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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Meet My Gauze And Crochet Romper
You see what you like, so go for it in this cute romper! It has a sleeveless V-neckline, adjustable straps that create a cross-back design, and a fully lined lace bodice. A sheer crochet panel highlights your waist. Shorts are composed of unlined gauze fabric and offer a flowy fit. Complete look with wedges and sunglasses for a fab day out.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross at back
- Sheer crochet panel at waist
- Flowy shorts
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06303-0157
Category Name: Vacation Looks
Price: $14.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Day Sleeveless Linen Romper
It's a perfect day to rock a romper for a casual moment! The romper features a sleeveless V-neckline, a cami-styled bodice, multi-button down front, adjustable spaghetti straps, and a smocked back. The waist features a cinching tie waist belt. hidden side pockets, and cuffed shorts. The romper is composed of a lined linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and a denim jacket.
Fit & Features
- Sleeveless V-neckline
- Multi-button down front
- Adjustable spaghetti straps
- Smocked back
- Tie waist belt, hidden side pockets
- Lined linen fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06303-0205
Category Name: Vacation Looks
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chase The Cheetah Tie-Front Top
You may wanna chase this cheetah tie-front top before it's gone! Features long peasant sleeves, a plunging neckline, and a cropped hem on texture woven fabric with no stretch. Complete the look in high-rise jeans and heels.
Fit & Features
- Long peasant sleeves
- Plunging neckline
- Tie-front detail
- Cropped hem
- Cheetah pattern
- Texture woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1164
Category Name: Vacation Looks
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hit The Tropics High Slit Maxi Skirt
Channel a tropical paradise in a skirt that makes waves! The skirt features a fun palm leaf print, an elastic high rise waist, and a maxi length with a high side slit. The skirt is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a crop top and wedges.
Fit & Features
- Palm leaf print
- Elastic high rise waist
- Maxi length
- High side slit
- Lined smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0655
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual And Chic Linen Shorts
Keep it casual and carefree in shorts that are perf for everyday! The shorts feature a high-rise waist, slant pockets, and a wide leg hem. The shorts are composed of a linen fabric that offers a relaxed fit with minimal stretch. Complete look with the matching top.
Shop Matching Top: Casual And Chic Tie Front Top
Fit & Features
- High rise waist
- Slant pockets
- Wide leg hem
- Lined linen fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06303-0134
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual And Chic Tie Front Top
Keep it casual and carefree in a top that is perf for every day! The top features a sleeveless sweetheart neckline with a tie-front accent, ruffled cap sleeves, a smocked bodice, and a cropped hem. The top is composed of a lined linen fabric that offers a form-hugging fit with minimal stretch. Complete look with the matching shorts.
Shop Matching Shorts: Casual And Chic Linen Shorts
Fit & Features
- Sleeveless sweetheart neckline
- Tie-front accent
- Ruffled cap sleeves
- Smocked bodice
- Cropped hem
- Lined linen fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1402
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Class Act Cowl Neck Cami Top
Classy and chic, you'll adore this cami top perfect for dressing up on date night! It features a stunning, sleeveless cowl neck with adjustable spaghetti straps and a flowy cropped hem on chiffon textured fabric with no stretch. Finish the look with a rhinestone bracelet.
Fit & Features
- Sleeveless, cowl neck
- Adjustable spaghetti straps
- Flowy cropped hem
- Chiffon textured fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1779
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylishly Sleek High Waist Satin Shorts
Keep it stylishly sleek with a pair of shorts that bring the luxe. The shorts feature a high-rise elastic waist, drawstring, hidden side pockets, and a cheeky bottom. The shorts are composed of a satin fabric that offers a relaxed fit with minimal stretch. Complete the look with the matching long sleeve top.
Shop Matching Top: Stylishly Sleek Satin Button Down Top
Fit & Features
- Elastic high-rise waist
- Drawstring
- Hidden side pockets
- Cheeky bottom
- Satin fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0230
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tequila Diet Script Cap
Let this cap say it all, babe! The sassy cap features a traditional baseball design and a contrasting script that reads: "Tequila Diet". Complete look with a crew neck top and cargo joggers.
Fit & Features
- Traditional baseball cap design
- Script: "Tequila Diet"
Style Number/Barcode: 07302-0503
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Blanco Reposado Anejo Script Cap
Let this cap get the party started! The fun cap features a traditional baseball design and a contrasting script that reads: "Blanco Reposado Anejo". Complete look with a crew neck top and cargo joggers.
Fit & Features
- Traditional baseball cap design
- Script: "Blanco Reposado Anejo Script Cap"
Style Number/Barcode: 07302-0504
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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With A Twist Gold Hoops
Like a cocktail, these gold hoops come with a twist! They have an omega-back closure with a rubber stopper for a secure fit. Complete the look in a classic LBD.
Fit & Features
- Twist design
- Omega-back closure
- Rubber stopper for a secure fit
- Metal material
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1206
Category Name: Vacation Looks
Price: $5.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vintage Rose Crepe Ruched Mini Dress
It's vintage-inspired, darling! Have your moment in this rose print mini dress featuring a square neck, long peasant sleeves, and curve-accentuating ruching, and a bodycon silhouette. Composed of a crepe-lined fabric with no stretch. Style with lace-up heels.
Fit & Features
- Squareneck, long peasant sleeves
- Ruching, back zipper closure
- Bodycon silhouette
- Mini-length hem
- Rose floral pattern
- Crepe-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 05101-1409
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destination Dinner Paisley Halter Mini Dress
Dinner plans? You're gonna need this perfect halter mini dress! It features a sleeveless bodice on an open-back with dual tie-back closure, a front slit accent, bodycon silhouette, and a paisley pattern throughout. Complete the look in lace-up heels.
Fit & Features
- Sleeveless, halter neckline
- Dual tie-back closure
- Front slit accent
- Bodycon silhouette
- Mini-length hem
- Paisley pattern
- Knit fabric, partial front knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4410
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Schedule Full Oversized Square Sunglasses
An essential pair of oversized square sunglasses to slip on when you're on the go!
Fit & Features
- Oversized design
- Square shape
- Tinted lenses
- Chain link detail on arms
Style Number/Barcode: 07008-1129
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Girl Next Door Crochet Crop Top
Keep it effortless with a cute crochet top that is totally fab for a day out! The top features a square neckline, cap sleeves, and a stunning lace-up back. The top is composed of an unlined crochet knit fabric that offers a relaxed fit. Complete look with cutoff shorts and sandals.
Fit & Features
- Square neckline
- Cap sleeves
- Lace-up back
- Cropped hem
- Unlined crochet fabric
- Runs true to size
Style Number/Barcode: 06005-1345
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Your Moment Slinky Wrap Crop Top
Flaunt your fashionista status in this cute wrap crop top featuring long sleeves, a plunge V-neck, and a twist front with a wrap-tie closure. Composed of slinky knit fabric with a moderate stretch. Complete the look in faux leather leggings for a chic fit.
Fit & Features
- Long sleeves
- Plunge V-neck
- Twist front
- Wrap-tie closure
- Cropped hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4105
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Nothing Bud Fun Floral Halter Dress
Have nothing but fun in this flirty floral halter dress perfect for a brunch date! It features a sleeveless, halter v-neck with adjustable neck tie, a babydoll style bodice leading to a flowy, ruffled short hem. Showcase some skin in the open-back with tie closure. Complete the look in lace-up sandals.
Fit & Features
- Sleeveless, halter v-neck, adjustable necktie
- Babydoll style bodice
- Flowy ruffled short hem
- Open-back, tie closure
- Ditsy floral print, woven-lined fabric
- Fits true to size, no stretch
Style Number/Barcode: 05102-4364
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bring The Edge Denim Skirt
Bring the edge with a mini skirt that shows off your affinity for the bold life! The skirt features a high-rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, heavy destruction, and a frayed hem. The skirt is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with a crop top and sandals.
Fit & Features
- High-rise waist
- Single-button with zipper closure
- Traditional five-pocket with belt loops
- Heavy distressing, frayed hem
- Dark wash denim fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0064
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring The Charm Floral Corset Top
Bring the charm to your spring 'fits with this adorable corset top! It features a romantic sweetheart neckline, short puff sleeves with a ruffle trim, front hook and eye closures, an all-over blooming floral print, and a cropped, form-hugging fit. Style with a denim mini skirt and mules.
Fit & Features
- Sweetheart neckline, padded cups
- Short puff sleeves, ruffle trim
- Front hook and eye closures
- Floral print
- Cropped, fitted silhouette
- Woven fabric
- Runs true to size
Style Number/Barcode: 06003-1588
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Staple High Waist Denim Skirt
Turn to this staple skirt that is perf for styling with your dressy and casual tops! The skirt features a high-rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, and a frayed hem. The skirt is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with a crop top and sandals.
Fit & Features
- High-rise waist
- Light distressing, frayed hem
- Single-button with zipper closure
- Traditional five-pocket with belt loops
- Light-medium wash denim fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0065
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Babe Low-Rise Swim Bottoms
Elevate your poolside look this season with these chic swim bottoms! They feature a low-rise waist with a cheeky fit and O-ring accents at the hips. Style with the matching swim top.
Shop Matching Top: Chic Babe Tank Swim Top
Fit & Features
- Low-rise waist
- Cheeky fit
- O-ring accents at the hips
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0839
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Babe Tank Swim Top
Elevate your poolside look this season with this chic swim top! It features a sleeveless tank design with a scoop neckline, adjustable spaghetti straps, and dual sleek O-ring accents at the front with sultry cutouts. Style with the matching swim bottoms.
Shop Matching Bottoms: Chic Babe Low-Rise Swim Bottoms
Fit & Features
- Sleeveless tank design
- Scoop neckline
- Adjustable spaghetti straps
- Dual O-ring accents, cutouts
- Back strap, slide hook closure
- Runs true to size
Style Number/Barcode: 07104-0692
Category Name: Vacation Looks
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On Trend Double Buckle Sandals
Step out in style in these trendy sandals that are perf for casual brunch dates! They feature an open almond toe, a dual strap design with double buckle detailing, and a slide-on fit. Pair these sandals with your favorite casual dress and a classic denim jacket.
Fit & Features
- Open almond toe
- Dual strap design
- Double buckle detailing
- Slide-on styling
Style Number/Barcode: 07404-0945
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take A Dip Mesh One Piece Swimsuit
Take a dip and look fab in this one-piece swimsuit featuring a one-shoulder strap design with a sheer mesh insert and removable padding. Complete the look in cute sunglasses.
Fit & Features
- One-Shoulder strap design
- Sheer mesh insert
- Removable padding
- Pull-on/off styling
- Fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0300
Category Name: Vacation Looks
Price: $4.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free