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.

Fashionably Fierce One-Piece Swimsuit
Keep your poolside look fashionably fierce in this chic one-piece swimsuit. It features adjustable spaghetti straps, a scoop neckline, a low scoop back, a belted waist, and a semi-cheeky fit. The swimsuit showcases a leopard print pattern for a trendy vibe. Pair it with a sheer flowy duster and cute sandals.

Fit & Features
- Adjustable spaghetti straps
- Scoop neckline with padded cups
- Low scoop back
- Belted waist
- Circular buckle
- Semi-cheeky fit
- Leopard print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0221

Category Name: Vacation Looks

Price: $5.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Taking the Plunge Mesh One Piece Swimsuit
Take the plunge in this stunning swimsuit that raises the heat this season! The swimsuit features a plunging V-neckline, a triple row of mesh insets, supportive shoulder straps, and a high cut with a cheeky bottom. Complete look with sunnies for a chic poolside look.

Fit & Features
- Sleeveless plunging V-neckline
- Wide shoulder straps
- Triple row of mesh insets
- High cut
- Cheeky bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0176

Category Name: Vacation Looks

Price: $5.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Ribbed Knit Tie-Front Top
Level up your basic everyday look with this trendy top! It features long fitted sleeves, a V neckline, an open front with a tie closure, a merrow edge trim, and a cropped fit. The brushed ribbed knit fabric offers plenty of stretch for comfortable wear. Pair this top with mom jeans and chunky sneakers.

Fit & Features
- Long fitted sleeves
- V neckline
- Open front with a tie closure
- Merrow edge trim
- Cropped fit
- Brushed ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 06202-0134

Category Name: Vacation Looks

Price: $12.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wild At Heart Swim Bottoms
Showcase your wild and trendy style at the beach in these leopard print swim bottoms! They feature a high waist with a semi-cheeky fit. Pair these swim bottoms with the matching swim top and a chic flowy duster.

Shop Matching Swim Top: Wild At Heart Swim Top

Fit & Features
- High waist
- Semi-cheeky fit
- Leopard print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0632

Category Name: Vacation Looks

Price: $1.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Effect Abstract Wide-Leg Pants
Printed to perfection in a flattering wide-leg silhouette, these pants boast a classic high-rise waist. Pair with the matching top.

Fit & Features
- Abstract print, stretchy knit fabric
- Cowl halter neckline, tie straps
- Open back
- Fitted crop hem
- Runs true to size
Shop The Matching Top: Sultry Effect Abstract Cowl Halter Crop Top
Style Number/Barcode: 06502-000022

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wild At Heart Swim Top
Showcase your wild and trendy style at the beach in this leopard print swim top! It features removable spaghetti straps, a sweetheart neckline, and a tie front detail. Wear this swim top with the straps for additional support, or style it strapless. Pair it with the matching swim bottoms and a chic flowy duster.

Shop Matching Bottoms: Wild At Heart Swim Bottoms

Fit & Features
- Removable spaghetti straps
- Padded cups
- Sweetheart neckline
- Tie front detail
- Leopard print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0484

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bold Babe Bandeau Swim Top
Yes babe, give your poolside look a trendy and bold vibe in this swim top! It features a bandeau design with a strapless square neckline, padded detailing, and a cropped fit. Pair this swim top with the matching swim bottoms and a lightweight flowy duster.

Shop Matching Swim Bottoms: Bold Babe Cheeky Swim Bottoms

Fit & Features
- Bandeau design
- Strapless
- Square neckline
- Padded
- Cropped
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0352

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bold Babe Cheeky Swim Bottoms
Yes babe, give your poolside look a trendy and bold vibe in these swim bottoms! They feature a high V-cut design and a cheeky fit. Pair these swim bottoms with the matching swim top and a lightweight flowy duster.

Shop Matching Swim Top: Bold Babe Bandeau Swim Top

Fit & Features
- High V-cut design
- Cheeky fit
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0503

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chasing the Sun One-Piece Cutout Swimsuit
Chase that glow this season with a trendy swimsuit that is perfect for a bachelorette weekend or that dream vacay! The one-piece swimsuit features an asymmetrical one-shoulder neckline, a sexy-cut out at the waist, and a high waist with a full-coverage bottom. Complete your look with a floppy hat and sunglasses.

Fit & Features
- Asymmetrical one-shoulder neckline
- Cutout at the bust
- Waist cutout
- High waist
- Full coverage bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0214

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sultry Vibes Glitter Lurex Bodycon Dress
Bring luxe appeal with a one-shoulder bodycon that showcases sultry vibes! The dress features a one-shoulder neckline with a fitted long sleeve and an asymmetrical mini-length silhouette. The ruching detail throughout enhances your natural curves while offering a form-hugging fit. Composed of a glitter lurex-lined fabric with a moderate stretch. Style with mules and rhinestone earrings.

Fit & Features
- One shoulder neckline. strapless bra friendly
- Fitted long sleeve
- Ruching detail, form-hugging fit
- Back zipper, hook-eye closure
- Asymmetrical mini length silhouette
- Glitter lurex-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-0947

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lace Affair Ruched Mini Dress
Fall for this lace mini dress as you head out for a date night with bae! The dress features a sleeveless square neckline, spaghetti straps, ruched side seams, and a floral lace body. Complete your look with rhinestone hoops and mules.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruched side seams with tie details
- Sheer floral lace body with a knit lining
- Moderate stretch
- Mini length silhouette
- Form-hugging fit
Style Number/Barcode: 05101-0958

Category Name: Vacation Looks

Price: $19.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty In Floral Tie Swim Bottoms
Give your poolside look an adorable flirty vibe in these floral tie swim bottoms! They feature a high cut design with side ties, a cheeky fit with smocked detailing, and the cutest floral print. Pair these swim bottoms with the matching swim top and a sheer tie-front top for the perfect cover-up.

Shop Matching Swim Top: Flirty In Floral Smocked Swim Top

Fit & Features
- High cut design
- Side ties
- Cheeky fit
- Smocked detailing
- Floral print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0628

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty In Floral Smocked Swim Top
Give your poolside look an adorable flirty vibe in this floral swim top! It features tie shoulder spaghetti straps, a square neck and back, padded cups, smocked detailing, a cropped fit, and the cutest floral print. Pair this swim top with the matching swim bottoms and a sheer tie-front top for the perfect cover-up.

Shop Matching Swim Bottoms: Flirty In Floral Tie Swim Bottoms

Fit & Features
- Tie shoulder spaghetti straps
- Padded cups
- Square neck and back
- Smocked
- Cropped fit
- Floral print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0480

Category Name: Vacation Looks

Price: $11.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Color Block High Waist Swim Bottoms
Color block your look babe in these adorable multi-colored high waisted swim bottoms! Pair with the matching top and take your look poolside!

Shop Matching Top: Color Block Tie Front Swim Top

Fit & Features
- High rise waist
- Cheeky bottom
- Color-block 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: 07105-0520

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Color Block Tie Front Swim Top
Color block your look babe in this adorable multi-colored tie front swim top! Pair with the matching bottoms and take your look poolside!

Shop Matching Bottoms: Color Block High Waist Swim Bottoms

Fit & Features
- Adjustable spaghetti straps
- Triangle design
- Tie front detail
- Back hook and bar closure
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: 07104-0371

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Breeze High Waist Swim Bottoms
Look like a total trendsetter as you relax on the beach in these swim bottoms! They feature a high rise waist with side cut outs and a high cut, semi-cheeky fit. Pair these swim bottoms with the matching swim top and some adorable sandals.

Shop Matching Swim Top: Coastal Breeze Triangle Swim Top

Fit & Features
- High rise waist
- Side cut outs
- High cut, semi-cheeky fit
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0638

Category Name: Vacation Looks

Price: $5.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Coastal Breeze Triangle Swim Top
Look like a total trendsetter as you relax on the beach in this swim top! It features a triangle design with adjustable spaghetti straps, a small front cut out at the bust, a lace-up back, and a banded hem. Pair this swim top with the matching swim bottoms and some adorable sandals.

Shop Matching Swim Bottoms: Coastal Breeze High Waist Swim Bottoms

Fit & Features
- Triangle design
- Adjustable spaghetti straps
- Small front cut out at the bust
- Lace-up back
- Banded hem
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0490

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Good Vibes Belted One-Piece Swimsuit
Showcase good vibes as you chill poolside in this adorable one-piece swimsuit! It features wide tank-like shoulder straps, a plunging V neckline with padded cups, an open back, a belted waist, ruched detailing at the hips, and a high cut, semi-cheeky fit. Pair this swimsuit with chic sandals.

Fit & Features
- Wide tank-like shoulder straps
- Deep V neckline with padded cups
- Open back
- Belted waist
- Ruched detailing at the hips
- High cut, semi-cheeky fit
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0241

Category Name: Vacation Looks

Price: $18.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Statement Gleam Buckle Thong Sandals
Make a statement in these buckle thong sandals perfect for elevating your spring to summer style!

Fit & Features
- Square toe
- Buckle accent thong strap
- Flat sole
- Style Options: solid black, zebra print, ivory
- Runs true to size
Style Number/Barcode: 07404-1247

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: In Stock

Available Color: ZEBRA

Available Size: 5.5, 6
Product Badge:
- Sale
Cut To The Chase One-Piece Swimsuit
Let's cut to the chase - this one-piece swimsuit will bring major sultry and stylish vibes! It features a wrap-around neck design with a front center keyhole cut out, padded cups, an open back, side cut outs, and a cheeky bottom. Pair this swimsuit with a sheer flowy duster for the perfect poolside look.

Fit & Features
- One-piece swimsuit
- Wrap-around neck design with padded cups
- Front keyhole cut out
- Open back
- Side cut outs
- Cheeky bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0239

Category Name: Vacation Looks

Price: $18.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Can't Be Tamed One-Piece Swimsuit
Rule the pool in this feisty and fashionable one-piece swimsuit! It features a scoop neckline with halter straps, removable padding, a front belt with a detailed lion face on the buckle, and a high cut bottom with a semi-cheeky fit. Style this swimsuit with a flowy duster and chic sandals.

Fit & Features
- Scoop neckline with removable padding
- Halter straps
- Front belt
- Detailed lion face on the buckle
- High cut bottom
- Semi-cheeky fit
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0240

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunkissed Cutie Monokini
Get that sunkissed look with a chic monokini! The monokini features a plunging scoop neckline with padded cups, adjustable spaghetti straps, waist cutouts, a lower back cutout, and a cheeky fit bottom. Complete your look with sunnies!

Fit & Features
- Sleeveless scoop neckline
- Padded cups
- Adjustable spaghetti straps
- Waist cutouts
- Lower back cutout
- Cheeky fit
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0218

Category Name: Vacation Looks

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual And Chic Cut Off Shorts
Keep it casual and chic in shorts that are perfect for creating an effortlessly stylish look! The shorts feature a high-rise waist, a multi-button down front, a traditional five-pocket and belt loop design, heavy destruction, and a cut-off hem with a cheeky fit. Complete the look with a basic tank and sneakers.

Fit & Features
- High-rise waist
- Heavy destruction
- Cut-off hem, cheeky fit
- Multi-button down front
- Traditional five-pocket and belt loop design
- Denim fabric, form-hugging fit, no stretch
- Runs true to size
Style Number/Barcode: 06603-0220

Category Name: Vacation Looks

Price: $15.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Floral Mesh Duster
Get a flirty vibe when you layer on this adorable sheer mesh duster! It features long fitted sleeves, an open front, a flowy fit, and an all-over floral print. Pair this duster with a bustier and denim for a casual-chic date night look.

Fit & Features
- Long fitted sleeves
- Open front
- Flowy fit
- Floral print
- Sheer mesh fabric
- Plenty of stretch
Style Number/Barcode: 06202-0137

Category Name: Vacation Looks

Price: $13.97 $29.90

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