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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Stunning Beauty Floral Chiffon Tie-Front Top
Let your stunning beauty radiate in this breezy chiffon top! It features long blouson sleeves with elastic banded hems, a V neckline leading to a tie-front closure, and a cropped, form-hugging fit. The sheer chiffon fabric showcases a pretty floral print that will pair perfectly with light-wash denim. Accessorize with sleek hoop earrings for a stylish look.
Fit & Features
- Long blouson sleeves with elastic banded hems
- V neckline
- Tie-front closure
- Cropped, form-fitting style
- Sheer floral chiffon fabric
- No stretch
- Runs true to size
Style Number/Barcode: 06204-0808
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunkissed Tropical Bandeau Bikini Top
Channel a sunkissed look with a bikini top that will have you beach-ready! The top features a bandeau-style, a tropical print, a tortoise-hued O-ring at the center, supportive flexible boning at the sides, and removable padding. Complete look with the matching bikini bottoms and t-strap sandals.
Shop Matching Bikini Bottoms: Sunkissed Tropical High Waist Bikini Bottoms
Fit & Features
- Bandeau-style
- Tropical print
- Removable padding
- Tortoise-hued O-ring at the center
- Flexible boning
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0535
Category Name: Vacation Looks
Price: $5.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunkissed Tropical High Waist Bikini Bottoms
Channel a sunkissed look with bikini bottoms that will have you beach-ready! The bottoms feature a high-rise waist, a tropical print, and a cheeky bottom. Complete look with the matching bikini top and t-strap sandals.
Shop Matching Bikini Top: Sunkissed Tropical Bandeau Bikini Top
Fit & Features
- High rise waist
- Tropical print
- High cut
- Cheeky bottom
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0683
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic And Cinched One Piece Swimsuit
Channel a chic and cinched look with a swimsuit that shows curves off in all the right places. The swimsuit features a sleeveless square neckline, adjustable spaghetti straps, removable padding, dual drawstrings, and a high cut with a cheeky bottom. The swimsuit is composed of a lined textured waffle-knit fabric that offers a form-hugging fit. Complete look with sunnies.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Removable padding
- Dual drawstrings
- High cut
- Cheeky bottom
- Form hugging fit, moderate stretch, runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0263
Category Name: Vacation Looks
Price: $16.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Read Between The Lines Bikini Bottoms
Have em' read between the lines with bikini bottoms that stun. The bikini bottoms feature a low-rise waist, a high-cut front, contrasting trim, and a cheeky bottom. Complete look with the matching bikini top and sandals.
Shop Matching Bikini Top: Read Between The Lines Bikini Top
Fit & Features
- Low-rise waist
- High-cut front
- Contrasting trim
- Cheeky bottom
- Form hugging fit, moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0708
Category Name: Vacation Looks
Price: $5.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Read Between The Lines Bikini Top
Have em' read between the lines with a bikini top that stuns. The bikini top features a plunging V-neckline, supportive tank straps, contrasting trim, and a slide hook closure at the back. Complete your look with the matching bikini bottoms and sandals.
Shop Matching Bikini Bottoms: Read Between The Lines Bikini Bottoms
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Contrasting trim
- Slide-hook fasten at the back
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0561
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Fave Flowy V-Neck Midi Dress
This breezy lightweight midi dress will be your new casual fave for weekend plans. Designed with a sleeveless V-neck, low back, and mid-length flowy fit, style with a layered necklace and strappy sandals.
Fit & Features
- Gauze woven fabric, mini-length stretchy knit lining
- Sleeveless V-neckline
- Adjustable spaghetti straps, low back
- Hidden side pockets
- High side slit
- Midi-length flowy silhouette
- Runs true to size
Style Number/Barcode: 05102-000185
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sealed With Edge Jelly Sandals
These sandals are part glam, part edgy. The sandals feature a t-strap design with studded embellishments, a bow accent, an open almond toe, and composed of jelly material. Complete the look with a cute swimsuit and coverup.
Fit & Features
- Open almond toe
- T-strap design
- Studs
- Bow accent
- Jelly material
Style Number/Barcode: 07404-0684
Category Name: Vacation Looks
Price: $12.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Muse Tropical Floral Tie-Front Top
Serving island goddess energy with every step. This mesh tie-front top brings the vacay vibes with tropical floral drama and an ultra-cropped fit that moves with you from golden hour to after-party. Style with the matching maxi skirt for a look that slays.
Shop Matching Bottoms: Island Muse Tropical Floral Maxi Skirt
Fit & Features
- Sheer mesh fabric, high stretch
- Tropical floral print
- V-neckline
- Tie-front design
- Long bishop sleeves
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06202-000036
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet And Chic Ruffled Lace Romper
Keep it sweet and chic with a romper that brings pretty details. The romper features a sleeveless sweetheart neckline with a ruffled trim, tank-like shoulder straps, a lined lace body throughout, and wide-leg shorts with a cheeky fit. Complete look with wedges for a brunch ready look.
Fit & Features
- Sleeveless sweetheart neckline
- Ruffles
- Tank shoulder straps
- Lace body
- Wide leg shorts, cheeky fit
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06503-0098
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Stunner Tulip Pants
This spring season, bring those stunning bohemian vibes to your look with these chic tulip pants. They feature a high-rise waist with an elastic banded back, a flowy, wide-leg fit, and high front slits. The lightweight woven fabric has an all-over boho-inspired print that will pair perfectly with the matching top. Complete your look with strappy sandals.
Shop Matching Top: Bohemian Stunner Long Sleeve Crop Top
Fit & Features
- High-rise waist
- Elastic banded back
- Wide-leg fit
- High front slits
- Woven fabric with no stretch
- Boho-inspired print
- Runs true to size
Style Number/Barcode: 06302-0179
Category Name: Vacation Looks
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Stunner Long Sleeve Crop Top
This spring season, bring those stunning bohemian vibes to your look with this chic crop top. It features a deep V neckline, long loose sleeves with elastic cinched hems, and a cropped, form-hugging fit with an elastic banded back hem. The lightweight woven fabric has an all-over boho-inspired print that will pair perfectly with the matching pants. Complete your look with strappy sandals.
Shop Matching Bottoms: Bohemian Stunner Tulip Pants
Fit & Features
- V neckline
- Long loose sleeves with cinched hems
- Cropped, form-fitting style
- Elastic banded back hem
- Woven fabric with no stretch
- Boho-inspired print
- Runs true to size
Style Number/Barcode: 06003-1182
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Off The Shoulder Asymmetrical Midi Dress
Keep it fab in a floral midi dress that brings the romance to your outfit! The dress features an off the shoulder neckline, off the shoulder straps, a sweetheart bust with padded cups, a built-in no-slip strip, and a floral print. The relaxed fit bodice leads to a stunning asymmetrical midi length silhouette. Complete look with wedges.
Fit & Features
- Off the shoulder neckline
- Sweetheart bust, padded cups, gel no-slip strip
- Floral print
- Asymmetrical midi-length silhouette
- Lined smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0465
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make A Splash Smocked Bikini Bottoms
Make a splash in chic bikini bottoms! The bikini bottoms feature a high-rise waist, dual O-ring accents at the hips, high cut, and a cheeky bottom. The swim bottoms are composed of a smocked fabric. Complete look with the matching bikini top and sunnies.
Shop Matching Bikini Top: Make A Splash Smocked Bikini Top
Fit & Features
- High rise waist
- Dual O-ring accents at the hips
- Smocked fabric
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0658
Category Name: Vacation Looks
Price: $2.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make A Splash Smocked Bikini Top
Make a splash in a chic bikini top! The bikini top features triangle cups, an O-ring accent at the center, tank-straps, and composed of a smocked fabric. Complete look with the matching bikini bottoms and sunnies.
Shop Matching Bikini Bottoms: Make A Splash Smocked Bikini Bottoms
Fit & Features
- Plunging V-neckline
- Tank straps
- O-ring accent
- Smocked fabric
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0509
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Edgy Glam Studded Jelly Sandals
These sandals are part glam, part edgy. The sandals feature a t-strap design with studded embellishments, a bow accent, an open almond toe, and composed of jelly material. Complete the look with a cute swimsuit and coverup.
Fit & Features
- Open almond toe
- T-strap design
- Studs
- Bow accent
- Jelly material
- Patent-like finish
Style Number/Barcode: 07404-0683
Category Name: Vacation Looks
Price: $12.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Stunner Boho Flare Pants
Showcase your stunning style in these dreamy boho-chic flare pants! They feature a high-rise elastic banded waist, form-fitting pant legs, and a flared-out hem. The stretchy knit fabric has an all-over paisley print that will pair perfectly with a basic crop top. Complete your look with strappy sandals.
Fit & Features
- High-rise elastic banded waist
- Form-fitting pant legs
- Flared hem
- Knit fabric with plenty of stretch
- Paisley print
- Runs true to size
Style Number/Barcode: 06502-0488
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Budding Romance Strapless Floral Jumpsuit
Get a romantic look for date night this spring in this stunning floral printed jumpsuit! It features a strapless square neckline, a high waist, and flowy pant legs. The sheer mesh fabric has a gorgeous all-over rose print and includes a full knit lining. Complete your outfit with wedges and new earrings.
Fit & Features
- Strapless square neckline with an elastic banded hem
- High waist
- Flowy pant legs
- Sheer mesh fabric with a full knit lining
- Rose print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0382
Category Name: Vacation Looks
Price: $18.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Essential Staple Denim Mini Skirt
Slay your look with an essential denim skirt that goes with everything! The skirt features a high-rise waist and a mini-length silhouette with a mini side slit. The skirt is composed of a denim fabric that offers a form-hugging fit. Complete look with a cami and clear mules for a girl-next-door look.
Fit & Features
- High rise waist
- Mini length silhouette
- Mini side slit
- Form hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0014
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Babe Flowy Tie-Front Romper
You'll be a total boho babe in this flowy romper that is perf for the warmer months. It features an off-the-shoulder neckline that can also be worn on the shoulders, long wide bell sleeves, a tie-front belt, and flowy shorts. The lightweight gauze woven fabric has no stretch. Complete your look with statement earrings and strappy sandals.
Fit & Features
- Off-the-shoulder neckline
- Long bell sleeves
- Elastic high waist
- Tie-front belt
- Flowy shorts
- Gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0106
Category Name: Vacation Looks
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love At First Sight Mini Dress
With you in this adorable ditsy floral dress, it will be love at first sight. The dress features thin ruffle shoulder straps, a V neckline with subtle ruching, and a short, curve-hugging silhouette. The lightweight knit fabric offers plenty of stretch. Complete your look with a classic denim jacket and sneakers.
Fit & Features
- Thin ruffle shoulder straps
- V neckline with ruching
- Mini-length, form-hugging fit
- Knit fabric with plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-1429
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Retro Tie Dye Bodysuit
Channel a retro feel with a bodysuit that makes a colorful impression. The bodysuit features a sleeveless scoop neckline, tank shoulder straps, a tie-dye print, and a thong bottom with dual snap button closure. Complete look with a high waist mini skirt.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Tie-dye print
- Thong bottom with dual snap button closure
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3248
Category Name: Vacation Looks
Price: $11.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropic Time Halter Cutout Wide-Leg Jumpsuit
Bring on the summer weather in this tropical wide-leg jumpsuit for your next vacation or any weekend plans! This eye-catching jumpsuit features a flattering halter neckline and strategic cutouts that accentuate your curves.
Fit & Features
- Tropical print, stretchy knit fabric
- Halter neckline with spaghetti strap ties
- Cutout bodice
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000013
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Stripes Strapless Romper
Stun with a striped romper that channels those stylish vibes! The romper features a strapless square neckline, a tie-waist belt, and striped wide-leg shorts. Complete your cute brunch outfit with a pair of wedges and sleek hoops.
Fit & Features
- Strapless square neckline
- Tie-waist belt
- Striped wide-leg shorts
- Elastic banded back hem
- Form-hugging fit
- Knit top with a moderate stretch
- Lightweight woven shorts with a knit lining
- Runs true to size
Style Number/Barcode: 06303-0107
Category Name: Vacation Looks
Price: $16.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale