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.

Cabo Calling Boho Tube Top
Answer the call! Look fab on vacay in this boho tube top featuring an eye-catching tie-front, halter neckline, a smocked back, and a cute boho-inspired print on lined woven fabric with no stretch. Complete the look in matching pants and sandals.

Shop The Matching Pants: Cabo Calling Boho Tulip Pants

Fit & Features
- Sleeveless, halter neckline
- Tie-front design
- Ultra cropped hem
- Smocked back
- Boho-inspired print
- Woven lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1581

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Gorgeous Blooms Sleeveless Crop Top
Style up your summer date looks with this gorgeous blooming floral crop top. It features adjustable spaghetti straps, a sweetheart neckline, a underwire bust, front hook-eye closures, and a cropped fit. Complete the outfit with a mini skirt and your favorite heels.

Fit & Features
- Adjustable spaghetti straps
- Sleeveless sweetheart neckline
- Underwire bust, hook-eye closures
- Smocked back
- Cropped hem
- Floral print pattern
- Woven lined fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1863

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feeling Playful In Floral Babydoll Dress
You'll be feeling playful in this floral babydoll dress perfect for bridal showers or dressy weekend brunches! It features a sleeveless square neck, adjustable spaghetti straps, an empire seam, and a flared short-length hem. The dress is designed with flower appliques on airy chiffon fabric with a woven lining. Complete the look in cute wedges.

Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Empire seam, babydoll silhouette
- Flared, short-length hem
- Flower appliques, chiffon fabric, woven lining
- Runs true to size
Style Number/Barcode: 05101-2470

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Captivate In Floral Strapless Dress
Captivate the crowd in this floral strapless dress at brunches or parties! It features non-slip grip lining along the neckline, side ruched seams that hug your curves along the bodycon silhouette, and a mini-length hem. The dress is designed with a watercolor floral print on mesh fabric with a stretchy knit lining. Complete the look in metallic block heels.

Fit & Features
- Strapless neckline, non-slip grip lining
- Back zipper and hook-eye closure
- Side ruched seams
- Bodycon silhouette, mini-length hem
- Watercolor floral print
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2271

Category Name: Vacation Looks

Price: $5.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Spring Vibes Floral Skater Dress
This adorable floral skater dress will bring those sweet spring vibes to your look! It features a sweetheart neckline, short puff sleeves, a high waist, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight chiffon fabric features a dainty floral print pattern. Style with strappy sandals.

Fit & Features
- Sweetheart neckline, short puff sleeves, elastic cinched hems
- High waist seam, smocked back design
- Short skater skirt, ruffled hem
- Fit and flare silhouette
- Small floral print
- Chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2080

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Golden Hour Floral Ruffled Skater Dress
Snap a dreamy pic for golden hour in this floral skater dress and watch the likes come through! It features an off-the-shoulder, sweetheart neckline with ruffle trim, peasant long sleeves, a smocked bodice with a front adjustable drawstring, a cutout waist, and a flowy tiered ruffled short-length hem. Complete the look in chic clear strap mules.

Fit & Features
- Off-the-shoulder, sweetheart neck, ruffle trim
- Peasant long sleeves
- Smocked bodice, front adjustable drawstring
- Cutout waist, skater silhouette
- Tiered ruffle short hem
- Watercolor floral print, non-stretch woven fabric
- Runs true to size
Style Number/Barcode: 05101-1987

Category Name: Vacation Looks

Price: $5.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bright As Day Platform Block Heel Sandals
Today's forecast calls for these bright and cheery platform sandals perfect for a beach day or daytime party! They feature an almond toe, wide clear PVC strap, and lucite low block heel, and are composed of faux leather material. Complete the look with cute sunglasses.

Fit & Features
- Almond toe
- Wide clear PVC strap
- Lucite low-block heel
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4202

Category Name: Vacation Looks

Price: $12.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Artsy Cute Geo Print Chain Strap Dress
Express your artsy side in this cute mini dress perfect for parties and a vacation look! The sleeveless dress features eye-catching chain straps, a sweetheart neck, a bodycon silhouette, side ruched seams, and a trendy geometric print on mesh fabric. Style with a choker and platform heels.

