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.

Easy Stunner Sleeveless Lace Trim Bodysuit
Easily stun in this sleeveless bodysuit to layer under your favorite sheer blouses or layered with a cute jacket! The bodysuit is crafted from a double-lined rib knit stretchy fabric for comfort. It features a delicate lace trim square neckline, adjustable spaghetti straps for a perfect fit, a form-hugging fit that shows your shape, and a thong bottom with snap-button closures. Complete the look with a midi skirt, jacket, and heels for a date!

Fit & Features
- Double-lined rib knit stretchy fabric
- Adjustable spaghetti straps
- Lace trim
- Form-hugging fit
- Thong bottom, snap-button closures
- Runs true to size
Style Number/Barcode: 06002-1782

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lively Elegance Smocked Floral Babydoll Dress
Indulge in elegance in this elegant floral babydoll dress perfect for wedding showers or graduations! With its stretchy smocked bodice and adjustable straps, you'll get a perfect fit. The chiffon fabric and vibrant floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem. Complete the look in sandals.

Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Stretchy smocked bodice
- Babydoll silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05102-5470

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charming Presence Strapless Slit Floral Maxi Dress
Your presence will always be charming in this ditsy floral maxi dress at wedding showers, brunch, or casual parties! Adorned in a stunning disty floral print, this strapless dress features a ruffle trim neckline and padded bra cups for flattering support. The curve-hugging silhouette, front slit, and maxi-length hem create a captivating look, while the brushed knit stretchy fabric ensures comfort. Pair with earrings and strappy sandals.

Fit & Features
- Ditsy floral print
- Brushed knit stretchy fabric
- Padded bra cups
- Front slit
- Curve-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5541

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunset Vibes Braided Strap Platform Sandals
These trendy braided strap platform sandals are perfect for sunset happy hours this season! They feature a cork block heel and platform sole, an open square-shaped toe, and multi-colored braided straps in a criss-cross design. The open back offers effortless on-and-off styling. Pair these sandals with gold hoops!

Fit & Features
- 4.5" Cork block heel, platform sole
- Faux leather upper
- Open square toe
- Criss-cross multi-colored braided straps
- Open back
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07401-4843

Category Name: Vacation Looks

Price: $16.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Next Level Gladiator Flat Platform Sandals
Take your style to the next level in these gladiator flat platform sandals perfect for spring to summer wear! Featuring an almond toe and a strappy caged design, these sandals are both chic and comfortable. The adjustable ankle strap with buckle closure ensures a perfect fit while the flat platform sole adds a touch of height to faux leather material. Complete the look in a trendy denim jacket.

Fit & Features
- Almond toe
- Strappy caged design
- Flat platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1171

Category Name: Vacation Looks

Price: $24.90

Availability: Out of Stock
Product Badge:
- Ships Free
Flirt In Full Bloom Lace Halter Top
A little sheer, a little sweet—this lace halter brings all the romance with a ring-front detail and breezy flyaway silhouette. Pair with denim or maxi skirts for your next IG-worthy moment.

Fit & Features
- Lace fabric, bust knit lining
- Halter neckline, spaghetti strap ties
- Hoop insert
- Center split design
- Sheer cropped hem
- Runs true to size
Style Number/Barcode: 06001-000161

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Glitzy Rhinestone Strappy Faux Leather Sandals
Step out in glitzy style with these rhinestone strappy sandals! Made with faux leather material, they feature an open square toe, a wide twisted strappy design across the foot with rows of mini rhinestones, and a mini rhinestone outline on the flat sole for more sparkle. The open back offers effortless on-and-off styling. Pair these sandals with a fab handbag.

Fit & Features
- Faux leather upper
- Square toe
- Twisted strappy design with rhinestones
- Rhinestone trim
- Open back, flat sole, faux leather padded insole
- On-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1181

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bloom With A View High Rise Floral Mini Skirt
Take in your beauty in this floral mini skirt on vacation! Designed with a stretchy sheer mesh fabric with a lining, the delicate floral bloom print will bring out a touch of chic to any outfit. Featuring a high-rise elasticized waist, flattering side ruching to accentuate your curves on the bodycon fit, and a mini-length hem, this skirt is perfect for any getaway. Complete the look with the matching crop top!

Shop Matching Top: Bloom With A View V-Neck Floral Crop Top

Fit & Features
- Stretchy sheer mesh fabric, sewn-in knit lining
- Floral bloom print
- High-rise elasticized waist
- Bodycon fit
- Ruched side seams
- Runs true to size
Style Number/Barcode: 06501-0965

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chasing Rainbows Press On Nail Kit
Color your everyday style in this rainbow press-on nail kit including everything you need to achieve a fun look. The exclusive kit offers two sets of colorful press-on nails with artsy designs, one mini nail file, a prep pad, and glue. Follow the easy instructions on the prep pad for the best results. Complete the look in sandals for a daytime brunch or party!

Fit & Features
- Press on nail kit
- Two sets of colorful press-on nails, artsy designs
- One mini nail file
- One prep pad with easy instructions
- One glue tube
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07307-0190

Category Name: Vacation Looks

Price: $3.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Forever Rogue Long Press On Nail Kit
Embolden your vibe in this press on nail kit including everything you need to achieve a trendy look. The exclusive kit offers two sets of bold long press-on nails, one mini nail file, a prep pad, and glue. Follow the easy instructions on the prep pad for the best results. Complete the look with a tee and cargo pants for casual plans or travel!

Fit & Features
- Press on nail kit
- Two sets of bold long press-on nails
- One mini nail file
- One prep pad with easy instructions
- One glue tube
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07307-0185

Category Name: Vacation Looks

Price: $3.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flawless Duo Ruched Tube Crop Top
You can't go wrong while on vacay in this tube crop top! Featuring a sleeveless V-neckline, spaghetti straps, and a ruched bust, this top is designed to flatter your figure. The elasticized ultra-cropped hem adds a trendy touch while the soft woven fabric ensures comfort while you're relaxing under the sun or having a dinner with a view! Complete the look with the matching skirt.

Shop Matching Skirt: Flawless Duo Tiered Maxi Skirt

Fit & Features
- Woven fabric, bust lining, slight stretch
- Spagehtti straps
- Elasticized cropped hem
- Runs true to size
Style Number/Barcode: 06003-2469

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flawless Duo Tiered Maxi Skirt
You can't go wrong while on vacay in this maxi skirt! Featuring a high-rise elasticized waistband and a flowy tiered silhouette, this skirt is designed to flatter your figure. The maxi-length hem adds a trendy touch while the soft woven fabric ensures comfort while you're relaxing under the sun or having dinner with a view! Complete the look with the matching top.

Shop Matching Top: Flawless Duo Ruched Tube Crop Top

Fit & Features
- Woven fabric, slight stretch
- High-rise elasticized waist
- Tiered flowy silhouette
- Runs true to size
Style Number/Barcode: 06401-0654

Category Name: Vacation Looks

Price: $12.97 $29.69

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Admiration Button Peplum Tank Top
Take on a sweet look in this peplum tank top that everyone will admire! Designed to flatter with a sweetheart neckline, adjustable spaghetti straps for a custom fit, and a stretchy smocked back while the button front and peplum ruffled hem add charming details to this woven fabric. Complete the look in a trendy denim mini skirt for casual plans!

Fit & Features
- Woven fabric
- Adjustable spaghetti straps
- Stretchy smocked back
- Button front
- Peplum ruffled hem
- Runs true to size
Style Number/Barcode: 06003-2461

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Above Average Oval Metal Trim Sunglasses
Take your look above average in these oval metal trim sunglasses perfect for driving and everyday styling! The sleek oval metal trim frame and tinted lenses provide 100% UV protection while the rubber nose supports and plastic arms ensure comfort and durability. Complete the look with a trendy shoulder bag.

Fit & Features
- Oval metal trim frame
- 100% UV protection
- Tinted lenses
- Rubber nose supports
- Plastic arms
Style Number/Barcode: 07008-1056

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Classic Icon Round Sunglasses
Channel your classic and iconic look in these round sunglasses to shade your eyes and keep your outfit looking fab! They feature a wide round plastic frame, 100% UV protective tinted lenses, and comfortable plastic arms. Complete the look in chic stiletto pumps.

Fit & Features
- Round plastic frame
- 100% UV protection
- Tinted lenses
- Comfortable plastic arms
Style Number/Barcode: 07008-1054

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunniest Day Flat Top Square Sunglasses
These flat-top sunglasses are perfect for wearing on the sunniest day! The flat top design and plastic square frame provide a unique and fashionable look while offering 100% UV protection tinted lenses for your eyes. Complete the look with a sleek shoulder bag for any occasion!

Fit & Features
- Plastic square frame
- Flat top design
- 100% UV protection tinted lenses
- Comfortable fit
Style Number/Barcode: 07008-1055

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Everywhere Stunner Aviator Metal Sunglasses
Everywhere you go in these aviator metal sunglasses you're sure to stun! Featuring sleek colored metal frames and tinted lenses, you'll be turning heads while enjoying 100% UV protection. Rubber nose supports and plastic arms provide comfort and durability, all in a classic aviator design. Complete the look with a dainty charm necklace.

Fit & Features
- Sleek-colored metal frame
- Classic aviator design
- 100% UV protection
- Tinted lenses
- Rubber nose supports
- Plastic arms
Style Number/Barcode: 07008-1058

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glowing Up Rhinestone Flat Jelly Sandals
Glow up in these exclusive jelly sandals for a sparkling spring and summer! These chic sandals feature a trendy square toe and rhinestone embellished asymmetrical straps for a touch of glamour. The adjustable ankle strap with buckle closure and flat sole provides a secure and comfortable fit, while the clear jelly material with a rhinestone embellished edge trim provides a remarkable shine! Complete the look with a tote bag for a beach day or vacation!

Fit & Features
- Flat sole, rhinestone embellished edge trim
- Square toe
- Rhinestone embellished asymmetrical straps
- Adjustable ankle strap, buckle closure
- Clear jelly material
- Runs true to size
Style Number/Barcode: 07404-1202

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sittin' Pretty Tiered Chiffon Maxi Skirt
Sit pretty in this chiffon maxi skirt for effortless elegance on vacation or a weekend escape! The high-rise elasticized waist, flowy tiered silhouette, and maxi-length hem create a flattering look on sheer chiffon fabric. Complete the look in a crop top.

Fit & Features
- Sheer chiffon fabric
- High-rise elasticized waist
- Flowy tiered silhouette
- Runs true to size
Style Number/Barcode: 06401-0653

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
She Came to Slay Floral Maxi Skirt
When your outfit speaks before you do. This abstract floral maxi skirt brings the drama with a back slit accent and a flawless, form-hugging fit made for rooftop nights and flirty first dates.

Shop Matching Top: She Came to Slay Floral Corset Tube Top

Fit & Features
- Sheer mesh fabric with full knit lining, high stretch
- Abstract floral print
- High-rise waist
- Maxi-length hem, back slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000050

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: In Stock

Available Color: FUCHSIA

Available Size: S, M
Product Badge:
- Sale
Alluring Daydream Off-The-Shoulder Crop Top
Be an alluring daydream come to life in this off-the-shoulder crop top to bare some skin on a breezy sunshine day! Made from smooth woven fabric, this top boasts romantic peasant long sleeves and ruffled trim, a front adjustable ruched drawstring that lets you customize the style, and a stretchy smocked back for easy wear. Complete the look in high-rise jeans and sandals for any occasion!

Fit & Features
- Smooth woven fabric
- Off-the-shoulder
- Ruffled trim
- Adjustable ruched drawstring
- Stretchy smocked back
- Runs true to size
Style Number/Barcode: 06003-2437

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Day To Night Charm Lace-Up Ditsy Floral Mini Dress
Be effortlessly charming in this ditsy floral mini dress day to night! This dress features a flattering sweetheart neckline, sleek spaghetti straps, and a mini bow along the bust to accentuate your figure. The open lace-up back and bodycon silhouette add a touch of sexiness, while the ditsy floral print on stretchy ribbed knit fabric keeps you comfortable and looking cute! Complete the look in boots to edge up your allure.

Fit & Features
- Stretchy ribbed knit fabric, knit lining
- Ditsy floral print
- Sweetheart neckline, mini bow detail
- Spaghetti straps
- Open lace-up back
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5650

Category Name: Vacation Looks

Price: $6.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Travel Pal Twist Chain Straw Panama Hat
Make this straw panama hat your new stylish travel pal! Handmade woven straw creates this sunny-day essential featuring a wide brim to help shade, a twisted chain accent band for a luxe allure, and inner adjustable drawstrings to customize the fit. Complete the look in a dreamy vacation outfit to pack with you for a getaway!

Fit & Features
- Handmade woven straw material
- Wide brim
- Twisted chain band
- Inner adjustable drawstrings
Style Number/Barcode: 07302-1560

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Here To Play Bow Ruffled Ditsy Floral Romper
This ditsy floral romper is here to play up your flirtatious energy at parties and brunch! Short puff sleeves and a sweetheart neckline add a touch of cuteness to the fitted bodice with a playful bow along the back. The flowy layered ruffled short-length hem on woven fabric makes this romper perfect for a day full of fun. Complete the look in strappy thong sandals.

Fit & Features
- Ditsy floral print, woven fabric, partial lining
- Back zipper and hook-eye closure
- Back bow
- Flowy layered ruffled short-length hem
- Runs true to size
Style Number/Barcode: 06403-0430

Category Name: Vacation Looks

Price: $20.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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