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.

  • Work Your Angles Chunky Platform Heels

    These faux leather heels work every angle for your feet! They feature a square toe, wide toe strap, an ankle strap with buckle closure, a platform sole, and a square-shaped chunky block heel. Style with a mini tote bag to complete the fab look!

    Fit & Fetaures

    • Square toe
    • Wide toe strap
    • Ankle strap, buckle closure
    • Square-shaped chunky block heel
    • Platform sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4132

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Next Level Luxe Rhinestone Strap Wedges

    Step out to impress in these luxe cork wedges perfect for sunset wine tastings to dinner out with the girls! They feature an almond toe, rhinestone embellished toe and ankle strap, and a cork platform sole. Complete the look with sparkly rhinestone earrings.

    Fit & Features

    • Almond toe
    • Rhinestone embellished toe and ankle strap
    • Cork platform sole
    • Runs true to size

    Style Number/Barcode: 07406-0327

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Silhouette Scoop Neck Tank Top

    This smooth basic tank top will be a staple in your wardrobe! The crop top features a sleeveless scoop neckline, comfortable tank shoulder straps, a racerback design, and a form-hugging fit. The double-lined stretchy knit fabric offers a seamless design and has an ultra-soft buttery feel. Style with best-selling bottoms and clear heels for a chic look!

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Racerback design
    • Form-hugging fit
    • Double-lined, buttery knit fabric
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 06002-1578

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Moment A-Line Mini Dress

    Step out in this iconic little black dress for many chic moments of the night! The dress features a sleeveless V-neckline, spaghetti straps, a flattering A-line silhouette, and a mini-length hem on slinky knit fabric. Complete the look in lace-up heels for a date night!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • A-line silhouette
    • Mini-length hem
    • Slinky knit fabric, knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5066

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Butterfly Kisses Rhinestone Mini Dress

    Every heart will flutter with your winged beauty! This rib knit mini dress features a sleeveless scoop neck, spaghetti straps, a rhinestone butterfly design, and a bodycon silhouette. Complete the look in cute sandals for a casual party or lunch!

    Fit & Features

    • Sleeveless scoop neck
    • Spaghetti straps
    • Rhinestone butterfly design
    • Bodycon silhouette
    • Mini-length hem
    • Soft rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4944

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Fly Butterfly Rhinestone Earrings

    You'll be feeling fly all night with these shimmering butterfly earrings featuring mini rhinestone embellishments and a post-back closure. Style with glam platform heels to complete your semi-formal or special occasion look!

    Fit & Features

    • Butterfly earrings
    • Mini rhinestone embellishments
    • Post-back closure

     

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

    Style Number/Barcode: 07001-1632

    Category Name: Vacation Looks

    Price: $2.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glitzy Trendsetter Rhinestone Body Chain

    Earn your status as a glitzy trendsetter with this glam rhinestone body chain! It features a choker leading to a lariat and a double-layered design with sparkling rhinestone embellishments. Includes back adjustable chains and lobster clasp closures. Style over a crop top or a mini dress for a festival vibe!

    Fit & Features

    • Choker
    • Lariat
    • Double-layered design
    • Rhinestone embellishments
    • Back adjustable chains, lobster clasp closures

    Style Number/Barcode: 07002-1511

    Category Name: Vacation Looks

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fashionably Late Chiffon Lattice Top

    Whatever you're late for, look fashionable in this sheer chiffon top to elevate your fit! It features long flared sleeves, a collared V-neckline, and a lattice front design with a split flowy hem. Complete the look in distressed jeans and mules.

    Fit & Fetaures

    • Long flared sleeves
    • Collared V-neckline
    • Lattice front design
    • Split flowy hem
    • Sheer chiffon fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2113

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Looking Like A Day Dream Eyelet Lace Dress

    Look like a daydream come true in this eyelet lace mini dress for your next date! It features adorable puff sleeves with ruffle trim, a sweetheart neck, a ruched bust seam, and a bodycon silhouette with a flirty tiered ruffle hem. Complete the look in cute stiletto heels.

    Fit & Features

    • Puff short sleeves, ruffle trim
    • Sweetheart neck
    • Ruched bust seam
    • Bodycon silhouette
    • Tiered ruffle mini-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2184

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raise The Bar Strappy Block Heel Mules

    Raise the bar for everyone when you step out in these eye-catching faux leather mules! They feature a square toe, a strappy design, and a thin block heel. Style with a flirty sundress for a graduation or birthday brunch!

    Fit & Features

    • Square toe
    • Strappy design
    • Thin block heel
    • Faux leather material, subtle cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4403

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Many Admirers Linen Wrap Midi Skirt

    You'll have many admirers when they see you in this linen midi skirt on a weekend getaway! It features a flattering high-rise waist, a hip-hugging fit, a ruched side seam, and a wrap-style hem that creates a flirty front slit. The skirt is composed of a linen-blend woven fabric with a sewn-in knit lining and slight stretch. Complete the look in a sultry bustier and sandals.

    Fit & Features

    • High-rise waist
    • Side zipper and hook-eye closure
    • Hip-hugging fit
    • Front slit accent
    • Wrap-style midi-length hem
    • Linen-blend fabric, sewn-in knit lining, slight stretch
    • Runs true to size

    Style Number/Barcode: 06301-0156

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Call Of The Wild Satin Zebra Bandeau Top

    Answer the call of the wild in this fierce satin zebra printed top for a sultry vacay look! It features a sleeveless halter neckline with a tie-neck closure, a bandeau-style silhouette, and an elasticized cinched back band. The sleek satin woven fabric features a trendy zebra print pattern. Style with the matching midi skirt.

    Shop Matching Bottoms: Call Of The Wild Satin Zebra Midi Skirt

    Fit & Features

    • Sleeveless halter neckline, tie closure
    • Bandeau-style silhouette
    • Elasticized cinched back band
    • Zebra print
    • Lined satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2131

    Category Name: Vacation Looks

    Price: $3.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Paradise Strappy Cutout Maxi Dress

    You'll be pretty in paradise in this stunning maxi dress for vacation or a bachelorette weekend! The dress features a sleeveless V-neckline, spaghetti straps that lace up along the open back, flirty waist cutouts, and a high front slit along the flowy hem. Complete the look with earrings and clear block heels for a chic style!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Lace-up open back
    • Waist cutouts, high front slit
    • Maxi-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4752

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cue The Charm Linen Off-The-Shoulder Dress

    This linen skater dress cues the charm you'll be bringing to wine tasting with the ladies or a birthday brunch! It features a cute off-the-shoulder ruffle trim neckline with elasticized short-sleeve cuffs, a tie-waist belt, and a flattering short-length tiered ruffle hem. Complete the look with a dainty tennis bracelet and sandals.

    Fit & Features

    • Off-the-shoulder ruffle trim neckline
    • Elasticized short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Tie-waist belt
    • Skater silhouette, short-length tiered ruffle hem
    • Linen fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2341

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Funky Fresh Swirl Mesh Mini Skirt

    You'll be funky and fresh in this retro-inspired swirl print mini skirt perfect for a backyard bash or birthday party! It features a high-rise waist, bodycon fit, and a flirty side slit. Complete the look with matching top and lace-up heels.

    Shop Matching Top: Funky Fresh Swirl Mesh Crop Top

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Slit accent, mini-length hem
    • Swirl print
    • Partially lined mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0801

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Style Muse Boho Print Flare Pants

    You'll be such a summer style muse in these trendy boho-chic printed flare pants. They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the leg, a flared hem, and a bohemian-inspired multi-print pattern. Complete the look with a crop top and sandals.

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Form-hugging fit throughout the leg
    • Flared hem
    • Multi-print pattern
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-0904

    Category Name: Vacation Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Made You Marvel Straw Tassel Crossbody Bag

    One look at this metallic straw crossbody bag and you'll definitely be marveling! It features a stylish envelope front flap with a snap-button closure and fringe tassel, a detachable chain strap, and a spacious lined interior for keeping your must-haves in. Complete the look in trendy platform wedges for a graduation ceremony or semi-formal party!

    Fit & Features

    • Envelope front flap, snap-button closure
    • Fringe tassel
    • Detachable chain strap
    • Spacious lined interior
    • Metallic straw woven material

    Style Number/Barcode: 07203-1130

    Category Name: Vacation Looks

    Price: $11.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seaside Escape Tropical Print Romper

    Pack this cute tropical print romper for your next weekend escape to the coastline! It features a sleeveless square neckline, adjustable spaghetti straps, a tie-back design, an open lower back, a fitted high waist seam, and flowy shorts. The lightweight woven fabric features a tropical palm leaf print. Style with strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Tie-back design, open lower back
    • Fitted high waist seam, elasticized back waistband, flowy shorts
    • Tropical palm leaf print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0291

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Getaway Halter Crop Top

    Style up this lightweight mesh crop top to look like you're ready for an island getaway! It features a sleeveless halter neckline, ruched seams down the front and back, a cropped, form-hugging fit, and an all-over palm leaf print. Style with the matching mini skirt.

    Shop Matching Bottoms: Island Getaway Faux Wrap Mini Skirt

    Fit & Features

    • Sleeveless halter neckline
    • Ruched seams down the front and back
    • Cropped, form-hugging fit
    • Palm leaf print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4009

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Getaway Faux Wrap Mini Skirt

    Style up this lightweight mesh mini skirt to look like you're ready for an island getaway! It features a high-rise waist, ruched side seams, a short, curve-hugging fit with a faux wrap-front design at the hem, and an all-over palm leaf print. Style with the matching crop top.

    Shop Matching Top: Island Getaway Halter Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Ruched side seams
    • Mini-length, form-fitting silhouette, faux wrap-front hem
    • Palm leaf print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0598

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She Knows Style Eyelet Lace Skater Dress

    Breeze into every occasion in this stylish eyelet lace skater dress! It features a sleeveless square neck, spaghetti straps, a ruched bust, and a flattering fit and flare short-length hem. The sheer eyelet lace fabric includes a full knit lining and offers plenty of stretch. Complete the look with statement block heels for a wedding shower or birthday lunch!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Ruched bust
    • Fit and flare, skater silhouette
    • Short-length hem
    • Sheer eyelet lace fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4998

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • '90s Mood Square Frame Sunglasses

    Get in a '90s mood with these trendy sunglasses you've seen all over the gram. They feature a plastic square-shaped frame with tinted lenses. Complete your cool-girl look with large hoop earrings.

    Fit & Features

    • Plastic square-shaped frame
    • Tinted lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0985

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro-Chic Ombre Aviator Sunglasses

    Accessorize your summer 'fits with these retro-chic sunglasses! They feature an aviator design with a thin metal frame and ombre-tinted lenses. Includes rubber nose pads. Style with a halter crop top and printed flare pants.

    Fit & Features

    • Aviator design
    • Thin metal frame
    • Ombre-tinted lenses
    • Rubber nose pads
    • 100% UV Protection

    Style Number/Barcode: 07008-0986

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beach Mode Chiffon Belted Kimono

    Enter into beach mode in this effortlessly chic sheer chiffon kimono perfect for layering over your outfit or swimwear! It features flowy half sleeves, an open front design, a tie-waist belt, side slit accents, and a mid-length hem. Complete the look in trendy denim shorts.

    Fit & Features

    • Flowy half sleeves
    • Open front design
    • Tie-waist belt
    • Side slit accents
    • Mid-length hem
    • Sheer chiffon fabric
    • Runs true to size

    Style Number/Barcode: 06204-1576

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance