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.

  • Sunny POV Tropical Print Jumpsuit

    Get in the sunny state of mind with this tropical printed jumpsuit featuring a deep V-neckline, tie-back halter straps, and a wide-leg silhouette.

    Fit & Features

    • Knit fabric, high stretch
    • Tropical print
    • Sleeveless deep V-neckline
    • Tie-back halter straps, open back
    • High waist seam, ruched sides
    • Hip-hugging fit, wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000014

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: RUST

    Available Size: XS, S, M, L

  • Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress

    Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.

    Fit & Features

    • Eyelet fabric lined with stretchy knit
    • Sweetheart neckline
    • Adjustable bust drawstring, cutout
    • Skater silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5430

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Twist Cutout Knit Midi Dress

    Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Knit fabric, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • Twist back cutout
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1950

    Category Name: Vacation Looks

    Price: $17.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Like A Dream High-Rise Ponte Skort

    Make weekend styling simple with this ponte skort! Designed with a flattering high-rise waist and sleek side slits, this form-hugging skort offers both comfort and a chic silhouette. 

    Fit & Features

    • Ponte fabric, moderate stretch
    • High-rise waist
    • Side slits
    • Form-hugging fit
    • Skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000065

    Category Name: Vacation Looks

    Price: $27.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Best Seller
  • Artsy Scene Mock Neck Abstract Mini Dress

    Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5630

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Legendary Style Western Buckle Faux Leather Sandals

    It's impossible not to make an iconic fashion statement in these faux leather sandals! Featuring a sleek square toe, a flat sole, and a Western-inspired buckle along the strap for added flair. Complete the look with a trendy denim jacket.

    Fit & Features

    • Square toe
    • Flat sole
    • Western-inspired buckle on strap
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1239

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Link Up Luxe Lariat Statement Necklace

    Not just jewelry—this one’s a full style statement. With oversized links and a sculptural drop detail, this lariat chain adds instant edge to blazers, bustiers, or strapless looks.

    Fit & Features

    • Bold oversized chain links
    • Drop lariat silhouette with center dangle link
    • Adjustable lobster clasp

    Style Number/Barcode: 07002-000022

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Done In One Ribbed Knit Bodycon Midi Dress

    Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

    Fit & Features

    • Ribbed knit fabric, sewn-in knit lining, moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5666

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dazzle Me Rhinestone Square Toe Sandals

    Bring a dazzling aura in these square toe sandals embellished with sparkling rhinestones, perfect for day or night.

    Fit & Features

    • Square toe
    • Rhinestone-embellished strap
    • Fat sole with rhinestone-embellished trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000034

    Category Name: Vacation Looks

    Price: $20.90

    Availability: In Stock

    Available Color: SILVER

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

  • Girlycore Off-The-Shoulder Ruffled Skater Dress

    Embrace a girly-core coquette aesthetic in this skater dress perfect for sunny days! The sweetheart neckline and cutout waist add a flirty touch, while the stretchy smocked bodice hugs your curves, and the ruffled tier short-length hem adds a feminine flair. Complete the look in wedge sandals.

    Fit & Features

    • Airy woven fabric with lining
    • Stretchy smocked bodice with bust tie
    • Cutout waist
    • Ruffled tier skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3054

    Category Name: Vacation Looks

    Price: $10.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Glam To Care Oversized Braid Sunglasses

    These oversized sunglasses with braided arms bring instant luxe vibes. Whether you’re blocking out the sun or the shade, they’ve got your back in style.

    Fit & Features

    • Oversized sleek frames
    • Braided detail on the arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000061

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

  • Cherry On Top Lace Trim V-Neck Mesh Mini Dress

    This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.

    Fit & Features

    • Cherry print, mesh fabric, stretchy knit lining
    • Lace trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5798

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knot Your Basic Flyaway Tube Top

    Giving effortless cool with a twist—literally. With a twist front and flyaway design, this ribbed knit tube top is your not-so-basic basic, perfect for rooftop drinks and summer dates.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Strapless sweetheart neckline
    • Twist-front bust detail
    • Front fly-away design
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000041

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: WHITE, BLUE

    Available Size: S, M, L, XS

  • Pick Me Halter Floral Eyelet Crop Top

    Pick this floral crop top for the sweetest look! This halter crop top features a flattering V-neckline with a spaghetti strap tie for a perfect fit, while a sweet bow detail adds a touch of charm. The fitted crop hem and floral printed eyelet fabric give off a playful, summertime vibe. Complete the look in high-rise jeans for any casual plans!

    Fit & Features

    • Floral printed eyelet fabric, minimal stretch
    • Halter V-neckline, spaghetti strap tie
    • Bow along the bust
    • Fitted crop length
    • Runs true to size

    Style Number/Barcode: 06001-5365

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Highly Favored Triangle Rhinestone Lariat Necklace

    This lariat necklace will be highly favored over the rest! It features a dainty chain adorned with rhinestone charms leading to a sleek triangle charm with rhinestone trim and a single fringe chain with a rhinestone. Complete the look in a sultry cocktail dress for a rehearsal dinner or reception!

    Fit & Features

    • Dainy chain lariat necklace
    • Rhinestone charms
    • Triangle charm with rhinestone trim
    • Single fringe chain with rhinestone
    • Lobster clasp closure

    Style Number/Barcode: 07002-1872

    Category Name: Vacation Looks

    Price: $2.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Yoga And Tequila Graphic Halter Top

    Balance is hot girl behavior. This graphic top says namaste, then time for shots. Stretchy enough for yoga, spicy enough for last-minute plans, this cheeky top features a halter V-neck and fitted, mid-length hem.

    Fit & Features

    • Knit fabric, moderate stretch
    • Sleeveless V-neckline
    • Halter strap, partially open back
    • Front script that reads, "I do yoga & drink tequila"
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06002-000163

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

  • Confident Flirty Strappy One-Shoulder Crop Top

    Make your crush stop and stare at you in this sleeveless crop top! It boasts a flirty strappy one-shoulder neckline, and a fitted crop hem, and is made from a stretchy rib knit fabric. Complete the look in a denim mini skirt for any casual plans!

    Fit & Features

    • Stretchy rib knit fabric
    • Strappy one-shoulder neckline
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1878

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun Soaked Espadrille Strappy Wedges

    Step into sunny style with these espadrille wedges in a strappy design that elevates any look! 

    Fit & Features

    • Wedge heel
    • Square toe
    • Criss cross straps
    • Closed ankle, back zipper closure
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000011

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

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

  • Fall Into Fashion Crew Neck Open Back Maxi Dress

    You'll be the cutest thing around in this sleeveless maxi dress all season! With its sleek crew neckline, alluring strappy open back, and flattering form-hugging fit, this dress is both stylish and versatile. Complete with a side slit and maxi-length hem, it's the perfect piece for any occasion. Style this maxi dress with earrings and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Strappy open back
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5654

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt In Full Bloom Lace Halter Top

    A little sheer, a little sweet—this lace halter brings all the romance with a ring-front detail and breezy flyaway silhouette. Pair with denim or maxi skirts for your next IG-worthy moment.

    Fit & Features

    • Lace fabric, bust knit lining
    • Halter neckline, spaghetti strap ties
    • Hoop insert
    • Center split design
    • Sheer cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000161

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Vacay Ready Tropical Knit Wide-Leg Pants

    These alluring tropical wide-leg pants will have you ready for a dreamy vacay! The stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The pants are shaped with a high-rise elasticized waistband for comfortable wear and a relaxed wide-leg silhouette for a trendy look. Style with the matching crop top and hoop earrings.

    Shop Matching Top: Vacay Ready Tropical Knit Halter Crop Top

    Fit & Features

    • Abstract tropical print
    • Stretchy knit
    • High elasticized waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2481

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Crush Striped Crochet Midi Skirt

    POV: you just found your new fave beach-to-brunch vibe. This striped crochet midi skirt serves laid-back heat with a form-hugging fit and thigh-high slit made for turning heads from sunrise to sunset.

    Shop Matching Top: Summer Crush Striped Crochet Bralette Top

    Fit & Features

    • Crochet knit fabric
    • Striped pattern
    • High-rise waist
    • Thigh-high side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000027

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Much Love Sweetheart Swiss Dot Mesh Mini Dress

    It's too easy to fall for this flirty swiss dot mesh mini dress perfect for soirees! The sweetheart neckline and padded bra cups provide a flattering fit, while the adjustable spaghetti straps and dual front ruched drawstrings allow for a customizable look. The bodycon fit and mini-length hem showcase your figure, all in a beautiful swiss dot mesh fabric. Complete the look in sandals.

    Fit & Features

    • Swiss dot mesh fabric, sewn-in knit lining, stretchy
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Padded bra cups
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3253

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale