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.

Show filters

Sort:

Size

Color

Price

All filters

Sort

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

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.

Such A Flirt Floral Crop Top
Give off major flirty vibes in this adorable floral crop top! Keep it casual with some high rise denim shorts, or dress it up with a satin midi skirt!

Fit & Features
- Thin tie shoulder straps
- Slight sweetheart neckline | Ruffle trim
- Bust seam detailing
- Partial stretchy smocked back
- Hidden side zipper
- Cropped
- All over floral print
- Woven fabric
Style Number/Barcode: 06003-0902

Category Name: Vacation Looks

Price: $11.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bold Beauty Floral Maxi Dress
Just as bold as it is beautiful, this maxi dress is designed with a statement floral print on a body-skimming silhouette. It's perfect for your next vacation or weekend plans!

Fit & Features
- Floral print, mesh fabric, soft stretchy knit lining
- Strapless neckline
- Form-hugging bodice
- Relaxed maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6118

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dive In Tie Dye Hipster Swim Bottoms
Don't call it a comeback, tie-dye has always been here to stay. Add a splash of color to your look in the Dive In swim bottoms! Make sure you add to cart the matching top to complete the look!

Shop Matching Top: Dive In Tie Dye Swim Top

Fits & Features
- Mid-Rise Fit
- Hipster Design
- Fully Lined
- Tie Dye Design
- Matching Top Sold Separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0563

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dive In Tie Dye Swim Top
Don't call it a comeback, tie-dye has always been here to stay. Add a splash of color to your look in the Dive In swim top! Make sure you add to cart the matching bottoms to complete the look!

Shop Matching Bottoms: Dive In Tie Dye Hipster Swim Bottoms

Fits & Features
- Wide Shoulder Straps
- V Neckline I Square Back
- Knot At Center Front
- Pull-Over Design
- Tie-Dye Design
- Matching Bottoms Sold Separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0415

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Paradise Ready Halter Swmsuit
You're ready for paradise bby! Take this gorg tropical printed one piece swimsuit on your trip & get ready for some fun in the sun.

Fit & Features
- Halter neck | Back hook and bar closure
- Large front and back keyhole cut out
- Lattice detailing down the sides
- High rise waist
- Cheeky bottom
- All over tropical print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0192

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Feelin' The Floral Off The Shoulder Top
You'll be totally feelin' the floral vibe in this adorable off the shoulder top! Pair with some light wash jeans and sneaks for a more casual look.

Fit & Features
- Off the shoulder square neckline | Ruffle trim
- Short puff sleeves | Ruffle trim
- Faux button down front
- Stretchy smocked back
- Ruffle cropped hem
- All over floral print
- Woven fabric
Style Number/Barcode: 06003-0884

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sea Me Now Ruffle Trim Molded Swim Top
Wait till they see you! Turn heads in this flirty and fun swimsuit. Make sure you add the matching bottoms to cart to complete the look!

Shop Matching Bottoms: Sea Me Now Tie Side Hipster Swim Bottoms

Fits & Features
- Spaghetti Straps Cross & Tie At The Back
- Molded Padded Cups With Ruffle Trim
- Fully Lined
- Matching Bottoms Sold Separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0431

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dreaming of Summer Ombre Swim Top
We're dreaming of sunny days and poolside vibes in this ombre swim top! Don't forget to pair these must haves with the matching bottoms!

Shop Matching Swim Bottoms: Dreaming of Summer Ombre Swim Bottoms

Fit & Features
- Scoop Neckline
- Flexible Boning at Sides
- Removable Padding
- Tank-Like Straps
- Tie-Dye Ombre Pattern
- Back Strap Closure
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0448

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Mid Rise Rolled Hem Shorts
Girl, stow away those pants! It's time to bust out the shorts with the incoming sunny days. Complement your look with a flowy blouse and cute heels!

Fits & Features
- Elastic Mid Rise Waistband
- Button Waist I Zip Fly
- Slant Hand Pockets
- Belt Loops
- Fitted Leg Openings I Rolled Hem
- Stretchy Woven Fabric
- Moderate Stretch
Style Number/Barcode: 06303-0054

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Wrapped Around My Finger One Piece Swimsuit
Have them wrapped around your little finger while you lounge poolside in this sexy one piece bb!

Fit & Features
- Slanted neckline
- Adjustable single spaghetti strap
- Wrap around sheer mesh detailing
- Cheeky bottom
- High hips
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0209

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
All About Summer Crochet Halter Top
This summer, it's all about breezy lightweight fabrics like this trendy crochet halter top. It features a tie-back halter neckline and cropped, curved hanky hem perfect for pairing with denim shorts.

Fit & Features
- Crochet cotton fabric, partial stretch, cotton lining
- Sleeveless halter neckline, tie-back straps
- Partially open back
- Cropped curved hanky hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000050

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flowy Floral Kimono Sleeve Duster
Make floral your go-to print of the season! This flowy kimono sleeve duster can easily be draped over a cute simple mini dress and paired with some strappy heels!

Fit & Features
- Short kimono sleeves
- Tie front detail | Elastic banded back
- Flowy maxi length
- Sheer floral printed chiffon fabric
- No stretch
Style Number/Barcode: 06204-0492

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tiki Tropic Queen Swim Bottoms
Channel a tropical paradise in these vibrant swim bottoms! All you need is a fruity drink in hand and an Insta-worthy view for vacay goals! Pair with matching swim top to complete your look!

Shop Matching Top: Tiki Tropic Queen Swim Top

Fit & Features
- High Rise Waist
- Wooden O-Ring Belt Accent
- Tropical Floral Print
- Full Coverage
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0594

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tiki Tropic Queen Swim Top
Channel a tropical paradise in this vibrant swim top! All you need is a fruity drink in hand and an Insta-worthy view for vacay goals! Pair with matching swim bottoms to complete your look!

Shop Matching Bottoms: Tiki Tropic Queen Swim Bottoms

Fit & Features
- Bandeau Neckline
- Removable Padding
- Wooden O-Ring Accent
- Tropical Floral Print
- Back Metal Fasten Closure
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0447

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Paradise Swim Bottom
Catch those rays this season as you live it up in a floral paradise with this floral swim top!

Shop The Matching Top: Floral Paradise Bikini Top

Fit & Features
- Hipster Style
- Hip Tie Accents
- Floral Print
- Cheeky Bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0524

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Staple Ribbed Knit Bodycon Midi Dress
A stylish staple like this bodycon midi dress needs to be in your closet. The ribbed knit fabric offers plenty of stretch, while the form-hugging fit flaunts your curves.

Fit & Features
- Lined ribbed knit fabric, high stretch
- Sleeveless square neck and back design
- Spaghetti straps
- High side slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000066

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wavy Baby High Hip Swim Bottoms
Keep it wavy in a new sexy swim suit baby! Also don't forget to pick up the matching top for a full on beach babe lewk!

Shop Matching Top: Wavy Baby Wired Swim Top

Fit & Features
- High hip swim bottoms
- Cheeky bottom
- Lined
- Moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0547

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wavy Baby Wired Swim Top
Keep it wavy in a new sexy swim suit baby! Also don't forget to pick up the matching bottoms for a full on beach babe lewk!

Shop Matching Bottoms: Wavy Baby High Hip Swim Bottoms

Fit & Features
- Adjustable spaghetti straps
- Wired cups
- Hook closure
- Lined
- Moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0399

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Paradise Bikini Top
Catch those rays this season as you live it up in a floral paradise with this floral bikini top!

Shop The Matching Bottoms: Floral Paradise Swim Bottom

Fit & Features
- Bikini Style Cups
- Twist Front Accent
- Spaghetti Straps
- Cross-Strap Back
- Floral Print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0375

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bright Side Of Things Neon Swim Bottoms
Add a pop of color with your look this summer, we are loving these tonez, they pair perfect with a bronzey goddess glow! Don't forget your matching top to complete your look!

Shop Matching Top: Bright Side Of Things Neon Swim Top

Fit & Features
- Low rise fit
- Bungee hips with snap adjustments
- Cheeky bottom
- Triangle design
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0485

Category Name: Vacation Looks

Price: $8.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bright Side Of Things Neon Swim Top
Add a pop of color with your look this summer, we are loving these tonez, they pair perfect with a bronzey goddess glow! Don't forget to pick up your matching bottoms to complete the look!

Shop Matching Bottoms: Bright Side Of Things Neon Swim Bottoms

Fit & Features
- Halter top neckline
- Straight back-line
- Adjustable bungee hemline
- Neon
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0333

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feline Wild Cut Out Swimsuit
You'll be feelin' totally wild & fierce in this bold cut out one piece swimsuit! Pair with some oversize sunnies and get ready to strut down that beach!

Fit & Features
- Single adjustable spaghetti strap
- Square neckline
- Back bar closure
- Large center cut out
- Cheeky bottoms
- All over zebra print in orange and black hues
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0193

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Viva Las Vegas Rhinestone Swim Top
We can already see it now, you are getting that V.I.P treatment and hitting vegas looking like a true sparkling qween! Don't forget to pick up the matching bottoms to complete ur look!

Shop Matching Bottoms: Viva Las Vegas Rhinestone Swim Bottoms

Fit & Features
- Triangle design
- Tie straps
- Removable padding
- Iridescent rhinestone detailing
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0444

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Viva Las Vegas Rhinestone Swim Bottoms
We can already see it now, you are getting that V.I.P treatment and hitting vegas looking like a true sparkling qween! Don't forget to pick up the matching top to complete ur look!

Shop Matching Top: Viva Las Vegas Rhinestone Swim Top

Fit & Features
- Triangle design
- Low rise fit
- Thong bottom
- Iridescent rhinestone detailing
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0592

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

Reset Your Password

Email Sent

Order Status

Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials