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.

Bohemian Glam Cutout Romper
Channel your free-spirited side with a cute romper! The romper features a bohemian print, a halter neck with a racer bust, a sexy cutout at the midriff, and cheeky shorts. Complete look with sandals and butterfly hair clips.

Fit & Features
- Bohemian print
- Halter neck, racer bust
- Cutout at midriff
- Cheeky shorts
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0240

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Bound Palm Leaf Duster
Set off on that dream vacay with a chic duster! The lightweight duster is perf to layer over your beachside looks or styled for a date night. The duster features a vibrant palm leaf print, kimono sleeves, a tie waist belt, and a flowy long length.

Fit & Features
- Tropical print
- Draped open front
- Kimono sleeves
- Tie waist belt
- Long length
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-1049

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Button Up Darling Mid-Rise Denim Shorts
Upgrade your summer wardrobe with these denim shorts for a darling look all season! These stylish shorts feature a flattering mid-rise waist and unique button trim pockets for added flair.

Fit & Features
- Dark wash denim fabric
- Mid-rise waist
- Button trim front pockets, belt loops
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-000054

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mesh Moment Tie-Front Top
Have a chic and stylish moment in this sheer mesh top! It features flowy kimono-style sleeves, a V-neckline, a tie-front detail, and a relaxed fit. Layer this airy top over your fave bikini to wear as a cute coverup.

Fit & Features
- Kimono-style sleeves
- V-neckline
- Tie-front
- Relaxed fit
- Sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0230

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keeping Knit Boho Crochet Crop Top
Channel a boho feel with a crop top that keeps your look effortlessly stylish! The top features a sleeveless V-neckline, spaghetti straps, a crochet knit bodice, and a cropped hem. Complete the look with an adhesive bra and maxi skirt.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Crochet knit bodice
- Cropped hem
- Relaxed fit, moderate stretch
Style Number/Barcode: 06005-1185

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Double Take Paisley Cutout Mini Dress
Make them take a double-take with a sexy mini dress that commands attention on your next GNO! The dress features a trendy paisley print, a halter neck, a twisted neck strap that allows you to customize the coverage of the bodice, cutout at the bodice, ruching, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Paisley print
- Halter neck
- Twisted neck strap, allows for adjustable coverage
- Cutout at the bodice
- Ruching
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4083

Category Name: Vacation Looks

Price: $19.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Passion For Florals Asymmetrical Mini Dress
Show off your passion for florals with a mini dress that brings the charm! The dress features a sleeveless V-neckline, bungee straps that cross at the back, a floral print, and an asymmetrical mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules and hoops.

Fit & Features
- Sleeveless V-neckline
- Bungee straps, cross at back
- Floral print
- Asymmetrical mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2205

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bold Impressions One Shoulder Crop Top
Make a bold impression with a crop top that brings the drama! The top features a one-shoulder neckline, an adjustable spaghetti strap, and a cropped hem. The top is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching maxi skirt.

Shop Matching Maxi Skirt: Bold Impressions High Slit Maxi Skirt

Fit & Features
- One-shoulder neckline
- Adjustable spaghetti strap
- Cropped hem
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3460

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bold Impressions High Slit Maxi Skirt
Make a bold impression with a maxi skirt that brings the drama! The skirt features a high rise waist, a high side slit, and a maxi-length silhouette. Complete look with the matching crop top and heels.

Shop Matching Crop Top: Bold Impressions One Shoulder Crop Top

Fit & Features
- High rise waist
- High side slit
- Maxi length silhouette
- Form hugging fit
- Runs true to size
Style Number/Barcode: 06501-0434

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Feels Ruffled Mini Dress
This pretty floral dress has us in our feels, bby! The dress features a floral print, an off-the-shoulder neckline with a ruffled popover, ruffled short sleeves, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a metal cuff.

Fit & Features
- Ditsy floral print
- Off the shoulder neckline
- Ruffled popover, ruffled short sleeves
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2096

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Go With The Flow Smocked Maxi Dress
Go with the flow in a casual maxi dress that keeps your look effortlessly chic! The dress features a sleeveless square neckline, a smocked bodice, halter neck ties, a triple-row bar strap design, and a flowy maxi length silhouette. The dress is composed of a lined gauze fabric that offers a relaxed fit with slight stretch. Complete look with wedges and a floppy hat.

Fit & Features
- Sleeveless square neckline
- Smocked bodice
- Halter neck ties
- Triple-row bar strap
- Maxi length silhouette
- Lined gauze knit fabric
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 05102-1362

Category Name: Vacation Looks

Price: $6.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Radiance Eyelet Mini Dress
Radiate in a gorge floral mini dress for your next brunch date! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of an eyelet knit fabric that offers a form hugging fit with minimal stretch. Complete look with mules and hoops.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Eyelet knit fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4091

Category Name: Vacation Looks

Price: $9.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Crochet Cutie Linen Maxi Dress
Keep it cute in a crochet maxi dress! The dress features a sleeveless V-neckline, a lined floral lace bodice, adjustable spaghetti straps, an unlined crochet waist, and a flowy maxi-length silhouette. The dress is composed of a linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops.

Fit & Features
- Sleeveless V-neckline
- Lined floral lace bodice
- Adjustable spaghetti straps
- Unlined crochet waist
- Maxi length silhouette
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4184

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Eve One-Shoulder Ruched Midi Dress
Special Occasion

Sultry and stunning, the Eve midi dress is perf for your next night out. She features a sleeveless one-shoulder neckline, an open back with a strappy lace-up design, ruched detailing, and a mid-length, curve-hugging silhouette with a trendy side drawstring. Style this dress with clear heels.

Fit & Features
- Sleeveless one-shoulder neckline
- Open back, strappy lace-up design
- Ruching
- Mid-length, form-hugging fit
- Side drawstring
- Knit fabric, addtional mini skirt length lining
- Runs true to size
Style Number/Barcode: 05001-0734

Category Name: Vacation Looks

Price: $29.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Details Ombre Sunglasses
It's all in the details! Top off your look with sunglasses that slay! The sunglasses feature oversized square-shaped lenses with an ombre hue, nose pads, studded detail, and sleek metal arms. Complete look with a romper.

Fit & Features
- Square-shaped lenses
- Ombre hue
- Nose pads
- Studded detail
- Metal arms
Style Number/Barcode: 07008-0853

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Wonder Ruffled Skater Dress
Make em' awestruck with a pretty mini dress! The dress features a floral print, an off-the-shoulder neckline, ruffled off-the-shoulder straps, a mini tie-front accent at the bust, a smocked bodice, a tie waist belt, and a skater silhouette with a ruffled hem. The dress is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with wedges and butterfly earrings.

Fit & Features
- Floral print
- Off the shoulder neckline with ruffled shoulder straps
- Smocked bodice, mini-tie front
- Tie waist belt
- Skater silhouette
- Chiffon fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4227

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunny Muse Floral Eyelet Chiffon Romper
You'll be a total sunny muse in this adorable romper made with airy eyelet chiffon fabric and a dainty floral print pattern. The sweetheart neck features a lace-up bust design, leading to the cutest fit-and-flare silhouette with flowy shorts.

Fit & Features
- Sheer eyelet chiffon fabric with floral print, stretchy knit lining
- Sleeveless sweetheart neckline, lace-up bust, padded bra cups
- Adjustable spaghetti straps
- Smocked back, zipper hook-eye closure
- High-rise seam
- Flowy shorts, fit-and-flare silhouette
- Runs true to size
Style Number/Barcode: 06403-000008

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Picture Perfect Knit Mini Dress
Create a picture-perfect moment in a cute mini dress! The dress features a scoop neckline, spaghetti straps, an exposed seam pattern, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with heels and hoops.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Exposed seam pattern
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4180

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Rush Ruched Mini Dress
Get caught in a floral rush with a pretty mini dress! The dress features a floral print, a sleeveless V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a drawstring. Complete look with clear heels and butterfly hoops.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Ruched body
- Mini length silhouette with drawstring
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1035

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep It Trendy Cutout Mini Dress
Keep your look trendy and chic in this ribbed knit mini dress that is a summer staple! It features a sleeveless crew neckline, a front O-ring accent, dual waist cutouts, and a short, curve-hugging silhouette. Style this dress with sneakers for everyday wear, or cute mules for date night.

Fit & Features
- Sleeveless crew neckline
- Front O-ring detail
- Dual waist cutouts
- Mini-length, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4115

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek Satin Floral Mini Dress
This sleek satin floral mini dress is perf for a date night out with bae! It features a sleeveless cowl neckline, spaghetti straps that lead to a cross-back, lace-up design, ruched detailing with side drawstrings, and a short, curve-hugging fit. The lightweight satin fabric has a pretty all-over floral print for a romantic look. Style this dress with dainty earrings and heels.

Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Open back, cross-back, lace-up design
- Ruching, side drawstrings at the hem
- Mini-length, form-hugging silhouette
- Satin fabric, floral print, no stretch
- Runs true to size
Style Number/Barcode: 05101-0636

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Sleek O Ring Fanny Pack Belt
Keep your look so sleek with a fanny pack belt to carry all your essentials in. The belt features a sleek faux leather band, a mini fanny pack with envelope closure, a metal O-Ring, and a swag chain accent. Complete look with high waist jeans and a corset.

Fit & Features
- Faux leather belt
- Mini fanny pack
- Envelope closure
- Metal O-Ring
- Swag chain accent
Style Number/Barcode: 07203-0549

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Bound Raffia Straw Tote
You'll be vacay bound with this cute tote to carry all your beach and resort essentials! The tote features an oversized square body, a woven material, raffia ribbon trim, and a top handle. Complete your look with a matching top and skirt set.

Fit & Features
- Oversized square body
- Woven material
- Raffia ribbon trim
- Top handle
Style Number/Barcode: 07203-0695

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Sleek Double Band Mules
Keep your look so sleek with stylish mules! The mules feature an open back, a double-row strap design, an open square toe, and low block heel. The mules are composed of a faux leather material. Complete look with a floral romper and butterfly earrings.

Fit & Features
- Open back
- Double-row strap design
- Open square toe
- Low block heel
- Faux leather material
Style Number/Barcode: 07401-2822

Category Name: Vacation Looks

Price: $7.97 $24.90

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