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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STYLE SPOTLIGHT

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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.

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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Flourishing Floral Midi Dress
Flourish in florals! Look cute for spring in this midi dress featuring a sleeveless square-neck bodice, spaghetti straps, and side ruched seams to accentuate your curves. Composed of soft knit fabric with a moderate stretch. Style with a trendy panama hat.

Fit & Features
- Squareneck, spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Midi-length hem
- Floral pattern
- Soft knit fabric
- Fits true to size, moderate stretch
Style Number/Barcode: 05101-1434

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ruffle Party Chiffon V-Neck Babydoll Dress
Make a ruffle at the party in this chiffon babydoll dress featuring a sleeveless V-neckline, adjustable spaghetti straps, criss-cross back, flowy silhouette, and a ruffled trim throughout. Composed of a chiffon woven fabric with an inner skirt lining. Perfect for styling with a mini tote bag.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Criss-cross back
- Babydoll flowy silhouette
- Ruffled trim throughout
- Chiffon woven fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1465

Category Name: Vacation Looks

Price: $6.67 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cherry Blossom Slit Midi Dress
Warmer temps call for showing off your shoulders! This stylish floral midi dress features a sleeveless, v-neckline, spaghetti straps, a front slit accent, and a cherry blossom pattern throughout. Complete the look in heels for a perf brunch fit'.

Fit & Features
- Sleeveless, v-neckline
- Sleek spaghetti straps
- Form-fitting silhouette
- Front slit, midi hem
- Cherry blossom floral print
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05101-1364

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Turn Heads Tie-Dye Open Back Maxi Dress
Serving body, back, and bold energy! This mesh maxi turns heads with a sultry cowl halter, hoop details, and a tie-dye print that does the most in the best way.

Fit & Features
- Tie-dye print, mesh fabric, stretchy knit lining
- Cowl halter neckline
- Hoop inserts, tie-back straps
- Open back
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000115

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials