Vacation Looks

HomeVacation Looks

Resortwear
Sundresses
Matching Sets
Maxi Dresses
Women's Shorts
Sandals
Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...
tag of the document. This will help to improve the load of the images // during color swatches interaction on PLP const preloadBackground = (entries, observer) => { entries.forEach(async (entry) => { if (entry.isIntersecting) { const swatch = entry.target; const images = swatch.dataset.varimg.split(','); images.forEach((img, index) => { // preload image const link = document.createElement('link'); link.href = buildSrc(img); link.imagesrcset = getSrcset(img); link.imagesizes = cssImageMediaCondition; link.rel = 'preload'; link.as = 'image'; document.getElementsByTagName('head')[0].appendChild(link); }); swatch.removeAttribute('data-varimg'); switchObserver.unobserve(swatch); } }); }; const switchObserver = new IntersectionObserver(preloadBackground, { root: null, // Default is the viewport rootMargin: '30px', threshold: 0.05, // Load image when 10% of the div is visible }); // Sort options function getPageParam() { const urlParams = new URLSearchParams(window.location.search); const pageParam = urlParams.get('page'); return pageParam ? parseInt(pageParam, 10) : 1; } domLoadedPage = getPageParam(); setupSortDropdown('.fs_sort_by_wrap_desktop', '.fs_sort_by_options_desktop', '.fs_sort_by_select_desktop'); const sortBySelect = document.getElementById('sortByDesktop'); let sortByValue = getSortBy(); // call the function and store the returned value sortBySelect.value = sortByValue; // update the desktop dropdown value on page load // update sort mobile dropdown value on page load const validSortOptions = ['price_min_to_max', 'price_max_to_min', 'creation_date', 'relevency']; sortByValue = validSortOptions.includes(sortByValue) ? sortByValue : 'relevency'; const inputField = document.querySelector(`form [data-value="${sortByValue}"]`); if (inputField) { inputField.checked = true; // update the value of the option } else { console.error(`No radio button found with data-value="${sortByValue}"`); } const form = document.getElementById('sortForm'); if (form) { form.addEventListener('change', (event) => { if (event.target.name === 'sort') { const selectedValue = event.target.getAttribute('data-value'); if (selectedValue && validSortOptions.includes(selectedValue)) { setUrlParam('sortBy', selectedValue, true); resetPageAndScroll(); updateOtherDropdown(selectedValue); } } }); } updateOtherDropdown(getSortBy()); if (sortBySelect) { sortBySelect.addEventListener('change', function () { if (sortBySelect.value && validSortOptions.includes(sortBySelect.value)) { setUrlParam('sortBy', sortBySelect.value, true); } }); } // Description 'read more' function toggleReadMore(button) { const container = button.parentNode; const isExpanded = container.getAttribute('aria-expanded') === 'true'; container.setAttribute('aria-expanded', !isExpanded); if (isExpanded) { button.querySelector('.button-text').textContent = 'more'; } else { button.querySelector('.button-text').textContent = 'Show less'; } } function visibleReadMore() { const toggleButtons = document.querySelectorAll('.fs_collection_top_toggle'); toggleButtons.forEach(button => { const description_children = button.previousElementSibling.children; let description_scroll_width = 0; let description_client_width = 0; for(const child of description_children) { description_scroll_width += child.scrollWidth; description_client_width += child.clientWidth; }; button.style.display = (description_scroll_width > description_client_width) ? 'block' : 'none'; }); } window.addEventListener('DOMContentLoaded', visibleReadMore); // category pills GTM const categories = document.querySelectorAll('.category-pills__pill'); let category; let categoryHandle; let categoryId; const pushCategoryPills = (category, categoryHandle, categoryId, typeCategory) => { if (category && categoryHandle && categoryId && typeCategory) { const categoryPills = { event: `categoryPills`, category: category, categoryHandle: categoryHandle, categoryId: categoryId, typeCategory: typeCategory }; window.dataLayer.push(categoryPills); } } categories?.forEach(category => { category.addEventListener('click', function(e) { try { category = e.currentTarget.getAttribute('data-category'); categoryHandle = e.currentTarget.getAttribute('data-collection-handle'); categoryId = e.currentTarget.getAttribute('data-collection-id'); typeCategory = e.currentTarget.getAttribute('data-type-category'); pushCategoryPills(category, categoryHandle, categoryId, typeCategory); } catch (error) { console.error('Error in category click event:', error); } }) })

Now Trending

STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Wild Life Leopard Ruched Swimsuit

    It's now or never. Live your best life and don't let anyone tell you otherwise! 

    Fits & Features

    • Narrow Spaghetti Straps
    • Low, Open Back 
    • Plunging V Neckline 
    • Ruching Along The Side With Ties 
    • Cheeky Fit & Coverage 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

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

    Style Number/Barcode: 07109-0134

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Layin' Low Platform Espadrille Sandals

    Lay low and and keep it chill in these adorable lace up espadrille sandals! Style them with a relaxing flowy dress!

    • Open open toe
    • Single band over the toe
    • Wrap around lace up ankle
    • Faux suede
    • Espadrille + Cork platform

    Style Number/Barcode: 07404-0574

    Category Name: Vacation Looks

    Price: $26.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Just Grow For It Floral Wrap Top

    Who needs a bouquet when you're wrapped up in this gorge top? Look adorbs and fresh by pairing it with some jeans and booties! 

    Fits & Features

    • Surplice V Neckline
    • Long Sleeves I Elastic Cuffs
    • Tie Front Wrap Design At Side
    • Lightweight Chiffon Fabric I Floral Print 
    • Minimal Stretch 

    Style Number/Barcode: 06003-0581

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Watch Me Do My Thing Swim Top

    Leave them in awe when you step out in this sexy simple swim suit! Catch some rays and serve some lewks. Don't forget to pick up the matching swim bottoms!

    Shop Matching Bottoms: Watch Me Do My Thing Thong Swim Bottoms

    Fit & Features

    • Triangle design
    • Non-padded
    • Halter neckline
    • String closures
    • Fully lined
    • Moderate stretch

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

    Style Number/Barcode: 07104-0290

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Ditzy Floral Smocked Top

    Look oh so darling in this adorable ditsy floral chiffon smocked top! Pair with some distressed denim for a casual cute 'fit.

    Fit & Features

    • Short puff sleeves with smocked ruffled details
    • Wrap front V neckline
    • Back button closure | Keyhole cut out
    • Stretchy smocked waist
    • Mid-length, form hugging fit
    • Chiffon fabric

    Style Number/Barcode: 06003-0475

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Asymmetrical Maxi Skirt

    Take it to the next level and show off a sultry and edgy look in this maxi skirt! Top it off with your fave crop top, add a denim jacket, and slip into some chic booties! 

    Fits & Features

    • High Rise Elastic Waistband 
    • Smooth Jersey Knit Fabric 
    • Maxi Length Silhouette 
    • Asymmetrical High Slit 
    • Ample Stretch | Form Hugging Fit 

    Style Number/Barcode: 06501-0227

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • New Love Ditsy Smocked Mini Dress

    Something sweet, something new. Charm them all by slipping into the New Love mini dress! Pair with some sneakers for a girls' day and switch to some heels for date night with the boo! 

    Fits & Features 

    • Adjustable Spaghetti Straps
    • Square Neckline
    • Mini Length Silhouette
    • Woven Fabric I All Over Smocking 
    • Ditsy Floral Print I Tiered Ruffle Design 
    • Form Hugging Fit I Ample Stretch 

    Style Number/Barcode: 05102-0522

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Crochet Chic High Low Dress

    Keep it cute in crochet girl! This dress is giving us major boho vibes and perfectly pairs with your fav headband and wedges! 

