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.

Found Love Corset Rhinestone Lace Skater Dress
Celebrate your romantic era in this strapless skater dress designed with a corset bodice that snatches your figure and rhinestone embellishments for a glam allure!

Fit & Features
- Lace-lined fabric, rhinestone embellishments
- Strapless sweetheart neckline
- Corset bodice, flexible boning
- Skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3935

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Soak Up The Rays O-Ring Bikini Bottoms
Get ready to soak up the rays in these chic O-ring bikini bottoms, which have a flattering low-rise waist and flirty, cheeky bottom coverage! Pair with the matching bikini top.

Fit & Features
- Lined knit fabric
- Low-rise waist, spaghetti strap side ties
- O-ring insets
- Cheeky bottom coverage
- Runs true to size
- Returns are not accepted without the hygienic liner
Shop The Matching Bikini Top: Soak Up The Rays O-Ring Bikini Top
Style Number/Barcode: 07105-0869

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Too Cute to Care Babydoll Mini Dress
Low effort, high reward kind of vibe. This babydoll mini dress features a strappy cutout back and hidden pockets—aka your new throw-on-and-slay essential.

Fit & Features
- Poplin woven fabric
- Square neckline
- Spaghetti straps
- Spaghetti strap tie-back and cutout accent
- Hidden side pockets
- Babydoll silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000092

Category Name: Vacation Looks

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Getaway Bound Lace-Up Print A-Line Dress
With an Italian-inspired print, this A-line dress is perfect for packing with you! This dress is designed in a flattering A-line mini silhouette with a stylish lace-up front and a chic cutout back that turns heads.

Fit & Features
- Multi-printed, woven fabric, woven lining
- V-neckline with lace-up bust
- Adjustable spaghetti straps
- Cutout back
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000150

Category Name: Vacation Looks

Price: $10.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Everyday Allure Plunging Linen Corset Top
Show off an everyday allure in this sultry plunging linen corset top! Designed with a lightweight linen-blend fabric, it features a sleeveless sweetheart plunging neckline, pleating at the bust, an angled underwire and flexible boning to provide structure, and thin tank shoulder straps. The back hook and eye closures offer a secure fit, and the fitted, angled, cropped hem gives that snatched silhouette. Style with distressed jeans and booties!

Fit & Features
- Linen-blend woven fabric lined with knit, slight stretch
- Sleeveless plunging sweetheart neckline
- Pleated bust, angled underwire, flexible boning
- Thin tank straps
- Back hook and eye closures
- Fitted, angled, cropped hem
- Runs true to size
Style Number/Barcode: 06003-2307

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Stud Strappy Jelly Sandals
Put an edgy-cute foot forward in these jelly sandals with dual straps and studded accents that elevate your everyday look.

Fit & Features
- Round toe
- Dual straps with studded accents
- Flat sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-1260

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK, GOLD

Available Size: 5, 6, 7, 8, 9, 10
Product Badge:
- Sale
Bold And Beautiful Rosette Halter Cutout Maxi Dress
Step out like a bold beauty in this printed maxi dress for brunch, shower celebrations, or parties! This stunning maxi features an elegant halter neckline adorned with rosette detail, flirty cutouts that flatter your silhouette, and a flowing skirt that moves gracefully with every step.

Fit & Features
- Abstract print, woven fabric
- Halter neckline with rosette detail, bust knit lining
- Side cutout accents
- Flowy ruffled maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000054

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Subtle Charm V-Neck Ruffled Floral Skater Dress
Embrace your inner charm in this floral skater dress at showers or birthdays! The flattering V-neckline and adjustable spaghetti straps provide a perfect fit, while the tiered ruffled skater silhouette adds a touch of feminine flair. With its tie-back design, short-length hem and beautiful floral print, this dress will make you feel effortlessly stylish. Complete the look in mules and earrings!

Fit & Features
- Ditsy floral print
- Chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Tie-back design
- Tiered ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3022

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Playful Mood Strapless Ruffled Skater Dress
Frolicking is expected in this playful ruffled skater dress at brunch, shower celebrations, or graduation parties!

Fit & Features
- Chiffon lined fabric
- Strapless sweetheart neckline
- Stretchy smocked bodice
- Ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05101-3999

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: In Stock

Available Color: IVORY

Available Size: M
Product Badge:
- Sale
Gorgeous Perfection Halter Floral Chiffon Crop Top
Be gorgeous and perfect all season in this floral chiffon crop top at formal soirees! Made with floral and leaf print chiffon fabric, this top is a must-have for any fashion-forward girlie. Its sleeveless halter neckline and cropped hem create a flattering fit. Complete the look with the matching skirt.

Shop The Matching Skirt: Gorgeous Perfection Ruffled Floral Chiffon Maxi Skirt

Fit & Features
- Floral and leaf print, chiffon fabric lined with stretchy knit
- Halter neckline
- Back zipper hook-eye closure
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2505

Category Name: Vacation Looks

Price: $6.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Breezy As Can Be Strapless Ruffled Midi Dress
This midi dress will be your go-to choice from shower celebrations to sunset dinners. Cascading ruffles create a feminine silhouette that flows with your movements, while the midi hem lets you show off your shoes.

Fit & Features
- Gauze woven fabric, woven lining
- Strapless smocked stretchy bodice
- Ruffled cascading silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000027

Category Name: Vacation Looks

Price: $15.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Impressive Style Strappy Sandals
Step out in impressive style in these flat sandals showcasing a strappy design with trendy inserts for the cutest look.

Fit & Features
- Square toe
- Strappy design with inserts
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1282

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK, WHITE

Available Size: 5.5, 6, 6.5, 7, 7.5, 8.5
Product Badge:
- Sale
Pretty Picture Striped Midi Dress
With an ice cream in hand and strappy sandals on, this striped midi dress will have you looking pretty everywhere you go! Featuring a flattering square neck and curve-hugging fit, this dress accentuates your figure down to the midi hem.

Fit & Features
- Striped print, stretchy knit fabric, sewn-in knit lining
- Square neckline
- Wide shoulder straps
- Curve-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5860

Category Name: Vacation Looks

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charmingly Perfect Floral A-Line Midi Dress
Step out in this charming and perfect floral midi dress to graduations, brunch, or shower celebrations! With adorable puff short sleeves, a flattering A-line silhouette, and a flirty front slit, you'll turn heads everywhere you go.

Fit & Features
- Floral print, woven fabric, stretchy knit lining
- Puff short sleeves
- Square neckline, bust tie
- Back zipper and hook-eye closure
- A-Line silhouette, front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-4067

Category Name: Vacation Looks

Price: $11.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Gone Coastal Snake Triangle Bikini Top
If you're heading on vacay or the beach, this snake triangle bikini top will keep you fiercely stylish on and off the shore! Pair with the matching bikini bottoms.

Fit & Features
- Snake print, lined fabric
- Triangle cups, removable padded bra cups
- Adjustable spaghetti straps
- Back spaghetti strap tie
- Runs true to size
Shop The Matching Bikini Bottoms: Gone Coastal Snake Side Tie Bikini Bottoms
Style Number/Barcode: 07104-0729

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Moment Of Beauty Lace Up Floral Maxi Dress
Have your moment of beauty during soiree hour in this floral maxi dress perfect for showers or garden parties! The vibrant floral print adds an extra touch of fun to this maxi length dress. Featuring a playful lace up back, adjustable spaghetti straps, and a high front slit, this dress will have you looking effortlessly chic! Complete the look with earrings and block heels.

Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Lace up back
- V-neckline, padded bra cups
- High front slit
- Maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3047

Category Name: Vacation Looks

Price: $26.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Style One-Shoulder Slit Tropical Maxi Dress
Get that tropical feeling when you're in this one-shoulder maxi dress, whether you're on vacay or having some weekend fun! The curve-hugging silhouette offers a show of skin with a side cutout and high slit.

Fit & Features
- Tropical print, stretchy knit fabric, short knit lining
- One-shoulder neckline
- Side cutout
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6089

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Up A Notch Cork Platform Block Heels
Kick your outfit up a notch in these cork platform heels for showers, birthdays, or graduations! These quirky heels feature a square toe and faux leather wide strap for a unique touch. The cork platform sole and block heel provide added height, while the faux leather adjustable ankle strap with buckle closure ensures a comfortable fit. Complete the look with a crossbody purse.

Fit & Features
- 4.5" Cork Block Heel
- Square toe
- Cork platform sole
- Faux leather straps
- Adjustable ankle strap, buckle closure
- Runs true to size
Style Number/Barcode: 07401-4853

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfect Pair Bow Detail Thong Strap Sandals
The perfect pair of sandals for casual weekend plans! The thong strap design features a bow accent for the cutest detail.

Fit & Features
- Faux leather material
- Almond-shaped toe
- Thong strap design, bow detail
- Open back, on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1253

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: In Stock

Available Color: SILVER

Available Size: 6.5, 7.5, 8, 8.5, 9, 10
Product Badge:
- Sale
Make Some Noise Strapless Printed Bustier
Prepare to receive all the compliments when you're in this strapless printed bustier on vacay or a weekend away! Featuring a chic strapless sweetheart neckline with a padded bust, a stretchy smocked back, and a fitted cropped hem, this top is 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 palazzo pants.

Shop Matching Bottoms: Make Some Noise Printed Palazzo Pants

Fit & Features
- Watercolor print
- Linen-blend woven fabric with woven lining
- Strapless sweetheart neckline, padded bust
- Stretchy smocked back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06003-2408

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Here To Be Loved V-Neck Eyelet Skater Mini Dress
Layered or worn solo, this stunning skater dress features a forever flattering mini-length silhouette and an adorable eyelet pattern for the perfect femme finish.

Fit & Features
- Eyelet woven fabric, stretchy knit lining
- V-neckline, bust tie
- Adjustable spaghetti straps
- Stretchy smocked bodice
- Skater silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3950

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Silhouette Drop Waist Skater Dress
You'll be ready to frolic and twirl with the sweet silhouette of this short skater dress. The tie-back halter straps offer an adjustable fit, while the V-shaped drop waist creates a flattering fit.

Fit & Features
- Poplin woven fabric, woven lining, no stretch
- Sleeveless V-neckline
- Tie-back halter straps, partially open back, zipper with hook-eye closure
- Faux button-down front, pleated accents
- V-shaped drop waist
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3996

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunny Dream V-Cut Scrunched Bikini Bottoms
Shop Matching Top: Sunny Dream Ruffled Off-The-Shoulder Bikini Top

Fit & Features
- Ribbed knit fabric with smooth lining, plenty of stretch
- Mid-rise waist, V-cut design
- Scrunched sides and back
- Cheeky bottom
- Form-hugging fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-0860

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic On Vacay Geometric Print Maxi Tube Dress
You'll be chic on vacay in this trendy maxi tube dress designed with a lightweight woven fabric with a bold geometric print. The strapless bodice features a V-shaped front overlay with a fringe trim, leading to a long-length fitted silhouette with a thigh-high side slit to show off some leg.

Fit & Features
- Woven fabric with woven lining, no stretch
- Geometric print
- Strapless straight-across neckline, no-slip strip
- V-shaped front overlay, fringe trim
- Tie-back design, lower open back, hidden zipper with hook-eye closure
- High-cut side slit
- Maxi-length fitted silhouette
Style Number/Barcode: 05102-000142

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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