures.
Style Number/Barcode: 07001-4288
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free