Vacation Dresses & Outfits

HomeVacation Dresses & Outfits

Sundresses
Matching Sets
White Outfits For Women
Maxi Dresses
Women's Shorts
Sandals
Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...
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.

  • Pair To Perfection Metallic Lace-Up Sneakers

    These metallic sneakers pair perfectly with your everyday outfits. They feature a round-toe, a lace-up front closure, and a rubber gum sole. 

    Fit & Features

    • Round toe
    • Metallic material
    • Lace-up front closure
    • Rubber gum sole
    • Runs true to size

    Style Number/Barcode: 07407-0231

    Category Name: Vacation Dresses & Outfits

    Price: $28.90

    Availability: In Stock

    Available Color: SILVER

    Available Size: 5.5, 6

  • Stole Your Heart Charms Shield Sunglasses

    These shield sunglasses will steal your heart! They showcase side heart charms for a trendy vibe, oversized tinted lenses, rubber nose supports, and comfortable arms. Complete the look in a cute jumpsuit.

    Fit & Features

    • Shield style oversized tinted lenses
    • Side heart charms
    • Rubber nose supports
    • Comfortable arms

    Style Number/Barcode: 07008-1093

    Category Name: Vacation Dresses & Outfits

    Price: $11.90

    Availability: Out of Stock

  • Adorable Chic Bow Cutout Bodycon Mini Dress

    Adorable chic and ready to be seen, this sleeveless mini dress is everything! It features adjustable spaghetti straps for a customizable fit, a sweetheart neckline adorned with a statement bow, and a cutout bust to show a peak of skin along the bodycon silhouette. Complete the look in high heels.

    Fit & Features

    • Smooth knit fabric lined with knit
    • Adjustable spaghetti straps
    • Sweetheart neckline with bow
    • Cutout bust
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5697

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Icing On The Cake V-Neck Lace Skater Dress

    The perfect lace skater dress that'll take your day somewhere magical! Perfect for rehearsal dinners, birthdays, or graduation. This dress features a flattering V-neckline, spaghetti straps, and a playful cross-back design. Its skater silhouette and surplice ruffled short-length hem will keep you twirling all day! Complete the look in strappy block heels.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • V-neckline, spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3667

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • Strut And Snap Ribbed Knit Midi Dress

    Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Square neckline
    • Tank shoulder straps
    • Metal button accents
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1167

    Category Name: Vacation Dresses & Outfits

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Raise The Bar Wide-Leg Jumpsuit

    Raise the bar and strut in this sleeveless jumpsuit featuring a statement design with a plunge halter neckline and an alluring open back. Complete the look with earrings.

    Fit & Features

    • Smooth knit fabric, plenty of stretch
    • Plunging sleeveless halter neckline
    • Halter neck ties
    • Open back
    • Wide-leg silhouette
    • Jumpsuit in size small is 58" shoulder to hem with a 13" front rise and a 30" inseam
    • Runs true to size

    Style Number/Barcode: 06502-2551

    Category Name: Vacation Dresses & Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: RUST, BLACK

    Available Size: L

  • Effortless Style Short Sleeve Ribbed Knit Crop Top

    This adorable short sleeve crop top will make everyday styling effortless. Made with stretchy double-lined ribbed knit, it features a classic crew neckline, short sleeves, and a fitted cropped hem. The perf basic, pair with straight-leg jeans and sneakers.

    Fit & Features

    • Stretchy double-lined ribbed knit fabric
    • Crew neckline
    • Short sleeves
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1859

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Your Stripe Off-The-Shoulder Crop Top

    This striped crop top is just what you're looking for! It's designed on stretchy rib knit fabric with a trendy striped print, an off-the-shoulder neckline to bare some skin, and a flirty cropped hem. Complete the look in denim shorts for casual plans.

    Fit & Features

    • Striped rib knit stretchy fabric
    • Off-the-shoulder neckline
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-1972

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Example Tie-Front Lace Trim Crop Top

    You'll be giving off plenty of sweet and sexy vibes in this crop top! Featuring delicate cap sleeves, a flattering lace trim scoop neckline, and dual tie-front closures, this crop top effortlessly adds a touch of romance to any outfit. Complete the look in denim jeans for any casual plans!

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Cap sleeves
    • Lace trim scoop neckline
    • Dual tie-front closures
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06202-0476

    Category Name: Vacation Dresses & Outfits

    Price: $24.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Confident Cutie Sleeveless V-Neck A-Line Mini Dress

    Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!

    Fit & Features

    • Soft and stretchy rib knit fabric, full knit lining
    • V-neckline
    • Spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5651

    Category Name: Vacation Dresses & Outfits

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One Take V-Neck Ruffle Skater Romper

    One take in this skater romper and you'll be so obsessed! Its adjustable spaghetti straps and bust tie enhance the ruffled V-neckline, while the tie-back design provides a flattering silhouette. The ruffled layered short-length hem adds a cute touch. Complete the look with a dainty necklace.

    Fit & Features

    • Knit fabric, moderate stretch
    • Adjustable spaghetti straps
    • Ruffle V-neckline
    • Tie-back design
    • Skater silhouette
    • Ruffle layered short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1142

    Category Name: Vacation Dresses & Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK, PINK, IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Instant Fave Faux Suede Platform Sneakers

    A pair of faux suede sneakers feature a round toe, rubber gum platform sole that elevates the look, a lace-up front, and a side striped design. Perfect for everyday styling.

    Fit & Features

    • Faux suede material
    • Round toe
    • Rubber gum platform sole
    • Lace-up front
    • Side striped design
    • Runs true to size

    Style Number/Barcode: 07407-0232

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dancing Moves High-Rise Side Ruffle Midi Skirt

    Dance all night in this midi skirt featuring a flattering high-rise waist, form-hugging silhouette, and a high side slit with a flirty ruffled trim perfect for styling with heels. The smooth knit fabric hugs your curves and offers plenty of stretch.

    Fit & Features

    • Smooth knit-lined stretchy fabric
    • High-rise waist
    • High-side slit with ruffle trim
    • Form-hugging
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-1063

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Daring Texture Knit Mini Skirt

    Feel daringly stylish with this mini skirt! This ultra-trendy skirt features a high-rise waist, a bodycon silhouette, and a flirty mini-length hem on texture knit fabric. Dare to stand out and shop the matching top to complete the look!

    Shop Matching Top: Feeling Daring Texture Knit Crop Top

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Mini-length hem
    • Texture knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 06501-0999

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M

    Product Badge:
    • Sale
  • Set For Good Cap Sleeve Slit Texture Crop Top

    You'll be set for good in this stylish texture crop top all season! Featuring adorable cap sleeves, a V-neckline, and an adjustable bust drawstring atop a flirty slit along the cropped hem. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Set For Good High Rise Texture Mini Skirt

    Fit & Features

    • Texture sheer fabric, bust lining, minimal stretch
    • Cap sleeves
    • V-neckline
    • Adjustable bust drawstring, center slit
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5287

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Cowgirl Colored Stone Straw Western Hat

    Top off your cowgirl core look with this straw western hat at bachelorettes, festivals, or country bar nights! Made from distressed straw material for a rustic feel.  Featuring a string tie bow adorned with a colorful stone and metal ball trim, this hat adds a touch of glam to the classic curved wide brim. Complete the look in cowboy boots.

    Fit & Features

    • String tie bow, colored stone and metal ball trim
    • Classic curved wide brim
    • Distressed straw material
    • Adjustable inner strings for a snug fit

    Style Number/Barcode: 07302-1604

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Boho Sheer Lace Asymmetric Maxi Skirt

    Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties.

    Fit & Features

    • Sheer lace fabric with mini-length knit lining, plenty of stretch
    • High-rise waist
    • Ruching, adjustable drawstring
    • High side slit
    • Asymmetric maxi-length hem
    • Flowy fit
    • Runs true to size

    Style Number/Barcode: 06501-1065

    Category Name: Vacation Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY, BLACK

    Available Size: M, L, S

  • Chic Beauty Strappy Back Knit Midi Dress

    This chic sleeveless midi dress is designed with a jacquard patterned sweater knit fabric and features a square neckline, halter spaghetti straps, and a bold open back with cross-back straps and tie-back straps. The midi-length form-hugging silhouette is detailed with a high front slit.

    Fit & Features

    • Knit fabric with jacquard pattern, moderate stretch
    • Square neckline, halter spaghetti straps
    • Open back, cross-back straps, tie-back straps
    • Contrast seam design at the bodice
    • High front slit
    • Midi-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-2227

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sporty Luxe Corduroy Baseball Cap

    Fit & Features

    • Corduroy material 
    • Wide brim
    • Baseball cap design
    • Adjustable back strap

    Style Number/Barcode: 07302-1736

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Vision Chain Link Trim Sunglasses

    Any on-trend, sunny day look isn't complete without these sunglasses! They feature angular square-tinted lenses, rubber nose supports, and chain-link accent arms. Complete the look in sandals.

    Fit & Features

    • Angular square-tinted lenses
    • Rubber nose supports
    • Chain-link accent arms

    Style Number/Barcode: 07008-1094

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

  • Confident Moves Crew Neck Ruffled Mini Dress

    Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.

    Fit & Features

    • Smooth double-lined knit fabric, moderate stretch
    • Crew neck
    • Bodycon fit
    • Tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5792

    Category Name: Vacation Dresses & Outfits

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Charming Sweetness V-Neck Lace Trim Floral Crop Top

    Unlock a charming sweetness in this floral crop top to dress up your everyday look! With delicate spaghetti straps and a lace trim V-neckline, it exudes a romantic appeal with a tiered ruffled silhouette and cropped hem. Complete the look in shorts and strappy sandals. 

    Fit & Features

    • Floral print, mesh fabric, bust knit lining
    • Spagehtti straps
    • Lace trim V-neckline
    • Tiered ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 06001-5389

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Summer Vibes Wrap-Front Romper

    Show off a fresh summer vibe in this elevated and chic woven romper. It features a sleeveless V-neckline, tank shoulder straps that lead to an open back with a cross-back lace-up design, a lower back cutout, a flattering high waist seam, a ruched wrap-front design with a short skirt overlay, and fitted shorts. Style with espadrille wedges for a cute daytime party look.

    Fit & Features

    • Sleeveless V-neckline
    • Tank shoulder straps
    • Open back, cross-back lace-up design, tie closure
    • Lower back cutout, zipper and hook-eye closure
    • High waist seam, ruched wrap-front, short skirt overlay, fitted shorts
    • Lined smooth woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0407

    Category Name: Vacation Dresses & Outfits

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Does It Square Neck Rib Knit Bodysuit

    You do flirty well in this rib knit bodysuit perfect for styling with your favorite high-waisted bottoms! Featuring a sleeveless square neckline with a V-wire notch and wide shoulder straps, it hugs your figure with a form-hugging fit. The thong bottom has convenient snap-button closures. Complete the look in best-selling bottoms and heels.

    Fit & Features

    • Rib knit stretchy fabric
    • Square neckline with V-wire notch
    • Wide shoulder straps
    • Form-hugging fit
    • Thong bottom, snap-button closures
    • Runs true to size

    Style Number/Barcode: 06002-1814

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale