Vacation Looks

HomeVacation Looks

Resortwear
Sundresses
Matching Sets
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); } }) })

Now Trending

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.

  • Stay Sweet Short Sleeve Button Romper

    Stay sweet for everything on your social calendar in this short sleeve button romper designed with a layered ruffled hem that gives a flirty allure!

    Fit & Features

    • Woven fabric, knit lining, shorts underneath
    • Short sleeves
    • V-neckline, faux button details
    • Back zipper and hook-eye closure
    • Layered ruffled short hem
    • Runs true to size

    Style Number/Barcode: 06403-1102

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Bombshell Bikini Top

    Beachy bombshell will be your vibe in this sweetheart bikini top designed with lurex knit fabric for a trendy metallic sheen. Pair with the matching bikini bottoms and sarong for a sun-kissed look!

    Shop Matching Set: Beachy Bombshell One-Shoulder Bikini Top, Beachy Bombshell V-Cut Bikini Bottoms, Beachy Bombshell Short Sarong

    Fit & Features

    • Lurex knit fabric, metallic sheen
    • Structured sweetheart bust with underwire, padded bra cups
    • Adjustable spaghetti straps
    • Back hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-0724

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Choice Sleeveless Lace-Up Floral Romper

    A flirty floral romper like this is perfect for upcoming summer parties! Designed with a lightweight floral-printed woven fabric, it features a square neckline, a small keyhole cutout with a bust tie, thin shoulder straps, a lace-up back that adds a touch of flair, and a flowy short-length hem that keeps you trendy. Complete the look with hoop earrings.

    Fit & Features

    • Floral print
    • Woven fabric with smooth woven lining, no stretch
    • Square neckline with keyhole cutout and bust tie
    • Thin shoulder straps
    • Lace-up back, lower back zipper
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 06303-0256

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Burst With Beauty Rhinestone Star Necklace

    Burst with dainty beauty with this rhinestone star charm necklace! Complete the look with a stackable ring set for extra glam. 

    Fit & Features

    • Rhinestone star charm 
    • Lobster clasp closure
    • Chain

    Style Number/Barcode: 07002-1866

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Thriving Allure Sweetheart Floral Romper

    Cue the weekend trip or brunch! This sweetheart floral romper will sweeten up all of your social plans.

    Fit & Features

    • Floral print, woven fabric, stretchy knit shorts lining
    • Lace trim sweetheart neckline, underwire bust
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1255

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Captivating Cutie Eyelet Floral Babydoll Dress

    Captivate everyone with your cuteness in this eyelet floral babydoll dress at parties or brunch! Made with delicate eyelet floral chiffon fabric, this dress is perfect for any occasion.  The puff short sleeves and V-neckline add a touch of playfulness, while the babydoll silhouette and tiered ruffled hem offer a flattering fit. Complete the look in edgy booties.

    Fit & Features

    • Eyelet floral print chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Babydoll silhouette
    • Tiered ruffle short length hem
    • Runs true to size

    Style Number/Barcode: 05101-3144

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glittery Goals Triangle Rhinestone Threader Earrings

    Enchant everyone in these unique threader earrings featuring a dainty chain adorned with a triangle charm with mini rhinestone trim for a glittery effect. Complete the look with a ring set.

    Fit & Features

    • Dainty chain
    • Triangle charm with mini rhinestone trim
    • Threader-style silhouette
    • Rubber back stopper

     

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

    Style Number/Barcode: 07001-2060

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Girl Studded Western Buckle Sandals

    Slide into these studded western buckle sandals for a cool-girl vibe all spring to summer!

    Fit & Features

    • Round toe
    • Studded buckle dual straps
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1256

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Bombshell Short Sarong

    Beachy bombshell will be your vibe in this short sarong designed with lurex knit fabric for a trendy metallic sheen. Layer over the matching bikini top and bottoms for a sun-kissed look!

    Shop Matching Set: Beachy Bombshell Bikini Top, Beachy Bombshell One-Shoulder Bikini Top, Beachy Bombshell V-Cut Bikini Bottoms

    Fit & Features

    • Lurex knit fabric, metallic sheen
    • Mini-length hem
    • Tie closure

    Style Number/Barcode: 07105-000003

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Honky Tonk Honey Two-Tone Baseball Cap

    This baseball cap features a trendy two-tone design embroidered with a script reading, "Honky Tonk Honey," and includes a back adjustable strap for a customized fit. Pair with a basic tee and jean shorts!

    Fit & Features

    • Cotton material
    • Curved brim
    • Two-tone design
    • Embroidered script reads, "Honky Tonk Honey"
    • Back adjustable strap

    Style Number/Barcode: 07302-1685

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soak Up The Rays O-Ring Bikini Top

    Get ready to soak up the rays in this triangle bikini top with O-ring insets and a flirty knotted bust. Pair with the matching bikini bottoms.

    Fit & Features

    • Lined knit fabric
    • Knotted bust, removable padded bra cups
    • Spaghetti straps
    • Back hook closure
    • O-ring insets
    • Runs true to size

     

    Shop The Matching Bikini Bottoms: Soak Up The Rays O-Ring Bikini Bottoms

    Style Number/Barcode: 07104-0723

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutout Crush Hour Midi Dress

    Warning: This midi dress is sure to cause double takes. From the front-tie detail to the high leg slit, it’s giving effortless bombshell, perfect for pool parties or a cute brunch!

    Fit & Features

    • Sweater knit stretchy fabric
    • V-neckline with tie bust design
    • Adjustable spaghetti straps
    • Underbust cutout accent
    • Front slit
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000014

    Category Name: Vacation Looks

    Price: $12.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M

    Product Badge:
    • Sale
  • Tropical Vacay High-Rise Slit Midi Skirt

    The perfect tropical floral midi skirt to look stylish on your vacay! With its high-rise waist and cheeky panty lining, this skirt offers a comfortable fit and sleek silhouette. The high front slit and eye-catching tropical floral print add a touch of boldness to your look. Pair with the matching crop top and espadrille wedges!

    Shop Matching Top: Tropical Vacay Spaghetti Strap Tie-Back Crop Top

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric, cheeky panty lining
    • High-rise waist
    • High front slit
    • Midi-length
    • Runs true to size

    Style Number/Barcode: 06501-1010

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Check Strappy Straw Denim Block Heels

    When the sun is shining, these denim block heels come out! It's open-toe season and these heels are a must-have for vacations or strolling downtown. They feature a square toe and straw denim strappy design, a sturdy block heel, and a closed ankle with an adjustable strap and buckle closure. Complete the look with a crossbody purse.

    Fit & Features

    • 4" Block Heel
    • Square toe
    • Denim straw strappy design
    • Closed ankle
    • Adjustable ankle strap with buckle closure
    • Runs true to size

    Style Number/Barcode: 07401-4882

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Days A-Line Midi Tube Dress

    Effortless days call for this woven midi tube dress designed with a smocked bodice with a geometric pattern and a flowy pleated A-line silhouette. Perfect for weekend plans, style with strappy sandals.

    Fit & Features

    • Poplin cotton woven fabric
    • Strapless sweetheart neckline
    • Smocked bodice, geometric pattern
    • High-rise waist
    • Side pockets
    • Midi-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000007

    Category Name: Vacation Looks

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ocean Dreams Seashell Mesh Bikini Bottoms

    Get beach-ready in these mesh bikini bottoms. The adjustable side ties ensure your perfect fit, while the seashell trim adds a touch of beachy glamour. Pair with the matching bikini top!

    Shop Matching Top: Ocean Dreams Seashell Mesh Bikini Top

    Fit & Features

    • Mesh-lined fabric
    • High-rise waist
    • Adjustable side ties with seashell trim
    • Cheeky coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000004

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Trend Oversized Cateye Sunglasses

    A pair of sleek, trendy sunglasses featuring an oversized cateye design, tinted lenses with 100% UV protection, and nose supports. Perfect for everyday wear.

    Fit & Features

    • Oversized cateye design
    • Tinted lenses
    • 100% UV protection
    • Nose supports

    Style Number/Barcode: 07008-1104

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Retreat Lace Up Embroidered Skater Dress

    Indulge in the ultimate feminine look in this floral skater dress for parties and dressy occasions! Featuring a delicate V-neckline, spaghetti straps, and a figure-flattering lace-up design, this dress is perfect for any event. The skater silhouette and short-length hem add a touch of playfulness, while the intricate floral embroidery adds a romantic and elegant touch. Complete the look in fringe earrings and heels!

    Fit & Features

    • Floral embroidery, mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Lace up
    • Skater silhouette
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05101-2931

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Confidence Floral Jacquard Skater Dress

    Let everyone know you've got the perfect style in this floral jacquard skater dress! Crafted from a jacquard floral embroidery, this dress exudes chic vibes. The ruffle trim sweetheart neckline and tie spaghetti straps add a touch of femininity, while the flexible boning ensures a perfect fit. The skater silhouette and short-length hem will have you twirling! Complete the look in strappy heels.

    Fit & Features

    • Floral jacquard embroidery, woven fabric, chiffon lining
    • Tie spaghetti straps
    • Ruffle trim sweetheart neckline
    • Back zipper and hook-eye closure
    • Flexible boning
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3166

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Sensation Lace A-Line Mini Dress

    A sweetly sensational lace A-line mini dress for chic brides-to-be, birthday girls, or graduates!

    Fit & Features

    • Lace-lined fabric
    • V-neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3982

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • More To Come Twist Tube Crop Top

    Elevate your look with this tube top perfect for everyday styling! It boasts a twist strapless neckline and a fitted crop hem that flaunts your figure.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless tube sweetheart neckline
    • Twisted bust
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000372

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: GREEN, BURGUNDY

    Available Size: XS, S, M, L

  • Sunny And Sweet Off-The-Shoulder Floral Crop Top

    Nothing's sweeter than a sunny day spent in this floral crop top! Featuring a ruffle trim neckline, short puff sleeves, and a stretchy smocked bodice, this top is as comfortable as it is stylish. The ruffled crop hem and floral print knit fabric add cuteness to any outfit. Complete the look in trendy denim shorts.

    Fit & Features

    • Floral print knit fabric, moderate stretch
    • Off-the-shoulder ruffle trim neckline
    • Short puff sleeves
    • Stretchy smocked bodice
    • Ruffled crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5337

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Floral High Rise Wide-Leg Satin Pants

    You can't go wrong stepping out in this floral satin pants on a getaway or having a sunset dinner! Show off your fashion sense with these pants with a flattering high-rise waist, wide-leg detail, and a dainty floral print. Complete the look with the matching top.

    Shop Matching Top: Flawless Floral Kimono Tie-Front Satin Crop Top

    Fit & Features

    • Dainty floral print, satin fabric, no stretch
    • High-rise waist, back elastic waistband
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1393

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Glow Floral Satin Maxi Dress

    Looking like a postcard, feeling like a getaway. This floral satin maxi dress brings paradise to the party with a silky flow, vacay-approved vibes, and a strappy open back that says “catch flights and feelings.”

    Fit & Features

    • Premium satin fabric
    • Large floral print
    • Sleeveless V-neckline
    • Spaghetti straps
    • Open cross-back strappy design, tie closure
    • Fitted flowy silhouette, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000172

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free