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.

  • Tag Along Strappy Buckle Sandals

    Whatever your summer plans are, these strappy buckle sandals are perfect for tagging along on any adventure! 

    Fit & Features

    • Round toe
    • Dual buckle straps
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-000007

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: WHITE, BLACK

    Available Size: 5, 6, 7, 8, 9, 10

  • Feeling Daring Texture Knit Crop Top

    Feel daringly stylish with this crop top! This ultra-trendy top features a sleeveless V-neckline, bungee spaghetti straps, an alluring open back with a strappy design, and a vivid V-cut cropped hem on sheer texture knit fabric. Dare to stand out and shop the matching bottoms to complete the look!

    Shop Matching Bottoms: Feeling Daring Texture Knit Mini Skirt

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Open back, strappy design, tie closure
    • V-cut cropped hem
    • Sheer texture knit fabric, lined bust
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-5214

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • To Be Adored Scoop Neck Floral Lace Mini Dress

    You're certain to be adored in this floral lace mini dress wherever you go! The scoop neckline with a bust tie adds a touch of feminine charm while the adjustable spaghetti straps provide a perfect fit. Its bodycon silhouette and mini-length hem accentuate your curves, making you feel confident and stylish. Complete the look with a mini handbag.

    Fit & Features

    • Ditsy floral print, lace fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Scoop neckline with bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5717

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Mood Tortoiseshell Oval Sunglasses

    Lowkey iconic, highkey essential. These tortoiseshell oval sunglasses give your everyday 'fits that effortless vintage vibe—perfect for rooftop brunches, market strolls, or literally anytime you want to look cool.

    Fit & Features

    • Small oval-shaped design
    • Tortoiseshell plastic frame
    • Built-in nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000048

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: TORTOISE

    Available Size: NS

  • Dreamy Muse Watercolor Chiffon Flowy Midi Dress

    You'll be a dreamy muse in this gorgeous watercolor chiffon flowy midi dress! The airy lined chiffon fabric is detailed with a mesmerizing watercolor print for the perf summertime vibe. The mid-length dress features a sleeveless halter neckline with a center stone accent, tie-back spaghetti straps, a partially open back for a touch of allure, and a lower-smocked back design for added stretch. The fitted high waist flows out to a gorgeous A-line silhouette with an asymmetrical hemline for beautiful movement. Style this long dress with espadrille wedges.

    Fit & Features

    • Watercolor print
    • Sheer chiffon fabric with smooth woven lining
    • Halter neckline, stone detail, tie-back straps
    • Partial open back, lower stretchy smocked back
    • Flowy A-line silhouette
    • Asymmetrical hemline
    • Runs true to size

    Style Number/Barcode: 05101-3306

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Neutrals Halter Strappy Tropical Midi Dress

    Unveil this chic tropical midi dress on the island! The cowl halter neckline and strappy open back add a touch of allure, while the bodycon silhouette and asymmetrical cut hem flatter your figure. Complete the look with cute block heel sandals and sunglasses!

    Fit & Features

    • Tropical print, smooth knit stretchy fabric
    • Halter cowl neckline, spaghetti strap
    • Strappy open back
    • Bodycon fit
    • Asymmetrical cut hem
    • Runs true to size

    Style Number/Barcode: 05102-5185

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Tropics Halter Lace Tropical Mini Dress

    Hit the tropics in this stylishly sultry tropical mini dress perfect for dinner and cocktails! Crafted from a tropical patterned lace fabric, this mini-length dress features a halter neckline with tie closure and a stunning bodycon silhouette to show off your curves. Complete the look in sandals and earrings!

    Fit & Features

    • Tropical patterned lace fabric, stretchy knit lining
    • Halter neckline, tie closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5796

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Girls Are Girling Trucker Hat

    Keep it cute and sassy in this trucker hat that says it all! It features a classic curved brim, an embroidered script that reads "The Girls Are Girling" and a mesh back with an adjustable strap. Complete with denim shorts. 

    Fit & Features

    • Curved brim
    • Embroidered script reads "The Girls Are Girling"
    • Mesh back with adjustable closure 

    Style Number/Barcode: 07302-1667

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Vibe Floral Bodycon Mini Dress

    Radiate a gorgeous vibe in this bold floral print mini dress designed with a strapless neckline and bodycon silhouette to flaunt your curves.

    Fit & Features

    • Smooth knit fabric with knit lining, high stretch
    • Large floral print
    • Strapless straight neckline, no-slip strip
    • Mini-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000147

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tied Up In Vibes Crochet Sweater

    Cute from the front—but that back? Straight-up stunning. With open-tie drama and airy crochet texture, this sweater is here to steal stares and soak up sunsets.

    Fit & Features

    • Sheer crochet fabric
    • Crew neck
    • Flare long sleeves
    • Open tie-back design
    • Cropped length hem
    • Runs true to size

    Style Number/Barcode: 06005-000076

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Fun And Games Tie Strap Bodycon Floral Mini Dress

    This floral mini dress is here for fun and games this summer! Perfect for casual weekend fun, this dress features spaghetti strap ties, a sweetheart neckline, and all-over ruched seams that accentuate your curves along the bodycon fit. Complete the look with a trendy purse.

    Fit & Features

    • Floral ditsy print, brushed knit fabric
    • Spaghetti strap ties
    • Sweetheart neckline
    • Ruched bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5728

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You Love Me Graphic Tank Top

    Unapologetically bold and playful, this graphic tank top is a must-have for those who want to make a statement. Featuring a cropped design and eye-catching "You Look Like You Love Me" graphic, this tank top exudes attitude.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neck
    • Racerback design
    • "You Look Like You Love Me" graphic script
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000072

    Category Name: Vacation Looks

    Price: $18.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Show Off Your Glow Tropical Lace-Up Midi Dress

    Show off your vacation glow in this tropical midi dress all over the island or resort! With a square neckline, spaghetti straps, and a lace-up back, this side slit dress hugs your body in all the right places with side ruched seams and a bodycon fit. Complete the look in sandals.

    Fit & Features

    • Tropical print, mesh fabric, sewn-in knit lining, moderate stretch
    • Spaghetti straps
    • Square neckline
    • Lace-up back
    • Ruched side seams, bodycon fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5866

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Vibes Cutout Geometric Mesh Maxi Dress

    Serve major vibes in this geometric mesh maxi dress out by the beach this weekend or for a getaway! The square neckline, adjustable spaghetti straps, and form-hugging fit show off your curves while the cutout sides and back add a touch of sass. Complete with a center-back slit and maxi-length hem for effortless movement. Style this sleeveless dress with earrings and sandals.

    Fit & Features

    • Geometric print, mesh fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Square neckline
    • Cutout sides and back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5759

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Weekend Lace-Up Espadrille Wedges

    Unlock coastal vibes in these cute lace-up espadrille wedges for a picnic or strolling the boardwalk.

    Fit & Features

    • Almond toe
    • Lace-up ankle straps
    • Wedge heel
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000004

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 8.5, 9, 10

  • Beachy Glam Rhinestone Palm Tree Metallic Sandals

    Level up your fabulous vacay 'fits with these glam rhinestone metallic sandals! Made with sleek faux leather with a metallic sheen, they feature a square-shaped toe, a thong strap with a glitzy rhinestone-embellished palm tree design, an adjustable ankle strap with a buckle closure, and a flat sole for comfortable wear. Style with a flowy sundress and hoop earrings for a beachside dinner!

    Fit & Features

    • Faux leather upper, metallic sheen
    • Square toe
    • Thong strap
    • Rhinestone-embellished palm tree design
    • Adjustable ankle strap with buckle closure
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1229

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Attention Abstract Split Crop Top

    Command attention in this striking halter crop top featuring a flattering twisted neckline, a daring split design, and a cropped length that perfectly highlights your figure.

    Fit & Features

    • Abstract print, mesh fabric, sewn-in knit lining
    • Halter plunge twist neckline, tie closure
    • Center split design
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000167

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • Sweet Charm Lace-Up Babydoll Crop Top

    You'll radiate sweet charm in this babydoll crop top all season! With delicate spaghetti straps and a V-neckline, this top boasts a stretchy smocked bust that hugs your curves for a flattering fit. The lace-up back adds a touch of allure, while the ruffled cropped hem adds a playful touch. Complete the look in a denim skirt and block heels for any occasion!

    Fit & Features

    • Gauze woven fabric, no stretch
    • V-neckline
    • Stretchy smocked bust
    • Spagehtti straps, lace-up back
    • Babydoll silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 06003-2524

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Flower Strap Stiletto Mules

    You'll be ready for your next vacay in these fab faux leather mules featuring a thin strappy design with a bold flower accent and short stiletto heel.

    Fit & Features

    • Stiletto heel
    • Faux leather material
    • Open almond-shaped toe
    • Thin strappy design, flower accent
    • Open back, on-and-off styling
    • Cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000085

    Category Name: Vacation Looks

    Price: $30.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Resort Calling Mesh Slit Maxi Skirt

    Booked the trip? This skirt is already packed. Featuring a high-rise waist and dramatic slit skirt, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails.

    Shop The Matching Top: Resort Calling Mesh Tie Front Top

    Fit & Features

    • Floral print, attached panty knit lining
    • High-rise waist
    • High front slit
    • Flowy maxi length hem
    • Runs true to size

    Style Number/Barcode: 06501-000037

    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
  • Refreshing Charm Smocked Striped A-Line Mini Dress

    This sleeveless striped mini dress features a flattering square neckline and a smocked A-line silhouette with a trendy drop waist seam. The ruffled hem adds a flirty touch perfect for picnics or a day at the beach. 

    Fit & Features

    • Striped woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Smocked A-line silhouette
    • Drop waist seam
    • Mini-length ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5826

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Life Beaded Straw Cowboy Hat

    A straw cowboy hat featuring a distressed wide brim with a beaded string trim and a snug fit. Style with cowboy boots.

    Fit & Features

    • Distressed wide brim
    • Beaded string trim
    • Snug fit
    • Straw material

    Style Number/Barcode: 07302-1702

    Category Name: Vacation Looks

    Price: $4.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl Next Door Tie Front Gingham Tube Top

    Get cute for summer in this gingham tube top, perfect for casual events! This flirty, figure-flattering crop top features a charming gingham pattern and adjustable tie front detail that creates the perfect silhouette.

    Fit & Features

    • Gingham print, cotton woven fabric
    • Strapless tube neckline
    • Tie-front detail
    • Stretchy smocked silhouette
    • Ultra cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000076

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: RED

    Available Size: M, L

  • Coastal Cutie Halter Cutout Striped Linen Jumpsuit

    Hit the coast in this breezy cute striped linen jumpsuit! This playful piece features a halter neckline with a spaghetti strap tie and a cutout bodice to flaunt some skin. The stretchy smocked back and wide-leg silhouette provide comfort and style, while the striped print adds a pop of personality to the linen-blend fabric. Complete the look in platform sandals.

    Fit & Features

    • Striped print, linen blend fabric
    • Halter neckline, spaghetti strap tie
    • Cutout bodice
    • Back zipper and hook-eye closure, stretchy smocking
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0817

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale