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.

Fierce And Fashionable Sheer Mesh Bodysuit
Fierce and fashionable will be your vibe in this sultry sheer mesh bodysuit. It features a crew neckline, long fitted sleeves, and a thong bottom with a dual snap button closure. The sheer mesh fabric showcases a trendy all-over flocked velvet leopard print pattern. Complete the look with faux leather shorts and mules.

Fit & Features
- Crew neckline
- Long fitted sleeves
- Thong bottom, dual snap button closure
- Sheer mesh fabric, flocked velvet leopard print
- Form-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-3627

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chic Silhouette Long Sleeve Maxi Dress
Create a chic silhouette in this curve-hugging maxi dress. It features a crew neckline, long fitted sleeves, a stylish cutout at the lower back, and a floor-length form-hugging fit with a side slit. Style this dress with clear heels.

Fit & Features
- Crew neckline
- Long fitted sleeves
- Cutout at the lower back
- Floor-length, form-hugging fit
- Side slit
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4137

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Casual Crew Cropped Sweater
Rock it out in a casual sweater to warm up those chilly days! The sweater features a crew neckline with a raw edge hem, long sleeves, and a cropped hem with a raw edge. The sweater is composed of a knit fabric that offers a relaxed fit with a moderate stretch. Complete look with high waist jeans.

Fit & Features
- Crew neckline
- Long sleeves
- Cropped hem
- Distressing throughout
- Knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1048

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Oh So Classic Block Heels
You'll be so classic in this pair of block heels! They're complete with an open toe, a buckled ankle strap, and a faux leather material. Wear them with a blazer and denim for a chic everyday look.

Fit & Features
- Ankle strap
- Open toe
- Faux leather
- Fits true to size
Style Number/Barcode: 07401-3183

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
In The Details Cutout Mini Dress
A fab look is all in the details! This mini dress brings the style with a trendy sweetheart neckline with a cinching tie front, short sleeves, a daring cutout at the midriff, and a mini-length silhouette. The dress is composed of a double-layered knit fabric that offers a form hugging fit with a moderate stretch. Complete look with dainty rings and chunky sneakers.

Fit & Features
- Sweetheart neckline
- Tie-front
- Short sleeves
- Cutout at midriff
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05103-4239

Category Name: Vacation Looks

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Enticing Sass Halter Cutout Wide-Leg Jumpsuit
Unlock the sass in this sleeveless knit jumpsuit featuring a sultry halter neckline, a cutout front, and a flattering wide-leg silhouette perfect for styling with sandals. The smooth knit fabric offers a comfortable stretch.

Fit & Features
- Smooth knit fabric, moderate stretch
- Halter neckline, spaghetti strap tie
- Cutout front
- Wide-leg silhouette
- Jumpsuit has a 12.5” front rise with a 33” inseam
- Runs true to size
Style Number/Barcode: 06502-2535

Category Name: Vacation Looks

Price: $14.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
New Heights Chiffon Cutout Maxi Dress
Take your look to new heights in a maxi dress that slays your look! The dress features a plunging V-neckline with padded cups, a large O-Ring at the center of the bodice, dual cutouts at the waist, long sleeves with elastic cuff, a double-row of tie-back ties, and a flowy A-line silhouette with a high side slit. The dress is composed of a lined chiffon fabric that offers a minimal stretch. Complete look with wedges and a snake charm necklace.

Fit & Features
- V-neckline, padded cups
- O-Ring, dual waist cutouts
- Long sleeves with elastic cuff
- Double-row of tie-back ties
- A-line silhouette, high side slit
- Lined chiffon fabric, mini skirt length knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1265

Category Name: Vacation Looks

Price: $26.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Back To Basics Knit Hoodie
Bring your look back to basics with a hoodie that keeps it casual and comfy! The hoodie features a zippered front, a hood, long sleeves, side pockets, and a cropped hem. The hoodie is composed of a knit fabric that offers a relaxed fit with a moderate stretch. Complete look with the matching joggers.

Shop Matching Joggers: Back To Basics Knit Joggers

Fit & Features
- Zippered front
- Hood
- Long sleeves
- Side pockets
- Cropped hem
- Knit fabric
- Relaxed fit, moderate stretch, runs true to size
Style Number/Barcode: 06202-0196

Category Name: Vacation Looks

Price: $14.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Back To Basics Knit Joggers
Bring your look back to basics with joggers that keep it casual and comfy. The joggers feature a high-rise waist with a drawstring, zippered side pockets, and a straight leg fit with a ribbed hem. Complete look with the matching zipper hoodie.

Shop Matching Hoodie: Back To Basics Knit Hoodie

Fit & Features
- Elastic high rise waist
- Drawstring
- Zippered side pockets
- Straight leg fit
- Knit fabric
- Relaxed fit, moderate stretch, runs true to size
Style Number/Barcode: 06502-0582

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Living Large Trendy Twist Hoops
Showcase how extra you are with hoops that take the spotlight! The earrings feature extra-large hoops with a trendy twist design and a post-back closure. Complete look with a matching crop top and mini skirt set.

Fit & Features
- Extra-large hoops
- Twist design
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0953

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Picturesque Cutie Corset Lace-Up A-Line Midi Dress
Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette.

Fit & Features
- Woven fabric lined with stretchy knit
- Sweetheart neckline, tie-front detail
- Thin adjustable straps
- Corset bodice, lace-up back
- High waist seam
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3069

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glamour Chic Panama Hat With Pearls
Channel a glam vibe with a hat to adorn tresses with. The hat features a traditional Panama design, a short brim, and a faux pearl trim. The hat is composed of faux wool. Complete look with a bustier and mom jeans.

Fit & Features
- Traditional Panama design
- Short brim
- Faux pearl trim
- Faux wool material
Style Number/Barcode: 07302-0448

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simple And Elevated Faux Leather Booties
These simple sleek faux leather booties will elevate your looks! They feature a pointed toe, an inner zipper closure, an ankle-high design, and a low stacked block heel. Style these booties with a cute shoulder bag.

Fit & Features
- Pointed toe
- Inner zipper closure
- Ankle-high design
- Low stacked block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1410

Category Name: Vacation Looks

Price: $12.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Who's That Girl Chic Cabby Hat
Throw on this cabby hat to leave them asking who's that girl? That hat features a traditional cabby design and a short faux leather brim. Complete look with a crop top and faux leather mini skirt.

Fit & Features
- Traditional cabby design
- Faux leather short brim
- Brushed faux wool material
- Nylon lining
Style Number/Barcode: 07302-0396

Category Name: Vacation Looks

Price: $5.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
A Stylish Twist Midi Dress
Bring a stylish twist to your look with a sleek midi dress that slays! The dress features a sleeveless scoop neckline, spaghetti straps, a high side slit with a twist knot accent, and a midi-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 PVC heels and a faux leather clutch.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- High side slit
- Twist knot accent
- Midi length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1540

Category Name: Vacation Looks

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Everyday Chic Faux Suede Lace Up Heels
Lace-up in these everyday heels that dress up your casual outfits! The heels feature an open back, lace-up straps, a double-row strap design, an open square toe, and a block heel. The heels are composed of a faux suede material. Complete look with a midi skirt and blouse for a chic workwear outfit.

Fit & Features
- Open back
- Lace-up straps
- Double-row strap design
- Open square toe
- Block heel
- Faux suede material
- Runs true to size
Style Number/Barcode: 07401-3602

Category Name: Vacation Looks

Price: $14.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Stunner Faux Wool Boater Hat
Keep it trendy with a boater hat that completes your effortless outfits! The hat features a traditional Panama design, a short brim, and a cute ribbon trim. The hat is composed of a faux wool material. Complete look with a bodysuit and cargo pants.

Fit & Features
- Panama design
- Short brim
- Ribbon trim
- Faux wool material
Style Number/Barcode: 07302-0378

Category Name: Vacation Looks

Price: $5.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Mood Faux Wool Panama Hat
Channel a basic mood with a fab hat that adds that effortless touch to your look! The hat features a traditional Panama design, a short brim, a faux leather trim with a small buckle. The hat is composed of a faux wool material. Complete look with a bodysuit and high waist jeans.

Fit & Features
- Traditional Panama design
- Short brim
- Faux leather trim with a small buckle
- Faux wool material
Style Number/Barcode: 07302-0377

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wild Thing Zebra Halter Top
Tap into your wild side with a halter top that makes a fierce impression! The top features a trendy zebra print, a halter neck, a drawstring tie front, 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 midi skirt.

Shop Matching Midi Skirt: Wild Thing Zebra Midi Skirt

Fit & Features
- Zebra print
- Halter neck
- Drawstring tie front
- Cropped hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3797

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Criss Cross Chic PVC Sandals
Keep it chic with sandals that gave your look that finishing touch! The sandals feature an open back, clear PVC straps that criss-cross, and an open almond toe. The sandals are composed of a faux leather and PVC material. Complete look with mom jeans and a crop top.

Fit & Features
- Open back
- Clear PVC straps
- Open almond toe
- Faux leather and PVC material
- Runs true to size
Style Number/Barcode: 07404-0887

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Hitting The Mark Faux Suede Boots
Hit the style mark with boots that complete your layered outfits! The boots feature an over-the-knee fit, an inner zipper closure, ruching, a pointed toe, and a block heel. The boots are composed of a faux suede material. Complete look with a chunky cable knit sweater and skinny jeans.

Fit & Features
- Over the knee fit
- Ruching
- Inner zipper closure
- Pointed toe
- Block heel
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0750

Category Name: Vacation Looks

Price: $12.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Luxe Satin A-Line Cutout Mini Dress
Keep it so luxe and vibrant with a mini dress that takes your look to the next level! The dress features a plunging V-neckline, a mini keyhole at the back, long balloon sleeves, dual cutouts at the waist, and a mini-length A-line silhouette. The dress is composed of a satin fabric that offers a relaxed fit with minimal stretch. Complete look with mules and a faux leather crossbody.

Fit & Features
- Plunging V-neckline
- Long balloon sleeves
- Dual cutouts at the waist
- Mini length
- A-line silhouette
- Satin fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1303

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bring On Basics Sleeveless Midi Dress
Bring on those basic vibes with a dress that is perf for every day! The dress features a sleeveless V-neckline, tank shoulder straps, and a midi-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.

Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Midi-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4221

Category Name: Vacation Looks

Price: $32.90

Availability: Out of Stock
Product Badge:
- Sale
Clear Things Up PVC Strap Block Heels
Take the time to clear things up in this chic pair of block heels! They feature a clear PVC strap, block heel, and buckled ankle strap. Wear them with a bodycon dress to get them talking.

Fit & Features
- PVC strap
- Buckled ankle strap
- Block heel
- Fits true to size
Style Number/Barcode: 07401-3162

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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