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.

Sassy Chic Snake Print Ruched Mini Dress
Keep it sassy with a snake print mini dress! The dress features a sleeveless square neckline, spaghetti straps, snake print, dual ruched drawstrings, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Snake print
- Dual ruched drawstrings
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1093

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Flirty Eyelet Knit Skater Romper
So flirty, this adorable eyelet knit skater romper is perf for weekend brunch. You'll love the fit-and-flare silhouette with hidden shorts for coverage.

Fit & Features
- Eyelet knit fabric
- Sleeveless V-neckline, knot-front bust design
- Spaghetti straps
- High-rise waist
- Mini-length overlay, skater silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-1278

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Fusion Satin Mini Dress
Add a burst of florals to your look with this pretty mini dress! The dress features a sleeveless cowl neckline, spaghetti straps that cross at back, a mini lace-up back, a floral print, and a mini-length silhouette. The dress is composed of a satin fabric that offers a form hugging fit with minimal stretch. Complete look with sandals.

Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps, cross at back
- Mini-lace-up back
- Floral print
- Mini length silhouette
- Satin fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1056

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Charm Sleeveless Mini Dress
Bring the floral charm with a pretty mini dress! The dress features a sleeveless square neckline, smocked tie-shoulder straps, a floral print, and a mini-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals.

Fit & Features
- Sleeveless square neckline
- Smocked tie-shoulder straps
- Floral print
- Mini length silhouette
- Lightweight woven fabric, knit lining
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-1905

Category Name: Vacation Looks

Price: $19.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Sweetheart Striped Mini Dress
Bring the sweet vibes to your summer look with this adorable mini dress. It features a sleeveless square neckline, spaghetti straps, a tie-back detail, and a short, curve-hugging silhouette. The ribbed knit fabric has a cute all-over striped print. Style this dress with casual sneakers.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-back detail
- Mini-length, form-hugging fit
- Ribbed knit fabric, striped print
- Runs true to size
Style Number/Barcode: 05102-0443

Category Name: Vacation Looks

Price: $7.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dainty Rhinestone Cross Charm Ring Pack
Stack on the style with a ring pack that brings the luxe! The ring pack includes ten rings that vary in band size. The rings feature a mix of rhinestone cross charms and metal bands. Complete look with a mini dress and mules for your next brunch look.

Fit & Features
- Pack includes ten rings
- Cross charm
- Flat metal bands
- Rhinestones
Style Number/Barcode: 07004-0126

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Sensation Off-The-Shoulder Top
Keep it sensational in a floral top this season! The top features an off-the-shoulder neckline, a sweetheart bust with ruching, short sleeves, a ditsy floral print, and a cropped hem. Complete look with the matching high waist pants.

Shop Matching Pants: Floral Sensation High Waist Pants

Fit & Features
- Off-the-shoulder neckline
- Sweetheart bust
- Ruching
- Short sleeves
- Stretchy knit fabric, ditsy floral print
- Cropped hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-3471

Category Name: Vacation Looks

Price: $4.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Butterfly Claw Multi Clip Pack
Treat tresses to stylish updos with these fab clips! The multi-pack features three clips in neutral hues, a claw closure, and a butterfly design. Complete look with a crop top and denim shorts.

Fit & Features
- Pack includes three clips
- Neutral tones
- Claw closure
- Butterfly design
Style Number/Barcode: 07006-0255

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunny Days Ahead Straw Visor
You'll be totally beach-ready with this adorable straw visor! It features an open-top design, a wide front brim, and a stretchy adjustable band at the back. Style this hat with a pair of chic sunglasses.

Fit & Features
- Open-top design
- Wide front brim
- Straw-like material
- Stretchy adjustable band
Style Number/Barcode: 07302-0365

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropic Dreams Tie Front Top
Set off on those tropical dreams in a cute tie-front top! The top features a plunging V-neckline, tie-front accent, long sleeves, and a tropical palm leaf print. The top is composed of a sheer mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with the matching maxi skirt.

Shop Matching Skirt: Tropic Dreams Mesh Maxi Skirt

Fit & Features
- Plunging V-neckline
- Tie-front accent
- Long sleeves
- Tropical palm leaf print
- Mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0180

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropic Dreams Mesh Maxi Skirt
Set off on those tropical dreams with a cute maxi skirt! The skirt features a high-rise waist, a tropical palm leaf print, and a maxi-length silhouette with a high side slit. Includes a mini skirt-length knit lining. Complete look with the matching tie-front top.

Shop Matching Top: Tropic Dreams Tie Front Top

Fit & Features
- High rise waist
- Tropical palm print
- Maxi length, high side slit
- Miniskirt length knit lining
- Sheer mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0415

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Stunning Asymmetrical Maxi Skirt
Keep it so stunning with a stylish maxi skirt! The skirt features a high-rise waist, an asymmetrical high side slit, and a maxi-length silhouette. The skirt is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching tube top.

Shop Matching Top: So Stunning Ruched Tube Top

Fit & Features
- High-rise waist, elastic waistband
- Asymmetrical high side slit
- Maxi-length silhouette
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0428

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Stunning Ruched Tube Top
Keep it so stunning with a stylish tube top! The top features a sleeveless sweetheart neckline with a ruched center and an asymmetrical cropped hem. The top is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching maxi skirt.

Shop Matching Maxi Skirt: So Stunning Asymmetrical Maxi Skirt

Fit & Features
- Sleeveless sweetheart neckline
- Ruched center
- Asymmetrical cropped hem
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3391

Category Name: Vacation Looks

Price: $2.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bling It On Rhinestone Anklet
Bring on the bling with this glamorous rhinestone anklet! It features three rows of rhinestones in a layered design with gold, silver, and pink hues. Style this anklet with your fave pair of mules.

Fit & Features
- Three rows of rhinestones
- Layered design
- Gold, silver, and pink hues
Style Number/Barcode: 07003-0251

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sealed With Elegance Rhinestone And PVC Sandals
Bring an elegant touch to the everyday with chic sandals! The sandals feature an open back, an open square toe, a clear PVC strap over the toe and a rhinestone embellished bow accent on the strap. Complete look with a bodysuit and cutoff shorts.

Fit & Features
- Open back
- Open square toe
- Clear PVC strap over toe
- Rhinestone bow
- Faux leather footbed
Style Number/Barcode: 07404-0777

Category Name: Vacation Looks

Price: $7.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Summer Cherry Charm Necklace
Create sweet looks this summer with this cherry charm necklace!

Fit & Features
- Cherry charm
- Dainty chain
- Lobster clasp closure
Style Number/Barcode: 07002-000070

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dragon Print Swim Coverup
Keep it trendy with a swim coverup that is all the rage! The coverup features a dragon print and an oversized fit. The coverup can be worn as a coverup skirt or headwrap. Complete look with a swimsuit and sandals.

Fit & Features
- Dragon print
- Oversized fit
- Runs true to size
Style Number/Barcode: 07305-0294

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sultry Floral Asymmetrical Midi Dress
Keep your summertime look sexy and chic with this sultry floral midi dress. It features a sleeveless V-neckline with spaghetti straps that can be worn in a front cross-strap design, an open back with a tie detail, ruching, and a mid-length, curve-hugging silhouette with an asymmetrical hem. Style this dress with sleek hoop earrings.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps that can be worn in a front cross-strap design
- Open back, tie detail
- Ruching at the waist
- Mid-length, form-hugging fit, asymmetrical hem
- Knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-1037

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Denim Days Button Up Mini Dress
Button up in a denim dress that is part stylish, part edgy! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a button-down front, side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit. Complete look with mules and hoops.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Button-down front
- Side pockets
- Mini-length silhouette, form-hugging fit
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0499

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Splash Of Style Tie Dye Midi Dress
Add a splash of style with a pretty midi dress! The dress features a sleeveless cowl neckline, spaghetti straps, a strappy back design, a tie-dye print, and a midi-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with clear mules.

Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Strappy back design
- Tie-dye print
- Midi length silhouette
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1659

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Romance Ruched Mini Dress
Start a floral romance with this pretty mini dress! The dress features an off-the-shoulder neckline, ruching at the bust, short sleeves, a cutout at the midriff, a ditsy floral print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and earrings.

Fit & Features
- Off the shoulder neckline
- Ruching at bust
- Short sleeves
- Cutout at the midriff
- Ditsy floral print
- Smooth knit fabric, form-hugging fit, runs true to size
- Mini length silhouette
Style Number/Barcode: 05102-1103

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Daydream Floral Mini Dress
You'll look like such a daydream in this adorable floral mini dress. It features a sleeveless V-neckline, bungee spaghetti straps, a mini-length fitted silhouette, and a slightly flared-out hem with a front slit. Complete the look with hoop earrings and strappy sandals.

Fit & Features
- V-neckline
- Bungee spaghetti straps
- Short, fitted silhouette
- Slightly flared-out hem, front slit
- Knit fabric, plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-4172

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Style Icon Gauze Cutout Maxi Dress
Create a stylish moment with a maxi dress that is perf for the season! The dress features a plunging V-neckline, waist cutouts with bar straps, a high side slit, and a maxi silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

Fit & Features
- Sleeveless V-neckline
- Waist cutouts with bar straps
- Maxi silhouette
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-1314

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
For The Thrill Of Knit Mini Dress
Keep it stunning with a mini dress that wows! The dress features a sleeveless scoop neckline, spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1154

Category Name: Vacation Looks

Price: $4.97 $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