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.

Major Headturner Cutout Bikini Top
Make a head-turning statement with bikini bottoms that will have you vacay ready! The bottoms feature a high-rise waist, dual cutouts at the waist, and a cheeky bottom. Complete look with the matching bikini top.

Shop Matching Bikini Bottoms: Major Stunner High Waist Bikini Bottoms

Fit & Features
- Scoop neckline
- Tank shoulder strap
- Adjustable spaghetti strap
- Asymmetrical cutout front and back
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0689

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
High Tides Minimal Bikini Top
Cool off beachside with a bikini top that is totally effortless! The bikini top features a halter neck with neck ties, triangle cups with removable padding, and adjustable back ties. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: High Tides Minimal Bikini Bottoms

Fit & Features
- Halter neck
- Adjustable neck ties
- Triangle cups
- Removable padding
- Adjustable back ties
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0658

Category Name: Vacation Looks

Price: $4.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ring Bling Lurex Bikini Top
Bring the bling with a cute bikini top that is too glam! The bikini top features a halter neck, neck ties, triangle cups, a metal o-ring accent at the center, and wrap-around ties at the midriff. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Ring Bling Lurex Bikini Bottoms

Fit & Features
- Halter neck
- Neck ties
- Triangle cups
- Metal O-Ring accent
- Wrap around ties at midriff
- Lined lurex fabric
- Form hugging fit, runs true to size
Style Number/Barcode: 07104-0646

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Rhinestone Glam Bikini Top
Bring on the bling with a glam bikini top that brings the sparkle! The bikini top features a plunging scoop neckline, a double o-ring rhinestone design at the center, flexible boning, adjustable spaghetti straps, and tie back ties. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Rhinestone High Rise Bikini Bottoms

Fit & Features
- Plunging scoop neckline
- Double O-ring rhinestone accent
- Flexible boning
- Adjustable spaghetti straps
- Tie back accent
- Form hugging fit
- Runs true to size
Style Number/Barcode: 07104-0650

Category Name: Vacation Looks

Price: $4.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Knits Halter Midi Dress
The cooler spring days call for your best knits! Set the tone in this halter midi sweater dress featuring a sleeveless high neck, adjustable spaghetti straps, space-dye knit pattern, bodycon silhouette, and a side slit accent to showcase some leg. Complete the look in cute mules.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless high neck, halter design
- Adjustable spaghetti straps
- Bodycon silhouette
- Side slit, midi-length hem
- Space-dye knit pattern
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1257

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summertime Chic Straw Wedges
Step up your summertime 'fits with these boho-chic wedges. They feature an open almond-shaped toe, a wide toe strap, a tall wedge heel, and a braided straw design. Style these wedges with a breezy floral dress.

Fit & Features
- Open almond-shaped toe
- Wide toe strap
- Open back
- Wedge heel
- Braided straw design
- Faux leather insole
- Runs true to size
Style Number/Barcode: 07406-0295

Category Name: Vacation Looks

Price: $12.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Lovin' Basket Weave Sandals
Summer lovin' all-over these trendy sandals featuring an almond toe, dual basket weave straps, and a flat sole. Complete the look in a darling sundress.

Fit & Features
- Almond toe
- Dual basket weave straps
- Comfort fit
- Runs true to size
Style Number/Barcode: 07404-0972

Category Name: Vacation Looks

Price: $12.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Basic Vibes Bikini Top
Channel those basic vibes with a bikini top that will have you ready to bask in the sun! The bikini top features wired demi-cups, adjustable spaghetti straps, and a slide-hook closure. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Basic Vibes Bikini Bottoms

Fit & Features
- Wired demi cups
- Adjustable spaghetti straps
- Slide hook closure at back
- Form-hugging fit, slight stretch
- Runs true to size
Style Number/Barcode: 07104-0668

Category Name: Vacation Looks

Price: $4.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunset Drip Retro Aviator Sunglasses
With retro-inspired frames and luxe metal detailing, these aviator sunglasses give the final touch for pool parties, matcha runs, and paparazzi-level entrances.

Fit & Features
- Lightweight metal frame with retro aviator shape
- Gradient-tinted lenses with UV protection
- Slim bridge with supportive nose pads
Style Number/Barcode: 07008-000018

Category Name: Vacation Looks

Price: $11.90

Availability: In Stock

Available Color: GOLD

Available Size: NS
Boho Bell Sleeve Wrap Top
Play up your look in patterns! This boho-inspired top features flowy bell sleeves, a plunge v-neckline, and a surplice wrap-tie bodice on a cropped hem. Complete the look in lace-up sandals for a cute day out.

Fit & Features
- Long bell sleeves
- Plunge v-neckline
- Surplice wrap-tie bodice
- Cropped hem
- Boho-inspired pattern
- Sleek knit stretchy fabric
- Fits true to size
Style Number/Barcode: 06001-3773

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cute And Dainty Floral Blouse
This adorable floral printed blouse is perfect for elevating your everyday spring look. It features an off-the-shoulder neckline, long bishop sleeves, a cropped fit with a cinched hem, and an all-over dainty floral print. Style this woven blouse with denim shorts and espadrille sandals.

Fit & Features
- Off-the-shoulder neckline, elasticized hem
- Long bishop sleeves, elastic cinched hems
- Cropped fit, elastic cinched hem
- Dainty floral print
- Woven fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1562

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Toucan Ruched Mini Skirt
Slip on this tropical mesh mini skirt for instant island vibes! It features a high-rise waist, chic ruched detailing down the sides, a short, curve-hugging fit, and a palm leaf print on sheer mesh knit fabric with a moderate stretch. Complete the look with the matching crop top for the perfect vacay 'fit.

Shop Matching Top: Tropical Toucan Mesh Crop Top

Shop Matching Duster: Tropical Toucan Long Mesh Duster

Shop Matching Jumpsuit: Tropical Toucan Strapless Jumpsuit

Fit & Features
- High-rise waist
- Side ruching
- Mini-length, form-fitting silhouette
- Palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0539

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Toucan Mesh Crop Top
Slip on this tropical mesh crop top for instant island vibes! It features a sleeveless square neckline, thin bungee straps, a cropped, form-hugging fit, and a palm leaf print on sheer mesh knit fabric with a moderate stretch. Complete the look with the matching mini skirt for the perfect vacay 'fit.

Shop Matching Bottoms: Tropical Toucan Ruched Mini Skirt

Shop Matching Duster: Tropical Toucan Long Mesh Duster

Shop Matching Jumpsuit: Tropical Toucan Strapless Jumpsuit

Fit & Features
- Sleeveless square neckline
- Thin bungee straps
- Cropped, form-hugging fit
- Palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3749

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Happily Glam Ever After Corset
Create a storybook moment with a corset that seems too good to be true! The corset features a sleeveless square neckline, an airy mesh overlay, flexible boning, and a cropped hem. The top is composed of a lined mesh fabric that offers a form hugging fit with minimal stretch. Complete look with high waist jeans and mules.

Fit & Features
- Sleeveless square neckline
- Flexible boning
- Mesh overlay
- Cropped hem
- Lined mesh fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1734

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Flair Paisley Crop Top
Showcase a bohemian flair with this effortlessly chic crop top. It features a deep V-neckline with a trendy lattice front, long bishop sleeves, a cropped, form-hugging fit, and an all-over paisley print. The lightweight woven gauze fabric has a subtle pretty metallic thread woven throughout. Style this top with light wash jeans and mules.

Fit & Features
- Low V-neckline
- Lattice front, tie closure
- Long bishop sleeves, elastic cinched hems
- Cropped, form-hugging fit
- Woven gauze fabric, subtle metallic thread detailing, no stretch
- Runs true to size
Style Number/Barcode: 06003-1498

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sweet Home Lace-Up Gingham Corset Top
Perfect for a day out, this sweet gingham corset top is designed to charm! With a lace-up back and gingham pattern, this top will give you a flattering silhouette while adding a touch of vintage flair to any outfit.

