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.

  • Miami Nights Sleeveless Tropical Slit Maxi Dress

    Turn up the heat in Miami in this tropical maxi dress on vacay! The square neckline and spaghetti straps accentuate your curves in a form-hugging fit while the high side slit adds a touch of sassy sophistication. Let the tropical print and maxi-length hem transport you to a paradise getaway! Complete the look in sandals.

    Fit & Features

    • Tropical print, knit fabric, stretchy short lining
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5624

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Effect Abstract Wide-Leg Pants

    Printed to perfection in a flattering wide-leg silhouette, these pants boast a classic high-rise waist. Pair with the matching top.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • Cowl halter neckline, tie straps
    • Open back
    • Fitted crop hem
    • Runs true to size

    Shop The Matching Top: Sultry Effect Abstract Cowl Halter Crop Top

    Style Number/Barcode: 06502-000022

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • In My Element V-Neck Bow Ruffled Floral Romper

    Time to show your playful side in this sleeveless ditsy floral romper for spring-to-summer fun! With a surplice V-neckline, adjustable spaghetti straps, and an open crisscross back, you'll turn heads. The front bow tie waist and ruffled short-length hem add a touch of fun to the ditsy floral print woven fabric. Complete the look in stiletto mules and earrings!

    Fit & Features

    • Ditsy floral print woven fabric, partial knit lining, minimal stretch
    • Surplice V-neckline
    • Adjustable spaghetti straps, open back, cross-back strap design
    • Back zipper with hook and eye closure
    • High waist seam, tie-front bow
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 06403-0379

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Perfection Strappy Straw Block Heels

    These straw heels are the definition of beachy perfection! They feature a square toe with dual straps, an adjustable ankle strap with buckle closure to secure the style, and a trendy circular block heel. Complete the look with a cute tote bag for a beach trip!

    Fit & Features

    • 2.5" Circular block heel
    • Square toe
    • Dual straps
    • Adjustable ankle strap with buckle closure
    • Straw material
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-4863

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Babe Halter Plunge Neck Romper

    Perfect for a day or night out, this romper will make you stand out from the crowd with its flowy and flattering design. The halter plunge neck adds a touch of daring while the open back enhances your silhouette. 

    Fit & Features

    • Knit fabric, stretchy knit shorts lining
    • Plunge halter neckline, tie straps
    • Open back
    • Flowy mini skirt overlay
    • Runs true to size

    Style Number/Barcode: 06503-000064

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: RED, OFF, WHITE

    Available Size: S, M, L, XS

  • Stylish In Stripes Strapless Wide Leg Knit Jumpsuit

    Spend your days looking stylish in this striped jumpsuit perfect for layering over your swimsuit or wearing on its own. The jumpsuit features a strapless neckline and an adjustable drawstring waist that cinches, leading to the flattering wide-leg silhouette. Complete the look with chic sunglasses.

    Fit & Features

    • Striped pattern, knit fabric, moderate stretch
    • Strapless neckline
    • Adjustable drawstring waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2539

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oasis Babe Floral Wrap Tie Sarong

    Perfect for poolside lounging or beachfront dining, this sarong adds instant babe status to your vacation wardrobe. This mesh sarong can be styled as a swimsuit cover-up or a stylish skirt with its adjustable tie design, with a vibrant floral print that captures tropical vibes.

    Fit & Features

    • Mesh fabric, floral print, stretchy
    • Wrap tie adjustable waist
    • Sheer design

    Style Number/Barcode: 07105-000015

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heart Eyes Only Slide Sandals

    These comfy-cute slides feature a clear strap topped with a bold heart charm—perfect for pool days, park hangs, or running errands like a style icon.

    Fit & Features

    • Round toe
    • Clear PVC strap with heart cutout
    • Comfortable footbed
    • Platform sole
    • Runs true to size

    Style Number/Barcode: 07404-000005

    Category Name: Vacation Looks

    Price: $20.90

    Availability: In Stock

    Available Color: CLEAR

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Sunny Dreams High-Rise Distressed Denim Shorts

    Keep it cute and casual all season in these denim shorts from fun at the beach to weekend hangs! They feature a flattering high-rise waist, trendy distressed accents along the form-hugging silhouette, and a raw cut-off hem. Complete the look in a basic tee and sneakers!

    Fit & Features

    • Denim material with stretch
    • High-rise waist
    • Distressed accents
    • Form-hugging
    • Front button and hidden zipper closure
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06603-0397

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Poolside Flirt String Bikini Top

    Sit flirty and pretty in this eyelet string bikini top at a pool party or on vacation! Pair with the matching bikini bottoms.

    Fit & Features

    • Eyelet lined fabric
    • Triangle cups
    • Dual string spaghetti back ties
    • Runs true to size 

     

    Shop The Matching Bikini Bottoms: Poolside Flirt Eyelet String Bikini Bottoms

    Style Number/Barcode: 07104-0719

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serve Attitude Cat Eye Sunglasses

    These aren’t just sunglasses—they’re your armor of IDGAF. With a sleek cat eye shape that oozes retro cool and mystery, these frames instantly upgrade your fit and your mood.

    Fit & Features

    • Cat eye frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000065

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

    Product Badge:
    • Best Seller
  • Perfect Striped Halter V-Neck Mini Dress

    This striped mini dress will easily become your perfect favorite piece this season! The halter V-neckline and open back highlight your alluring figure, while the bodycon fit and mini-length hem flatters your curves on the striped mesh-lined fabric. Complete the look with sunglasses and sandals for a day out or on vacation!

    Fit & Features

    • Striped print, mesh fabric, soft stretchy knit lining
    • Halter V-neckline
    • Open back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5811

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Vacay Vibes High Slit Tropical Knit Maxi Dress

    Give off effortless vacay vibes in this high slit tropical knit maxi dress. The tropical palm leaf print on the lightweight knit fabric will have you looking like you're ready for a getaway, even if you're just grabbing drinks at a local happy hour! The dress is shaped with a sleeveless V-neckline and spaghetti straps, and features a high-cut side slit to showcase some leg on the form-hugging mid-length silhouette. Style with gold hoops and strappy wedges!

    Fit & Features

    • Stretchy knit fabric with a bust lining
    • Tropical print
    • Sleeveless V-neckline
    • Spaghetti straps
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5537

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Company Sleeveless Button-Up Vest

    Never worry about looking stylish with this sleeveless vest in your lineup! Designed from a linen-blend woven fabric, this vest offers a classic and trendy vibe with a collar neckline, button-up front closures, faux pockets, and a cropped hem. Complete the look in denim shorts.

    Fit & Features

    • Linen-blend woven fabric, no stretch
    • Collar neckline
    • Button-up front closures
    • Buttoned chest pockets
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1785

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Covetable Charm V-Neck Ruffled Maxi Dress

    You'll covet the charm of this sleeveless maxi dress all season!  With a flattering V-neckline and adjustable spaghetti straps, this dress will hug you in all the right places. The crisscross and smocked back add a trendy touch, while the flowy silhouette and ruffled long-length hem offer a breezy style. Complete the look in sandals.

    Fit & Features

    • Woven fabric, bust lining, no stretch
    • Adjustable spaghetti straps
    • Crisscross and smocked back
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5546

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Chic High Slit Crochet Maxi Skirt

    Create a sunny chic 'fit with the cutest crochet maxi skirt! Designed with a breezy sheer crochet knit fabric with a built-in panty lining, this skirt was made for summer getaways. It features a high-rise banded waist with a front adjustable drawstring for a customized fit, a high-cut back slit, and a slim-fit silhouette. Complete your look with the matching crop top and a pair of slip-on sandals!

    Shop Matching Top: Sunny Chic Halter Ruched Crochet Crop Top

    Fit & Features

    • Sheer crochet knit fabric, moderate stretch
    • Built-in knit panty lining
    • High-rise elastic banded waist
    • Front adjustable drawstring
    • High back slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 06501-0917

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Think Sunshine Long Sleeve Cutout Crochet Mini Dress

    Get in the summer vibe with this crochet mini dress perfect for pool parties or vacation! Featuring sheer flared long sleeves for a trendy touch, a sexy V-neckline, and a cutout waist and back for a daring look. The hoop insert adds a unique twist and the tie-back design creates a flattering look along the bodycon silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Crochet fabric, sewn-in knit lining, slight stretch
    • Sheer flared long sleeves
    • V-neckline
    • Hoop insert, cutout waist and back
    • Tie-back design
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5732

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Of All Paisley Crop Top

    A paisley crop top that adds boho sweetness to your favorite bottoms!

    Fit & Features

    • Paisley graphic print, stretchy knit fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Fitted pointy crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000055

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: S, M, L

  • Pretty In Paradise One-Shoulder Tropical Maxi Dress

    You'll be looking so pretty as you stroll the beach in paradise in this tropical maxi dress! The smooth stretchy knit fabric showcases a bold tropical print perfect for an island vacay. The long dress is shaped with a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap. The sultry ruched cutout at the waist features an adjustable drawstring for a customized look. Reveal some leg with the sexy high-cut side slit on the maxi-length silhouette. Style this slim-fit dress with espadrille wedges.

    Fit & Features

    • Stretchy knit fabric, knit lining at the bust
    • Tropical print
    • Asymmetric one-shoulder neckline, spaghetti strap
    • Ruched side cutout, adjustable drawstring
    • High side slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5542

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meant To Be Surplice V-Neck Strappy Chiffon Romper

    This chiffon romper was meant to be adored by everyone at showers or celebrations! The surplice V-neckline and adjustable spaghetti straps provide a flattering fit, while the crisscross open back adds a touch of playful charm. The tie waist cinches in at the perfect spot, and the layered ruffled short-length hem adds a flirty and feminine touch. Complete the look in wedge sandals.

    Fit & Features

    • Textured chiffon fabric, chiffon woven lining
    • Surplice V-Neckline, adjustable spaghetti straps
    • Criss-cross open back, zipper and hook-eye closure
    • Layered ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 06403-0418

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Never A Dull Moment Strapless Cutout Maxi Dress

    Bring a stunning look in this strapless maxi dress for your look-back-it moment! The strapless neckline and cutout bust add a touch of allure, while the strappy back and form-hugging fit emphasize your figure. With a center-back slit, you'll be able to move in style. Complete the look with earrings and a clutch!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Cutout bust, strappy back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5766

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Prowl Strapless Zebra Crop Top

    On the prowl and ready to unleash fierceness in this zebra print crop top! It features a strapless neckline, a tie-back design, and a fitted crop hem that flaunts your figure. Complete the look with the matching skirt.

    Shop Matching Skirt: On The Prowl High Rise Zebra Maxi Skirt

    Fit & Features

    • Zebra print, woven fabric, bust knit lining
    • Strapless neckline
    • Tie-back design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2507

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiji Feeling Sleeveless Lace-Up Tropical Maxi Dress

    Escape to the island or look like you did in this tropical maxi dress for an effortless summer style! With a flattering V-neckline and delicate spaghetti straps, this dress will keep you stylish all day long. The lace-up back adds a touch of playful detail, while the A-line silhouette and maxi-length hem create a flowy and romantic look.

    Fit & Features

    • Palm leaf tropical and border print, woven fabric with lining, no stretch
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • A-line maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5864

    Category Name: Vacation Looks

    Price: $11.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale