Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.

Show filters

Sort:

Size

Color

Price

All filters

Sort

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.

Sunday Girl Eyelet Lace-Up Skater Dress
This eyelet skater dress is perfect for Sunday brunch! It features adorable short puff sleeves, a square neck, an elasticized waist, an open-back design with lace-up closure, and a flared skirt. Composed of breathable cotton fabric with an inner lining. Finish the look in strappy sandals.

Fit & Features
- Short puff sleeves
- Squareneck
- Elasticized waist
- Open-back design, lace-up closure
- Flared, skater silhouette, short-length hem
- Eyelet lace cotton fabric, inner lining
- Fits true to size, no stretch
Style Number/Barcode: 05102-4428

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Totally Fab Plaid Skort
Rock a totally fab vibe with a mini skirt that channels those preppy vibes! The skort features a plaid print, a high-rise waist, a pleated body, wide leg shorts with a mini skirt overlay. The skort is composed of a lined lightweight woven fabric that offers a form hugging fit with a minimal stretch. Complete look with a crop top and lug booties!

Fit & Features
- Plaid print
- High rise waist
- Pleated
- Wide leg shorts, skirt overlay
- Lined lightweight woven fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 06301-0142

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Too Glam To Shade Square Rhinestone Trim Sunglasses
These sleek square frames with rhinestone-embellished trim bring full diva energy wherever you go!

Fit & Features
- Rhinestone-embellished trim on arms
- Sleek square metal frames
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000008

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: BLACK

Available Size: NS
Luxe Locks Tassel Earrings
Flaunt your luxe locks! These glam earrings feature snake chain tassels with a post-back closure. Complete the look in a satin dress for a night out.

Fit & Features
- Snake chain tassels
- Post-back closure
- Metal material
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1176

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep It Lowkey Hoops
Downplay the drama with some simple lowkey hoop earrings. With their thin etched design and easy latch closure, they provide comfortable wear. A definite must-have for happy hour with your girls! Wear them with a flirty midi dress and some trendy clear mules.

Fit & Features
- Dainty textured shimmer design
- Latch closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-0114

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Darling Ditsy Floral Tie-Front Top
Keep your everyday look darling and sweet with this adorable top! It features short flutter cap sleeves, a V-neckline with a tie-front design, a cropped fit, and an all-over ditsy floral print. Style with the matching mini skirt and espadrille wedges.

Shop Matching Bottoms: Darling Ditsy Floral Mini Skirt

Fit & Features
- Short flutter cap sleeves
- V-neckline
- Tie-front
- Cropped
- Ditsy floral print
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06202-0272

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Darling Ditsy Floral Mini Skirt
Keep your everyday look darling and sweet with this adorable skirt! It features a high-rise waist, ruched detailing leading to a front slit, a short, curve-hugging fit, and an all-over ditsy floral print. Style with the matching crop top and espadrille wedges.

Shop Matching Top: Darling Ditsy Floral Tie-Front Top

Fit & Features
- High-rise waist
- Ruching
- Front slit
- Mini-length, form-fitting silhouette
- Ditsy floral print
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06501-0567

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
All Night Wrap Maxi Skirt
Look sexy in this maxi skirt for your next all-nighter! It features a high-rise waist, wrap-twist front, and sultry slit. Composed of sleek knit fabric with a moderate stretch. Style with the matching top.

Shop The Matching Top: All Night Plunge Halter Top

Fit & Features
- High-rise waist
- Wrap twist
- Front slit
- Maxi length hem
- Sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0587

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All Night Plunge Halter Top
Look sexy in this halter top for your next all-nighter! It features a halter plunge neckline with dual button closure and an ultra-cropped hem. Composed of sleek knit fabric with a moderate stretch. Style with the matching bottoms.

Shop The Matching Skirt: All Night Wrap Maxi Skirt

Fit & Features
- Halter plunge neckline
- Dual button closure
- Ultra cropped hem
- Sleek knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06001-3970

Category Name: Vacation Looks

Price: $9.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Toucan Long Mesh Duster
Slip on this breezy tropical mesh duster for instant island vibes! It features long sleeves, an open-front design, and a palm leaf print on sheer mesh knit fabric with a moderate stretch. Complete the look in a bikini set for poolside lounging.

Shop Matching Top: Tropical Toucan Mesh Crop Top

Shop Matching Bottoms: Tropical Toucan Ruched Mini Skirt

Shop Matching Jumpsuit: Tropical Toucan Strapless Jumpsuit

Fit & Features
- Long fitted sleeves
- Open-front design
- Longline hem
- Palm leaf print
- Sheer mesh knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0257

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bring The Trendy Vibes Mesh Bodysuit
Bring the trendy vibes to your festival look with this bold mesh bodysuit. It features long fitted sleeves, a front cutout creating a bandeau design with a halter neckline and a below-the-bust cutout, a thong bottom, and a fab tie-dye swirl print. Style this bodysuit with cutoff denim shorts and clear mules.

Fit & Features
- Long fitted sleeves
- Front cutout, bandeau design, halter neckline, below-the-bust cutout
- Thong bottom, dual snap-button closure
- Form-hugging fit
- Tie-dye swirl print
- Sheer mesh fabric, front knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4056

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Hello Weekend Straw Floppy Hat
A true weekender like you will adore this straw hat! It features a floppy design with a script on the wide brim that reads, "Hello Weekend". Complete the look in a cute bikini to soak up the sun.

Fit & Features
- Floppy design
- Wide brim
- Script reads, "Hello Weekend"
- Straw material
Style Number/Barcode: 07302-0502

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trip To The Coast Tie-Front Top
Be sure to pack this effortless tie-front top for your next beachside trip! It features flowy three-quarter-length kimono-style sleeves, a V-neckline with a tie-front design, and a cropped fit. The lightweight woven rayon fabric features a crinkled texture. Pair this top with cutoff denim shorts and cute shades.

Fit & Features
- Three-quarter-length kimono-style sleeves
- V-neckline
- Tie-front design
- Cropped
- Rayon fabric, crinkle detailing, no stretch
- Runs true to size
Style Number/Barcode: 06204-1191

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Reese Distressed Mom Shorts by Windsor Denim
With these denim mom shorts, you're ready for music festivals and beyond! The shorts by Windsor Denim feature a high-rise waist, distressed detailing on front and back, a mom-style silhouette, and a frayed cut-off hem. The premium denim fabric offers no stretch. Complete the look in a beaded bustier and sandals.

Fit & Features
- High-rise waist
- Mom style silhouette
- Distressed detail on front and back
- Frayed cut off hem
- Front button and hidden zipper closure
- Premium denim fabric, no stretch
- Fits true to size
Style Number/Barcode: 06603-0228

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
High Waist Acid Wash Shorts
Step up your denim game with shorts that bring that chic touch to your outfit! The shorts feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, heavy distressing throughout, and a cutoff hem. The shorts are composed of an acid wash denim fabric that offers a relaxed fit with minimal stretch. Complete look with boots and a crochet top for a festival ready look!

Fit & Features
- High rise waist
- Single-button, zipper closure
- Traditional five-pocket belt loop design
- Heavy distressing
- Cutoff hem
- Acid wash denim fabric
- Form hugging fit, minimal stretch, runs 1/2 smaller
Style Number/Barcode: 06603-0291

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Uptown Babe Crinkle Tie-Front Top
Head uptown looking like a babe in this tie-front top featuring trendy long peasant sleeves, a plunge v-neckline, and a cropped hem on crinkle woven fabric. Complete the look in a panama hat and shades.

Fit & Features
- Long peasant sleeves
- Plunge v-neckline
- Tie-front
- Cropped hem
- Crinkle woven fabric, no stretch, fits true to size
Style Number/Barcode: 06204-1183

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hidden Gem Lace-Up Halter Crop Top
Uncover this cute crop top for the perfect summer look! Featuring a sultry string lace-up halter and a flattering split center design, this crop top will make you stand out in any crowd.

Fit & Features
- Stretchy rib knit fabric
- String lace-up plunge halter neckline
- Split center accent
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-2283

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sparkling Intrigue Rhinestone Body Chain
Intrigue the crowd with your sparkle! This glam body chain features an intricate rhinestone chain in a wrap-around design with dual lobster-clasp closure. Complete the look in a chic bodycon dress.

Fit & Features
- Intricate rhinestone chain
- Wrap-around design
- Dual lobster clasp closure
Style Number/Barcode: 07002-1205

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Talk O-Ring Strappy Jumpsuit
Don't just talk the talk but walk the walk in this sultry strappy jumpsuit perf for vacationing in Cabo! It features a sleeveless, halter neckline with tie closure, front keyhole, cutout bodice with a ring insert, and slightly flared legs. Complete the look in statement earrings.

Fit & Features
- Sleeveless, halter neckline, tie-closure
- Front keyhole, cutout bodice with ring insert
- Cutout strappy bodice, back tie-closure
- Slightly flared legs
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0805

Category Name: Vacation Looks

Price: $6.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cute Classic Denim Shortall
Cute and classic, these denim shortalls are an effortless staple with a relaxed fit and trendy cuffed hem.

Fit & Features
- Medium wash denim fabric
- Adjustable shoulder straps
- Racerback design
- Front bib pocket
- Side button closures, belt loop accents, front pockets
- Relaxed fit, cuffed hem
- Runs true to size
Style Number/Barcode: 06603-0485

Category Name: Vacation Looks

Price: $6.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Burst Ruffled Short Dress
Bring a burst of florals with a short dress that will have you brunch ready! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and a cutout at the midriff. The smocked waist leads to a flowy skater silhouette with tiered ruffles. The dress is composed of a lined chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Cutout at midriff, smocked waistband
- Floral print
- Skater silhouetted, tiered ruffles
- Lined chiffon fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1505

Category Name: Vacation Looks

Price: $6.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Love Tie-Front Top
Showcase your sweet side with a cute tie-front top that adds the romance to your look! The tie-front features a dainty floral print, a V-neckline with tie-front hem, long sleeves, and a cropped hem. The top is composed of an airy chiffon fabric that offers a relaxed fit. Complete the look with a lace bustier.

Fit & Features
- Floral print
- V-neckline
- Tie-front hem
- Long sleeves, elasticized cinched hems
- Cropped hem
- Chiffon fabric, no stretch, relaxed fit
- Runs true to size
Style Number/Barcode: 06204-1165

Category Name: Vacation Looks

Price: $14.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Baby Tube Side Ruched Romper
Embrace your boho roots! This cute tube romper features a strapless neckline, side ruched seams, and high-rise shorts on soft stretch-jersey knit fabric. Complete the look in a panama hat for a trendy brunch look.

Fit & Features
- Strapless tube neckline, elasticized hem
- Side ruched seams
- High-rise shorts
- Boho border print
- Soft and stretchy jersey knit fabric
- Runs true to size
Style Number/Barcode: 06503-0988

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Walkin' On Sunshine Floral Puff Romper
Flirty and floral, this puff sleeve romper is perfect for soaking up the sun! It features short sleeves, a square neck, and a smocked bodice atop flowy shorts. Complete the look in trendy sandals for a day out.

Fit & Features
- Short puff sleeves
- Square neck
- Smocked bodice
- Flowy shorts
- Floral print
- Gauze woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06303-0208

Category Name: Vacation Looks

Price: $14.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

Reset Your Password

Email Sent

Order Status

Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials