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.

Dainty Butterfly Charm Earrings
Add a stunning, subtle touch of glam to your look with these adorable earrings! They feature a linear design with a butterfly charm post and a cascading dainty chain link with more butterfly charms. The charms are embellished with sparkly rhinestones. Pair these earrings with your fave blouse for a pretty vibe.

Fit & Features
- Linear design
- Butterfly charm post
- Chain link design with butterfly charms
- Rhinestone embellishment
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0718

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Three Pack Mini O-Ring Belt Set
Add a layer of glam with a belt to your favorite high rise jeans! The variety pack includes three faux leather belts that feature a mini-double o-ring design. The pack includes a black, ivory, and brown belt.

Fit & Features
- Pack includes 3 belts
- Faux leather
- Adjustable
- Mini-double O-ring design
Style Number/Barcode: 07301-0222

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dainty Mama Charm Necklace
Shout out to all the mamas out there! Let this necklace say it all with love! The necklace features a dainty chain link and a script charm that reads: "Mama". Complete look with a bodysuit and high waist jeans.

Fit & Features
- Dainty chain link
- Mama script charm
- Lobster clasp closure
Style Number/Barcode: 07002-0571

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Five Pack Bohemian Bangle and Bracelet Set
Channel those boho vibes with a bracelet that shows off your free spirit. The bracelet pack includes a variety of bohemian-inspired bracelets and bangles. They can be worn alone or layered for that boho look. Complete the look with a crochet top and flared pants.

Fit & Features
- Pack includes 5 bracelets and bangles
- Bohemian-inspired design
- Metal
Style Number/Barcode: 07003-0208

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish And Chic Rhinestone Statement Earrings
Look oh-so-stylish and chic when you accessorize with these glam statement earrings! They feature a square-shaped rhinestone adorned post linked to a large square-shaped layered design with all-over rhinestones. Pair these earrings with a trendy jumpsuit for a date night.

Fit & Features
- Square-shaped post
- Large square-shaped layered design
- All-over rhinestones
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0484

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dainty Snake Chain and Coin Charm Necklace
Layer up in a necklace that brings a chic look to your outfit! The necklace features a layered design including a snake chain, a flat coin charm, and a bar charm. Complete your look with a matching lounge set to create a casual vibe.

Fit & Features
- 3 layered design
- Snake chain
- Flat coin charm
- Bar charm
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0587

Category Name: Vacation Looks

Price: $7.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Two-Pack Rhinestone Butterfly Bobby Pins
Style up your pretty tresses with this gorgeous set of butterfly bobby pins! The pack features two pins with a butterfly design and partial rhinestone detailing. Pair these pins with a casual mini dress and heeled mules.

Fit & Features
- Two-pack bobby pins
- Butterfly design
- Partial rhinestone detailing
Style Number/Barcode: 07006-0197

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Butterfly Babe Hoop Earrings
Add a pretty vibe to your everyday 'fit with these adorable hoop earrings! They feature a hoop design with rhinestone adorned butterfly detailing. Pair these earrings with a chic crop top and high waist denim.

Fit & Features
- Hoop design
- Rhinestone adorned butterfly detailing
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0687

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cubic Zirconia Butterfly Charm Necklace
Accessorize with this simple charm necklace to add a touch of glam to your look. It features a dainty chain with a center butterfly charm with cubic zirconia detailing. Layer this necklace over a basic bodysuit for a cute everyday outfit.

Fit & Features
- Dainty chain
- Center butterfly charm
- Cubic zirconia
- Gold: 18K gold dipped
- Silver: Rhodium dipped
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0589

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glam Glitter Face Mask
This glitter face mask will keep you safe and let you showcase major glam vibes! It features a woven material with exterior glitter detailing and ear loops. Complete your look with a little black dress and heels.

Fit & Features
- Woven material
- Exterior glitter detailing
- Ear loops
- This is not a medical-grade mask nor is a substitute for medical-grade equipment
- Wash before and after use is recommended
- Please consult local health authority for guidance on the use of non-medical grade masks
Face masks are final sale merchandise and may not be returned or exchanged.
Style Number/Barcode: 07305-0250

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Three Pack Leopard Print Face Mask
Style with a face mask to keep it fierce and safe. This variety pack includes three masks that feature a solid black mask, a warm-toned leopard print mask, and a cool-toned leopard print mask. Each mask includes stretchy earloops for a customized comfortable fit. Complete your look with a ribbed lounge set.

Fit & Features
- Includes three masks
- Solid black and leopard print
- This is not a medical-grade mask nor is a substitute for medical-grade equipment
- Wash before and after use is recommended
- Please consult local health authority for guidance on the use of non-medical grade masks.
Face masks are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07305-0219

Category Name: Vacation Looks

Price: $5.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Classic Cropped Corset Top
Keep it classy in a corset top that brings the chic factor to your look. The top features a sleeveless square neckline, corset-like bodice, piping detailing, and a cropped hem. Complete your look with high waist jeans.

Fit & Features
- Sleeveless square neckline
- Corset-like bodice
- Piping detailing
- Cropped hem
- Sheer mesh fabric with knit lining
- Stretchy smocked back
- Form-hugging fit
Style Number/Barcode: 06003-1059

Category Name: Vacation Looks

Price: $4.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Moody Baseball Cap
Keep it moody in a cap that says it all! The cap features a traditional baseball-style brim and a text graphic that reads: "Moody" in a contrasting white script. Complete look with a matching lounge set.

Fit & Features
- Traditional baseball-style brim
- Text graphic
- "Moody" in contrasting white script
Style Number/Barcode: 07302-0291

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Get Your Flirt On Floral Open Back Crop Top
Have yourself a summer romance in this flirty floral crop top designed with a sultry open strappy back and a cropped hem that flaunts your figure!

Fit & Features
- Floral print, mesh-lined fabric
- Scoop neckline
- Sleek spaghetti straps
- Open strappy back
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000076

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Butterfly Babe Linear Earrings
You'll for sure flutter some hearts in these gorgeous statement earrings! They feature a linear design with cascading dainty and detailed butterfly charms. Pair these earrings with a cute mini dress and chunky sneaks for an adorable everyday look.

Fit & Features
- Linear design
- Dainty and detailed butterfly charms
- Fish hook closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0750

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortlessly Chic Sleeveless Mini Dress
You'll look so effortlessly chic in this simple yet stylish mini dress! It features a sleeveless bodice, a high neckline, and a mini length, curve-hugging silhouette. The knit fabric is lined and offers plenty of stretch for comfortable wear. Pair this dress with a denim jacket for a casual look or a blazer for an elevated vibe.

Fit & Features
- High neckline
- Short, form-hugging fit
- Lined knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0994

Category Name: Vacation Looks

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Clearly Chic Box Clutch
Stay on-trend, girl! Keep all your essentials close to you in this cute box clutch. The clutch features a clear box design, a top fasten closure, and a chain shoulder strap. Clutch is composed of a hard acrylic material. Complete the look with joggers and a crop top for a casual vibe.

Fit & Features
- Clear box design
- Top fasten closure
- Chain shoulder strap
- Composed of a hard acrylic material
Style Number/Barcode: 07203-0423

Category Name: Vacation Looks

Price: $14.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Twisted Detail Headband
Style up your pretty tresses with this trendy headband! It features a twisted design with a braided woven material. Pair this headband with a chic off the shoulder top for a brunch date with the girls.

Fit & Features
- Twisted design
- Braided woven material
Style Number/Barcode: 07006-0212

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Nirvana Graphic Vintage Tee Shirt
Pay homage to Nirvana with a graphic tee shirt fitting for the rocker babes out there. The tee shirt features a crew neckline, short sleeves, and a graphic featuring the iconic In Utero album cover. The tee shirt is composed of a cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with distressed jeans.

Fit & Features
- Crew neckline
- Short sleeves
- In Utero album cover graphic
- Cotton knit fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 06002-0658

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casually Cozy Basic Joggers
Get an effortless, casual, and cozy look in these basic joggers! They feature a high rise elastic banded waist with a front adjustable drawstring, slanted zippered front pockets, and a relaxed fit with a tapered jogger hem. Pair these joggers with chunky sneakers for a perf look for a girl on the go like you!

Shop Matching Jacket: Casually Cozy Zip Front Jacket

Fit & Features
- High rise elastic banded waist
- Front adjustable drawstring
- Slanted zippered front pockets
- Relaxed fit
- Tapered jogger hem
- Knit fabric with soft lining and moderate stretch
Style Number/Barcode: 06502-0493

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Casually Cozy Zip Front Jacket
Get an effortless, casual, and cozy look in this chic jacket! It features a mock neckline with an adjustable drawstring with gold metal hardware, a complete zip front, long loose dolman style sleeves, and a mid-length, relaxed fit. Pair this jacket with chunky sneakers for a perf look for a girl on the go like you!

Shop Matching Bottoms: Casually Cozy Basic Joggers

Fit & Features
- Mock neckline with adjustable drawstring
- Complete zip front
- Long dolman sleeves
- Front zippered pockets
- Mid-length, relaxed fit
- Knit fabric with soft lining
- Moderate stretch
Style Number/Barcode: 06202-0125

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Stunner Rhinestone Charm Necklace
Showcase stylish and stunning looks by layering on this gorgeous necklace! It features a dainty chain with a center rhinestone adorned star charm. Pair this necklace with a trendy knit mini dress to add some pretty sparkle.

Fit & Features
- Dainty chain
- Center rhinestone adorned star charm
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0603

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Top It Off Faux Wool Cabby Hat
Top off your fabulous 'fit with this chic cabby hat! It features a traditional cabby design with a faux leather brim and braided trims with button accents. Pair this hat with a trendy crop top and denim for a casual slay you can wear everyday.

Fit & Features
- Traditional cabby design
- PU brim
- Braided trims with button accents
- Faux wool material
Style Number/Barcode: 07302-0278

Category Name: Vacation Looks

Price: $7.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Three Pack Butterfly Detail Face Masks
Stay safe while adding a cute factor to your 'fit with these butterfly face masks! The set features three pairs of face masks with varying butterfly designs. Pair these face masks with your everyday look for an adorable vibe.

Fit & Features
- Three pack of face masks
- Varying butterfly designs
- Reusable
- Earloops
- This is not a medical-grade mask nor is a substitute for medical-grade equipment
- Wash before and after use is recommended
- Please consult local health authority for guidance on the use of non-medical grade masks
Face masks are final sale merchandise and may not be returned or exchanged
Style Number/Barcode: 07305-0220

Category Name: Vacation Looks

Price: $7.97 $15.90

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