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.

  • Abstract Chic Straight-Leg Pants

    Showcase your artsy side in these abstract chic straight-leg pants! They feature a high-rise banded waist, a hip-hugging fit, a straight-leg silhouette, and an all-over multi-colored swirl print pattern. Style with the matching crop top for a bold allure. 

    Shop Matching Top: Abstract Chic Twist-Front Crop Top

    Fit & Features

    • High-rise banded waist
    • Hip-hugging fit
    • Straight-leg silhouette
    • Multi-colored abstract swirl print
    • Knit slinky fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2364

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Finders Keepers Tie Dye Mini Dress

    Lucky you to have found this tie-dye mini dress! Perfect for summer fun, this sleeveless dress features a square neckline, spaghetti straps, adjustable side drawstrings let you customize the style, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in strappy sandals for a backyard dinner party!

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Adjustable side drawstrings
    • Bodycon silhouette
    • Mini-length hem
    • Unique tie-dye print
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5224

    Category Name: Vacation Looks

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer In Tie Dye Cutout Midi Dress

    Spend your summer in this tie-dye midi dress perfect for backyard dinners to sunset cocktails! It features a sleeveless V-neckline, spaghetti straps, a sexy cutout waist, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in trendy doorknocker earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Cutout waist
    • Bodycon silhouette
    • Midi-length hem
    • Tie-dye print, stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5225

    Category Name: Vacation Looks

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meet Your Match Bandage Crop Top

    Meet your match! This bandage crop top is the style you'll be obsessed with all season. It features a sleeveless plunge V-neckline, tank shoulder straps, a square low-cut back, and underbust seam detail. The crop top is designed from a bandage-seamless knit fabric that fits like a glove. Complete the look with the matching bottoms for a Miami vacation or club night!

    Shop Matching Bottoms: Meet Your Match Bandage Midi Skirt

    Fit & Features

    • Sleeveless plunge V-neckline
    • Tank shoulder straps
    • Square low-cut back
    • Underbust seam detail
    • Cropped hem
    • Bandage-seamless knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1723

    Category Name: Vacation Looks

    Price: $3.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meet Your Match Bandage Midi Skirt

    Meet your match! This bandage midi skirt is the style you'll be obsessed with all season. It features a flattering high-rise waist, bodycon silhouette, center-back slit accent, and a midi-length hem. The midi skirt is designed from a bandage-seamless knit fabric that fits like a glove. Complete the look with the matching top for a Miami vacation or club night!

    Shop Matching Top: Meet Your Match Bandage Crop Top

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Center back slit accent
    • Back zipper and hook-eye closure
    • Midi-length hem
    • Bandage-seamless knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0865

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fierce And Fine Satin Leopard Midi Dress

    Fierce, fine, and looking flawless in this satin leopard midi dress! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust, and a relaxed slim silhouette. Complete the look with a dainty bracelet and strappy heels for a birthday lunch!

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Knotted bust
    • Relaxed slim silhouette
    • Midi-length hem
    • Leopard print, smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5120

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine Lover Crochet Maxi Coverup

    All you need is the sunshine and this crochet maxi coverup for the perfect beach-day vibe! Features a sleeveless, crew neck, form-fitting silhouette, and a sexy side slit. Complete the look in a bikini set and sunglasses.

    Fit & Features

    • Sleeveless, crew neck
    • Form-fitting silhouette
    • Side slit
    • Maxi-length hem
    • Diamond crochet knit pattern
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06005-1435

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fashion Reputation Chiffon Tie-Back Crop Top

    You've got a fashion reputation to uphold and this chiffon crop top will keep you in check! It features breezy sheer peasant long sleeves, a V-neckline with non-slip grip lining, a ruched bust, and a wrap-style hem with tie-back closure. Complete the look in high-rise skinny pants for a dinner party!

    Fit & Features

    • Sheer peasant long sleeves
    • V-neckline, non-slip grip lining
    • Ruched bust
    • Wrap-style cropped hem
    • Tie-back closure
    • Chiffon fabric, bust lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2200

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Definite Yes High Slit Maxi Dress

    This sleek high slit maxi dress is a definite yes for leveling up your casual looks! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem with a thigh-high front slit to showcase some leg, and a slim-fit silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy sandals for a lunch date! 

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Maxi-length hem
    • High front slit
    • Slim-fit silhouette
    • Smooth and stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5194

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Girl Rib Knit Cutout Jumpsuit

    For all the girls going on a getaway this rib knit jumpsuit will keep you flawless on the island or European adventure! The jumpsuit features a sleeveless V-neckline, spaghetti straps, a flirty bust knot tie accent, a cutout waist and back design, and a flattering straight-leg silhouette. Complete the look in PVC mules for a seamless-chic style!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Bust knot tie accent
    • Cutout waist and back
    • Straight-leg silhouette
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2340

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Back To Basics Halter Rib Knit Crop Top

    Take your style back to basics with this sleeveless crop top perfect for pairing with your go-to bottoms! It features a halter neckline, spaghetti strap, an exposed underbust seam, and a fitted hem on stretchy rib knit fabric. Complete the look in distressed denim for a casual day out.

    Fit & Features

    • Sleeveless halter neckline
    • Spaghetti strap
    • Exposed underbust seam
    • Fitted crop hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1599

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Rhythm Halter Sweater Midi Dress

    Shimmy to the island rhythm with a cocktail in hand wearing this sweater midi dress for the cutest vacation look! It features a sleeveless halter neckline with wood bead accents, spaghetti straps that shape the open lace-up back design, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in chic wedges.

    Fit & Features

    • Sleeveless halter neckline, wood bead accents
    • Spaghetti straps, open lace-up back design
    • Bodycon silhouette
    • Miid-length hem
    • Sweater rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1698

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfection Vibes Chiffon Skater Romper

    Look like perfection in this chiffon skater romper for a night of fun vibes! It features adorable sheer puff short sleeves, a scoop neckline with a flirty bust tie front and keyhole, a sheer elasticized waist, and a flowy short-length hem. Complete the look in strappy heels for a celebration!

    Fit & Features

    • Sheer puff short sleeves
    • Scoop neckline, front bust tie and keyhole
    • Sheer elasticized waist
    • Skater silhouette
    • Flowy short-length hem
    • Airy chiffon fabric, partial knit stretchy lining
    • Runs true to size

    Style Number/Barcode: 06403-0316

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Romance Floral Chiffon Skater Romper

    Find your summer love in this charming floral chiffon skater romper! It features a square neckline with a dainty tie-front design, short puff sleeves with ruffled trims, dual high waist seams, and a fit and flare silhouette with flowy shorts and a short skater skirt overlay with ruffled hems. The all-over blooming floral print on the airy chiffon fabric is perfect for the season. Style with butterfly charm earrings.

    Fit & Features

    • Square neckline, tie-front design
    • Short puff sleeves, ruffled trims
    • Dual high waist seams, fit and flare silhouette
    • Flowy shorts, short skater skirt overlay, ruffled hems
    • Blooming floral print
    • Sheer chiffon fabric, knit bust lining and skirt lining
    • Runs true to size

    Style Number/Barcode: 06403-0319

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Dreams Linen Tropical Wide Leg Pants

    Your next getaway calls for these linen tropical pants to look stunning on vacay! They feature an elasticized high-rise waist, a flowy wide-leg silhouette, and a palm leaf print on lightweight linen woven fabric. Complete the look in a casual crop top for sipping a marg by the beach!

    Fit & Features

    • High-rise elasticized waist
    • Flowy wide-leg silhouette
    • Palm leaf tropical print
    • Lightweight linen woven fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06302-0776

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Style Strappy Back Midi Dress

    Simple yet so alluring, you'll love the sultry style of this strappy back midi dress. It features a sleeveless V-neckline, spaghetti straps that lead to an open back with cross-back lace-up straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Complete your look with clear heels and a chic handbag.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Open back, cross-back lace-up straps, tie closure
    • Midi-length hem
    • Bodycon silhouette
    • Ribbed knit fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4835

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stand Out Marble Print Cutout Midi Dress

    Stand out this season and have all eyes on you in this marble print midi dress perfect for weekend getaways or sunset cocktails! The dress features a sleeveless square neck, spaghetti straps, a cutout bodice, and side ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker necklace.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cutout bodice
    • Side ruched seams, bodycon silhouette
    • Midi-length 
    • Marble print, smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5235

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living In Color Chiffon Halter Maxi Dress

    Live life in color! Easy and breezy, this chiffon maxi dress is perfect for all of your summer activities. It features a sleeveless halter V-neckline, a unique braided neck strap with tie closure, a stretchy smocked back, and a flowy silhouette. The dress is designed with an airy chiffon fabric showcasing a watercolor print and a woven lining. Complete the look with a sleek arm cuff bracelet.

    Fit & Features

    • Sleeveless halter V-neckline
    • Braided neck strap, tie closure
    • Stretchy smocked back
    • Flowy silhouette
    • Maxi-length hem
    • Airy chiffon fabric, watercolor print, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5269

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Simple Smooth Knit Mini Dress

    This chic and simple smooth knit mini dress is the elevated basic you need! It features a sleeveless mock neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The buttery-soft and smooth double-lined knit fabric offers plenty of stretch. Style with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Mini-length hem
    • Bodycon silhouette
    • Soft and smooth double-lined knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5198

    Category Name: Vacation Looks

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss. Fashion Strapless Marble Print Mini Dress

    They'll call you Miss. Fashion when you step out in this mesh mini dress! It features a strapless neckline, a bodycon silhouette, an adjustable side drawstring that lets you customize the style, a slit accent, and an asymmetrical hem. Style with lucite heels for a seamless-chic look!

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Adjustable side drawstring, slit accent
    • Asymmetrical mini-length hem
    • Marble print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5268

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Cute Things Layered Charm Neckalce

    Adorn your look with all the cute things this Y2K layered necklace has to offer! It features a three-layered design, one beaded heart charm layer, one dainty chain butterfly charm layer, and one dainty chain flower charm layer. Complete the look with statement earrings for a party!

    Fit & Features

    • Three-layered necklace design
    • One beaded heart charm layer
    • One dainty chain butterfly charm layer
    • One dainty chain flower charm layer
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07002-1508

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Free Wanderer Butterfly Lariat Necklace

    Enchant your vacation outfits with this lovely lariat necklace to bring those wanderlust vibes! It features a choker chain with an attached dainty chain with a rhinestone butterfly charm. Complete the look in sleek hoop earrings.

    Fit & Features

    • Choker chain
    • Attached dainty lariat chain
    • Rhinestone butterfly charm

    Style Number/Barcode: 07002-1509

    Category Name: Vacation Looks

    Price: $2.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Art Of Style Abstract Print Midi Dress

    Show everyone how it's done! This sleeveless midi dress features a square neck, spaghetti straps, a side ruched seam that accentuates your curves along the bodycon silhouette, and a high side asymmetrical slit. The dress is designed with an artsy abstract print on smooth knit fabric. Complete the look with earrings for an art gallery opening!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Side ruched seam, bodycon silhouette
    • High side asymmetrical slit
    • Midi-length hem
    • Abstract print, smooth knit fabric, moderate stretch
    • Bust lining
    • Runs true to size

    Style Number/Barcode: 05102-5206

    Category Name: Vacation Looks

    Price: $5.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Remy High-Rise Frayed Hem Denim Shorts by Windsor Denim

    Level up your casual summer outfits with the Remy frayed hem denim shorts by Windsor Denim. They feature a high-rise waist, a color-faded design for a vintage look, and a cute frayed hem with side slit accents. Includes a five-pocket and belt loop design. Style with a basic bodysuit and slip-on sandals.

    Fit & Features

    • High-rise waist
    • Color-faded design
    • Frayed hem, side slit accents
    • Five-pocket and belt loop design
    • Button-front and hidden zipper closure
    • Denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06603-0341

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free