Fit & Features
- Gingham print, woven fabric, no stretch
- Square neckline
- Adjustable spaghetti straps, halter tie strap
- Flexible boning
- Bungee cord lace-up back, smocked panel
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-000019

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek Coin Drop Belly Chain
Give your look a sleek touch with a belly chain that is perfect to accentuate your skin-baring looks! The belly chain features a dainty chain link, a single row of flat coin charms, and a lobster clasp closure. Complete look with a bathing suit.

Fit & Features
- Single row of flat coin charms
- Dainty chain link
- Lobster clasp closure
Style Number/Barcode: 07002-1202

Category Name: Vacation Looks

Price: $12.90

Availability: Out of Stock
Product Badge:
- Ships Free
Under Wraps Triangle Bikini Top
This bikini top is best kept under wrap till it's time to unveil! It features plunge, triangle cups, a wrap-around tie closure, and a satin-like fabrication. Complete the look in the matching bikini bottoms.

Shop The Matching Bikini Bottoms: Under Wraps Tie Bikini Bottoms

Fit & Features
- Triangle cups
- Plunge neckline
- Wrap-around tie closure
- Satin-like fabrication
- Lined fabric, minimal stretch, fits true to size
Style Number/Barcode: 07104-0642

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Beach Party Hoop One Piece Swimsuit
Flaunt your figure in this one-piece swimsuit for your next beach party! It features a plunge, deep v-neckline atop a cutout bodice with a hoop inset, an open-back, and a hipster fit. Complete the look in cute shades.

Fit & Features
- Plunge, deep v-neckline
- Cutout bodice
- Hoop inset
- Open-back
- Hipster fit
- Sleek knit fabric, moderate stretch, fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0288

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Night Swim Satin One Piece Swimsuit
Take a night swim looking so sultry in this satin one-piece swimsuit featuring an eye-catching, one-shoulder cutout, an open bodice with a sleek hoop inset, and a hipster fit bottom. Complete the look in a chic cover-up.

Fit & Features
- One-shoulder cutout
- Open bodice
- Hoop inset
- Hipster fit bottoms
- Satin-like fabrication
- Minimal stretch
- Fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0287

Category Name: Vacation Looks

Price: $4.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sealed With A Twist Shorts
Seal your look with stylish shorts that add that chic twist to your look! The shorts feature a high-rise paper bag waist, a tie-waist belt with belt loops, hidden side pockets, and a wide-leg hem. The shorts are composed of a semi-sheer crepe fabric that offers a form-hugging fit with a moderate stretch. Complete the look with a bustier and wedges.

Fit & Features
- High-rise paper bag waist, elasticized back hem
- Tie-waist belt with loops
- Hidden side pockets
- Wide-leg hem
- Crepe fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-0956

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pop The Cork Sling Back Wedges
Your next wine tasting calls for these cork wedges featuring a sling-back ankle with adjustable buckle closure, almond toe, and a faux leather footbed. Complete the look in a flowy maxi dress.

Fit & Features
- Almond toe
- Sling back ankle, adjustable buckle closure
- Faux leather footbed
- Cork wedge heel
- Runs true to size
Style Number/Barcode: 07406-0293

Category Name: Vacation Looks

Price: $15.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spring Break Vibes Sarong
Bring the spring break vibes to your look with this bold sarong! The coverup features a mid-rise waist, a twist-front design, a short, curve-hugging fit, and a trendy all-over swirl print. Style with the matching swim top and bottoms for the perf poolside 'fit!

Shop Matching Top: Spring Break Vibes Bandeau Swim Top

Shop Matching Bottoms: Spring Break Vibes Swim Bottoms

Fit & Features
- Mid-rise waist
- Twist-front design
- Mini-length, form-fitting silhouette
- Swirl print
- Moderate stretch
Style Number/Barcode: 07305-0371

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Too Cute Crochet Sweater Topper
From days by the beach to summer nights, this crochet sweater topper will keep you cute all season!

Fit & Features
- Sheer crochet fabric
- Fitted long sleeves with flare cuffs
- Crew neck
- Ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06005-000025

Category Name: Vacation Looks

Price: $6.97 $34.90

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