Fit & Features
- Sleeveless sweetheart neckline
- Chain straps
- Bodycon silhouette
- Side ruched seams
- Mini-length hem
- Geometric print, mesh fabric
- Runs true to size
Style Number/Barcode: 05103-4911

Category Name: Vacation Looks

Price: $9.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paradise Bound Tropical Print Crop Top
Jet set off to paradise with this fabulous crop top packed in your carry-on! It features a sleeveless square neckline, bungee spaghetti straps, ruched side seams, a fitted, cropped hem, and a tropical palm leaf print that radiates vacay vibes. Style with the matching mini skirt!

Shop Matching Bottoms: Paradise Bound Tropical Print Mini Skirt

Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched side seams
- Fitted, cropped hem
- Tropical palm leaf print
- Mesh fabric
- Runs true to size
Style Number/Barcode: 06001-4751

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Paradise Bound Tropical Print Mini Skirt
Jet set off to paradise with this fabulous mini skirt packed in your carry-on! It features a high-rise waist, ruched side seams, a mini-length hem, a curve-hugging fit, and a tropical palm leaf print that radiates vacay vibes. Style with the matching crop top!

Shop Matching Top: Paradise Bound Tropical Print Crop Top

Fit & Features
- High-rise waist
- Ruched side seams
- Mini-length hem
- Form-hugging silhouette
- Tropical palm leaf print
- Mesh fabric
- Runs true to size
Style Number/Barcode: 06501-0803

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Plunging Into Basics Surplice Jumpsuit
Take the plunge into a basic jumpsuit that keeps it part casual, part stylish. The jumpsuit features a sleeveless wrap V-neckline with spaghetti straps, an elastic waistband, hidden side pockets, and a straight leg fit with an elastic hem. The jumpsuit is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete the look with mules and statement earrings.

Fit & Features
- Sleeveless wrap V-neckline
- Spaghetti straps
- Elastic waistband
- Hidden side pockets
- Straight leg fit with elastic hem
- Lightweight woven fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0729

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Babe Knit High-Rise Mini Skirt
Channel a boho babe vibe in this sweater knit mini skirt featuring a high-rise waist and a short, curve-hugging fit. Style with the matching tube top for a chic and seamless look!

Shop Matching Top: Bohemian Babe Knit Cutout Tube Top

Fit & Features
- Sweater knit fabric, ribbed hems, high stretch
- High-rise waist
- Mini-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000022

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Life Floral Chiffon Skater Dress
Live the sweet life twirling in this floral chiffon dress at birthday parties or baby showers! Featuring an adorable off-the-shoulder neckline with ruffle trim, short-sleeve cuffs, a bust keyhole cutout with a tie accent, and a short skater silhouette. The dress is composed of a dainty floral print chiffon fabric with a knit lining. Complete the look in simple platform heels.

Fit & Features
- Off-the-shoulder neckline, ruffle trim
- Short-sleeve cuffs, elasticized hems
- Keyhole bust with tie, back zipper, hook and eye closure
- Short skater silhouette
- Dainty floral print
- Sheer chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2038

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Aren't I Grand Crepe Chiffon Romper
Make an entrance in this crepe chiffon romper at your next chic soiree! Features a sleeveless V-neckline, adjustable spaghetti straps, wrap-around straps, and a ruffled layer short hem. Complete the look in colorful heels.

Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Back zipper and hook-eye closure
- Wrap-around straps
- Ruffled layer short hem
- Crepe chiffon fabric, partial lining
- Runs true to size
Style Number/Barcode: 06403-0296

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Just A Crush Satin Pleated Top And Shorts Set
It'll start out as just a crush, but you'll totally be smitten with this top and shorts set for all of your styling needs! The top features long sleeves, a collar neckline, a button-down front, and a flowy cropped hem. The shorts feature a high-rise elastic waist and a short-length hem. Each is composed of a satin pleated fabric. Complete the look in chic clear heels.

Fit & Features
- Satin pleated top and shorts set
- Top, long sleeves, collar neckline
- Button-down front, flowy cropped hem
- Shorts, high-rise elastic waist
- Short-length hem
- Non-stretch fabric
- Runs true to size
Style Number/Barcode: 06503-1040

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cali Palms Smocked Mini Skirt
Feel the breeze in Cali or wherever you vacay! Look cute in this mini skirt featuring a high-rise waist, smocked detail, bodycon silhouette, and a palm leaf print on woven fabric. Complete the look with the matching top.

Shop Matching Top: Cali Palms Cap Sleeve Tie-Front Top

Fit & Features
- High-rise waist
- Smocked detail
- Bodycon silhouette
- Mini-length hem
- Palm leaf print
- Runs true to size
Style Number/Barcode: 06301-0112

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cali Palms Cap Sleeve Tie-Front Top
Feel the breeze in Cali or wherever you vacay! Look cute in this tie-front top featuring puff cap sleeves, sweetheart neck, a smocked bodice, and a palm leaf print on woven fabric. Complete the look with the matching skirt.

Shop Matching Bottoms: Cali Palms Smocked Mini Skirt

Fit & Features
- Puff cap sleeves
- Sweetheart neck
- Tie-front detail
- Smocked bodice
- Cropped hem
- Palm leaf print
- Runs true to size
Style Number/Barcode: 06003-1683

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Coastal Cute Linen Top And Shorts Set
The perfect linen top and shorts set for your drive up the coast or beach cottage vacay! The oversized top features long sleeves with button cuffs, a collar neckline, a front pocket, and a button-down front. The matching shorts feature a smocked elastic high-rise waist. tie accent, side pockets, and a short-length hem. Complete the look in trendy sandals.

Fit & Features
- Linen top and shorts set
- Oversized top, long sleeves, button cuffs
- Collar neckline, front pocket
- Button-down closures
- Smocked elastic shorts, high-rise waist
- Tie accent, side pockets, short hem
- Runs true to size
Style Number/Barcode: 06303-0227

Category Name: Vacation Looks

Price: $21.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Brunch Date Floral Chiffon Skater Dress
This adorable floral chiffon skater dress is perfect for brunch dates! The mini dress features a sleeveless square neckline, spaghetti straps, a smocked bust, a short skater skirt with a fit and flare silhouette, and a dainty floral print pattern, this dress is a must-have for the spring and summer seasons. Style with heeled sandals.

Fit & Features
- Sleeveless square neckline, spaghetti straps
- Smocked bust
- Short skater skirt, fit and flare silhouette
- Dainty floral print
- Swiss dot chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2282

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Social Butterfly Mesh Corset Top
Got plans? You'll adore this charming mesh corset top for festivals and parties! Featuring a sleeveless scoop neckline, adjustable spaghetti straps, a bust cutout accent with lattice trim, underwire cups, a fitted crop hem, and back hook and eye closures. Style with sleek faux leather leggings to complete the look!

Fit & Features
- Sleeveless scoop neckline, adjustable spaghetti straps
- Bust cutout accent with lattice trim
- Underwire cups, fitted crop hem
- Back hook and eye closures
- Butterfly appliques
- Partially lined mesh fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4883

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pencil Me In Bandage Midi Skirt
Add chic and sophisticated vibes by adding this bandage midi skirt to your closet! It features a smooth high-rise fit and is crafted from bandage-seamless knit fabric that offers a form-hugging fit and moderate stretch. Complete the look in a sultry corset top for a wine bar with the ladies!

Fit & Features
- Smooth high-rise fit
- Form-hugging
- Midi-length hem
- Bandage-seamless knit design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0837

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Strike Again Marble Print Mini Dress
Strike a stunning look every time you're in this knit mini dress at parties or nights out! It features a sleeveless one-shoulder neckline, dual spaghetti straps with a sultry cutout, a bodycon silhouette, and a trendy marble print on stretchy knit fabric. Complete the look in sandals.

Fit & Features
- Sleeveless one-shoulder neckline
- Dual spaghetti straps
- Cutout bust
- Bodycon silhouette
- Mini-length hem
- Marble print, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4932

Category Name: Vacation Looks

Price: $5.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Made You Flirt Lace Skater Dress
Make your crush flirt with how cute you'll be looking in this lace eyelet short dress perfect for birthday brunches or parties! Featuring a sleeveless scoop neck, ruffled straps, a ruched bust, and a fit-and-flare skater silhouette. Style with a chic bracelet and heels to complete the look.

Fit & Features
- Sleeveless scoop neck, ruffled straps
- Ruched bust
- Fit and flare skater silhouette
- Short-length hem
- Lace eyelet fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2155

Category Name: Vacation Looks

Price: $5.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sandy Beaches Palm Bandeau Top
Can't you imagine strolling the beach in this palm print bandeau top? Embrace vacay in this tropical stunner featuring a sleeveless, strapless neckline, tie-front closure, and a smocked bodice. Complete the look with the matching bottoms.

Shop Matching Bottoms: Sandy Beaches Palm Wide-Leg Pants

Fit & Features
- Sleeveless, strapless neckline
- Tie-front closure
- Smocked bodice
- Cropped hem
- Palm print, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1809

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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