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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.

  • Flirtatious Florals Smocked Crop Top

    Feel oh so flirtatious in florals in this adorable smocked crop top! Pair with some high waist jeans for the perf spring time look!

    Fit & Features

    • Three quarter length sheer woven sleeves | Elastic banded ruffle hems
    • Square neckline | Faux tie front detail
    • Stretchy smocked bodice
    • Cropped, form hugging fit
    • All over small floral print

    Style Number/Barcode: 06003-0810

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Like Me Sleeveless Ruffled Maxi Dress

    An effortless woven maxi dress for shower celebrations, graduations, or meet-ups with the girls! It boasts a flowy ruffled silhouette and a floor-length hem perfect for styling with cute sandals.

    Fit & Features

    • Cotton fabric, woven lining
    • Square neckline
    • Adjustable spaghetti straps
    • Flowy ruffled silhouette
    • Maxi-length floor hem
    • Runs true to size

    Style Number/Barcode: 05102-6022

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Comin' Up Short Belted Cuffed Dress Shorts

    Don't come up short this season, get your shorts lined up for the warm weather! Style these gorg belted shorts with a tucked in tee, or dress up with a loose button up blouse!

    Fit & Features

    • High waist fit
    • Belt detail with matching square buckle
    • Slanted pockets
    • Soft woven knit material | Minimal stretch

    Style Number/Barcode: 06403-0090

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Runnin' On The Beach Strappy Swim Top

    Go for a little run on the beach in a swimsuit that accentuates that bronze tan! Don't forget to pick up your matching swim bottoms for the complete look!

    Shop Matching Bottoms: Runnin' On The Beach Hipster Swim Bottoms

    Fit & Features

    • V-neckline
    • Tank straps with a mesh trim
    • Criss cross strap detailing
    • Removable padding
    • Bar hook closure 
    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0398

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Make It Clear Thong Chunky Heels

    Make a clear statement in a pair of chunky heels! Style these with high waist denim and a tucked in tee, and make them the star of the show!

    • Open square toe
    • Clear thong design
    • Faux suede
    • Chunky block heel

    Style Number/Barcode: 07401-0666

    Category Name: Vacation Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Lust For Lavender Mini Purse

    Our new fav color is lavender! This pop of color adds a touch of femininity to your look, and we are obsessed! Get a little extra and pair with matching lavender heels!

    • Extra mini purse
    • Square structure
    • Single handle
    • Faux leather
    • Chain link shoulder strap
    • Snap closure

    Style Number/Barcode: 07201-0012

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Scallop Trim Tie Front Romper

    This playful romper is a wardrobe must-have! Make sure to add a fedora and some wedges for a springtime look! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • Tie Front Design 
    • Back Zipper With Hook & Eye Closure I Smocked Back 
    • Crochet Scallop Trim Along The Neckline, Bust, & Hem 
    • Wide Leg Openings 
    • Woven Fabric I Fully Lined 
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 06303-0050

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lively In Linen High Waist Shorts

    You'll be lookin' lively in linen in these spring break ready high waist shorts! Perf for a day out in the sun with the girls, the shorts and matching top make the cutest set!

    Shop Matching Top: Lively In Linen Crop Top

    Fit & Features

    • High rise waist
    • Belt loops
    • Front button | Hidden zipper closure
    • Two slanted front pockets
    • Cuffed
    • Linen fabric | Woven lining

    Style Number/Barcode: 06303-0063

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lively In Linen Crop Top

    You'll be lookin' lively in linen in this spring break ready crop! Perf for a day out in the sun with the girls, the top and matching shorts make the cutest set!

    Shop Matching Bottoms: Lively In Linen High Waist Shorts

    Fit & Features

    • Strapless sweetheart neckline
    • Tie front detail
    • Stretchy smocked back
    • Zipper closure
    • Cropped
    • Linen fabric

    Style Number/Barcode: 06003-0818

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forever Chill Cat Eye Sunglasses

    Shade the BS, and stay forever chill with a pair that gives you a lil' sassy finish! Perfectly style with a one piece bathing suit, and a chain belt!

    • Straight cat eye
    • Tortoise shell frame
    • Dark lenses

    Style Number/Barcode: 07008-0725

    Category Name: Vacation Looks

    Price: $4.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss Always Right Matte Jelly Crossbody Purse

    Hey there miss always right, you are making the right move when you pair this luxurious matte jelly with that all white 'fit! 

    • Rectangular structure
    • Matte jelly
    • Quilted design
    • Golden turn lock closure
    • Inner divider
    • Convertible crossbody strap | Shoulder strap

    Style Number/Barcode: 07203-0294

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flutter Some Hearts Floral Crop Top

    You'll be sure to flutter some hearts in this adorable floral printed crop top!

    Fit & Features

    • Flutter short sleeves
    • V neckline
    • Stretchy smocked waist | Faux button detailing
    • Cropped ruffle hem
    • Small floral print
    • Woven fabric | No stretch

    Style Number/Barcode: 06003-0807

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Denim Puff Sleeve Crop Top

    Give your denim an updated look with a gorge puff sleeve! This fab crop goes perf for pairing with your favorite prints and fringe pieces!

    Fit & Features

    • Off The Shoulder Neckline | No-Slip Strip
    • Elastic Sweetheart Bust
    • Short Puff Sleeves
    • Bustier-Styled Cups
    • Cropped Hem 
    • Lined Denim Fabric 
    • Relaxed Fit | Minimal Stretch 

    Style Number/Barcode: 06003-0718

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pick A Side One Shoulder Swimsuit

    Every side will be your good one in this simply chic one shoulder swimsuit!

    Fit & Features

    • One shoulder neckline | Tortoise shell O-ring detail
    • High rise waist | High cut design
    • Tortoise shell O-ring accent at waist
    • Cheeky bottom

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07109-0141

    Category Name: Vacation Looks

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gummy Bear Bobby Pin 6 Pack

    O-M-G gummy bears baby! These are too adorable, and tbh we are getting as set for ourselves because we can't resist!

    • Set of six bobby pins
    • Gummy bear accents
    • Multi colored
    • Gold pin
    • Slide on

    Style Number/Barcode: 07006-0117

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Style Zebra Print Mini Skirt

    Show off a wild style in this trendy zebra print mini skirt! It features a high-rise waist, a ruched front seam leading to a chic slit, a mini-length hem, and a form-hugging fit. Complete the look with the matching crop top and a pair of clear heels.

    Shop Matching Top: Wild Style Zebra Print Crop Top

    Fit & Features

    • High-rise waist
    • Ruched front seam
    • Front slit
    • Mini-length hem, form-hugging fit
    • Zebra print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0786

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stand In The Sand Woven Double Buckle Sandals

    These beachy inspired slides are a summer must have! Perfect for resort wear, or a day at the beach! Style with cut off denim, or high waist shorts!

    • Open round toe
    • Adjustable double buckles
    • Low cork platform
    • Straw woven detailing

    Style Number/Barcode: 07404-0570

    Category Name: Vacation Looks

    Price: $11.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Girl Next Door Tie Front Gingham Tube Top

    Get cute for summer in this gingham tube top, perfect for casual events! This flirty, figure-flattering crop top features a charming gingham pattern and adjustable tie front detail that creates the perfect silhouette.

    Fit & Features

    • Gingham print, cotton woven fabric
    • Strapless tube neckline
    • Tie-front detail
    • Stretchy smocked silhouette
    • Ultra cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000076

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Standing Tall Flat Platform Sandals

    Stand a lil taller when these 90z inspired platform sandals! Style with a sweet summer dress, or some cut off denim!

    • Open round toe
    • Single band over the toe
    • Sling back ankle strap
    • Adjustable pin buckle closure
    • Faux leather 
    • Faux suede straps
    • Platform sole

    Style Number/Barcode: 07404-0138

    Category Name: Vacation Looks

    Price: $17.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bronzed To The Godz Shimmering Swim Top

    Bbydoll you are bronzed to the godz and this shimmering bronze swimsuit will just take you there! Next level beach babe, bronze goddess!

    Fit & Features

    • Wired swim top
    • No padding
    • Flattering seams | Glitter finish
    • Adjustable spaghetti straps
    • Bar hook closure 
    • Fully lined
    • Matching swim bottoms: 07105-0456

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0299

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shimmy And Shimmer Swim Tank

    Shimmy, shimmer, and catch the light in a perfectly sparkling swim suit! Don't forget to pick up the matching swim bottoms to finesse your look!

    Shop Matching Bottoms: Shimmy And Shimmer High Waist Swim Bottoms

    Fit & Features

    • Scoop neckline
    • Adjustable spaghetti straps 
    • Fully lined
    • Non-padded
    • Blush tone with silver reflects
    • Moderate stretch

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0317

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shimmy And Shimmer High Waist Swim Bottoms

     Shimmy, shimmer, and catch the light in a perfectly sparkling swim suit! Don't forget to pick up the matching swim top to finesse your look!

    Shop Matching Top: Shimmy And Shimmer Swim Tank

    Fit & Features

    • Extra high waist fit
    • High rise hips
    • Thick elastic waist band
    • Fully lined
    • Blush tone with silver reflects
    • Moderate stretch

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0473

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • West Coastin' Low Block Mules

    Keep it light and breezy with that west coast style! These sweet simple mules pair so well with cut off denim!

    • Square oval open toe
    • Double bands
    • Low block heel
    • Black & Tan are faux nubuck
    • White pair is faux leather

    Style Number/Barcode: 07401-2147

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy In Stripes Kimono

    Keep it sassy in stripes in this airy kimono! Layer on this basic must-have with the perfect tee and jeans for a laid-back look!

    Fit & Features

    • Drape Open Front
    • Kimono Sleeves
    • Stripe Pattern
    • Lightweight-Woven Fabric
    • Relaxed Fit
    • Minimal Stretch 

    Style Number/Barcode: 06204-0326

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance