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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Living The Lattice Life Swimsuit
Lattice life is the only life during swim season! Check out this pretty little swimsuit that features a triangle, underwire bust paired with a sexy, exposed lattice front and adjustable shoulder straps.Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07109-0041
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Icing On The Cake V-Neck Lace Skater Dress
The perfect lace skater dress that'll take your day somewhere magical! Perfect for rehearsal dinners, birthdays, or graduation. This dress features a flattering V-neckline, spaghetti straps, and a playful cross-back design. Its skater silhouette and surplice ruffled short-length hem will keep you twirling all day! Complete the look in strappy block heels.
Fit & Features
- Lace fabric lined with stretchy knit
- V-neckline, spaghetti straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3667
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek And Strappy Swimsuit
Have a sleek and strappy look with this sultry swimsuit! The black one piece features a plunging neckline with a criss cross front detail, thin adjustable straps that lead to a straight across back, and a partial coverage bottom.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0035
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Side Cut Out Swimsuit
Channel your wild side with this side cut out swimsuit! The leopard print one piece features a deep neckline, thin adjustable shoulder straps that lead to a back closure and an open back, trendy side cut outs, cute side ties, and a partial coverage bottom.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small.Style Number/Barcode: 07109-0039
Category Name: Vacation Looks
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Grab The Keys And Go Swimsuit
Grab the keys and drive off to the water's edge in this hot one piece! The swimsuit has a round neckline paired with a keyhole front and back and has padded cups. The bikini cut one piece also features sexy, lattice sides for a little extra exposure.Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07109-0037
Category Name: Vacation Looks
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Fab In Fringe Bandeau
Create a total fab in fringe look with this majorly glam black bandeau! It features a sleeveless strapless square neckline, a cropped hem, and long rhinestone fringe detailing dangling down the front. The bandeau is composed of a knit fabric with plenty of stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07107-0303
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Fab In Fringe Pantie
Create a total fab in fringe look with this majorly glam black skirt pantie! It features a mid rise waist, a partially covered bottom, and a rhinestone fringe overlay creating a skirt illusion. The pantie is composed of a knit fabric that offers plenty of stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07108-0007
Category Name: Vacation Looks
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Key Lime High Waist Swim Bottom
Give them a taste of sweet and tangy in this neon green swim bottom! It features high rise sides and a semi-cheeky bum. Don't forget the matching swim top!Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0431
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Double The Fun Strappy Swim Bottom
Double up the poolside fun in this pink swim bottom! It features a high waist, multi strap design and a cheeky fit. Don't forget the matching swim top!Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE IN TACTRETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0412
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Passport To Paradise Swim Bottoms
Transport yourself to a tropical paradise in these vacay ready swim bottoms! They feature a colorful tropical print, a high rise fit, side slit accents on each side and a cheeky bottom. Be sure to pick up the matching top to complete your look!RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'6" with a 34" bust, 26" waist and 38" hips. She is wearing a size small.Style Number/Barcode: 07105-0406
Category Name: Vacation Looks
Price: $8.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rainbow Bright Swim Bottom
Be bold and be bright in this one of a kind swim bottom! It features a V cut style, side ties, and a full coverage bum. don't forget the matching top!Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0424
Category Name: Vacation Looks
Price: $8.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pucker Up Lemon Swim Bottoms
Pucker up in this zesty inspired swim bottom! It features a cute lemon print, a high rise waist, lattice accent along the sides and a high cut with cheeky coverage. Be sure to pick up the matching bikini top to complete your beach side look!RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0407
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Oh My String Swim Bottoms
Make jaws drop baby girl! This super sexy taupe bikini bottom features a high-cut string design with minimal coverage and a thong back. Don't forget the matching top!RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0376
Category Name: Vacation Looks
Price: $14.87 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Transport To Tropics Swim Bottoms
Transport yourself to an island paradise with these tropical-inspired swim bottoms. They feature a high rise waist with a hipster cut, tie waist accents and a cheeky bottom. The all over palm leaf print features green and blue hues. Be sure to pick up the matching duster and swim top to complete your look.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0397
Category Name: Vacation Looks
Price: $17.87 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Adventure Swim Bottom
Get ready to take off on an island adventure in these must have swim bottoms! They feature a black hue, a high rise waist and a high cut with a partial coverage bottom. The tropical floral design features red hues with green foliage. Be sure to pick up the matching swim top and cover up to complete your look!Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0395
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Artsy Babe Paisley Bodycon Slit Midi Dress
Strut like an artsy babe in this paisley mesh midi dress showcasing a flattering bodycon silhouette with a flirty front slit. Complete the look with a handbag.
Fit & Features
- Paisley print, mesh fabric, stretchy knit lining
- Square neckline
- Spaghetti straps
- Bodycon silhouette
- Front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5932
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Waist Swim Bottom
Soak up those sunny days as you shake up your swim wear! These swim bottoms feature a high waist, and a cheeky fit! Be sure to pick up the matching top to complete your poolside look!RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0386
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Greek Key Swim Top
Vacay like a goddess in this chic black swim top! It features adjustable spaghetti straps, a triangle design with lined and padded cups, and an elastic banded hem with a gold Greek key design. Don't forget the matching swim bottoms!Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07104-0209
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Strappy And Sultry Swim Bottoms
These black swim bottoms give off major strappy and sultry vibes! They feature a high rise strap detailed waist paired with a partial coverage bottom. Don't forget the matching swim top!Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0375
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek And Simple Swim Bottoms
Sometimes sleek and simple is the look to go for! These black swim bottoms feature a basic hipster style with a low rise waist, thin side straps, and a partial coverage bottom. Don't forget the matching swim top!RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0362
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropic Lush Bikini Bottom
Indulge in a tropical paradise with this green printed bikini bottom! It features a high rise fit with a stretchy waist band, and a high-cut design that offers a moderate coverage. Don't forget the matching bikini top!Model is 5'6" with a 34" bust, a 24" waist, and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0072
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cut To The Chase Swim Bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.We don't want to waste your time, so let's get down to business! This cute swim bottom has a high cut waist, an extreme cheeky bottom, and is composed of a smooth knit that offers plenty stretch for the perfect fit.
Style Number/Barcode: 07105-0287
Category Name: Vacation Looks
Price: $16.90
Availability: Out of Stock
Product Badge:- Ships Free
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Getting Drunk Swimsuit
Because she can't celebrate this moment without you! Support her recent engagement with this cute swimsuit that has a scoop neckline paired with narrow straps that lead to a low back and a sexy, high-cut bikini bottom. The one piece features an iridescent shine and a large screen print that says "Getting Drunk" in large, block letters.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.Style Number/Barcode: 07105-0240
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Card Swimsuit
Surprise them all with this bold one piece as you soak up some sun poolside! This one piece features a plunging V neckline, padded cups, shoulder straps with a clasp closing at the back. The front features sexy triangle shaped waist cut outs and straps attached to a high waist contrast bottom. Includes a full bottom.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'7 with a 32" bust, 24" waist and 37" hips. She is wearing a size small.Style Number/Barcode: 07105-0284
Category Name: Vacation Looks
Price: $29.00 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free