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.

Glam Lace-Back One Piece Swimsuit
You're a glam one, babe! The swimsuit features a sleeveless scoop neckline with removable padding, adjustable spaghetti straps, a midriff cutout, a lace-up back with a lower back keyhole, and a cheeky fit bottom. Complete look with a floppy hat and sunnies.

Fit & Features
- Sleeveless scoop neckline
- Removable padding, spaghetti straps
- Midriff cutout
- Lower back keyhole
- Cheeky fit
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0270

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Ready Tie-Front Bandeau Crochet Crop Top
Heading on vacation? Don't forget to grab this vacay ready strapless crochet bandeau crop top with a sultry tie-front closure. Pair with the matching skirt and your fave shades!

Fit & Features
- Crochet fabric, stretchy knit lining
- Strapless neckline
- Tie-front closure
- Ultra-cropped hem
- Runs true to size
Shop The Matching Skirt: Vacay Ready High Rise Crochet Maxi Skirt
Style Number/Barcode: 06003-2777

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sealed With A Bow Floppy Straw Visor
Complete your look with a floppy visor that styles up tresses! The visor features a fitted brim, a floppy design, and a bow accent at the back. The convenient visor can be easily rolled up to throw in your bag for a beach day! Complete look with a bikini top and high waist bottoms.

Fit & Features
- Fitted brim
- Floppy design
- Bow accent at the back
- Straw material
- Can be rolled up with an elastic band
Style Number/Barcode: 07302-0308

Category Name: Vacation Looks

Price: $7.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glam Life Lace-Up Espadrille Wedges
Lace up in glam heels to live that glam life babe! The heels feature a lace-up design, closed-back, adjustable ankle strap, open almond toe with a clear strap over the toe, and an espadrille wedge heel. Complete the look with a tropical crop top and mini skirt set.

Fit & Features
- Faux leather metallic lace-up straps
- Closed-back
- Adjustable ankle strap
- Open almond toe, clear strap over the toe
- Espadrille wedge heel
Style Number/Barcode: 07406-0235

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Getaway Wrap Crop Top
Channel a tropical getaway with a crop top that channels those feel-good vibes! The top features a plunging wrap V-neckline, long bell sleeves, a cropped hem with tie waist accent, and a tropical print. Complete look with cutoff shorts and wedges.

Fit & Features
- Plunging wrap V-neckline
- Long bell sleeves
- Cropped hem with tie waist
- Tropical print
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3177

Category Name: Vacation Looks

Price: $11.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Island Vibes Floral Strapless Jumpsuit
Get a vacay on a tropical island vibe with this floral jumpsuit! It features a strapless square neckline, a high waist, and wide pant legs with a relaxed fit. Style this floral jumpsuit with cute wedges.

Fit & Features
- Strapless square neckline
- High waist
- Wide pant legs, relaxed fit
- Knit fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 06502-0569

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Mood Floral Skater Dress
This floral skater dress will have you totally summer-ready! It features a sleeveless bodice, a high neckline, spaghetti straps that lead to a strappy cross-back design, a high waist, and a flirty skater skirt. Complete the look with wedges.

Fit & Features
- High neckline
- Spaghetti straps
- Strappy cross-back design
- Back zipper closure
- High waist, skater skirt
- Nylon fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-0540

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bring The Romance Mini Dress
Bring the romance to date night in this gorgeous mini dress. It features a lined lace top with an off-the-shoulder square neckline, sheer short fitted sleeves, a front cutout at the waist, and a floral-printed knit skirt with a high waist and a mini-length, curve-hugging silhouette. Complete the look with clear heels and a sleek clutch.

Fit & Features
- Lined lace top
- Off-the-shoulder square neckline
- Sheer short fitted sleeves
- Front waist cutout, sheer scalloped trim
- Floral-printed scuba knit skirt
- High waist, short, form-hugging fit
- Runs true to size
Style Number/Barcode: 05101-0594

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Ready Sleeveless Skater Dress
This flirty sleeveless skater dress will have you totally summer-ready! It features a high square neckline, spaghetti straps that lead to a cross-back design, a fitted bodice, a high waist, and a short skater skirt. Complete the look with gold hoop earrings and cute wedges.

Fit & Features
- High square neckline
- Spaghetti straps, cross-back design
- Fitted bodice, high waist
- Short skater skirt, hidden side pockets
- Nylon Ponte fabric, knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0553

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Trendsetter Tie-Dye Mini Dress
Showcase your major trendsetter status in this cute tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps, ruching, and a mini-length, curve-hugging silhouette. Complete the look with sleek hoop earrings and sneakers.

Fit & Features
- Square neckline
- Spaghetti straps
- Ruching
- Short, form-hugging fit
- Knit fabric, plenty of stretch
- Tie-dye print may vary
- Runs true to size
Style Number/Barcode: 05102-2411

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ready For My Vacay Bikini Bottoms
You'll be totally ready for a summer vacay in these bright and bold bikini bottoms. They feature a high-rise waist, a criss-cross strap design at the back, and a semi-cheeky fit. The all-over tropical print will look so stylish with a sheer flowy duster. Complete your poolside outfit with the matching bikini top.

Shop Matching Top: Ready For My Vacay Bikini Top

Fit & Features
- High-rise waist
- Criss-cross strap design at the back
- Semi-cheeky fit
- Tropical print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0635

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Don't Be Jealous Graphic Halter Top
Serve icon attitude in this trendy graphic top featuring a halter V-neck, fitted cropped hem, and script reading, "Don't Be Jealous." Style with distressed denim and sneakers.

Fit & Features
- Cotton-blend fabric, moderate stretch
- Sleeveless V-neckline
- Halter strap, partially open back
- Front script reading, "Don't Be Jealous"
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06002-000159

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: In Stock

Available Color: PINK

Available Size: S, M
Product Badge:
- Sale
She's A Beauty Ditsy Floral Crop Top
Radiate a gorge look with a floral crop top! The crop top features an off-the-shoulder neckline with a sweetheart bust, a triple-row tie front, long sleeves with smocked cuff, a ditsy floral print, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with high waist jeans and mules.

Fit & Features
- Off the shoulder neckline
- Sweetheart bust
- Triple-row tie front
- Long sleeves with smocked cuff
- Ditsy floral print
- Cropped hem
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06003-1311

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chic Crochet Beauty Tie Front Crop Top
Keep it chic with a crop top that stuns with gorge details! The top features a plunging V-neckline, tie-front hem, long sleeves with crochet knit accent, and a cropped hem. Complete look with high waist shorts.

Fit & Features
- Plunging V-neckline
- Long sleeves with crochet detail
- Tie-front
- Cropped hem
- Lightweight woven fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0896

Category Name: Vacation Looks

Price: $13.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Leopard Print Cat Eye Sunglasses
Throw stylish shade with sunglasses to help you slay your look! The shades feature a cat-eye frame with a leopard print, dark lenses, and sleek arms. Complete look with a denim jumpsuit and wedges.

Fit & Features
- Leopard print
- Cat-eye frame
- Dark lenses
- Slim arms
- 100% UV protection
Style Number/Barcode: 07008-0835

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Make It Chic Strapless Jumpsuit
Make your look effortlessly chic in this strapless jumpsuit, a must-have for summer. It features a fitted top with a strapless square neckline, a high waist with a tie-front detail, and striped flowy pant legs with a relaxed fit. Style this jumpsuit with sleek earrings and cute wedges.

Fit & Features
- Fitted top, strapless square neckline
- High waist, tie-front
- Striped flowy pant legs, relaxed fit
- Woven fabric
- Runs true to size
Style Number/Barcode: 06302-0180

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
A Classic Vibe Linen Shorts
These summer-ready linen shorts will give your look a classic and chic vibe! They feature a high-rise waist, a tie-front belt, a button-down front, and a relaxed fit. Style these shorts with a basic bodysuit and cute mules.

Fit & Features
- High-rise waist
- Tie-front belt
- Button-down front
- Relaxed fit
- Linen fabric, pleated details
- Runs true to size
Style Number/Barcode: 06303-0122

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Mode Bikini Top
Let this bikini top instantly activate your vacay mode this season! The bikini top features a sleeveless scoop neckline, adjustable spaghetti straps, and an underbust cutout. Complete look with the matching bikini bottoms and thong sandals.

Shop Matching Bikini Bottoms: Vacay Mode Bikini Bottoms

Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Underbust cutout
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0581

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay Mode Bikini Bottoms
Let these bikini bottoms instantly activate your vacay mode this season! The bikini bottoms feature a high-rise waist with a cheeky bottom. Complete look with the matching bikini top and thong sandals.

Shop Matching Bikini Top: Vacay Mode Bikini Top

Fit & Features
- High rise waist
- Cheeky fit
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0728

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Stunner Circular Straw Bag
Go totally boho chic with an adorable circular straw bag! It features a round shape with top latch closure, a laser-cut design, a straw material body, and a faux leather should strap. Complete look with a romper and sandals for a cute brunch outfit.

Fit & Features
- Circular body
- Top latch closure
- Laser-cut design
- Straw material body
- Faux leather shoulder strap
Style Number/Barcode: 07203-0576

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Moment Paisley Tie Front Top
Create a bohemian moment with a tie-front top that is perfect for channeling your indie side. The top features a plunging V-neckline with cinching tie front, long kimono sleeves, a paisley print, and a cropped hem. The top is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with high waist shorts.

Fit & Features
- Plunging V-neckline
- Long kimono sleeves
- Paisley print
- Cropped hem
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0962

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ring Around The Florals Tie Front Top
Embrace florals this season with a top that makes a pretty impression! The top features a plunging V-neckline, a tie-front hem, long bell sleeves, a ditsy floral print, and a cropped hem. Complete look with cutoff shorts and wedges for a casual date outfit.

Fit & Features
- Plunging V-neckline
- Tie-front
- Long bell sleeves
- Ditsy floral print
- Cropped hem
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06204-0952

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Taking the Plunge Scoop Neck Midi Dress
Take the plunge in this stylish midi sweater dress! The dress features a sleeveless scoop neckline, tank shoulder straps, and a bodycon silhouette on rib-knit fabric. Complete the look with mules.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless scoop neckline
- Tank-shoulder straps
- Bodycon silhouette
- Midi-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1233

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blooming Beauty High-Low Skater Dress
You'll bloom with beauty in this stunning floral skater dress! It features a fitted bodice with an off-the-shoulder square neckline, short fitted sleeves, a high waist, and a flowy, high-low skater skirt. Style this dress with sleek earrings and new heels to attend a summer wedding.

Fit & Features
- Off-the-shoulder square neckline
- Short fitted sleeves
- High waist
- Flowy high-low skater skirt
- Scuba knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-0209

Category Name: Vacation Looks

Price: $9.97 $38.90

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