Vacation Looks

HomeVacation Looks

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.

  • Flirty Aura Puff Sleeve Floral Lace Skater Dress

    Captivate them with your flirty aura in the cutest floral lace skater dress! The dainty sheer floral lace fabric will give your look a soft feminine vibe and includes a partial woven lining for coverage. The bodice is shaped with a plunging V-neckline with a tie-front detail and sheer short puff sleeves with elasticized hems. The open back adds to the allure and features a tie-back design. The dual high waist seams lead to a fit-and-flare skater silhouette on a short-length hem that was made to twirl. Style this adorable dress with wedge heels for a spring or summer party!

    Fit & Features

    • Sheer floral lace fabric with partial woven lining, no stretch
    • Plunging V-neckline with tie-front
    • Short puff sleeves with elasticized hems
    • Open back, tie-back, lower back zipper with hook and eye closure
    • Dual high waist seams
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2967

    Category Name: Vacation Looks

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Vibes Belted Flared-Leg Denim Jumpsuit

    This fab belted flared-leg denim jumpsuit will give off major retro vibes for the spring and summer seasons! Designed with a cotton-blend denim fabric, this jumpsuit offers plenty of stretch for comfortable wear. The sleeveless bodice is shaped with a collared V-neckline, followed by a partial zip-front design. The high-rise belted waist will create a snatched look, leading to an iconic flared-leg silhouette. Style this denim jumpsuit with platform heels.

    Fit & Features

    • Cotton-blend denim fabric, plenty of stretch
    • Sleeveless collared V-neckline
    • Zip-front
    • High-rise belted waist
    • Front and back pockets
    • Form-hugging fit, flared-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06602-0484

    Category Name: Vacation Looks

    Price: $21.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Muse Floral Satin Maxi Dress

    Giving island goddess IRL. This floral satin maxi features a draped cowl neckline, crisscross back, and curve-skimming fit—perfect for destination weddings, summer soirées, or any RSVP that calls for a slay.

    Fit & Features

    • Floral print, satin fabric
    • Cowl neckline
    • Spaghetti straps
    • Open strappy back tie
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000121

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute In Chevron Print Mesh Crop Top

    You'll look cute in this chevron print top for festival season or hitting up the country bar! It features a sleeveless square neck, adjustable spaghetti straps, side ruched seams, and a fitted crop hem. Complete the look in the matching pants.

    Shop Matching Bottoms: Cute In Chevron Print Mesh Flare Pants

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Side ruched seams
    • Fitted crop hem
    • Chevron print 
    • Mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4709

    Category Name: Vacation Looks

    Price: $3.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's A Vision Abstract Cowl Slit Maxi Dress

    Make a statement and turn heads in this abstract maxi dress on vacation or at a chic pool party! The cowl neck, adorned with hoop trims, adds a touch of glamour, while the high side slit and maxi length hem elongate your silhouette and add a hint of allure.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • Cowl neckline with hoop trims, spaghetti strap
    • Open strappy back
    • High side slit, hoop insert
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6084

    Category Name: Vacation Looks

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Straight To Business V-Neck Paper Bag Jumpsuit

    From business to play, this paper bag jumpsuit isn't messing around when it comes to chic style! It features a sleeveless V-neck, adjustable spaghetti straps, a pleated tie-front belt waist design, hidden side pockets, and a skinny-leg silhouette on smooth woven fabric. Complete the look in this jumpsuit with a ring set and cropped blazer.

    Fit & Features

    • Sleeveless V-neck, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Paper bag pleated waist, tie-front belt design
    • Hidden side pockets
    • Skinny-leg silhouette
    • Smooth woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-1299

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Chic Wavy Striped Crochet Tube Top

    Fit & Features

    • Unlined crochet knit fabrication
    • Sleeveless sweetheart neckline
    • Keyhole cutout at the bust
    • Wavy striped pattern
    • Cropped hem
    • Runs true to size

     

    Shop Matching Skirt: Retro Chic Wavy Striped Crochet Midi Skirt

    Style Number/Barcode: 06005-2189

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, L

  • Forever Timeless Satin A-Line Slip Dress

    This satin slip dress will be a forever and timeless staple! The mini dress features a sleeveless V-neck, adjustable spaghetti straps, a flattering A-line silhouette and short hem on smooth non-stretch satin fabric. Complete the look with the matching top and heels for a cocktail reception.

    Shop Matching Top: Forever Timeless Satin Collared Top

    Fit & Features

    • Sleeveless V-neck
    • Adjustable spaghetti straps
    • A-line silhouette
    • Short-length hem
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2866

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Bliss Floral Corset Skater Dress

    Show off your effortless beauty in this adorable floral print skater dress at weekend brunches or day dates! The corset bodice and lace-up back will snatch your waist, while the short skater silhouette gives off a flirty flair.

    Fit & Features

    • Floral printed woven fabric, woven lining with lace trim, no stretch
    • Sleeveless sweetheart neckline, lace trim, tie-front detail, ruched bust, underwire
    • Thin adjustable tank straps with lace trim
    • Corset bodice, lace trim, pleating, flexible boning
    • Lace-up back design, zipper with hook-eye closure
    • V-shaped drop waist, short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000007

    Category Name: Vacation Looks

    Price: $31.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Look Tie-Front Ruffled Romper

    This adorable tie-front ruffled romper will create a flirty look for your weekend plans! Designed with a lightweight woven fabric, it features a sleeveless V-neckline with a tie-front design and a keyhole cutout under the bust, spaghetti straps, dual high waist seams, flowy shorts with a mini-length overlay, and a cute fit and flare silhouette. Style with clear heels for brunch.

    Fit & Features

    • Sleeveless V-neckline, tie-front, keyhole cutout
    • Spaghetti straps, back zipper closure
    • Dual high waist seams
    • Flowy shorts, mini-length overlay
    • Fit and flare silhouette
    • Woven fabric, knit lining at the bust, minimal stretch
    • Style runs large

    Style Number/Barcode: 06403-0435

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Always Bodycon Ruffle Mini Dress

    You'll always be remembered as stunning in this mini dress, perfect for brunch or casual parties and plans! The flattering scoop neckline with a delicate rose accent adds a touch of romance, while the bodycon fit showcases your curves and is finished with a flirty ruffled hem.

    Fit & Features

    • Stretchy knit fabric, knit lining
    • Scoop neckline with a rose accent
    • Spaghetti straps
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000152

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fuzzy Feels Chenille High-Rise Jogger Pajamas

    Get cozy lounging in these chenille jogger pajamas! They feature a high-rise elasticized waistband, a skinny jogger-leg silhouette, and ribbed cuffs on ultra-soft and cozy chenille knit fabric. Complete the look in the matching pajama top and robe for a chill night in!

    Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top

    Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe

    Fit & Features

    • High-rise elasticized waistband
    • Skinny jogger-leg silhouette
    • Ribbed cuffs
    • Ultra-soft chenille knit fabric
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 07103-0940

    Category Name: Vacation Looks

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Silhouette Bodycon Midi Dress

    Show off a stunning silhouette in this sleek knit midi dress featuring a sleeveless square neck, ruching to flaunt your figure, and a hanky hem with a chic flared fit. Style with stilettos for cocktail hour!

    Fit & Features

    • Smooth knit fabric, high stretch, stretch knit lining
    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching
    • Bodycon silhouette
    • Midi-length hanky hem
    • Runs true to size

    Style Number/Barcode: 05101-000553

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: LIGHT, MARSALA

    Available Size: XS, S, M, L, XL

  • Twice The Love Rib Knit Crop Top

    Dive into cozy rib knit love with this midi skirt! Perfect for everyday styling, this midi skirt features a high-rise elasticized waist and curve-flaunting bodycon silhouette and a side slit that shows some skin. Complete the look with the matching skirt.

    Shop Matching Skirt: Twice The Love Rib Knit Midi Skirt

    Fit & Features

    • Scoop neckline, plunging notched front design
    • Long fitted sleeves, flared hems
    • Cropped, form-hugging fit
    • Smaller notched front detail
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1806

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Inspired Charm Strapless Watercolor Print Mini Dress

    Envoke an inspired charm in this watercolor print mini dress and capture attention at parties or casual dinners!  With its strapless straight-across neckline and bodycon silhouette, this mini dress will accentuate your curves and flatter your figure. Made from airy lined mesh fabric with an eye-catching watercolor print, this dress is a must-have for any fashion-forward girlie! Complete the look in stiletto heels and a purse!

    Fit & Features

    • Watercolor print
    • Mesh fabric lined with stretchy knit
    • Strapless straight neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5605

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Shine Cubic Zirconia Circle Charm Necklace

    Give off the prettiest chic shine with this cubic zirconia circle charm necklace! It features a dainty chain with a small interlocking circle charm adorned with mini cubic zirconia stone embellishments for a subtle sparkle. Style with hoop earrings.

    Fit & Features

    • Dainty chain-link design
    • Small interlocking circle charm
    • Mini cubic zirconia stones
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1793

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Tones Smocked Eyelet Skater Dress

    Sunny tones and delicate eyelet lace embroidery? There's so much to love about this smocked skater dress that'll take you from brunch to a day date or party!

    Fit & Features

    • Eyelet lace embroidery, woven fabric lined with stretchy knit
    • Square neckline
    • Spaghetti strap ties
    • Stretchy smocked bodice
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3911

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Beauty Tropical Print Maxi Dress

    Show off your beauty at sunset happy hour in this tropical print maxi dress designed with sheer mesh fabric and a mini-length lining. The high-cut side slit adds an alluring detail to turn heads.

    Fit & Features

    • Sheer knit fabric with mini-length knit lining, high stretch
    • Tropical print
    • Sleeveless cowl neckline
    • Spaghetti straps, cross-back design
    • High side slit
    • Maxi-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6074

    Category Name: Vacation Looks

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Honey, I'm Home Faux Suede Bustier

    Flaunt your fab self for your honey in this faux suede bustier featuring a strapless bodice with non-slip grip lining, flexible boning inserts, a cropped hem, and a back zipper closure. Complete the look in a sleek mini skirt and basic heels. 

    Fit & Features

    • Lined faux suede fabric, minimal stretch
    • Strapless bodice
    • Non-slip grip lining
    • Flexible boning inserts
    • Cropped hem
    • Back zipper closure
    • Runs true to size

    Style Number/Barcode: 06003-1707

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coziest Cutie Oversized Cable Knit Cardigan

    The perfect cold-weather cable knit cardigan to layer over all of your cute outfits! The sweater features slouchy long sleeves with rib knit cuffs, an open front design, and an oversized silhouette on soft and cozy cable knit fabric. Complete the look in boots for casual day or night plans!

    Fit & Features

    • Slouchy long sleeves, rib knit cuffs
    • Open front design
    • Oversized silhouette
    • Soft cable knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1827

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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: 05101-4059

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: S, M, L

  • Hello Weekend Straw Tote Bag

    This straw tote bag is ready for a summery outing! Whether you're heading to the pool, beach, or a weekend away this must-have straw bag is perfect for carrying your essentials. The bag features faux leather handles, a front embroidered "Hello Weekend", and an inner zipper closure leading to a spacious woven lined interior with a pocket. Complete the look in cute sandals.

    Fit & Features

    • Straw tote bag
    • Front embroidered "Hello Weekend"
    • Faux leather handles
    • Inner zipper closure
    • Spacious woven lined interior with pocket

    Style Number/Barcode: 07203-1969

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek One-And-Done Seamless Tank Zip-Up Catsuit

    A sleek one-and-done, this seamless catsuit is essential for layering or on its own. Perfect for lounging in stylish comfort or heading out on errands, it features a flattering scoop neckline and front zip-up closure that adds a trendy detail, and a form-hugging silhouette on seamless, stretchy rib knit fabric. Complete the look in a cozy crop jacket and booties or your favorite slippers!

    Fit & Features

    • Seamless, stretchy rib knit fabric
    • Front zip-up closure
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 07109-0358

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wow Factor Cutout Maxi Dress

    In this strapless maxi dress, you'll be checking yourself out in every mirror you pass! It boasts a metal square accent with a chic drape, a cutout bodice to show some skin, and a high front slit for effortless movement.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, metal square accent, drape design
    • Padded bra cups
    • Cutout bodice, back zipper and hook-eye closure
    • High front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000116

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, BROWN

    Available Size: XS

    Product Badge:
    • Sale