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.

  • Oops I Slayed Again Denim Micro Skort

    Low rise, high key hot. This denim micro skort gives Y2K it-girl vibes with built-in shorts that keep up when you’re dancing at concerts or backyard parties!

    Fit & Features

    • Acid wash denim fabric, stretchy knit shorts lining
    • Low-rise waist
    • Bodycon fit
    • Micro mini-length hem
    • Front button and hidden zipper closure
    • Belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000082

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: LIGHT, DENIM

    Available Size: M, L

  • Dreaming Of You Floral A-Line Midi Dress

    You'll be dreaming of outdoor events and parties to wear this floral midi dress to! It's designed with dainty trim accents along the bodice and a flowy A-line silhouette.

    Fit & Features

    • Dainty floral print, woven fabric, stretchy knit lining
    • Square neckline, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Dainty trim accents in the bodice
    • Drop waist seam
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4023

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool In Camo Mid-Rise Denim Skirt

    Cool in camo, this mid-rise mini skirt is designed with a bodycon fit that flatters your figure while the frayed mini length hem adds an edgy touch!

    Fit & Features

    • Camouflage print, denim fabric, slight stretch
    • Mid-rise waist
    • Bodycon fit
    • Frayed mini-length hem
    • Front button and hidden zipper closure, belt loops
    • Two front pockets, two back flap pockets with button closures
    • Runs true to size

    Style Number/Barcode: 06601-0242

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: S, M, L

  • Here For Admiration Corset Lace-Up Eyelet Skater Dress

    Be prepared for much admiration when you're in this eyelet skater dress designed with the prettiest corset bodice and lace-up back that turns heads! Perfect for shower celebrations, graduations, and brunch.

    Fit & Features

    • Eyelet fabric, tulle and woven linings
    • Sweetheart neckline, bust tie, underwire bust, spaghetti strap ties
    • Lace-up back, side zipper and hook-eye closure
    • Corset bodice, flexible boning inserts
    • Drop waist seam with ruffle trim
    • Skater silhouette, short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3946

    Category Name: Vacation Looks

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Babe Tinted Denim Overalls

    The perfect pair of tinted denim overalls for a casual everyday vibe. Style with a graphic tee and sneakers.

    Fit & Features

    • Tinted denim fabric, no stretch
    • Sleeveless square neckline, bib pocket
    • Tank strap with adjustable buckles, racerback design
    • Mid-rise waist, belt loops, buttoned sides
    • Dual front and back pockets
    • Straight-leg silhouette, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06602-0574

    Category Name: Vacation Looks

    Price: $24.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MEDIUM, DENIM

    Available Size: L

    Product Badge:
    • Sale
  • Tea Time Corset Lace-Up Floral Skater Dress

    It's time to spill the tea at the garden party in this chic floral skater dress with a pretty corset bodice that snatches your waist and a lace-up back that turns heads!

    Fit & Features

    • Floral print, poplin woven lined lace trim fabric
    • Square neckline, lace trim, underwire bust, wide shoulder straps
    • Corset bodice, flexible boning, lace trim, lace-up back
    • Drop waist seam
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3923

    Category Name: Vacation Looks

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Main Stage Energy Fringe Denim Shorts

    Built for the spotlight and made to move—these denim shorts bring big fringe energy. The high-rise waist snatches your silhouette while the side fringe brings the drama.

    Fit & Features

    • Denim fabric
    • High-rise waist
    • Five-pocket and belt loop design
    • Front button closure
    • Side fringe detailing
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-000064

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: MEDIUM, DENIM

    Available Size: S, M, L

  • Super Star Mid-Rise Denim Shorts

    Creating trendy looks is easy with these mid-rise denim shorts with a head-turning star back design and a cut-off hem for a touch of edge!

    Fit & Features

    • Light wash denim fabric
    • Mid-rise waist
    • Star back design
    • Front seam details
    • Cut-off hem
    • Runs true to size

    Style Number/Barcode: 06603-000027

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: LIGHT, DENIM

    Available Size: L, XL

  • Daydream Date Bow-Front Skater Dress

    Giving total daydream vibes with a flirty twist. The bow-front detail and breezy skater silhouette make this short dress perfect for brunch, strolls, or spontaneous golden-hour photo ops.

    Fit & Features

    • Satin woven fabric, scenic print
    • Sleeveless V-neckline, bow-front detail
    • Adjustable spaghetti straps, smocked back
    • High-rise waist
    • Short skater silhouette, striped hem
    • Runs true to size

    Style Number/Barcode: 05102-000306

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

  • Stylish Day Out Straw Clutch Purse

    Whatever your destination, have a stylish day out accessorizing with this straw clutch purse featuring a detachable chain shoulder strap, a front flap, and a spacious interior for your essentials. Complete the look in a summer dress and sandals!

    Fit & Features

    • Detachable chain shoulder strap
    • Front flap 
    • Spacious interior, two pockets
    • Straw material

    Style Number/Barcode: 07203-2015

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stand And Deliver High-Rise Pocket Denim Skort

    Stand and deliver style in this denim mini skort perfect for casual plans! The high-rise waist and form-hugging fit will accentuate your curves, while the front skirt overlay with flap pockets adds a touch of flair. Plus, the shorts lining with back pockets provide convenience and comfort. Complete the look in a basic tee and boots!

    Fit & Features

    • Denim fabric, no stretch
    • High rise waist
    • Front button and hidden zipper closure
    • Four-pocket styling
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0402

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Life Rhinestone Strappy Faux Leather Sandals

    Live that fabulous glam life in these rhinestone strappy sandals perfect for adding that casual glitz to your looks! Made with a patent faux leather material, these sandals have a stylish sheen for that extra flair. The open square-shaped toe is followed by a thin strappy banded design with iridescent mini rhinestone embellishments for the prettiest sparkle. The open back and flat sole offer effortless on-and-off styling. Pair these sandals with a cute handbag.

    Fit & Features

    • Patent faux leather material
    • Open square toe
    • Thin strappy banded design
    • Iridescent mini rhinestones
    • Open back, flat sole
    • On-and-off styling
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1152

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Beauty Seashell Charm Anklet Set

    Create a coastal chic look radiating effortlessly glam vibes with this beachy anklet set! It features three dainty anklets including a small chain-link design, a beaded chain-link design, and a trendy paperclip chain accented with rhinestones, faux pearls, and seashell charms. Style with strappy sandals.

    Fit & Features

    • Three-pack anklet set
    • Small chain
    • Beaded chain
    • Paperclip chain with rhinestones, faux pearls, and seashell charms
    • Back adjustable chains, lobster clasp closures

    Style Number/Barcode: 07003-0556

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Cherry Charm Necklace

    Make your look sweet for summer with this cherry charm necklace featuring a delicate chain with a lobster clasp closure. Style this necklace with a summer dress for a backyard BBQ or carnival!

    Fit & Features

    • Cherry charm
    • Delicate chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-1806

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian-Chic Geometric Striped Halter Maxi Dress

    Channel a bohemian chic vibe with this breezy halter maxi dress perfect for summer. The lightweight woven fabric showcases a geometric striped print in stylish neutral hues. The long dress features a sleeveless plunging V-neckline, halter spaghetti straps that can be crossed in the front for a trendy look, and a tie-back design at the neck. The alluring open back leads to lower tie-back straps and a lower cutout accent. You'll love the hidden side pockets and high side slit on the effortless, flowy silhouette. Complete the look with strappy sandals.

    Fit & Features

    • Geometric striped print
    • Woven fabric, no stretch
    • Plunge V-neckline, halter spaghetti straps, tie-back design
    • Open back, lower tie-back straps, lower cutout
    • Side pockets
    • Side slit, flowy fit
    • Runs true to size

    Style Number/Barcode: 05102-5842

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Has Sprung Floral Woven Skater Dress

    Let your beauty bloom in this adorable floral woven skater dress! The lightweight lined woven fabric is accented with a dainty floral print for the sweetest allure. The short dress features a sleeveless sweetheart neckline with a padded bust and structured underwire for support. The corset-style bodice will snatch your waist and highlight your bust with a tie-front detail. The thin smocked shoulder straps lead to a smocked back design for added stretch with a zipper closure. The high waist flows out to a short skater skirt with a trendy bubble hem and a fit and flare silhouette. Pair with platform heels for the cutest party look!

    Fit & Features

    • Floral woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline, padded bust with underwire
    • Thin tank shoulder straps
    • Smocked back design, zipper and hook and eye closure
    • Corset bodice, tie-front detail, high waist seam
    • Short skater skirt with bubble hem, fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3187

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Instantly Chic Oversized Square Sunglasses

    These fabulous shades will instantly elevate your look and make it all the more chic! The sunglasses feature an oversized square slightly angled design, a sleek plastic frame and arms, built-in nose pads for support, and tinted lenses. Style with classic hoop earrings.

    Fit & Features

    • Oversized square-shaped design
    • Plastic frame and arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1082

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Rad Flat Top Rectangle Sunglasses

    Unlock a rad and cool vibe in these cute sunglasses! They feature a trendy flat top design, rectangular plastic frames, and tinted lenses to help protect your eyes from the sun. Complete the look with sleek hoop earrings for any occasion!

    Fit & Features

    • Flat top
    • Rectangular plastic frames
    • Tinted lenses

    Style Number/Barcode: 07008-1084

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Perfection Striped Crochet Straw Bucket Hat

    Create perfect summertime 'fits with this striped crochet straw bucket hat! Made with lightweight crochet straw material, this adorable hat features natural and green hues woven together to create the cutest striped pattern. Offers a flexible brim for effortless styling. Pair this bucket hat with a breezy crochet dress and lace-up sandals!

    Fit & Features

    • Crochet straw material
    • Striped woven design
    • Flexible brim

    Style Number/Barcode: 07302-1551

    Category Name: Vacation Looks

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Getaway Sleeveless Nylon Cargo Jumpsuit

    This sleek nylon cargo jumpsuit is essential for your next casual getaway! Designed with a lightweight smooth nylon-blend fabric, it features a square neckline with adjustable spaghetti straps for a customized fit. The high waist is detailed with belt loops and a faux button accent, leading to multiple pockets down the leg for a trendy design. The hem features adjustable drawcords to create a cinched jogger silhouette. Style this jumpsuit with strappy sandals.

    Fit & Features

    • Smooth nylon-blend woven fabric, no stretch
    • Sleeveless square neckline with adjustable spaghetti straps
    • High waist with belt loops and faux front button
    • Hidden back zipper
    • Dual front pockets, dual faux back pockets, cargo side pockets
    • Relaxed silhouette, adjustable drawcords at the hem
    • Runs true to size

    Style Number/Barcode: 06302-0816

    Category Name: Vacation Looks

    Price: $11.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Icon Chain-Link Rectangle Sunglasses

    Give off major cool girl vibes in these chain-link rectangle sunglasses. They feature a trendy rectangular-shaped design with a sleek plastic frame, shiny metal arms with a chain-link design, built-in nose pads for support, and tinted lenses. Style these iconic sunnies with hoop earrings.

    Fit & Features

    • Rectangular-shaped design
    • Plastic frame
    • Metal arms with chain-link design
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1074

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Nice Gal Beaded Straw Cowboy Hat

    Tip this straw cowboy hat looking like the nicest gal around town! Featuring a beaded faux leather band with a string bow tie, this hat adds a boho chic look. The curved wide brim not only provides stylish sun protection but also adds a playful flair. Made with straw material and an elasticized inner band for a comfortable and secure fit. Complete the look in cowboy boots.

    Fit & Features

    • Straw material
    • beaded faux leather band with string bow tie
    • Curved wide brim
    • Inner elasticized band for a snug fit

    Style Number/Barcode: 07302-1645

    Category Name: Vacation Looks

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miss America Baseball Cap

    Show your patriotic spirit in this cute and trendy baseball cap featuring a curved wide brim to help shade your eyes, a front embroidery that reads "Miss America" and an adjustable back strap for a snug fit. Complete the look in a denim romper for a backyard BBQ.

    Fit & Features

    • Curved wide brim
    • Front embroidery that reads "Miss America"
    • Adjustable back strap

    Style Number/Barcode: 07302-1639

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Staple Linen Strap Espadrille Wedges

    A chic summer staple, these linen strap espadrille wedges will elevate your summer 'fits! They feature an open almond-shaped toe with a wide linen toe strap, linen criss-cross adjustable ankle straps, an espadrille heel strap, and a tall espadrille wedge heel to give you that stylish height with a comfortable fit. Pair with a flowy skater dress!

    Fit & Features

    • 5" Espadrille wedge heel
    • Open almond toe
    • Wide linen toe strap
    • Linen criss-cross adjustable ankle straps
    • Espadrille heel strap
    • Runs true to size

    Style Number/Barcode: 07406-0348

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale