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.

  • Cute And Classic Cuffed Denim Jacket

    Layer on this cute and classic denim jacket over all your casual summer 'fits. It features a collared neckline, three-quarter length sleeves with buttons to cuff, a complete button-down front, and a cropped, fitted silhouette. Style with simple hoop earrings.

    Fit & Features

    • Collared neckline
    • Three-quarter length sleeves, buttons to cuff
    • Button-down front
    • Buttoned chest pockets, side pockets
    • Cropped fit
    • Light wash denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06203-0193

    Category Name: Vacation Looks

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Staycation High Slit Maxi Skirt

    Bare it all for a saucy night out in this high-rise maxi skirt featuring a sultry front slit on a form-fitting silhouette. Complete the look in the matching bottoms.

    Shop Matching Top: Staycation Twist Banded Crop Top

    Fit & Features

    • High-rise waist
    • Front slit
    • Form-fitting silhouette
    • Maxi-length hem
    • Sleek knit-lined fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0597

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chill Vision Small Rectangle Sunglasses

    For the days when you’re chill, but still need to serve a look. These small rectangle sunglasses are the perfect low-key statement for brunch hangs, solo city strolls, or golden hour selfies.

    Fit & Features

    • Small rectangular-shaped design
    • Plastic frame with glossy finish
    • Thin arms
    • Flexible nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000059

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vibe Out Y2K Lace-Up Block Heels

    Vibe out in 2000's style! These block heels will give your outfit a major throwback. Featuring an almond toe, block heel, a lace-up design, and a marble print. Complete the look in a cool denim jacket.

    Fit & Features

    • Almond toe
    • Block heel
    • Lace-up design
    • Marble print
    • Satin material
    • Runs true to size

    Style Number/Barcode: 07401-3894

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Staycation Twist Banded Crop Top

    Bare it all for a saucy night out in this crop top featuring a sleeveless V-neckline, adjustable spaghetti straps, and a sultry twisted bodice with an elasticized band. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Staycation High Slit Maxi Skirt

    Fit & Features

    • Sleeveless, V-neck, adjustable spaghetti straps
    • Twisted bodice
    • Elasticized band
    • Cropped hem
    • Sleek knit-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4008

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Coolest Vibe Midi Skirt

    Showcase the coolest vibe in this trendy midi skirt. It features a high-rise waist with a knot-front design, a midi-length asymmetrical hem with a high side slit, and an all-over marble print pattern. Complete the look with the matching crop top.

    Shop Matching Top: The Coolest Vibe Cropped Tank

    Fit & Features

    • High-rise waist
    • Knot-front design
    • Midi-length, asymmetrical hem, side slit
    • Curve-hugging silhouette
    • Marble print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0600

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Coolest Vibe Cropped Tank

    Showcase the coolest vibe in this trendy cropped tank. It features a sleeveless square neckline, thin tank shoulder straps, a cropped, form-hugging fit, and an all-over marble print pattern. Complete the look with the matching midi skirt.

    Shop Matching Bottoms: The Coolest Vibe Midi Skirt

    Fit & Features

    • Sleeveless square neckline
    • Thin tank shoulder straps
    • Cropped, form-hugging fit
    • Marble print
    • Lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4014

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunkissed Girl Slit Midi Skirt

    Embrace a sunkissed glow in this midi skirt perfect for strolling the boardwalk or hitting up cocktail hour. It features a high-rise elasticized waist, form-fitting silhouette, and a high-cut side slit on stretchy knit fabric. Complete the look in lace-up sandals.

    Fit & Features

    • High-rise elasticized waist
    • Form-fitting silhouette
    • High-cut side slit
    • Stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 06501-0677

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Sunset Tie-Back Crop Top

    Head to a spring sunset dinner with a view in this trendy crop top! It features a square neck, elasticized tank-style straps, and an open back with tie closure on stretchy, rib-knit fabric. Complete the look in the matching skirt.

    Shop Matching Skirt: Spring Sunset Slit Maxi Skirt

    Fit & Features

    • Sleeveless, square neck 
    • Elasticized tank-style straps
    • Cropped hem
    • Open-back, tie closure
    • Stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4070

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Sunset Slit Maxi Skirt

    Head to a spring sunset dinner with a view in this maxi skirt! It features a high-rise waist, bodycon silhouette, and a sultry front slit on stretchy, rib-knit fabric. Complete the look in the matching top.

    Shop Matching Top: Spring Sunset Tie-Back Crop Top

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Front slit
    • Maxi-length hem
    • Stretchy, rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 06501-0626

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty In Florals Short Dress

    Keep it pretty in a short dress that brings the charm! The dress features a pretty daisy print, a halter neck with neck ties, a square-neck smocked bodice, and a triple-row bar strap design at the back. The slim fit bodice leads to a fluttery A-line short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules. 

    Fit & Features

    • Halter neck with adjustable neck ties
    • Square-neck smocked bodice
    • Triple-row bar strap design 
    • Floral print
    • A-line, short length hem
    • Lined lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4401

    Category Name: Vacation Looks

    Price: $46.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Nights V-Neck Midi Dress

    Enjoy your nights in paradise in this tropical floral midi dress featuring a sleeveless, v-neck, adjustable criss-cross spaghetti straps, and a bodycon silhouette leading to the asymmetrical slit hem. Complete your vacay look in strappy heels.

    Fit & Features

    • Sleeveless, v-neck
    • Adjustable criss-cross spaghetti straps
    • Bodycon silhouette
    • Asymmetrical slit, side ruching
    • Midi-length hem
    • Tropical floral print, texture-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1455

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Eye Of The Tiger Bandeau Crop Top

    It's the eye of the tiger it's the thrill of wearing this cute bandeau crop top for your next island vacay! It features a sleeveless, strapless neckline with a flirty front knot-tie and a smocked back. Complete the look in the matching bottoms. 

    Shop The Matching Bottoms: Eye Of The Tiger Palazzo Pants

    Fit & Features

    • Sleeveless, strapless neckline
    • Front knot-tie closure
    • Smocked back, crop hem
    • Tiger print
    • Chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1742

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Tide Tropical Mini Skirt

    Feel the island breeze and enter paradise in this tropical mini skirt! It features a high-rise elasticized waist, a faux-wrap front, and a bodycon silhouette. Complete the look in the matching top.

    Shop Matching Top: Island Tides Tropical Tie-Front Top

    Fit & Features

    • High-rise elasticized waist
    • Faux wrap front
    • Bodycon silhouette
    • Mini-length hem
    • Tropical print fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0638

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eye Of The Tiger Palazzo Pants

    It's the eye of the tiger it's the thrill of wearing these cute palazzo pants for your next island vacay! It features a high-rise waist, a side hidden zipper closure, and a flowy palazzo-style leg. Complete the look in the matching top.

    Shop The Matching Top: Eye Of The Tiger Bandeau Crop Top

    Fit & Features

    • High rise waist
    • Side hidden zipper closure
    • Flowy palazzo-style leg
    • Tiger print
    • Chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06302-0633

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Island Tides Tropical Tie-Front Top

    Feel the island breeze and enter paradise in this tropical tie-front top! It features long bishop sleeves, a plunge V-neck, and a cropped hem. Complete the look in the matching skirt. 

    Shop Matching Skirt: Island Tide Tropical Mini Skirt

    Fit & Features

    • Long bishop sleeves
    • Plunge V-neck
    • Tie-front closure
    • Cropped hem
    • Tropical print fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0308

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry For The Summer Crochet Halter Mini Dress

    Create a sultry look for the summer in this sheer crochet mini dress featuring a halter V-neckline with wooden beaded accents and a short, curve-hugging silhouette to flaunt your figure.

    Fit & Features

    • Sheer crochet knit fabric, moderate stretch
    • Sleeveless V-neckline, wooden beaded accents
    • Tie-back halter straps, wooden beaded accents
    • Partially open back
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000063

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Season Floral Off-The-Shoulder Bustier

    Always in season and never dries out! Look fresh in this floral off-the-shoulder bustier featuring a fold-over, sweetheart bodice, detachable spaghetti straps, a built-in padded bust with underwire, front hook-eye closures, and flexible boning along the cropped hem. Complete the look in faux leather leggings for a chic-edgy vibe.

    Fit & Features

    • Foldover, off-the-shoulder neck
    • Sweetheart bodice, detachable spaghetti straps
    • Built-in padded bust with underwire
    • Front hook-eye closures, flexible boning
    • Cropped hem
    • Ditsy floral pattern, woven-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1758

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Made For You Tie Front Bandeau Top

    This bandeau top was made for you on vacation or pretending while sipping on cocktails poolside! It features a strapless, sleeveless, neckline with a flirty tie-front and a smocked back panel. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Made For You High Rise Palazzo Pants

    Fit & Features

    • Strapless, sleeveless neckline
    • Tie-front
    • Smocked back
    • Textured lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06001-4095

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made For You High Rise Palazzo Pants

    These palazzo pants are made for you on vacation or pretending while sipping on cocktails poolside! They feature a high-rise waist, pleat front detailing, and a wide-leg silhouette. Complete the look in the matching top.

    Shop Matching Top: Made For You Tie Front Bandeau Top

    Fit & Features

    • High-rise waist
    • Pleat front detailing
    • Wide-leg silhouette
    • Pull-on/off styling
    • Textured lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0631

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forever Chic Drawstring Halter Top

    Bring on the chic with a halter top that is perf for a time under the sun! The top features a halter neck, a drawstring neck ties, dual drawstrings at the sides, and cropped hem. The top is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with denim shorts.

    Fit & Features

    • Halter neck 
    • Drawstring neck ties
    • Dual drawstrings at sides
    • Cropped hem 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06001-4110

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Summer Days Cuffed Shorts

    These lightweight linen-blend shorts were made for those effortless summer days. They feature a mid-rise smocked waist, an adjustable tie-front drawstring, a cuffed hem, and a relaxed fit. Style these casual shorts with a fitted bodysuit and slides.

    Fit & Features

    • Mid-rise elasticized smocked waist
    • Adjustable tie-front drawstring
    • Front pockets, faux back pockets
    • Cuffed hem
    • Non-stretch woven linen fabric
    • Runs true to size

    Style Number/Barcode: 06303-0185

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunkissed Sultry Bikini Top

    Showcase a sunkissed sultry look in this alluring bikini top. It features a square neckline with a center square-shaped cutout at the bust, adjustable spaghetti straps for a customized fit, and a strappy tie-back design. Style with the matching bikini bottoms.

    Shop Matching Bottoms: Sunkissed Sultry Bikini Bottoms

    Fit & Features

    • Square neckline
    • Center square-shaped cutout
    • Adjustable spaghetti straps
    • Tie-back design
    • No padding
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0680

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho-Chic Celestial Charm Chain Belt

    Style up your festival 'fit with this boho-chic chain belt! It features a layered design with dangling moon, sun, and star charms for a trendy celestial vibe. Pair this belt over a curve-hugging mini dress with fab booties.

    Fit & Features

    • Layered design
    • Moon, sun, and star charms
    • Adjustable fit, lobster clasp closure

    Style Number/Barcode: 07301-0469

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale