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.

  • A Dose Of Attitude Lace-Up Flare Pants

    Serve major attitude in these faux suede pants with trending lace-ups and a flared hem perfect for country bars or festivals!

    Fit & Features

    • Faux suede fabric
    • High-rise waist
    • Dual front lace-ups
    • Hip-hugging fit
    • Flare hem
    • Runs true to size

    Style Number/Barcode: 06502-2577

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Day High-Rise Straight Leg Denim Jeans

    It's always a perfect day in these straight-leg denim jeans with a flattering high-rise waist perfect for crop tops or sweaters. 

    Fit & Features

    • Denim fabric
    • High-rise waist
    • Straight-leg fit
    • Front button closure
    • Front pockets, belt loops
    • Runs true to size

    Style Number/Barcode: 06602-0557

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Chic Sheer Lace Flare Pants

    So boho chic, these sheer lace flare pants are a style staple for festival season. Show off your curves with the hip-hugging fit that continues through the leg to the trendy flared hem.

    Shop Matching Black Top: Bohemian Chic Sheer Lace Tie-Front Top

    Fit & Features

    • Sheer floral lace fabric with knit panty lining, high stretch
    • High-rise elasticized waist
    • Hip-hugging fit
    • Form-hugging fit through the leg
    • Flared hem
    • Pants in size small have a 9" front rise with a 35" inseam
    • Runs true to size

    Style Number/Barcode: 06502-2582

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK, IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Stylish Crowd Hoop Drop Earrings

    These earrings will make any outfit stand out! They feature linked hoops in a drop design for the perfect statement. Complete the look in a cute matching set for upcoming plans!

    Fit & Features

    • Linked hoops
    • Drop design
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-2020

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Treat Yourself Mid-Rise Pleated Denim Mini Skirt

    Treat yourself to something new! This mid-rise pleated denim mini skirt is just the trend piece your weekly lineup needs for a cute refresh this season.

    Fit & Features

    • Non-stretch denim fabric
    • Mid-rise dual belted waist
    • Back zipper and hook-eye closure
    • Pleated silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06601-0232

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: DENIM

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Perfect View Smocked Cutout Skater Dress

    You'll be the prettiest and perfect view for all to see you in this smocked cutout skater dress with breezy long sleeves and a flattering silhouette.

    Fit & Features

    • Chiffon lined fabric, stretchy knit lining
    • Sheer peasant long sleeves
    • Sweetheart neckline
    • Stretchy smocked bodice with adjustable drawstrings
    • Cutout accent
    • Stretchy smocked back panel
    • Skater silhouette, drop waist seam, short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3991

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cuter Than Ever Lace Ruffle Shorts

    Romp around cuter than ever in these lace ruffle shorts for a flirtatious look everywhere you go!

    Fit & Features

    • Lace lined fabric
    • Low-rise waist
    • Tiered ruffled design
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06503-000018

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

    Product Badge:
    • Sale
  • Keep It Cute Pleated Denim Mini Skirt

    Keep your everyday 'fits cute and trendy with this pleated denim mini skirt. The distressed hem adds a casual flair to the adorable A-line silhouette.

    Fit & Features

    • Denim fabric
    • Mid-rise waist, belt loops
    • Front button closure
    • Pleated design
    • Mini-length distressed hem
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 06601-0227

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Caught Your Eye Strapless Lace-Up Skater Dress

    Catch every eye in this eyelet skater dress with a flirty lace-up bust and a flowy mini-length hem perfect for twirling at parties!

    Fit & Features

    • Eyelet cotton fabric with woven cotton lining
    • Strapless neckline, lace-up bust, padded bra cups
    • Skater silhouette
    • Flowy mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4009

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feels Like Spring Braided Slingback Sandals

    Step into fresh spring style in these braided flat sandals with a trendy closed pointed toe and mini block heel that elevates every outfit!

    Fit & Features

    • Mini block heel
    • Closed braided pointed-toe
    • Slingback adjustable strap with buckle closure
    • Cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-5316

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chill With Me Long Sleeve Square Neck Knit Romper

    Perfectly chill and cute, this lounge rib knit romper was made for relaxing at home and going for a coffee run in! Crafted from stretchy rib knit fabric, this romper features cozy fitted long sleeves, a flattering square neckline, and a form-hugging short-length hem. Pair with a cozy cardigan and slippers. 

    Fit & Features

    • Stretchy rib knit fabric
    • Fitted long sleeves
    • Square neckline
    • Form-hugging, short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1271

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Taste So Sweet Cherry And Faux Pearl Layered Necklace

    Sweeten up the vibe in this layered necklace with adorable colored rhinestone cherry charms and a luxe strand of faux pearls. Pair with a purse.

    Fit & Features

    • Layered necklace
    • Colored rhinestone cherry charms
    • Faux pearl strand
    • Lobster clasp closure

    Style Number/Barcode: 07002-2116

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Darling Babe Striped Drop Waist Skater Dress

    So darling, this striped woven skater dress is effortless perfection. The sleeveless square neckline is accented with a mini bow detail, and the drop waist design leads to a pleated fit-and-flare silhouette.

    Fit & Features

    • Striped woven fabric
    • Sleeveless square neckline, eyelet trim, mini bow detail
    • Tank shoulder straps
    • Square back, zipper closure
    • V-shaped drop waist
    • Short pleated skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000145

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutest Spirit Short Sleeve Knot Tie Mini Dress

    This short sleeve mini dress is the cutest for casual outings! Made from soft and stretchy rib knit fabric, this dress will keep you comfy and stylish all day long. With a flattering bodycon fit and a unique front knot tie detail, this dress exudes charm. The asymmetrical mini-length hem adds a touch of playfulness, making this a must-have. Complete the look in platform sneakers.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Crew neckline
    • Bodycon fit
    • Front knot tie detail
    • Runs true to size

    Style Number/Barcode: 05102-5762

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sporty Chick High-Rise Nylon Skort

    Show off your sporty style in this high-rise nylon skort, whether sitting on the sidelines or on the pickleball court! The skort is designed with an adjustable drawstring waist, convenient side pockets, and a sleek mini-length overlay with knit shorts lining. Pair with sneakers.

    Fit & Features

    • Nylon woven fabric, minimal stretch
    • High-rise elasticized and adjustable drawstring waist
    • Side pockets
    • Mini-length overlay
    • Stretchy knit shorts lining
    • Skort in size small has a 10" front rise with a 1.5" inseam
    • Runs true to size

    Style Number/Barcode: 06303-0292

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easily Gorgeous Strapless Cable Knit Midi Dress

    Flaunt your gorgeous curves in this chic cable knit midi dress for brunch or a casual party. The dress boasts a flattering bodycon silhouette and a center back slit for movement.

    Fit & Features

    • Cable knit design, soft stretchy knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5898

    Category Name: Vacation Looks

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Caught My Attention Floral Lace Bustier

    This floral bustier will attract all the attention with its flirty lace trim and flattering silhouette that snatches effortlessly!

    Fit & Features

    • Floral print, lace trim, woven-lined fabric
    • Sweetheart neckline, underwire bust
    • Adjustable straps
    • Back zipper and hook-eye closure
    • Flexible boning, lace trim
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2771

    Category Name: Vacation Looks

    Price: $7.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Fave Floral Ruffled Skater Dress

    This adorable ditsy floral skater dress will be your new flirty fave to style up all season! You'll love the tiered ruffled design and flowy fit-and-flare silhouette.

    Fit & Features

    • Woven fabric
    • Ditsy floral print
    • Strapless straight neckline
    • Smocked bodice
    • Tiered ruffled skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6052

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Elevated Era Ribbed Knit High Slit Midi Skirt

    Enter your elevated era with this chic staple ribbed knit midi skirt perf for everyday styling. Designed with a high-cut side slit and bodycon fit, pair with the matching cropped tank for a seamless look.

    Shop Matching Top: Elevated Era Ribbed Knit Cropped Tank Top

    Fit & Features

    • Ribbed knit fabric, high stretch
    • High-rise waist
    • High side slit
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1135

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Eyelet Bubble Hem Mini Dress

    You'll look effortlessly pretty in this floral eyelet mini dress featuring a strapless smocked bodice and adorable A-line silhouette with a bubble hem.

    Fit & Features

    • Floral eyelet woven fabric
    • Strapless straight neckline, ruffled trim
    • Stretchy smocked bodice, high waist
    • Mini-length A-line silhouette
    • Bubble hem
    • Runs true to size

    Style Number/Barcode: 05101-4152

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gives You Lemons Pajama Shorts

    When life gives you these lemon pajama shorts every lounge or sleep will look sweet! Pair with the matching pajama top to complete the look.

    Fit & Features

    • Lemon print, stretchy knit fabric
    • Mid-rise waist
    • Form-hugging fit
    • Cheeky bottom
    • Runs true to size

     

    Shop The Matching Pajama Top: Gives You Lemons Pajama Top

    Style Number/Barcode: 07103-000017

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Set Up Geometric Bandeau Halter Crop Top

    Super cute and perfect for getaways or weekend plans, this bandeau crop top is stylish and comfortable for anything on your calendar! It feature a flattering halter neckline with a spaghetti strap tie, an O-ring bust, a cropped hem, and a trendy geometric print on woven fabric. Complete the look with the matching pants.

    Shop The Matching Pants: All Set Up High Rise Geometric Palazzo Pants

    Fit & Features

    • Geometric print, woven fabric, no stretch
    • Halter neckline with spaghetti strap tie
    • O-Ring bust
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2551

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gives You Lemons Pajama Top

    When life gives you this lemon print pajama top will make every lounge or sleep will look sweet! Pair with the matching pajama bottoms to complete the look.

    Fit & Features

    • Lemon print, stretchy knit fabric
    • Short sleeves
    • Crew neckline
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Pajama Shorts: Gives You Lemons Pajama Shorts

    Style Number/Barcode: 07103-000016

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: L

    Product Badge:
    • Sale
  • All Day Cuteness Floral Corset Skater Dress

    For sunshine dressing, this cute floral skater dress is just the ticket! Designed with a figure-snatching corset bodice and flared short-length hem, this dress is a stylish option for shower celebrations or tea parties.

    Fit & Features

    • Floral print, cotton-blend woven fabric, smooth knit stretching lining
    • Square neckline, bust tie, wide shoulder straps
    • Corset bodice, back zipper hook-eye closure
    • Drop waist seam, pleated accents
    • Skater silhouette
    • Flared short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3886

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free