    Fit & Features 

    • V-Neckline 
    • Floral Crochet Bodice 
    • Adjustable Spaghetti Straps
    • Smocked Back 
    • High Low Silhouette| Mini Skirt Length Knit Lining
    • Lightweight Woven Fabric 
    • Relaxed Fit | Minimal Stretch 

     

    Style Number/Barcode: 05102-0617

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Queen Smocked Crop Top

    You'll be a stunning queen on vacay in this printed smocked crop top! Pair with the matching pants to complete the set.

    Shop Matching Bottoms: Vacay Queen Wide Leg Pants

    Fit & Features

    • Off the shoulder square neckline
    • Short puff sleeves | Ruffle trim
    • Stretchy smocked fabric
    • Cropped
    • All over palm print

    Style Number/Barcode: 06003-0842

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Makin' It Happen Paper-bag Dress Shorts

    Make things happen this summer with the perfect look! Starting with a pair of dress shorts! Style with a bodysuit, or dress down with a tucked in tee!

    Fit & Features

    • High waist fit
    • Hidden zipper closure center 
    • Button detailing
    • Slanted hidden pockets
    • Knit material | Moderate stretch

    Style Number/Barcode: 06403-0088

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrap Me In Ruffles Maxi Skirt

    Wrap yourself in ruffles and feel fun and flirty this summer! We are obsessed with this minimal maxi, pair with your favorite layers and sandals and live the simple life!

    Fit & Features

    • High waist fit
    • Ruffled trim
    • Wrap design with side button closure
    • Fully lined
    • Knit woven material | No stretch
    • Maxi length hemline

    Style Number/Barcode: 06301-0065

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Gorgeous Getaway Tropical Print Maxi Skirt

    This alluring tropical print maxi skirt will create a gorgeous getaway look! Designed with a trendy tropical print pattern on the airy mesh fabric, it features a high-rise waist, a maxi-length hem with a sultry high-cut side slit, and a slim-fit silhouette. Style with the matching crop top for your next destination vacay!

    Shop Matching Top: Gorgeous Getaway Tropical Print Crop Top

    Fit & Features

    • High-rise waist
    • Maxi-length hem
    • High-cut side slit
    • Slim-fit silhouette
    • Tropical print
    • Sheer mesh fabric, full-length knit lining
    • Runs true to size

    Style Number/Barcode: 06501-0956

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Back to Basics High Waist Jeans

    Bring it back to basics girl with these high waist jeans to create a girl next door vibe! Pair with hoops and a cute crop for a ready to go look!

    Fit & Features 

    • High Rise Waist 
    • Single Button And Zipper Closure 
    • Traditional Five Pocket and Belt Loop Design 
    • Straight Leg Fit | Raw Edge Hem 
    • Medium Wash Denim Fabric
    • Form Hugging Fit 
    • Moderate Stretch  

     

    Style Number/Barcode: 06602-0128

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Queen Wide Leg Pants

    You'll be a stunning queen on vacay in these printed wide leg pants! Pair with the matching top to complete the set.

    Shop Matching Top: Vacay Queen Smocked Crop Top

    Fit & Features

    • High rise elastic banded waist
    • Tie front belt
    • Wide pant legs
    • All over palm print
    • Woven fabric | No stretch

    Style Number/Barcode: 06302-0126

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Waist Ditsy Floral Printed Pants

    How spring ready are these pants?! The all over ditsy floral print is oh so adorable, and the wide pant legs are so flattering. Pair with a basic crop top for a cute 'fit!

    Fit & Features

    • High rise waist
    • Hidden back zipper | Hook and eye closure
    • Wide pant legs
    • Ditsy floral print
    • Woven fabric | No stretch

    Style Number/Barcode: 06402-0201

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kimono Sleeve Tie Front Top

    Effortless and flowy, this tie-front top has all the boho vibes! It features three-quarter-length kimono sleeves, a V-neckline, and a fitted crop hem on slinky knit fabric. Pair with a high-rise satin skirt to amp up your look.

    Fit & Features

    • Three-quarter-length kimono sleeves
    • V-neckline
    • Tie front
    • Cropped hem
    • Slinky knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06202-0068

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Charge Leopard Print One Piece Swimsuit

    You are in charge when you step out leopard print in a fierce way bae! This swimsuit tells it all, top it off with cat eye sunnies and you are set!

    Fit & Features

    • One piece swimsuit
    • V-neckline
    • Spotted O-rings at the straps
    • Low back with tie detail
    • Fully lined
    • Removable padding
    • Cheeky bottom

    Style Number/Barcode: 07109-0182

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life At Sea Strappy Hipster Swim Bottoms

    Spend your days out at sea, and catch some sun in a sexy swimsuit! Don't forget to pick up your matching top to complete the look!

    Shop Matching Top: Life At Sea Notch Swim Top

    Fit & Features

    • Mid-rise fit
    • Strappy hip detailing
    • Cheeky bottom
    • Fully lined
    • Sheen finish | Moderate stretch

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

    Style Number/Barcode: 07105-0249

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life At Sea Notch Swim Top

    Spend your days out at sea, and catch some sun in a sexy swimsuit! Don't forget to pick up your matching bottoms to complete the look!

    Shop Matching Bottoms: Life At Sea Strappy Hipster Swim Bottoms

    Fit & Features

    • V notch detailing
    • Adjustable spaghetti straps
    • Removable padding
    • Bar hook closure
    • Fully lined
    • Sheen finish | Moderate stretch

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

     

    Style Number/Barcode: 07104-0289

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Minimal High Waist Swim Bottoms

    Keep your vibe minimal yet flattering when you slip into our minimal swim tank swim top! Obvs don't forget to pick up the matching top to complete your beach babe lewk!

    Shop Matching Top: Minimal Tank Swim Top

    • High waist fit
    • Elastic banded waist
    • High cut design

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

    Style Number/Barcode: 07105-0254

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Minimal Tank Swim Top

    Keep your vibe minimal yet flattering when you slip into our minimal swim tank swim top! Obvs don't forget to pick up the matching bottoms to complete your beach babe lewk!

    Shop Matching Bottoms: Minimal High Waist Swim Bottoms

    • Tank straps
    • Low scoop neckline
    • Cropped hemline
    • Moderate stretch
    • No padding included

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

    Style Number/Barcode: 07104-0291

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Thowin' it Back Glitter Jelly Flats

    Throw it back with a pair of glitter jelly's! So cute with overalls or a pair of high waist shorts with a tank!

    • Closed almond toe
    • Caged detailing
    • Ankle strap 
    • Pin buckle closure
    • Composed of a clear jelly
    • Glitter reflects

    Style Number/Barcode: 07405-0026

    Category Name: Vacation Looks

    Price: $11.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring The Romance Off Shoulder Long Sleeve Skater Dress

    Date night calls for a sweet and pretty look! Style with some soft curls, a cute crossbody, and sparkly finishing touches and you'll be ready for the night! 

    Fits & Features

    • Elasticized, Off Shoulder Neckline I Tie At Center Front 
    • Off Shoulder Long Sleeves I Elastic Cuffs 
    • Crochet Waist Design 
    • Mini Length, Skater Style Skirt 
    • Brushed Knit Design I Floral Print 
    • Plenty Of Stretch 

    Style Number/Barcode: 05101-0401

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral In Love Smocked Top

    Fall in love with pretty florals in this adorable smocked waist top! The perf blouse to get that spring time vibe.

    Fit & Features

    • Long sleeves | Elastic banded hems
    • Wrap front V neckline
    • Back button closure | Large keyhole cut out
    • Stretchy smocked waist
    • Ruffle hem
    • Small floral print
    • Lightweight woven fabric | No stretch

    Style Number/Barcode: 06003-0809

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance