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.

  • Cutie Alert Cap Sleeve Swim Top

    Cutie alert! All eyes on you at the pool in this cap sleeve swim top featuring a scoop neck, removable padding, adjustable side ties, and a cropped hem on lined knit fabric. Complete the look in the matching swim bottoms.

    Shop The Matching Bottoms: Cutie Alert String Bikini Bottom

    Fit & Features

    • Cap sleeves
    • Scoop neck
    • Removable padding
    • Adjustable side ties
    • Cropped hem
    • Lined knit fabric
    • Fits true to size

     

    RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0672

    Category Name: Vacation Looks

    Price: $8.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Radar Lace-Up Flat Sandals

    Your glam radar is coming in hot! Create a sparkly look with these lace-up sandals featuring a round toe, rhinestone embellished straps, adjustable buckle closure, and a flat sole. Complete the look in a sleek satin dress.

    Fit & Features

    • Round toe
    • Rhinestone embellished straps
    • Lace-up design
    • Adjustable buckle closure
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-0975

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Catch Feels Dual Buckle Sandals

    Catch feels for these comfy and stylish sandals! They feature an open almond toe with strap, dual buckle strap design, and a slide-on styling. Complete the look in trendy denim shorts.

    Fit & Features

    • Open almond toe with toe strap
    • Dual buckle strap design
    • Slide-on/off styling
    • Runs true to size

    Style Number/Barcode: 07404-1034

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Forward Espadrille Flat Sandals

    Season's change and so should your shoe game! Slide into these espadrille sandals featuring a slightly square toe, single band, and a flat sole. Complete the look in a cute sundress for the farmer's market.

    Fit & Features

    • Slight square toe
    • Single-band
    • Flat sole
    • Espadrille trimming 
    • Slide-on/off design
    • Runs true to size

    Style Number/Barcode: 07404-1059

    Category Name: Vacation Looks

    Price: $12.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Beauty Tie-Front Top

    Showcase effortless vibes in this breezy tie-front top that is perfect for a beachside vacay. It features three-quarter length flowy sleeves, a tie-front design creating a V-neckline, and a cropped fit. Style with your favorite high waist bottoms and cute sandals.

    Fit & Features

    • Three-quarter length flowy sleeves
    • Tie-front
    • V-neckline
    • Cropped
    • Rayon gauze fabric, crinkle detailing
    • Runs true to size

    Style Number/Barcode: 06204-1190

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: Out of Stock

    Product Badge:
    • Ships Free
  • Beach Cottage Striped Linen Top

    This striped linen top is perfect for a beach vacay! It features cuffed dolman short sleeves, a collared neckline, a button-down front with a pocket, and a flirty tie-knot cropped hem. Complete the look in denim shorts.

    Fit & Features

    • Cuffed dolman short sleeves
    • Collared neckline
    • Button-down front
    • Front pocket
    • Tie-knot cropped hem
    • Striped pattern
    • Linen woven fabric, no stretch, fits true to size

    Style Number/Barcode: 06003-1796

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy-Chic Style Halter Midi Dress

    Showcase your trendy-chic status in this of-the-moment midi dress! It features a sleeveless halter neckline, spaghetti straps that lead to a cross-back lace-up strappy design, a sleek front O-ring accent, a midi-length, curve-hugging silhouette, and an all-over geometric striped pattern. Style this dress with heeled mules.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps
    • Open back, strappy cross-back lace-up design, tie closure
    • Front O-ring detail
    • Midi-length, form-fitting silhouette
    • Geometric striped pattern
    • Knit fabric, partial front knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4411

    Category Name: Vacation Looks

    Price: $4.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Speed Racer Graphic Lace-Up Tee

    Get in it to win it wearing this graphic tee featuring short sleeves, a square neck, and a front lace-up placket with exposed seam detail and a cropped hem. Complete the look in skinny jeans for a cute look.

    Fit & Features

    • Short sleeves
    • Square neck
    • Lace-up placket
    • Graphic detail
    • Exposed seams, cropped hem
    • Cotton blend fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06002-1163

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Palm Beach Linen Crochet Kimono

    Imagine yourself in this linen kimono walking the beach under the palm trees! It features 3/4 length sleeves, an open front design with tie waist, side slits, and crochet trim. Complete the look in a cute floppy straw hat.

    Fit & Features

    • 3/4 length sleeves
    • Open-front design
    • Tie waist, side slits, crochet trim 
    • Mid-calf length hem
    • Linen fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1415

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy And Chic Sheer Crop Top

    Breezy and chic, this sheer woven crop top will bring effortless vibes to your look. It features a sweetheart neckline, long bishop sleeves, an adorable tie-back design, a cropped fit, and an all-over swiss dot pattern. Style this top with denim shorts and sandals.

    Fit & Features

    • Sweetheart neckline
    • Long bishop sleeves, elastic cinched hems
    • Tie-back design
    • Cropped
    • Swiss dot pattern
    • Sheer woven fabric, partial front knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1653

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Current Mood Denim Belted Mini Skirt

    With this denim mini skirt, you'll always be in the mood to create fab looks! It features a high-rise waist, button, and hidden zipper closure, an adjustable belt with belt loops, front and back pockets on stretchy denim fabric. Complete the look in a bodysuit and knee-high boots.

    Fit & Features

    • High-rise waist
    • Button and hidden zipper closure
    • Adjustable belt and belt loops
    • Front and back pockets
    • Mini-length hem
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06601-0066

    Category Name: Vacation Looks

    Price: $8.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Plaid On Babe Pleated Skort

    Keep it chic in a plaid skort for a fab day out! The skort features a plaid print, a high-rise elastic waist, a pleated skirt overlay, and a pair of wide-leg shorts. The skort is composed of a woven fabric that offers a relaxed fit with a minimal stretch. Complete look with a bustier and sandals. 

    Fit & Features

    • Plaid print
    • Elastic high rise waist
    • Pleated skirt overlay
    • Wide leg shorts
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06303-0201

    Category Name: Vacation Looks

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blissful Blooms Crepe Floral Kimono

    Feel the bliss of these floral blooms! Step out for spring in this crepe kimono featuring three-quarter length sleeves, an open front, and a flowy longline hem. Complete the look in a casual bodycon dress.

    Fit & Features

    • Three-quarter length sleeves
    • Open front
    • Flowy longline hem
    • Floral pattern
    • Crepe fabric, no stretch

    Style Number/Barcode: 06204-1423

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ditsy Floral Off-Shoulder Crop Top

    Create a cute look in this disty floral off-the-shoulder crop top featuring short puff sleeves, dual drawstrings on the front, and pleat detail on stretchy knit fabric. Complete the look in high-rise jeans.

    Fit & Features

    • Off-the-shoulder
    • Short puff sleeves
    • Dual drawstrings on the front
    • Pleat detail, cropped hem
    • Ditsy floral pattern
    • Stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 06001-4284

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On A Roll Denim Mom Shorts

    Dang fashionista! You're on a stylish roll in these denim mom shorts featuring an on-trend high-rise waist, distressed accents, slight color fading effect, and a front side rolled hem on medium wash denim fabric. Complete the look in a cute crop top.

    Fit & Features

    • High-rise waist
    • DIstressed accents, front side rolled hem
    • Slight color fading effect
    • Mom-style silhouette
    • Front button and hidden zipper closure
    • Five-pocket design, belt loop accents
    • Fits true to size

    Style Number/Barcode: 06603-0284

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Denim Cutie High Rise Mom Shorts

    Flaunt your cuteness in these high-rise mom shorts featuring trendy distressed details, a raw cut hem, and cool color fading on medium wash denim fabric with minimal stretch. Complete the look in a bodysuit and sneakers.

    Fit & Features

    • High-rise waist
    • Mom style
    • Distressed details, color fade effect
    • Raw cut hem
    • Front button and hidden zipper closure
    • Five-pockets, belt loop accents
    • Medium wash denim, minimal stretch, fits true to size

    Style Number/Barcode: 06603-0283

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Fling Flowy Sleeve Kimono

    This three-quarter length sleeve kimono is in for the long haul! It features an open-front, side slit accents, and a floral pattern on gauze woven fabric. Complete the look in a chic midi dress and booties.

    Fit & Features

    • Three-quarter length sleeves
    • Open front
    • Side slit accents
    • Floral pattern
    • Gauze woven fabric, no stretch

    Style Number/Barcode: 06204-1425

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Comfort Level Criss-Cross Sandals

    Reach the perfect level of comfort in these criss-cross sandals featuring an almond toe, platform sole, and an adjustable ankle buckle closure. Complete the look in cute loungewear set for a chill day.

    Fit & Features

    • Almond toe
    • Platform comfort sole
    • Criss-cross strap design
    • Adjustable ankle buckle closure

    Style Number/Barcode: 07404-1038

    Category Name: Vacation Looks

    Price: $12.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Whispered Secrets Floral Mesh Maxi Dress

    Soft girl meets siren vibes. With delicate lace trim and a mesh maxi flow, this floral dress brings that effortlessly undone energy to every room.

    Fit & Features

    • Floral print, mesh fabric lined with stretch knit
    • Lace trim V-neckline
    • Spaghetti straps
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000230

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meet My Gauze And Crochet Romper

    You see what you like, so go for it in this cute romper! It has a sleeveless V-neckline, adjustable straps that create a cross-back design, and a fully lined lace bodice. A sheer crochet panel highlights your waist. Shorts are composed of unlined gauze fabric and offer a flowy fit. Complete look with wedges and sunglasses for a fab day out.

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps, cross at back 
    • Sheer crochet panel at waist
    • Flowy shorts
    • Gauze knit fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size 

    Style Number/Barcode: 06303-0157

    Category Name: Vacation Looks

    Price: $14.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Day Sleeveless Linen Romper

    It's a perfect day to rock a romper for a casual moment! The romper features a sleeveless V-neckline, a cami-styled bodice, multi-button down front, adjustable spaghetti straps, and a smocked back. The waist features a cinching tie waist belt. hidden side pockets, and cuffed shorts. The romper is composed of a lined linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and a denim jacket. 

    Fit & Features

    • Sleeveless V-neckline
    • Multi-button down front
    • Adjustable spaghetti straps
    • Smocked back 
    • Tie waist belt, hidden side pockets
    • Lined linen fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06303-0205

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chase The Cheetah Tie-Front Top

    You may wanna chase this cheetah tie-front top before it's gone! Features long peasant sleeves, a plunging neckline, and a cropped hem on texture woven fabric with no stretch. Complete the look in high-rise jeans and heels. 

    Fit & Features

    • Long peasant sleeves
    • Plunging neckline
    • Tie-front detail
    • Cropped hem
    • Cheetah pattern
    • Texture woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1164

    Category Name: Vacation Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hit The Tropics High Slit Maxi Skirt

    Channel a tropical paradise in a skirt that makes waves! The skirt features a fun palm leaf print, an elastic high rise waist, and a maxi length with a high side slit. The skirt is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a crop top and wedges. 

    Fit & Features

    • Palm leaf print
    • Elastic high rise waist
    • Maxi length 
    • High side slit
    • Lined smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06501-0655

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance