Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.

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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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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.

Glisten And Glow Swim Bottoms
Glisten and glow as you lounge poolside in these gorgeous swim bottoms! They feature a high rise waist, a semi-cheeky fit, and a shimmery fabric. Complete your look with the matching swim top and a chic flowy kimono.

Shop Matching Swim Top: Glisten And Glow Swim Top

Fit & Features
- High rise waist
- Semi-cheeky fit
- Shimmery fabric
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0504

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glisten And Glow Swim Top
Glisten and glow as you lounge poolside in this gorgeous swim top! It features tank-like shoulder straps, a deep V neckline, a tie front detail, and a shimmery fabric. Complete your look with the matching swim bottoms and a chic flowy kimono.

Shop Matching Swim Bottoms: Glisten And Glow Swim Bottoms

Fit & Features
- Tank-like shoulder straps
- Deep V neckline
- Tie front
- Banded back
- Shimmery fabric
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0353

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek and Minimal Swim Tank
Keep it minimal with a swim tank that rocks those basic vibes. The swim tank features a sleeveless scoop neckline, tank-straps, and a cropped hem. Complete your poolside look with the matching swim tank and sandals.

Shop Matching Bikini Bottoms: Sleek and Minimal High Waist Bikini Bottoms

Fit & Features
- Sleeveless
- Plunging scoop neckline
- Tank straps
- Cropped hem
- Form hugging fit
- Moderate stretch
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0517

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Trendsetter Clear Crossbody Purse
Showcase your chic trendsetter status with this adorable clear purse! It features a fold-over design with a faux leather top handle, a faux leather trim, and a removable faux leather shoulder strap to convert the purse to a crossbody. The faux leather on the clear bag showcases a cool snake print for an edgy vibe. Pair this cute accessory with your fave everyday outfits.

Fit & Features
- Fold-over design
- Faux leather top handle
- Faux leather trim
- Faux leather shoulder strap
- Snake print
- Clear material
Style Number/Barcode: 07203-0427

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ready to Slay Ruched Mini Dress
Babe, you'll be ready to slay in this sleek mini dress! Perfect for date night or a GNI, style this chic must-have with lucite heels and a sleek satin clutch. The dress features a sleeveless crew neckline, a ruched drawstring at the side seam, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch.

Fit & Features
- Crew neckline
- Sleeveless
- Ruched drawstring
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit
- Moderate stretch
Style Number/Barcode: 05103-3744

Category Name: Vacation Looks

Price: $6.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Ruffled High Waist Bikini Bottoms
Soak up the sun and bring the charm in these cute bikini bottoms! They feature a high rise waist with a ruffled trim, a waffle-print pattern, and a cheeky fit. Complete look with the matching bikini top.

Shop Matching Bikini Top: Flirty Ruffled Bikini Top

Fit & Features
- High rise waist
- Ruffled trim
- Waffle print pattern
- Cheeky fit
- Matching bikini top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0629

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vibrant Side Geometric Print Bodycon Midi Dress
Unleash your vibrant side in this stunning geometric midi dress on vacation, during weekend getaways, or at pool parties! Designed with a smooth knit fabric that effortlessly hugs your curves, it features a halter V-neck, open back, and center front slit for a trendy allure.

Fit & Features
- Smooth knit fabric, high stretch
- Geometric tropical print
- Sleeveless halter surplice V-neckline, open back
- Ruching
- Center front slit accent
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3929

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Ruffled Bikini Top
Soak up the sun and bring the charm in this cute bikini top! It features lightly padded triangle cups with a ruffled trim, adjustable spaghetti straps, a waffle-print pattern, and a single fasten closure. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Flirty Ruffled High Waist Bikini Bottoms

Fit & Features
- Lightly padded triangle cups
- Ruffled trim
- Adjustable spaghetti straps
- Waffle print pattern
- Single fasten closure
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0481

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek and Minimal High Waist Bikini Bottoms
Keep it minimal with bikini bottoms that rock those basic vibes. The bottoms feature a high rise waist, high cut, and a cheeky fit. Complete your poolside look with the matching swim tank and sandals.

Shop Matching Swim Tank: Sleek and Minimal Swim Tank

Fit & Features
- High rise waist
- High cut
- Cheeky fit
- Form hugging fit, moderate stretch
- Matching swim top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0666

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Minimal Swim Bottoms
Keep it basic as you soak up the sun in these cute swim bottoms! The swim bottoms feature a high rise elastic banded waist and a cheeky fit. Complete your poolside look with the matching swim top and chic sunnies!

Shop Matching Swim Top: The Minimal Swim Top

Fit & Features
- High rise elastic banded waist
- Cheeky bottom
- Matching swim top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0667

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Minimal Swim Top
Keep it basic as you soak up the sun in this cute swim top! The swim top features a sleeveless scoop neckline, lightly padded cups, supportive tank straps, and a cropped hem. Complete your poolside look with the matching swim bottoms and chic sunnies!

Shop Matching Swim Bottoms: The Minimal Swim Bottoms

Fit & Features
- Sleeveless scoop neckline
- Lightly padded cups
- Tank-straps
- Cropped hem
- Matching bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0518

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bling and Dazzle Faux Fur Slides
Bring the dazzle to your fit with glam slides! The slides feature a slip-on design, a square toe, a wide faux fur toe strap, and a luxe rhinestone trim. Complete look with a ribbed crop top and joggers set.

Fit & Features
- Slip-on design
- Square toe
- Wide toe strap
- Faux fur
- Rhinestone trim
Style Number/Barcode: 07404-0666

Category Name: Vacation Looks

Price: $12.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All That Luxe Rhinestone Sandals
Slip-on these glam sandals that bring the luxe to your look! The sandals feature a trendy slip-on design, a square toe, and a wide toe strap embellished with sparkling rhinestones. Complete look with a stunning swimsuit and sunglasses.

Fit & Features
- Slip-on design
- Square toe
- Wide toe strap
- Rhinestones
Please be advised that these sandals run 1/2 a size big.
Style Number/Barcode: 07404-0667

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Rhinestone Butterfly Charm Chain Link Anklet
Wrap yourself with a gorge anklet that brings the charm to your outfit. The anklet features a chunky chain link design and rhinestone embellished butterfly charms. Complete look with clear mules and a floral skater dress.

Fit & Features
- Chunky chain link design
- Rhinestone butterfly charms
- Lobster clasp closure
Style Number/Barcode: 07003-0203

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Under The Sun Tropical Tie-Front Crop Top
Perfect for any vacation or resort escape, this tropical top boasts a sultry tie-front and a cropped silhouette for a breezy allure. Pair with the matching skirt.

Fit & Features
- Tropical print, stretchy knit fabric
- Long sleeves
- V-neckline
- Tie-front closure
- Cropped hem
- Runs true to size
Shop The Matching Skirt: Under The Sun Tropical Slit Maxi Skirt
Style Number/Barcode: 06202-000014

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK

Available Size: S, M
Product Badge:
- Sale
Feelin' Chic Dainty Layered Necklace
Feel oh-so-chic in this dainty layered necklace, perfect for every day! It features two rows with dainty chains and center bar drop charms. Pair this necklace with a basic tee and denim to add a subtle hint of glam to your look.

Fit & Features
- Two-row layered design
- Dainty chains
- Bar drop charms
Style Number/Barcode: 07002-0582

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wave of Glam Low Rise Bikini Bottoms
Ride the glamour wave this season in a bikini bottom that is vacay-ready! The bikini bottom features a low rise waist, side ties, and a cheeky bottom. Complete your sunkissed look with the matching bikini top and stunning sunglasses.

Shop Matching Bikini Top: Wave of Glam Wrap Around Bikini Top

Fit & Features
- Low rise waist
- Side ties
- Cheeky bottom
- Matching bikini top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0625

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wave of Glam Wrap Around Bikini Top
Ride the glamour wave this season in a bikini top that is vacay-ready! The bikini top features triangle-cups, a halter neck-tie, and sleek wrap-around straps, and lower back tie-back straps. Complete look with the matching bikini bottoms and stunning sunglasses.

Shop Matching Bikini Bottoms: Wave of Glam Low Rise Bikini Bottoms

Fit & Features
- Triangle-cups
- Halter neck-tie
- Wrap around straps
- Lower back tie-back straps
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0477

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hey There Señorita One Piece Mesh Swimsuit
Hola Señorita, you look like a ten in your one piece bathing suit! Lay out, enjoy the vip treatment, and catch some rayss!

Fit & Features
- Plunging V-neckline
- Adjustable spaghetti straps
- Low back
- High hips with mesh cutout detailing
- Moderate stretch
- Cheeky bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0156

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Brighter Days High Cut Bikini Bottoms
Brighten up the season with a bikini bottom that radiates good vibes! The bikini bottom features a low-rise waist, a high cut, and a cheeky fit. Complete your look with the matching bikini top and a floppy hat.

Shop Matching Bikini Top: Brighter Days Wired Bikini Top

Fit & Features
- Low rise waist
- High cut
- Cheeky bottom
- Matching bikini top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0623

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Brighter Days Wired Bikini Top
Brighten up the season with a bikini top that radiates good vibes! The bikini top features a plunging sweetheart neckline, wired cups, adjustable spaghetti straps, and a fastening closure at the back. Complete your look with the matching bikini bottoms and a floppy hat.

Shop Matching Bikini Bottoms: Brighter Days High Cut Bikini Bottoms

Fit & Features
- Sleeveless sweetheart neckline
- Wired cups
- Adjustable spaghetti straps
- Fastening closure at back
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0475

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Chic High Waist Swim Bottoms
Keep it so chic as you cool off poolside in this chic swimsuit! The swim bottoms feature a high rise waist and a cheeky fit. Complete look with sunnies and the matching swim top.

Shop Matching Swim Top: So Haute One Shoulder Swim Top

Fit & Features
- High rise waist
- Cheeky bottom
- Matching swim top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0642

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Chic One Shoulder Swim Top
Keep it so chic as you cool off poolside in this chic swimsuit! The swim top features an asymmetrical one-shoulder neckline, a cap sleeve, and a cropped hem. Complete look with sunnies.

Shop Matching Swim Bottoms: So Haute High Waist Swim Bottoms

Fit & Features
- Asymmetrical one-shoulder top
- Cap sleeve
- Cropped hem
- Matching swim bottom sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0494

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beachside Babe One-Piece Swimsuit
You'll look like a total beachside babe in this stunning one-piece swimsuit! It features tank-like shoulder straps, a plunging V neckline, trendy side cut-outs leading to an open back, and a semi-cheeky fit. The swimsuit has a chic color block design with white, black, and mauve tones. Pair this one-piece with cute sandals and a sheer tie-front top.

Fit & Features
- Tank-like shoulder straps
- Deep V neckline
- Side cut-outs
- Open back
- Semi-cheeky fit
- Color block design
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0222

Category Name: Vacation Looks

Price: $18.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials