Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.

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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); } }) })

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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.

Make Some Noise Printed Palazzo Pants
Prepare to receive all the compliments when you're in these printed palazzo pants on vacay or a weekend away! Featuring a high-rise ruffled elasticized waist and a flowy wide-leg silhouette, these pants are perfect for any occasion. The beautiful watercolor print on the lightweight linen-blend fabric adds a touch of art. Complete the look with the matching bustier top.

Shop Matching Top: Make Some Noise Strapless Printed Bustier

Fit & Features
- Watercolor print
- Linen-blend woven fabric with woven lining
- High-rise ruffled elasticized waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0819

Category Name: Vacation Looks

Price: $8.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Breath Of Fresh Air Smocked Maxi Tube Dress
Step out looking like a breath of fresh air in this maxi tube dress on vacay or weekend plans! The strapless, stretchy, smocked bodice ensures a perfect and comfortable fit that flatters your figure while the flowy, maxi-length hem creates an effortless look.

Fit & Features
- Woven fabric, bust knit lining
- Strapless V-wired neckline
- Stretchy smocked bodice
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6076

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Statement Blooms Strapless Floral Maxi Dress
Perfect for any occasion, this floral maxi dress will make a statement! The strapless neckline and maxi hem create a flattering silhouette, while the vibrant floral print and side slit add a touch of playful elegance.

Fit & Features
- Floral print, mesh fabric, soft knit stretchy lining
- Strapless neckline
- Side slit
- Form-hugging fit
- Relaxed maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4098

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dreamy Boho Bell Sleeve Knit Mini Dress
Live out those dreamy boho vibes in this breezy knit mini dress featuring a plunging V-neck with beaded bust tie accents, sheer long bell sleeves, and an open back with a tie-back design.

Fit & Features
- Sheer textured knit fabric, partial knit lining
- Plunging V-neckline, dual bust ties with beaded detailing
- Sheer long bell sleeves
- Open back, tie-back spaghetti straps
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000129

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cutesy Girl Polka Dot Skater Dress
Create a cutesy vibe in this adorable polka dot skater dress featuring a halter V-neck, tie-back bow design, and a short fit-and-flare silhouette. Style with mules for weekend brunch!

Fit & Features
- Textured woven fabric, stretchy knit lining
- Polka dot embroidered pattern
- Sleeveless halter V-neckline
- Partially open back, lower zipper closure
- Tie-back bow design
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3942

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: In Stock

Available Color: WHITE

Available Size: L
Product Badge:
- Sale
Alluring Sensation Halter Open Back Maxi Dress
Wherever your summer takes you, this maxi dress will look sensational against any tropical or beach background! This dress features a striking cowl halter neckline, a sleek hoop insert, and a captivating form-hugging silhouette, while the open back adds a daring touch.

Fit & Features
- Slinky knit stretchy fabric
- Cowl halter neckline, hoop insert, tie back
- Open back
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000124

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: In Stock

Available Color: ORANGE

Available Size: M
Bright Beauty Halter Cutout Tropical Maxi Dress
You'll look bright and beautiful in this tropical maxi dress on vacation or at a weekend pool party! The halter neckline with a spaghetti strap tie highlights your shoulders, while the U-ring insert adds some structure. The cutout back with smocked detail flatters your figure along the flowy maxi-length silhouette. Complete the look with sunglasses and sandals for a chic vibe!

Fit & Features
- Tropical print, chiffon fabric, short stretchy knit lining
- Halter neckline with spaghetti strap tie, U-ring insert
- Cutout back with smocking
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5791

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Gorgeous Soul Floral Halter Bodycon Maxi Dress
This floral maxi dress is here to accentuate your gorgeous self for sunset cocktails while on vacation! The halter V-neck and bodycon silhouette accentuate your curves while the maxi-length hem adds a chic touch with a pair of sandals.

Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Halter V-neckline, tie straps
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4135

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Subtle Grace V-Neck Polka Dot Chiffon Skater Dress
Twirl with grace in this polka dot chiffon skater dress at graduations, celebration showers, or a birthday brunch!

Fit & Features
- Polka dot pattern, chiffon fabric, woven lining
- V-neckline, adjustable spaghetti straps
- Stretchy smocked bodice
- Ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-4136

Category Name: Vacation Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cheerful Cutie Gingham Skater Dress
From casual plans to picnics, this cheery gingham dress will have you feeling cute all day long! This delightful dress is designed with a smocked waist for a flattering fit, a cute mini-length hem, and a flared skater silhouette.

Fit & Features
- Gingham print, woven fabric, stretchy knit lining
- Sweetheart neckline with bust tie
- Adjustable spaghetti straps
- Stretchy smocked waist
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000093

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fairytale Daze Strappy Back Chiffon Skater Dress
This stunning skater dress is the perfect blend of effortless and ethereal. It is designed with flirty ruffles and a strappy tie-back that turns heads at parties!

Fit & Features
- Chiffon fabric, woven lining
- V-neckline, spaghetti straps
- Strappy tie-back, lower zipper and hook-eye closure
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4097

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dinner By The Sea Tube Crochet Midi Dress
You'll be a dreamy view in this crochet tube midi dress, enjoying a dinner by the sea. The form-hugging silhouette showcases your figure while the high side slit adds a daring touch of allure with seashell trim creates a captivating coastal-inspired look.

Fit & Features
- Crochet knit fabric, short knit stretchy lining
- Strapless tube neckline
- Form-hugging fit
- High side slit, seashell trim
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000109

Category Name: Vacation Looks

Price: $9.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cutest Look Ditsy Floral Ruched Knit Mini Dress
Create the cutest look for your weekend plans in this floral ruched knit mini dress! The adorable ditsy floral print on the soft and stretchy brushed knit fabric will give your casual look a flirtatious vibe! The short dress features a sleeveless square neckline with tie-shoulder spaghetti straps for a trendy detail and customized fit. The ruching down the side seams will show off your curves on the bodycon silhouette. Style this dress with hoop earrings and strappy mules for brunch with your girls!

Fit & Features
- Ditsy floral print
- Stretchy brushed knit fabric
- Sleeveless square neckline
- Tie-shoulder spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5533

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stealing Hearts Flocked Velvet Skater Dress
A flocked velvet skater dress that'll steal hearts left and right with a flattering sweetheart neckline and mini-length hem.

Fit & Features
- Flocked velvet pattern
- Mesh lined fabric
- Sweetheart neckline, wide shoulder straps
- Back zipper and hook-eye closure
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3866

Category Name: Vacation Looks

Price: $46.90

Availability: Out of Stock
Product Badge:
- Ships Free
Cutie Style Striped Knit Bodycon Mini Dress
Show off your cutie style in this adorable mini dress made with striped ribbed knit fabric with high stretch. The strapless sweetheart neckline features a knot detail at the bust and a small keyhole cutout for a trendy detail.

Fit & Features
- Striped ribbed knit fabric, knit bust lining, high stretch
- Strapless sweetheart neckline, no-slip strip
- Knot detail at the bust, small keyhole cutout
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000044

Category Name: Vacation Looks

Price: $19.97 $39.90

On Sale: Yes

Availability: In Stock

Available Color: TAUPE

Available Size: XS, S, M, L
Product Badge:
- Sale
Wild Thing Corset Zebra Print Top
Get wild for this zebra print corset top and flaunt your fierceness! Featuring a strapless neckline and flexible boning, a cropped hem adds a touch of flirty fun. Complete the look with the matching bottoms.

Shop Matching Bottoms: Wild Thing High Rise Zebra Print Skort

Fit & Features
- Zebra print, woven fabric, no stretch
- Strapless neckline
- Back zipper and hook-eye closure
- Flexible boning
- Runs true to size
Style Number/Barcode: 06003-2342

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sun And Blooms Floral Chiffon Skater Dress
Sunny weather is finally here to show off this floral chiffon skater dress with a flirty ruffled short-length hem! This dress is perfect for dressy occasions.

Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- V-neckline, back zipper and hook-eye closure
- Adjustable spaghetti straps
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-3470

Category Name: Vacation Looks

Price: $9.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Lace-Up Cutout Eyelet Skater Dress
Dainty eyelet details adorn every inch of this sweet skater dress, perfect for shower celebrations or any dressed-up occasion! With a lace-up back with a cutout and mini-length hem, you'll make every head turn.

Fit & Features
- Eyelet cotton fabric, woven lining
- Square neckline
- Adjustable spaghetti straps
- Lace-up back, cutout
- Side zipper and hook-eye closure
- Skater silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4018

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Forever Adorable Embroidered Sheer Head Scarf
Elevate any daytime 'fit with this adorable embroidered sheer head scarf! The sheer woven material is adorned with a delicate embroidered pattern for a trendy flair you'll love. Style this scarf as a pretty headwrap, around your neck, or tied on your bag as a chic accent! Complete the look in a basic sleeveless dress.

Fit & Features
- Sheer woven material, no stretch
- Embroidered pattern
- Multiple ways to style and wear
Style Number/Barcode: 07305-0497

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Enchanting Impression Butterfly Lace-Up Skater Dress
Impress in a flared skater dress with a gorgeous embroidered butterfly lace design throughout, a lace-up back design for a customized fit, ruffled straps, and a classic sweetheart neckline. Complete look with a sleek rhinestone clutch.

Fit & Features
- Knit and lace fabric, stretchy knit lining
- Sweetheart neckline
- Sleeveless with ruffled straps
- Lace-up back design, lower zipper and hook-eye closure
- Embroidered butterfly lace pattern
- Short skater fit
- Runs true to size
Style Number/Barcode: 05101-3941

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Hottie Tropical Halter Slit Maxi Dress
Look hot to trot around the island on vacation in this tropical maxi dress! This stunning maxi features a crisscross halter neckline for a touch of elegance and a front slit to show off those curves.

Fit & Features
- Tropical palm print, stretchy knit fabric, bust knit lining
- Crisscross halter neckline, beaded
- Front slit
- Curve-hugging fit
- Flowy maxi length hem
- Runs true to size
Style Number/Barcode: 05102-6117

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Check Me Out Puff Sleeve Cutout Gingham Crop Top
You'll check yourself in every mirror in this sweet gingham crop top perfect for spring to summer fun! This gingham crop top will surely turn heads, featuring puff sleeves, a cutout bust, and an open back with tie closure. Complete the look in high-rise denim shorts.

Fit & Features
- Gingham pattern, woven lined fabric, no stretch
- Sweetheart neckline with cutout
- Open back, tie closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-2368

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunshine Romance Floral Babydoll Dress
Indulge in the romantic allure of this floral dress for dressy events! With delicate ruffled shoulder straps and a charming babydoll silhouette, this dress offers a flirty and feminine look.

Fit & Features
- Floral print, chiffon fabric
- Square neckline
- Ruffled shoulder straps
- Babydoll silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3467

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fabulous Destination Tropical Cowl Neck Maxi Dress
Look fabulous heading to your destination in this tropical maxi dress for the cutest look on the island or beach resort! The cowl neckline creates a flattering drape and spaghetti strap tie while the low cowl back adds a touch of allure. The flowy maxi silhouette will make you feel like you're on a tropical escape! Complete the look in sunnies.

Fit & Features
- Tropical palm print, stretchy knit fabric
- Cowl neckline
- Low cowl back, spaghetti strap tie
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5727

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials