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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Paradise Tie Front Blouse
Get a piece of paradise with this tropic top! The taupe blouse has a flattering, tie front closure paired with long sleeves that feature a ball tassel trim. The woven top has a thin, light weight feel with a tropical, palm leaf print that has you dreaming of your tropic paradise.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06204-4628
Category Name: Vacation Looks
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tie Waist Lace Duster
Layer up that casual outfit for a stylish look! This black lace duster features short sleeves, an open front with a waist tie, and a calf length. Duster is unlined and completely sheer.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06204-4659
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go With The Flow Tie Front Top
Go with the flow of this pretty tie front top! It features short flowy kimono style sleeves paired with a tie front and a cropped hem. The top is composed of a woven fabric with no stretch and offers a relaxed and comfortable fit.
Style Number/Barcode: 06204-4646
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Ties Crop Top
Sweeten up your wardrobe with this cute top! It has a flattering, knot tie front paired with three-quarter sleeves and a cropped hem. The garment is composed of a thin woven fabric with a ribbed textured.Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.
Style Number/Barcode: 06204-4619
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ring Around In Florals Top
Surround yourself with pretty florals in this cute black top! It features a plunging knot bodice with tie strap accents, long bell sleeves and a cropped hem. The all over floral print features white and pink hues that complement the black background. Top is composed of lightweight textured woven fabric that offers a form hugging fit with minimal stretch.
Style Number/Barcode: 06204-0000
Category Name: Vacation Looks
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Making Hiss-Tory Snake Duster
You're an icon in the making girl! Stand out with this duster!
Fits & Features
- Open Front
- Fitted Long Sleeves
- Sheer Mesh Fabric With An All Over Snake Print Design
- Dramatic Slits At The Sides
- Relaxed Fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06202-1123
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Fit Crop Top
This ivory crop top is fitted, flattering, and so fun! It features a tie front detail that creates a deep V neckline, short cap sleeves, and a slim fit throughout. Top is composed of a stretchy, brushed knit fabric.Model is 5'7" with 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06202-1124
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Fresh Mesh Duster
Keep your summer 'fit fun and fresh with this long mesh duster! It features long loose sleeves with a cuffed hem, a drape front with a tie front belted waist, and a flowy, relaxed fit. The black duster is composed of a sheer mesh fabric with plenty of stretch.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 06202-1120
Category Name: Vacation Looks
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Don't Mesh Around Kimono
This trendy mesh kimono doesn't mess around! It features short kimono sleeves paired with a drape open front. The black kimono is composed of a sheer mesh fabric that offers moderate stretch and a relaxed fit.
Style Number/Barcode: 06202-1102
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make It Wild Duster
Make your 'fit wild and free with this animal print-inspired duster! It features long fitted sleeves, a drape open front, and a relaxed and comfortable fit. The duster is composed of a black and orange mesh fabric that offers plenty of stretch.Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06202-1104
Category Name: Vacation Looks
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Caught In A Mesh Top
Get caught up in this hot mesh of a top! This black, crop top has a flattering V neckline paired with a tie front, knot closure and long, narrow sleeves. The crop top is composed of a sheer, unlined mesh that offers plenty of stretch.Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.
Style Number/Barcode: 06202-1098
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tropic Touch Mesh Duster
Add a little tropic touch to your 'fit! This cute duster has an open front paired with fitted sleeves and is composed of a sheer, unlined mesh that offers plenty of stretch. The highlight of this beach-ready piece is the tropical print that feature shades of orange and green.
Style Number/Barcode: 06202-1091
Category Name: Vacation Looks
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Sweet Knot To Love
You're simply too sweet not to love in this cute pink top! it features an off the shoulder neckline with shoulder strap accents, a plunging sweetheart bust with knot accent, a merrow edge trim throughout and a cropped fit. Top is composed of a smocked fabric that offers a relaxed with a moderate stretch.Model is 5'8" with a 34" bust, 25" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-6365
Category Name: Vacation Looks
Price: $7.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Zesty Cutie Orange Print Pajama Top
Zesty and cute, this orange print pajama top makes sleeping or lounging juicy sweet! Pair with the matching pajama shorts to complete the look.
Fit & Features
- Orange print, stretchy rib knit fabric
- Short sleeves
- Crew neckline
- Fitted crop hem
- Runs true to size
Shop The Matching Pajama Shorts: Zesty Cutie Orange Print Pajama Shorts
Style Number/Barcode: 07103-000014
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take Me To Paradise Top
Who likes to vacay? We do! Get those relaxing vibes going in this tropical-inspired top! It features a red hue, a plunging knotted bodice, short sleeves and a cropped hem. The all over palm leaf print features green and blue hues. Top is composed of a lightweight unlined woven fabric that offers a relaxed fit with minimal stretch. Be sure to pick up the matching shorts!Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06202-0008
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Style Ribbed Midi Dress
Keep it sleek and stylin' with this yellow ribbed midi dress! It features a deep round neckline, spaghetti straps, and a traditional midi length. Ribbed knit offers plenty of curve hugging stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-6284
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
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Crochet Babe Tunic
All you need is sand and sun with this peach crochet tunic! It has a deep V neckline, lined cups, adjustable shoulder straps leading to a low square back, an exposed silver zipper closure, and a comfortable slim fit.Tunic is composed of an unlined crochet fabric with minimal stretch.Model is 5'7 with a 34" bust, 24" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-6289
Category Name: Vacation Looks
Price: $5.00 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway In Crochet Crop Top
Take a nice getaway in this vacay-ready crochet crop top! It features a crew neckline, long sleeves, a cropped hem, and a ribbed trim. The ivory top is composed of a sheer crochet knit fabric with no stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06005-6302
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Clearance
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Take A Snap Button Midi Dress
You'll want to take tons of snaps for the gram in this button down midi dress! It features a sleeveless bodice, tank-like shoulder straps, gold faux snap buttons, a front slit, and a midi length. The black dress is composed of a ribbed knit fabric with plenty of stretch.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 06005-6300
Category Name: Vacation Looks
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
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Such A Romantic Crop Top
Show your sweet, romantic side in this adorable crop top! It features a sleeveless bodice, spaghetti straps, a crossover front with a sweetheart neckline, and a cropped hem. The top is composed of a crepe fabric that offers moderate stretch and a form hugging style. Complete your romantic look with the matching high waist pants!
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9928
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Festive In Fringe Halter Top
Keep it festive in this adorable fringe halter top! It features a sleeveless bodice, halter straps that lead to a back tie closure, a deep V neckline, a sheer inset underneath the bust, and fringe detailing that flows down. The top is composed of a crochet fabric with moderate stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-0904
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Stuff Banded Crop Top
A little sweet, a little naughty. This black crop top features a daring strapless sweetheart neckline, a back zipper and a band hemline. Top is composed of a knit fabric with moderate stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9877
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smocked And Cropped Top
Keep cute and cropped in this white top! It features an off the shoulder neckline, a sweetheart bust, short sleeves, a drawstring bodice and a cropped hem. Top is composed of a smocked fabric that offers a stretchy fit.Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06003-9891
Category Name: Vacation Looks
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Button Up In Smock Top
Start the day looking fab in this top! It features a white hue, an off the shoulder neckline with a sweetheart bust, a ruffled trim, a keyhole accent with a tie detail and a button down front. Top is composed of a smocked fabric that offers a form hugging fit with a moderate stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06003-9885
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale