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.

  • Bold Muse Floral Print Tube Top

    Serve fab vibes on vacay in this cropped tube top featuring a bold floral print pattern. Style with the matching maxi skirt for an iconic 'fit.

    Shop Matching Bottoms: Bold Muse Floral Print Maxi Skirt

    Fit & Features

    • Smooth knit fabric, high stretch
    • Large floral print
    • Strapless straight-across neckline
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-000139

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: M, L

    Product Badge:
    • Sale
  • Casual And Chill Plaid Shacket

    Keep it casual and chill with a shacket that brings those girl-next-door vibes. The shacket features a plaid print, a multi-button down front, two chest pockets, long sleeves with a single-button cuff, and a longline length with a rounded hem. The shacket is composed of a soft faux wool fabric that offers a relaxed fit with a minimal stretch. Complete the look with thigh-high boots.

    Fit & Features

    • Plaid print
    • Collared neckline
    • Long sleeves with button cuff
    • Multi-button down front
    • Two chest pockets
    • Longline length, rounded hem
    • Faux wool fabric, relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06204-1657

    Category Name: Vacation Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Under The Sun Tropical Slit Maxi Skirt

    Perfect for any vacation or resort escape, this tropical maxi skirt boasts a sultry high front slit and a flowy silhouette for a breezy allure. Pair with the matching top.

    Fit & Features

    • Tropical print, stretchy knit fabric, knit panty lining
    • Low-rise waist
    • High front slit
    • Flowy silhouette
    • Maxi-length hem
    • Runs true to size

     

    Shop The Matching Top: Under The Sun Tropical Tie-Front Crop Top

    Style Number/Barcode: 06501-000014

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Better Half Cable Knit One Shoulder Sweater Top

    Wrap up in cozy style with this cable knit sweater top perfect for looking effortlessly cute in the chilly season! It features a one-shoulder neckline, a slouchy long sleeve with ribbed cuffs, a cropped hem, and a soft cable knit design. Complete the look in a faux leather mini skirt and boots for a coffee date.

    Fit & Features

    • One-shoulder neckline
    • Slouchy long sleeve, ribbed cuffs
    • Cropped hem
    • Soft cable knit design
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1746

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Golden Hour High-Rise Cargo Wide-Leg Linen Pants

    Stroll in these linen wide-leg pants during golden hour on vacation or a weekend by the beach! Designed with a high-rise elasticized waistband and linen fabric, these pants are perfect for all-day wear along with convenient cargo flap pockets and a wide-leg silhouette, you'll feel effortlessly chic and ready for anything. Complete the look with the matching vest and sandals.

    Shop Matching Vest: Golden Hour Tie-Front Linen Vest

    Fit & Features

    • Linen fabric lined with stretchy knit
    • High-rise elasticized waistband
    • Cargo flap pockets
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0810

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best Feeling Scoop Neck Cutout A-Line Midi Dress

    There's nothing better than enjoying a sunny day in this scoop neck midi dress! With adjustable straps and a stretchy smocked bodice with a flirty cutout, this dress offers the perfect look for any occasion. The A-line silhouette and midi-length hem add a touch of playful style. Complete the look with dainty earrings and sandals.

    Fit & Features

    • Modal blend woven fabric with lining
    • Adjustable spaghetti straps
    • Scoop neckline
    • Stretchy smocked bodice with cutout
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5718

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss Jetsetter Halter Tie-Back Print Crop Top

    Whether you're jet-setting to your next adventure, meeting friends for brunch, or creating the perfect vacation look, this dual tie-back printed crop top is essential for looking cute on the go! Shop the matching skirt to complete the look.

    Shop Matching Bottoms: Miss Jetsetter High-Rise Print Mini Skort

    Fit & Features

    • Printed design, cotton fabric, bust knit lining
    • Halter V-neckline
    • Dual tie-back details
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000022

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: M, L

    Product Badge:
    • Sale
  • Floral Sensation High Waist Pants

    Keep it sensational in floral pants this season! The pants feature a high-rise waist, a ditsy floral print, and a wide leg hem. Complete look with the matching crop top.

    Shop Matching Crop Top: Floral Sensation Off The Shoulder Top

    Fit & Features

    • High rise waist
    • Wide leg hem
    • Ditsy floral print
    • Form hugging fit
    • Runs true to size 

    Style Number/Barcode: 06502-0608

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Linked Up Dual Chain Link Belt

    Link up with this sassy dual-chain link belt featuring an adjustable lobster clasp closure. Complete the look in denim shorts for any casual occasion!

    Fit & Features

    • Dual chain link belt
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1112

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mystic Pearl Press On Nail Kit

    Mystify your alluring presence with this press on nail kit including everything you need to achieve a whimsical flair. The exclusive kit offers two sets of pearly press-on nails with a glowing effect for extra shimmer, one mini nail file, a prep pad, and glue. Follow the easy instructions on the prep pad for the best results. Complete the look with faux pearl earrings for a date!

    Fit & Features

    • Press on nail kit
    • Two sets of pearly press-on nails, glow effect
    • One mini nail file
    • One prep pad with easy instructions
    • One glue tube

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07307-0184

    Category Name: Vacation Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Repeat Lace Tube Mini Dress

    She’s sleek up top, party on the bottom—aka your new go-to for nights that need a little extra twirl. The strapless neckline and tiered ruffles make it an easy yes for going out.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Strapless tube neckline
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000171

    Category Name: Vacation Looks

    Price: $48.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Such A Flirt Floral Mini Dress

    Bring the flirtatious vibes in this adorable floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. Style this dress with sneakers for a cute and casual look.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Ruched detailing, drawstrings at the hem
    • Short, form-hugging fit
    • Ribbed knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-1404

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Paradise Halter Open Back Slit Midi Dress

    Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look.

    Fit & Features

    • Slinky knit fabric, smooth stretchy knit lining
    • Halter cowl neckline, beaded spaghetti strap tie
    • Open back with spaghetti strap tie
    • Bodycon silhouette
    • Slit accent, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000069

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Fave Ribbed Knit Mini Dress

    This basic casual ribbed knit mini dress will be a new fave for the season! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a mini-length hem, and a form-hugging silhouette. The lightweight ribbed knit fabric offers plenty of stretch. Style with a denim jacket and sandals for a cute everyday vibe.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Mini-length hem
    • Form-hugging bodycon fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5086

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Summer Babe Oversized Square Sunglasses

    These trendy oversized shades will have you looking like a total summer babe! The sunglasses feature an oversized square-shaped design, thin arms with sleek metal geometric chain-link accents, rubber nose pads for support, and tinted lenses with ombre shading. Style with a crop top, a mini skirt, and sandals.

    Fit & Features

    • Oversized square-shaped design
    • Thin arms, metal geometric chain-link accents
    • Rubber nose pads
    • Tinted lenses, ombre shading
    • 100% UV protection

    Style Number/Barcode: 07008-1024

    Category Name: Vacation Looks

    Price: $3.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seaside Vacay Criss Cross Straw Block Heels

    From summer parties to seaside vacays, these straw block heels are a cute essential all season! With an almond toe and crisscross straps adorned with a buckle accent, these straw block heels add a touch of style to your summer look. Complete the look with a matching set.

    Fit & Features

    • 3.5" Block heel
    • Almond toe
    • Crisscross straps, buckle strap
    • Straw material
    • Runs true to size

    Style Number/Barcode: 07401-4919

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crossed Over High-Rise Denim Shorts

    Designed with the best fit, these high-rise denim shorts are forever flattering! With a form-hugging fit and a cross-over hem that elevates your everyday look.

    Fit & Features

    • Medium wash denim fabric, slight stretch
    • High-rise waist
    • Front button and hidden zipper closure, belt loop accents
    • Two back pockets
    • Form-hugging fit
    • Cross-over hem
    • Runs true to size

    Style Number/Barcode: 06603-0487

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: S

  • Contemporary Acetate Oval Hoop Earrings

    Achieve contemporary style with these oval hoop earrings! Crafted with high-quality acetate, these hoops offer a modern take on a classic design.

    Fit & Features

    • Acetate design
    • Mini hoop trims
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged

    Style Number/Barcode: 07001-000064

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Queen Tropical Floral Mesh Tie-Front Top

    Slay your next vacay in this gorg tropical floral mesh tie-front top with long sleeves and an ultra-cropped hem. Style with the matching maxi skirt for a sultry vibe!

    Shop Matching Bottoms: Vacay Queen Tropical Floral Mesh Maxi Skirt

    Fit & Features

    • Sheer mesh fabric, high stretch
    • Large tropical floral print
    • V-neckline
    • Tie-front design
    • Long bishop sleeves
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000019

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Summer Glow Floppy Straw Hat

    Get a stunning glow this summer with this on-trend floppy hat! It features a fitted top, a wide floppy brim, and is composed of a straw-like material with all-over sequin sparkle details and a frayed hem. Complete your beach-ready look with strappy sandals.

    Fit & Features

    • Fitted top
    • Wide floppy brim
    • Straw-like material
    • Sequin sparkle details
    • Frayed hem

    Style Number/Barcode: 07302-0301

    Category Name: Vacation Looks

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep Me Cozy Slouchy Knit Sweater

    The perfect chilly day staple! Cozy up in this cute sweater featuring slouchy dolman sleeves, a boat neckline, and a relaxed crop hem on rib-knit fabric. Pair with casual trouser pants to complete the look!

    Fit & Features

    • Slouchy dolman sleeves
    • Boat neckline
    • Relaxed crop hem
    • Soft rib-knit sweater fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1522

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Era V-Neck Ruffled Romper

    Enter your sweet girl era in this eyelet romper perfect for brunch, graduations, or shower celebrations! The V-neck and form-hugging bodice create a flattering silhouette, while the ruffled hem adds a playful touch.

    Fit & Features

    • Eyelet knit fabric
    • V-neckline
    • Spaghetti straps
    • Form-hugging bodice
    • Ruffled skirt overlay, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000032

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Bejeweled Glitter Jelly Sandals

    You fancy huh! Radiate glam in these glitter jelly sandals featuring a round toe, bejeweled t-strap, and adjustable buckle closure. Complete the look in a day dress for a birthday lunch.

    Fit & Features

    • Round toe
    • Bejeweled t-strap
    • Adjustable buckle closure
    • Glitter jelly material

    Style Number/Barcode: 07404-0969

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Staple Sheer Button-Up Tunic

    This sheer button-up tunic is such a staple for layering over a cute bikini or a lacey bralette! It features long sleeves with button cuffs, a collared neckline, high side slits along a flowy, round hem. Composed of sheer gauze woven fabric with no stretch.

    Fit & Features

    • Long sleeves, button cuffs
    • Collared neckline
    • Button-up front closures
    • High-side slits
    • Flowy round hem
    • Sheer gauze woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1649

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance