Vacation Looks

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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.

  • Vintage Glam Oversized Denim Jacket

    Create a vintage glam moment with an oversized denim jacket that adds a layer of style to your look. The jacket features a collared neckline, long sleeves, big pockets, a multi-button down front, and a cropped hem. The denim jacket offers a relaxed fit with minimal stretch. Complete look a crop top and a mini skirt.

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Big Pockets
    • Multi-button down front
    • Cropped hem
    • Light distressing
    • Relaxed fit, minimal stretch

    Style Number/Barcode: 06203-0117

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovin' Lace Crochet Crop Top

    Lace-up in this charming crop top that creates a sweet impression. The crop top features an off the shoulder neckline, a square neck bust with a cute tie-front, unlined long sleeves with elastic hem, and a cropped hem with lace trim. The top is composed of a lined crochet lace fabric that offers a relaxed fit with a slight stretch. Complete your look with cut off shorts and knee-high boots. 

    Fit & Features

    • Off the shoulder neckline
    • Square neck with tie front
    • Unlined long sleeves
    • Crochet lace bodice 
    • Cropped hem
    • Relaxed fit, slight stretch 
    • Back zipper closure 

    Style Number/Barcode: 06001-3113

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Destructed Oversized Denim Jacket

    Layer on this trendy denim jacket for an effortlessly edgy vibe! It features a collared neckline, long sleeves with buttons, a complete button-down front, buttoned chest pockets, lower front pockets, distressed detailing, and a relaxed, oversized fit. Pair this denim jacket with a graphic tee and your fave pair of shorts.

    Fit & Features

    • Collared neckline
    • Long sleeves with buttons
    • Button-down front
    • Buttoned chest pockets
    • Lower front pockets
    • Destructed denim fabric
    • Oversized fit

    Style Number/Barcode: 06203-0116

    Category Name: Vacation Looks

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing The Sun Bikini Top

    Chase those warmer days with a cute bikini top that is vacay ready! The bikini top features a padded square neck, cute tie shoulder straps, and cropped hem. Complete your fit' with the matching bikini bottoms and sunglasses

    Shop Matching Bikini Bottoms: Chasing The Sun Bikini Bottoms

    Fit & Features

    • Sleeveless square neck
    • Padded 
    • Tie-shoulder straps
    • Cropped hem
    • Matching bikini bottoms sold separately 

     

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

    Style Number/Barcode: 07104-0356

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chasing The Sun Bikini Bottoms

    Chose those warmer days with cute bikini bottoms that are vacay ready! The bikini bottoms feature a high rise waist and a cheeky fit. Complete your fit' with the matching bikini top and sunglasses.

    Shop Matching Bikini Top: Chasing The Sun Bikini Top

    Fit & Features

    • High rise waist
    • High cut
    • Cheeky fit
    • Matching bikini top sold separately

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

    Style Number/Barcode: 07105-0508

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Moment Oversized Cropped Denim Jacket

    Create a trendy moment with an oversized denim jacket that adds a layer of style to your look. The jacket features a collared neckline, long sleeves, big pockets, a multi-button down front, and a cropped hem. The denim jacket offers a relaxed fit with minimal stretch. Complete look a crop top and a mini skirt

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Big Pockets
    • Multi-button down front
    • Cropped hem 
    • Light distressing 
    • Relaxed fit, minimal stretch 

    Style Number/Barcode: 06203-0118

    Category Name: Vacation Looks

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glamorous Vibes Rhinestone Trim Sunglasses

    These fabulous sunglasses will give you major gorgeous and glam vibes! They feature an oversized design with tinted lenses and a stylish rhinestone trim. Pair these sunnies with a rhinestone choker necklace to really bring the bling.

    Fit & Features

    • Oversized design
    • Plastic frame
    • Tinted lenses
    • Rhinestone trim

    Style Number/Barcode: 07008-0805

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Flirt Ditsy Floral Mini Dress

    Capture hearts in this flirty ditsy floral printed mini dress that is perfect for spring! It features short puff sleeves, a sweetheart neckline with a tie-front detail, and a mini-length, curve-hugging silhouette. The dress is composed of a lightweight, stretchy knit fabric with no lining. Style this floral dress with cute wedges for brunch with the girls.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Tie-front at the bust
    • Short, form-hugging fit
    • Ditsy floral print
    • Stretchy unlined knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1078

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Chic Tie-Front Crop Top

    Effortless for vacay or weekend fun, this chic top is designed with flowy short sleeves and a tie-front perfect for styling alone or layering!

    Fit & Features

    • Cotton woven fabric
    • Flowy short sleeves
    • V-neckline
    • Tie-front 
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000017

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Dreamer Lace Corset Crop Top

    Get a dreamy boho-inspired look in this sheer lace crop top! It features tank-like shoulder straps, a corset design with hook and eye front closures, a stretchy smocked back, and a cropped, form-hugging fit. Pair this top with high rise distressed jean shorts and some strappy sandals.

    Fit & Features

    • Tank-like shoulder straps
    • Corset design
    • Hook and eye front closures
    • Stretchy smocked back
    • Cropped
    • Form-fitting
    • Sheer lace fabric with moderate stretch

    Style Number/Barcode: 06001-3013

    Category Name: Vacation Looks

    Price: $11.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forever Fierce Micro Swim Top

    Feel forever fierce as you relax poolside in this adorable micro swim top! It features a triangle design with halter spaghetti straps, a padded bust, lower thin straps that tie at the back, and a trendy leopard print. Pair this swim top with the matching swim bottoms and a flowy sheer mesh duster.

    Shop Matching Swim Bottoms: Forever Fierce Micro Swim Bottoms

    Fit & Features

    • Triangle design
    • Halter spaghetti straps
    • Padded bust
    • Thin straps that tie at the back
    • Leopard print
    • Runs true to size

     

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

    Style Number/Barcode: 07104-0496

    Category Name: Vacation Looks

    Price: $9.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Fierce Micro Swim Bottoms

    Feel forever fierce as you relax poolside in these adorable micro swim bottoms! They feature a high-cut cheeky fit, thin side straps, and a trendy leopard print. Pair these swim bottoms with the matching swim top and a flowy sheer mesh duster.

    Shop Matching Swim Top: Forever Fierce Micro Swim Top

    Fit & Features

    • High-cut cheeky fit
    • Thin side straps
    • Leopard print
    • Runs true to size

     

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

    Style Number/Barcode: 07105-0644

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylishly Studded Flat-Top Sunglasses

    Accessorize your trendy look and get a cool, chic vibe with these sunglasses! They feature a flat-top design, a center cut-out, and tinted lenses with small stud detailing on each side. Pair these shades with a graphic tee and distressed denim.

    Fit & Features

    • Flat-top design
    • Center cut-out
    • Tinted lenses
    • Small stud detailing
    • Plastic frame and arms

    Style Number/Barcode: 07008-0819

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Greek Key Choker Necklace

    Accessorize your everyday 'fit with this chic choker necklace! It features a trendy greek key design with small chain links and an adjustable lobster clasp closure. Pair this necklace with a graphic tee for a cool vibe.

    Fit & Features

    • Greek key design
    • Small chain links
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07002-0643

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Chic Cat Eye Sunglasses

    Show off your effortlessly chic style when you accessorize your 'fit with these sunglasses! They feature a cat eye design with a tortoise-shell hued plastic frame and tinted lenses. Pair these sunnies with your fave loungewear set to elevate the look.

    Fit & Features

    • Cat eye design
    • Tortoise-shell hued plastic frame and arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-0821

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luxe Layered Three-Pack Necklace Set

    Add some luxe and trendy layers to your everyday 'fit with this necklace set! It features three necklaces, the shortest layer a thick round chain design, the middle layer a thick chain link design with mini rhinestone details, and the longest layer a dainty chain with a center lock charm. Pair this necklace set with a cool graphic tee.

    Fit & Features

    • Three-pack necklace set
    • Adjustable lobster clasp closures

    Style Number/Barcode: 07002-0633

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic On-Trend Two-Pack Necklace Set

    Layer on this chic necklace set to keep your look fab and on-trend! It features two necklaces, the shorter layer with a twisted chain and the longer layer showcasing a dainty chain with a center butterfly detailed tag charm. Pair this set with a basic tee and a classic denim jacket.

    Fit & Features

    • Two-pack necklace set
    • Twisted chain
    • Dainty chain
    • Center butterfly tag charm
    • Adjustable lobster clasp closures

    Style Number/Barcode: 07002-0644

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Falling For Florals Puff Sleeve Crop Top

    Fall for a floral crop top that brings on those charming feels! The crop top features a sweetheart neckline, a ruched bodice, long puff sleeves with cinched ruffled hems, a gorge floral print, a stretchy smocked back, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with a mini skirt and clear heels.

    Fit & Features

    • Sweetheart neckline 
    • Ruched bodice
    • Long puff sleeves with cinched ruffled hems 
    • Floral print
    • Stretchy smocked back, cropped hem
    • Lightweight woven fabric, relaxed fit, minimal stretch
    • Runs true to size 

    Style Number/Barcode: 06003-1159

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wanderlust Beauty Flared Pants

    You're a total wanderlust beauty, and these boho-chic flared pants are a must-have style for you. They feature a high-rise elastic banded waist, a form-hugging fit, and a flared-out hem. The stretchy knit fabric showcases an all-over paisley pattern for a trendy vibe. Complete your look with a crop top and sandals for the perf warm-weather outfit.

    Shop Matching Smock Top: Wanderlust Beauty Smocked Tube Top

    Shop Matching Tie-Front Top: Wanderlust Beauty Tie Front Top

    Shop Matching Lace-Up Top: Wanderlust Beauty Lace-Up Top

    Fit & Features

    • High-rise elastic banded waist
    • Form-fitting style
    • Flared hem
    • Knit fabric with plenty of stretch
    • Paisley print
    • Runs true to size

    Style Number/Barcode: 06502-0613

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strike A Pose Cat Eye Sunglasses

    Strike a pose in chic sunglasses to relax poolside! The sunnies feature an oversized cat eye frame, a sleek metal nose bridge, and a trendy print. Complete the look with a cute monokini and sandals.

    Fit & Features

    • Oversized cat-eye frame
    • Metal nose bridge
    • Trendy print

    Style Number/Barcode: 07008-0806

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Instant Classic Cat Eye Sunglasses

    Create an instantly classic look with these sunglasses that are simply stunning! The sunglasses feature a cat-eye frame, dark lenses, and sleek arms. Complete the look with a ribbed mini dress and mules for the perfect outfit to grab your favorite iced coffee! 

    Fit & Features

    • Cat-eye frame
    • Dark lenses
    • Sleek arms

    Style Number/Barcode: 07008-0807

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Textured Hoop Earrings

    Add a gorgeous glam vibe to your look with these trendy hoop earrings! They feature a large thick hoop with a textured wrap design and an omega closure. Pair these earrings with your fave chic catsuit and strappy heels.

    Fit & Features

    • Thick hoop
    • Textured wrap design
    • Omega closure

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0498

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Give Trendy Vibes High-Rise Button Mini Skort

    Stroll around in this adorable mini skort with button accents along a flattering high-rise waist and a flirty ruffled hem.

    Fit & Features

    • Woven fabric, shorts lining
    • High-rise waist
    • Side button accents
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06303-000012

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Golden Glow Chandelier Earrings

    Get a gorgeous golden glow when you accessorize your fancy 'fit with these chandelier earrings! They feature an intricately detailed tiered design with dangling diamond-shaped charms and a fish hook closure. Pair these stunning statement earrings with a classic little black dress to add a glam factor to your look.

    Fit & Features

    • Chandelier tiered design
    • Diamond-shaped charms
    • Fish hook closure

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0500

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free