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.

  • Too Cute Bubble Hem Mini Skirt

    It’s giving flirty, flowy, and fully obsessed. This bubble hem mini skirt with cute bow detailing adds instant playful energy to any 'fit—perfect for your next photo dump.

    Fit & Features

    • Woven fabric, stretchy knit shorts lining
    • High-rise elasticized waist
    • Drop waist seam, dual bow details
    • Mini-length bubble hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 06301-000006

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • In The Spotlight Strapless Ruched Corset Top

    You'll be the center of attention in this corset top everywhere you go! Made from a ruched woven fabric, this corset top sets the bar high with a strapless neckline, flexible boning, and a cropped hem to flaunt your figure. Plus, the hidden back hook and eye fasteners secure the style. Complete the look in cute jeans for any plans!

    Fit & Features

    • Ruched woven fabric
    • Strapless neckline
    • Hidden back hook and eye fasteners
    • Flexible boning
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2296

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All This Allure Strappy Halter A-Line Skater Dress

    You'll be irresistible in this A-line skater dress on a night out! This stunning dress features a plunging halter neckline and a strappy back, adding a touch of allure to any occasion, while the mini-length hem offers a flirty touch.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Plunge halter neckline, bar accent, tie straps
    • Strappy back with spaghetti strap tie
    • A-Line skater silhouette
    • Seam detailing, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000102

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

  • Sunny Mode V-Cut Bikini Bottoms

    Activate sunny mode with these hot bikini bottoms featuring a V-cut design, scrunched detailing at the back, and a cheeky fit. Style with the matching bikini top to be sitting pretty poolside!

    Shop Matching Top: Sunny Mode Ruched Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • V-cut waist
    • Scrunched back
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000008

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ultimate Chic Choice Floral Tie-Back Short Dress

    For the ultimate chic choice, pick this floral short dress for all your summer plans! The sweetheart neckline and spaghetti straps give a flirty touch, while the dual tie-back design ensures a perfect fit. The underwire bust and flexible boning offer support and structure, with a short-length hem for a stunning silhouette. Complete the look with dainty chic earrings.

    Fit & Features

    • Ditsy floral print, woven fabric lined with stretchy knit
    • Sweetheart neckline, underwire bust
    • Spaghetti straps
    • Dual tie-back design
    • Flexible boning
    • Short-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3447

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Staple Mid-Rise Denim Shorts

    A true forever staple, these flattering mid-rise denim shorts hug your curves and flatter with unique seam designs and the perfect length.

    Fit & Features

    • Light wash denim
    • Mid-rise waist, seam detailing
    • Form-hugging fit
    • Front button and hidden zipper closure, belt loops
    • Four-pocket styling
    • Runs true to size

    Style Number/Barcode: 06603-000009

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: LIGHT, DENIM

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

  • Ocean Dreams Seashell Mesh Bikini Top

    Get beach-ready in this mesh bikini top! The adjustable spaghetti straps ensure your perfect fit, while the alluring front cutout with string details and seashell trim adds a touch of beachy glamour. Pair with the matching bikini bottoms!

    Shop Matching Bottoms: Ocean Dreams Seashell Mesh Bikini Bottoms

    Fit & Features

    • Mesh-lined fabric
    • Adjustable spaghetti straps
    • Front cutout, strings with seashell trim
    • Back cutout with string trim
    • Runs true to size

    Style Number/Barcode: 07104-000001

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Occasion Satin Cargo Mini Skirt

    The perfect stylish satin mini skirt for any occasion! Crafted on silky stretch satin, this skirt features a flattering high-rise waist, a form-hugging fit, dual side flap pockets, and a mini-length hem. Complete the look with a sleek moto jacket and boots! 

    Fit & Features

    • High-rise waist
    • Front hidden zipper and hook closure
    • Form-hugging fit
    • Dual side flap pockets. mini-length hem
    • Silky stretch satin-lined fabric
    • Stretchy knit shorts lining
    • Runs true to size

    Style Number/Barcode: 06403-0438

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mentionable Flirt One-Shoulder Asymmetrical Crop Top

    For an effortless flirty outfit, pair this one-shoulder crop top with a trendy pair of denim! It features a single shoulder strap, an adjustable side drawstring to let you customize the fit, and an asymmetrical cropped hem on soft knit fabric. Complete the look in a denim midi skirt and sneakers.

    Fit & Features

    • Soft knit stretchy fabric, bust lining
    • One-shoulder neckline
    • Side adjustable drawstring
    • Asymmetrical cropped hem
    • Runs true to size

    Style Number/Barcode: 06002-1860

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Casual Everyday Ribbed Knit Midi Dress

    This ribbed knit midi dress is cute, casual, and perf for everyday styling! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem with a side slit accent, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a cropped denim jacket and strappy mules.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-4934

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All The Splendor A-Line Faux Pearl Lace Mini Dress

    Look and feel gorgeous in this lace A-line mini dress at parties and showers! This playful mini dress features a flattering V-neckline, spaghetti straps, and a lace-up back for the perfect fit. The A-line silhouette and faux pearl embellishments add a touch of whimsy to this lacey ensemble! Complete the look in block heels and a clutch.

    Fit & Features

    • Faux pearl embellishments
    • Lace fabric lined with stretchy knit
    • Spagehtti straps
    • V-neckline
    • Lace-up back, zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3018

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Match My Energy Three-Pack Hoop Earrings

    This three-pack of hoop earrings keeps up with the trends! This pack includes a pair of simple hoop earrings, glittering rhinestone hoop earrings, and intricately etched hoop earrings, perfect for any occasion. Complete the look in a bodycon dress for dinner and drinks!

    Fit & Features

    • Three-pack hoop earrings
    • One pair of simple hoop earrings, post-back closure
    • One pair of rhinestone hoop earrings, post-back closure
    • One pair of etched hoop earrings, omega closure

     

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

    Style Number/Barcode: 07001-1983

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Chic Halter Ruched Crochet Crop Top

    Create a sunny chic 'fit with the cutest crochet crop top! Designed with a breezy sheer crochet knit fabric with a partial lining, this top was made for summer getaways. It features a sleeveless halter neckline with a racerback design, and a small keyhole cutout at the back with beaded tie-back straps for a customized fit. The front features ruching with adjustable drawstring beaded straps and a fitted cropped hem for a snatched silhouette. Complete your look with the matching maxi skirt and a pair of slip-on sandals!

    Shop Matching Bottoms: Sunny Chic High Slit Crochet Maxi Skirt

    Fit & Features

    • Sheer crochet knit fabric, partial knit lining
    • Halter neckline, racerback design
    • Back keyhole cutout, tie-back straps
    • Ruched front with adjustable drawstring straps
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2251

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Botanic Chic Textured Leaf Earrings

    These gorgeous earrings feature a textured leaf design that gives your look a nature-meets-luxury allure—perfect for date nights or rooftop brunches!

    Fit & Features

    • Textured leaf design
    • Linear silhouette
    • Fish hook

     

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

    Style Number/Barcode: 07001-000124

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • More Than Sweet Tie Strap Fit-And-Flare Dress

    Who can imagine a look sweeter than this fit-and-flare dress? Showcase your darling side in this short eyelet dress at casual brunches or parties! This charming dress features a square neckline, tie shoulder straps, and a flattering fit-and-flare silhouette. With a tiered ruffled short-length hem and delicate eyelet lace fabric, this dress will have you looking and feeling your best. Complete the look in trendy sneakers for a cute style!

    Fit & Features

    • Sheer eyelet lace fabric with knit lining, moderate stretch
    • Square neckline
    • Tie shoulder straps
    • Fit-and-flare silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5532

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Layered Beaded Chain Charm Necklace

    The charm necklace features a four-row design with a sleek snake chain layer, a dainty beaded chain layer, a trendy flat chain layer, and a thin cord layer accented with beading and an oval-shaped metal pendant. Style with hoop earrings.

    Fit & Features

    • Four-row layered necklace
    • Snake chain
    • Dainty beaded chain
    • Flat chain
    • Beaded cord with oval pendant
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1878

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fierce And Flirty Leopard Floral Maxi Skirt

    Show up fierce and flirty in this leopard floral maxi skirt! The flattering high waist accentuates your curves while the daring side slit adds movement and drama to every step. Pair with the matching tie-front top.

    Shop Matching Top: Fierce And Flirty Leopard Floral Tie-Front Top

    Fit & Features

    • Leopard floral print, mesh fabric, stretchy knit lining
    • High-rise waist
    • High side slit
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000054

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Summer Allure Abstract Print Satin Crop Top

    Bring the allure to your summer 'fits with this abstract print satin crop top! Designed with a silky satin woven fabric with a trendy abstract pattern, this top features a sleeveless V-neckline, halter spaghetti straps with a tie-back design, a bold open back with an elasticized back strap for added stretch, and a cropped hanky-style hem with a form-hugging fit. Pair with denim shorts and sandals!

    Fit & Features

    • Abstract print
    • Satin woven fabric, knit bust lining
    • V-neckline
    • Halter tie-back spaghetti straps
    • Open back, elasticized back strap
    • Cropped hanky hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2587

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get Like Me Cutout Wide-Leg Jumpsuit

    Make a striking impression in this bold strapless jumpsuit on vacay or a summer night out! With O-ring inserts, a cutout bodice, and a flattering wide-leg fit, this jumpsuit will turn heads everywhere you go.

    Fit & Features

    • Smooth knit stretchy fabric, full knit lining
    • Strapless neckline
    • O-ring inserts, cutout bodice
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000036

    Category Name: Vacation Looks

    Price: $45.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Color Me Pretty Satin Abstract Wide-Leg Pants

    Color you pretty in these satin pants to brighten up this new season! They feature a flattering high-rise waist, an elasticized back band, front pleating, and a wide-leg silhouette on smooth satin with an abstract print. Complete the look with the matching top for a vacation!

    Shop Matching Top: Color Me Pretty Satin Abstract Crop Top

    Fit & Features

    • High-rise waist, elasticized back band
    • Front pleating
    • Wide-leg silhouette
    • Abstract print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1371

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Garden Of Roses Chiffon Midi Dress

    Frolic through the garden or your next soiree in this rose print chiffon midi dress! It features a sleeveless sweetheart neck, spaghetti straps, a ruched bust with a tie, and a slim A-line silhouette with a flirty front slit. Complete the look in strappy block heels.

    Fit & Features

    • Sleeveless sweetheart neck, spaghetti straps
    • Ruched bust with tie
    • Back zipper and hook-eye closure
    • Slim A-line silhouette
    • Front slit, midi-length hem
    • Rose print, airy chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2081

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylishly Striped Knit Off-The-Shoulder Mini Dress

    This trendy striped knit mini dress is designed with a chic off-the-shoulder straight neckline with a flattering fold-over design and a bodycon silhouette to show off your curves. Pair with sneakers for a cute everyday look.

    Fit & Features

    • Striped ribbed knit fabric, plenty of stretch
    • Off-the-shoulder straight neckline, fold-over design
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5853

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheerly A Good Time Halter Lace Romper

    You're in for a stylishly good time in this sheer lace romper at festivals or concerts! It boasts a sultry open strappy back and a sheer bodice that flaunts your figure.

    Fit & Features

    • Lace fabric
    • Halter V-neckline, spaghetti strap tie
    • Open back, spaghetti strap tie
    • Sheer fitted bodice
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 06503-000048

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK, IVORY

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Truly Radiant V-Neck Lace Bodycon Mini Dress

    This sleeveless lace mini dress features a flattering ruffle trim V-neckline, spaghetti straps, and a bodycon silhouette perfect for a date or brunch.

    Fit & Features

    • Lace-lined fabric
    • Ruffle trim V-neckline
    • Spaghetti straps
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3534

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale