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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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.

Sweet Then Sour Lemon Swim Bottoms
Are you sweet or sour? Lay out poolside in the cutest lemon print swim suit, and sip that lemonade! Don't forget to pick up your matching swim top!

Shop Matching Top: Sweet Then Sour Lemon Swim Top

Fit & Features
- Low rise fit
- Cheeky bottom
- Fully lined
- Lemon print pattern
- Moderate stretch
Model is 5'8" with 34" bust, 24" waist and 37" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0610

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glow Up Lace Front Swim Top
You'll totally glow girl in this lace front swim top! Pair with the matching hipster bottoms and get ready to own that beach!

Shop Matching Bottoms: Glow Up Hipster Swim Bottoms

Fit & Features
- Adjustable halter spaghetti strap | Strap is removable
- Padded molded cups
- Lattice front | Tie closure
- Back tie closure
- Fabric with a slight sheen
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: 07104-0454

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Rock The Boat Tie Side Hipster Swim Bottoms
When they see you in this....girl, you're going to be causing a commotion! Make sure you pick up the matching top for a finished look!

Shop Matching Top: Rock The Boat Lace Up Triangle Swim Top

Fits & Features
- Mid-Rise Waist
- Lattice Tie Sides
- Hipster Fit I Cheeky Coverage
- Ribbed I Fully Lined
- Matching Top Sold Separately
Model is 5'4" with a 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: 07105-0577

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Babe Next Door Gingham Swim Bottoms
Embrace your girl next door vibes with a sweet gingham two piece! So cute when you pair with red lipstick and cat eye sunnies! Don't forget to pick up your matching swim top!

Fit & Features
- Mid-rise fit
- Tie sides
- Cheeky bottom
- Moderate stretch
- Gingham pattern
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0608

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Rock The Boat Lace Up Triangle Swim Top
When they see you in this....girl, you're going to be causing a commotion! Make sure you pick up the matching bottoms for a finished look!

Shop Matching Bottoms: Rock The Boat Tie Side Hipster Swim Bottoms

Fits & Features
- Adjustable Spaghetti Straps
- Triangle Bralette Style I Removable Padded Bust
- Lace-Up Front
- Ribbed Fabric I Fully Lined
- Matching Bottoms Sold Separately
Model is 5'4" with a 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: 07104-0429

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Viper Vixen Lace Up High Waist Swim Bottoms
Girl, you're going to be making more than a splash at the pool party. Make your entrance be known in these fierce swim bottoms! Don't forget to pick up the matching top!

Shop Matching Top: Viper Vixen One Shoulder Swim Top

Fits & Features
- High Rise Waist
- Lace Up Design At Center Front
- Cheeky Bottoms
- Fully Lined I Snake Print Design
- Matching Top Sold Separately
Model is 5'4" with a 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: 07105-0571

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Viper Vixen One Shoulder Swim Top
Girl, you're going to be making more than a splash at the pool party. Make your entrance be known in this fierce swim top! Don't forget to pick up the matching bottoms!

Shop Matching Bottoms: Viper Vixen Lace Up High Waist Swim Bottoms

Fits & Features
- One Shoulder Strap
- Scoop Neckline I Removable Padded Bust
- Lace-Up Design At The Side
- Fully Lined I Snake Print Design
- Matching Bottoms Sold Separately
Model is 5'4" with a 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: 07104-0423

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Escape To The Tropics One Piece Swimsuit
Set that out-of-office email and escape to the tropics in this gorge one-piece swimsuit! Top off your look with some sunnies and cute slide sandals!

Fits & Features
- One Piece Swimsuit
- Halter Neckline With Ties At Nape
- Keyhole At Center Front
- Removable Padded Bust
- Cut Out Design At The Waists
- Full Coverage Bottoms
- Tropical-Inspired Prints
Model is 5'4" with a 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: 07109-0201

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sip Of Sultry Strapless Ruffle Mini Dress
Be the center of attention in this sultry strapless mesh mini dress! It features a strapless neckline with non-slip grip lining, and a ruffled trim adds a flirty touch while the bodycon silhouette highlights your curves down to the mini-length hem. Complete the look in heels and teardrop earrings.

Fit & Features
- Strapless neckline
- Non-slip grip lining
- Side zipper and hook-eye closure
- Ruffle trim, bodycon silhouette
- Mini-length hem
- Mesh fabric, sewn-in knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-3349

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sol Seeker High Waist Swim Bottoms
Frolic in the waves and lounge under that sun bb girl! The heat is finally here and you'll want to be keeping your cool in the Sol Seeker swim suit! Don't forget to add the matching swim top to cart and a pair of sunnies

Shop Matching Top: Sol Seeker Wired Swim Top

Fits & Features
- High Waist Fit
- Elastic Waist
- High Cut Design
Model is 5'4" with a 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: 07105-0576

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sol Seeker Wired Swim Top
Frolic in the waves and lounge under that sun bb girl! The heat is finally here and you'll want to be keeping your cool in the Sol Seeker swim suit! Don't forget to add the matching bottoms to cart and a pair of sunnies

Shop Matching Bottoms: Sol Seeker High Waist Swim Bottoms

Fits & Features
- Adjustable Spaghetti Straps
- V-Wired Cups I Unpadded
- Back Metal Bar Clasp Closure
- Fully Lined
- Matching Bottoms Sold Separately
Model is 5'4" with a 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: 07104-0428

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Under The Sun Ribbed Hipster Swim Bottoms
Kick back, relax, and just bask under the sun hunty!! Highlight that sunkissed glow in your new fave swim bottoms! Don't forget to add the matching top to cart ;-)

Shop Matching Top: Under The Sun Ribbed Underwire Swim Top

Fits & Features
- Mid-Rise Waist
- Ribbed I Fully Lined
- Hipster Fit I Cheeky Coverage
- Matching Top Sold Separately
Model is 5'4" with a 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: 07105-0578

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Under The Sun Ribbed Underwire Swim Top
Kick back, relax, and just bask under the sun hunty!! Highlight that sunkissed glow in your new fave swim top! Don't forget to add the matching bottoms to cart ;-)

Shop Matching Bottoms: Under The Sun Ribbed Hipster Swim Bottoms

Fits & Features
- Adjustable Spaghetti Straps
- Back Metal Bar Clasp
- Underwire I Unpadded I Dramatic Cup Design
- Ribbed I Fully Lined
- Matching Bottoms Sold Separately
Model is 5'4" with a 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: 07104-0430

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Let The Good Times Roll Wired Swim Top
Step out in a two piece and let the good times roll through! Perfect for a bronzed goddess like yourself, don't forget to pick up your matching swim bottoms!

Shop Matching Bottoms: Let The Good Times Roll Swim Bottoms

Fit & Features
- Padded cup design
- Wired
- Adjustable spaghetti straps
- Bar hook closure
- Minimal stretch
Model is 5'8" with 34" bust, 24" waist and 37" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0334

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stroll In The Sand Halter Crochet Crop Top
Make waves by the shore in this crochet top with a flirty halter V-neckline and crop hem that flaunts your figure. Pair with a flowy maxi skirt for any casual plans!

Fit & Features
- Crochet knit fabric
- Halter V-neckline, spaghetti strap tie
- Crop hem
- Runs true to size
Style Number/Barcode: 06005-000030

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Under The Sun Tank Swim Top
Get ready to bask under the sun & showcase what a stunna' you are in this tank swim top! Pair with the matching bottoms for a bright and bold look.

Shop Matching Bottoms: Under The Sun Hipster Swim Bottoms

Fit & Features
- Adjustable spaghetti straps
- Wired V front
- Hook back closure
- Ribbed knit fabric
- Light padding
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0410

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Under The Sun Hipster Swim Bottoms
Get ready to bask under the sun & showcase what a stunna' you are in these hipster swim bottoms! Pair with the matching top for a bright and bold look.

Shop Matching Top: Under The Sun Tank Swim Top

Fit & Features
- Hipster design
- Criss cross cut out sides
- Cheeky bottom
- Ribbed knit fabric
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0558

Category Name: Vacation Looks

Price: $8.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blame It On The Juice Colorful Swim Top
Introduce some color this summer! This cute fruity design would look soo cute in your beach front insta-worthy pics bby! Don't forget to pick up the matching bottoms!

Fit & Features
- Triangle designed swim top
- Juicy fruit colorful pattern
- Adjustable spaghetti straps
- Hook closure
- Moderate stretch
- Matching bottoms: 07105-0472
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0316

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blame It On The Juice Colorful High Waist Swim Bottoms
Introduce some color this summer! This cute fruity design would look soo cute in your beach front insta-worthy pics bby! Don't forget to pick up the matching top!

Fit & Features
- Triangle designed swim top
- Juicy fruit colorful pattern
- Adjustable spaghetti straps
- Hook closure
- Moderate stretch
- Matching top: 07104-0316
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0472

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Simply Sweet Clear Pointed Flats
Keep a sweet girl vibe when you slip into these adorable clear flats! Pair with cut off dress pants or a summer dress!
- Pointed toe
- Flat sole
- Transparent design
- Available in clear & gold glitter
Style Number/Barcode: 07405-0020

Category Name: Vacation Looks

Price: $11.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ray Of Sunshine Off-Shoulder Swim Top
Be that little ray of sunshine on the beach with this flirty swim look! Don't forget to pick up the matching bottoms, and style with a pair of chunky earrings!

Fit & Features
- Sweetheart neckline
- Off shoulder sleeves
- Tie front detail
- Non-removable padding
- Sip on fit | No closure
- Moderate stretch
- Matching bottoms: 07105-0491
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0339

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ray Of Sunshine Off-Shoulder Swim Bottoms
Be that little ray of sunshine on the beach with this flirty swim look! Don't forget to pick up the matching top, and style with a pair of chunky earrings!

Fit & Features
- High waist fit
- Ruched bottom
- Fully lined
- Moderate stretch
- Matching top: 07104-0339
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0491

Category Name: Vacation Looks

Price: $8.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In Tulum One-Shoulder Tropical Maxi Dress
Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing!

Fit & Features
- Tropical print, smooth knit fabric with short stretchy lining
- One-shoulder neckline
- One shoulder strap with metal accents
- Front ruffled slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6073

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hila Floral Chiffon A-Line Dress
Special Occasion

Decked with pretty florals, our lovely Hila will have you feeling oh-so-fine. She's the perfect plus one for any spring-time soiree! Her breezy chiffon skirt will look and feel as though it's forever-flowing as you glide from room-to-room. Look even more enchanting by adding a pair of glistening earrings and heels to complete the look!

Fits & Features
- Adjustable Spaghetti Straps
- Surplice V Neckline
- Back Zipper With Hook & Eye Closure
- Floor Length Hemline I A-Line Silhouette
- Fully Lined Chiffon Fabric
- Form Hugging Fit I Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0654

Category Name: Vacation Looks

Price: $19.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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