Dive into our stunning lineup of vacation outfits perfect for your getaway. Our collection ranges from trendy, tropical print dresses to breezy cover-ups and vibrant two-piece sets, all designed to tantalize your fashion sense and ignite wanderlust. Uncover an array of beautifully crafted, season-appropriate clothing that effortlessly blends comfort and style, helping you craft those Instagram-worthy looks. Whether you prefer the elegance of beachy maxis or the casual cool of denim shortalls, our collection lets you express your vacation vibes like never before.

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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); } }) })

STYLE SPOTLIGHT

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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.

There She Goes High-Rise Slit Boyfriend Jeans
These denim boyfriend jeans were made to be seen on you! They feature a flattering high-rise waist, trendy relaxed boyfriend style leg with knee slit accents on premium denim fabric. Style with a chic corset top for dinner and drinks with your honey!

Fit & Features
- High-rise waist
- Relaxed boyfriend-style leg
- Knee slit accents
- Front five-button closure
- Five-pocket styling, belt loop accents
- Premium denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0428

Category Name: Vacation Looks

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Out Of Office Lace-Up Tropical Crop Top
Turn your status to out of office and slip on this tropical crop top for your next weekend getaway or vacation! It flaunts a head-turning strappy lace-up back and a trendy palm print.

Fit & Features
- Tropical palm print, stretchy knit fabric
- Square halter neckline
- Spaghetti straps
- Strappy lace-up back
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000075

Category Name: Vacation Looks

Price: $24.90

Availability: In Stock

Available Color: OLIVE

Available Size: XS, S, M, L
Simple Glam Moment Bodysuit
Showcase simple glam vibes in this glitter knit bodysuit that was made for a night out. It features a wrap-front design with a V-neckline, long fitted sleeves, a high waist seam, and a knit bottom. Style this shimmery bodysuit with faux leather pants and strappy heels.

Fit & Features
- Wrap-front design, V-neckline
- Long fitted sleeves
- High waist seam
- Knit bottom
- Glitter knit fabric
- Runs true to size
Style Number/Barcode: 06001-4482

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Babe Lace Hanky Hem Maxi Skirt
Live out your boho era in this airy sheer lace maxi skirt with a mini-length lining for a chic look. The long flowy silhouette will create that effortlessly cool vibe.

Fit & Features
- Sheer lace fabric with mini-length knit lining
- High-rise waist
- Hip-hugging fit
- Maxi-length hanky hem
- Flowy silhouette
- Runs true to size
Style Number/Barcode: 06501-1131

Category Name: Vacation Looks

Price: $32.90

Availability: In Stock

Available Color: IVORY

Available Size: XS, S, M, L
Elevated Sleek Faux Leather Blazer
Layer on this elevated sleek faux leather blazer for a city-chic vibe. It features a lapel collar, long cuffed sleeves, front pockets, and a relaxed silhouette. The patent faux leather fabric offers a moderate stretch. Style with hoop earrings and a chain necklace.

Fit & Features
- Lapel collar
- Long sleeves, cuffed hems
- Front pockets
- Long-length hem
- Relaxed fit
- Patent faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-1485

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cute Adventures Halter Tie Front Crop Top
A halter crop top for all of your cute adventures this season! This top is designed with a flirty dual tie-front design and a bold center split and delicate sheer crop hem create the perfect balance of daring and feminine charm.

Fit & Features
- Crinkle texture sheer woven fabric, bust lining
- Plunge halter neckline with tie closure
- Dual tie front
- Center split, sheer crop hem
- Runs true to size
Style Number/Barcode: 06003-000039

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Country Vibes Cowboy Boot Bag
Show off those trendy country vibes with this adorable cowboy boot bag! Featuring a cowboy boot shape with a center star accent, a cow print pattern, and an included chain-link shoulder strap, this bag is perfect for music festivals to keep all of your essentials on hand. Style with a rhinestone fringe denim jacket and boots!

Fit & Features
- Cowboy boot shape
- Center star accent
- Cow print pattern
- Top zipper closure
- Included chain-link shoulder strap
- Faux leather material, woven interior
Style Number/Barcode: 07203-1151

Category Name: Vacation Looks

Price: $19.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wild Thing High Rise Zebra Print Skort
Get wild for this zebra print skort and flaunt your fierceness! Featuring a high-rise waist and form-hugging fit, a front skirt overlay adds a touch of flirty fun, while the short lining offers comfort and coverage. Complete the look with the matching top.

Shop Matching Top: Wild Thing Corset Zebra Print Top

Fit & Features
- Zebra print, woven fabric, no stretch
- High rise waist
- Back zipper and hook-eye closure
- Form-hugging fit
- Skirt overlay, shorts lining
- Runs true to size
Style Number/Barcode: 06303-0252

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Ditsy Floral Eyelet Strapless Mini Dress
Keep your summer date 'fits flirty and stylish with this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a sweet ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with platform sandals and hoop earrings.

Fit & Features
- Ditsy floral print
- Stretchy eyelet knit fabric with knit lining
- Strapless straight neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5799

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Muse Floral Maxi Dress
Beach date or rooftop night out? You’re covered. With a drapey neckline and bold floral print, this maxi gives you that effortless she’s glowing moment.

Fit & Features
- Floral print, mesh fabric lined with stretchy knit
- Cowl halter neckline
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000273

Category Name: Vacation Looks

Price: $49.90

Availability: In Stock

Available Color: BROWN

Available Size: S, M, L
Sultry Classic Plunge V-Neck Top
Ultra flattering and essential, this plunge v-neck top features long bishop sleeves and a ruched bodice for a figure-hugging fit. Complete the look in high-rise jeans for a dinner party.

Fit & Features
- Long bishop sleeves
- Plunge v-neck
- Ruched bodice
- Figure-hugging fit
- Sleek knit fabric
- Fits true to size
Style Number/Barcode: 06001-4393

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Breezy Charm Halter Babydoll Mini Dress
A charming halter dress for dinner dates or beachside strolls. Its lightweight babydoll silhouette offers a comfortable, flowy fit, while the playful ruffle mini hem brings a flirty finish!

Fit & Features
- Woven gauze fabric, woven lining
- Sweetheart halter neckline, hoop insert, spaghetti strap tie
- Cutout keyhole accent
- Padded bra cups
- Flowy babydoll silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6087

Category Name: Vacation Looks

Price: $44.90

Availability: In Stock

Available Color: NATURAL

Available Size: L
Trendsetting Vibes Faux Leather Shacket
Showcase chic trendsetting vibes when you layer on this sleek faux leather shacket. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, and a relaxed fit. The smooth faux leather fabric offers a moderate stretch. Style over a basic bodysuit with your fave pair of denim.

Fit & Features
- Collared neckline
- Long sleeves, single button detail
- Button-down front
- Buttoned chest pockets, dual lined side pockets
- Relaxed fit
- Faux leather fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1369

Category Name: Vacation Looks

Price: $21.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pop Star Rhinestone High-Rise Denim Shorts
Put on a show arriving in these rhinestone denim shorts! They feature a flattering high-rise waist, and stunning rhinestone swag chains across the front for a touch of glamour. The distressed accents add a trendy edge, while the fitted hem ensures a perfect fit. Complete the look in a bodysuit and boots for a concert or music festival!

Fit & Features
- High-rise waist
- Rhinestone swag chains across the front
- Distressed accents, fitted hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0364

Category Name: Vacation Looks

Price: $22.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Main Style Ribbed Knit Tank Mini Dress
This adorable tank mini dress will be your new main style to create the cutest everyday looks! Designed with a stretchy ribbed knit fabric for comfortable wear, it features a sleeveless scoop neck and back, thin tank shoulder straps, and a bodycon silhouette to flaunt your figure. Pair this short dress with a denim jacket and sneakers for a coffee date with friends.

Fit & Features
- Stretchy ribbed knit fabric
- Scoop neck and back
- Thin tank straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1975

Category Name: Vacation Looks

Price: $8.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Off Duty Babe Luxe Zip-Up Crop Hoodie
Elevate your off-duty look babe in this luxe crop hoodie perfect for running errands or coffee runs! It features relaxed long sleeves with elasticized cuffs, a hooded neckline, front zipper closure, functional pockets, and a cropped elasticized hem on stretchy scuba knit fabric. Layer over a basic top and pants.

Fit & Features
- Relaxed long sleeves, elasticized cuffs
- Hooded neckline
- Front zipper closure
- Functional pockets
- Cropped elasticized hem
- Stretchy and luxe scuba knit fabric
- Runs true to size
Style Number/Barcode: 06202-0379

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Schedule Full Oversized Square Sunglasses
An essential pair of oversized square sunglasses to slip on when you're on the go!

Fit & Features
- Oversized design
- Square shape
- Tinted lenses
- Chain link detail on arms
Style Number/Barcode: 07008-1129

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: BLACK

Available Size: NS
Casual Cute Striped Oversized Sweater
Layer on this casual cute striped oversized sweater for an adorable everyday 'fit! It features a high crew neckline, long dolman sleeves with tapered cuffs, and a mid-length hem with a relaxed fit. The knit fabric features an all-over striped pattern with thick and thin stripes. Pair with your favorite go-to jeans and ankle booties.

Fit & Features
- High crew neckline
- Long dolman sleeves, tapered cuffs
- Mid-length hem
- Oversized relaxed fit
- Striped pattern, thick and thin stripes
- Ribbed knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1436

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Shell We Dance Crochet Hanky Top
Your boho era just called and said to wear this. This crochet hanky top brings flirty vibes with a strapless fit and fringe shell trim, perfect for beach days, brunch dates, or dancing barefoot in the sand.

Fit & Features
- Crochet fabric, stretchy knit lining
- Strapless tube neckline
- Hanky hem with shell trim
- Runs true to size
Style Number/Barcode: 06005-000080

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Pearl-Fect Pick Sweater Maxi Dress
Forever a perfect pick for your next chic soiree! This sweater maxi dress features long fitted sleeves, a plunge V-neckline, a center front faux pearl button-down along the bodycon silhouette, and a slit accent. The ribbed knit fabric offers a moderate stretch. Complete the look with pointed-toe booties.

Fit & Features
- Sweater ribbed knit fabric, moderate stretch
- Long fitted sleeves
- Plunge V-neckline
- Center front faux pearl button-down
- Bodycon fit
- Front slit
- Runs true to size
Style Number/Barcode: 06005-1525

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ladies' Night Abstract Floral Crop Top
This stunning abstract floral crop top will turn heads with every wear on your next ladies' night!

Fit & Features
- Abstract floral print, mesh fabric, sewn-in knit lining
- Adjustable drawstring shoulder straps
- Plunge neckline
- Side ruched seams
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000137

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: PINK

Available Size: S, M, L
Product Badge:
- Sale
Glam Trendsetter Rhinestone Lace-up Skinny Jeans
You'll be a trendsetting muse in these glam rhinestone-accented skinny jeans! They feature a high-rise waist, a rhinestone embellished lace-up front, a skinny-leg silhouette, and a form-hugging fit. The denim fabric offers a moderate stretch. Complete the look with sparkly mules.

Fit & Features
- High-rise waist
- Rhinestone embellished lace-up front design
- Skinny-leg silhouette
- Five-pocket design, three belt loops
- Front button, hidden zipper closure
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06602-0389

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Energy High-Rise Midi Skirt
Bring the energy to your destination getaway in this tropical midi skirt, designed with a sleek high-rise waist and form-hugging silhouette. Pair it with the matching top.

Fit & Features
- Tropical print, mesh fabric, soft knit stretchy lining
- High-rise waist
- Form-hugging silhouette
- Midi-length hem
- Runs true to size
Shop The Matching Top: Tropical Energy Strapless Crop Top
Style Number/Barcode: 06501-000010

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: TAN

Available Size: S, M, L
Product Badge:
- Part of a Set
Style Warm Up Sweater Knit Dress
Cozy up this season in style! This sweater mini dress is the best of both worlds featuring cozy dolman sleeves, a surplice v-neckline, belted tie-front waist, and a bodycon silhouette. The dress is composed of soft cable and rib-knit fabric that offers plenty of stretch. Style with knee-high boots to complete the look!

Fit & Features
- Dolman sleeves
- Surplice v-neckline
- Belted tie-front waist, belt loop accents
- Bodycon silhouette, mini-length
- Cable and rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1572

Category Name: Vacation Looks

Price: $20.97 $49.90

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