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.

Butterfly Charm Bodychain
Accent your beachside looks with a cute body chain that accents your look! The body chain features a dainty chain link and flat metal butterfly charms. Includes a post-back closure.

Fit & Features
- Dainty chain link
- Butterfly charms
- Lobster clasp closure
Style Number/Barcode: 07002-0732

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casually Chic Ribbed Knit Mini Dress
Elevate your everyday look with this casually chic mini dress. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this ribbed knit dress with the matching jacket and sleek hoop earrings.

Shop Matching Jacket: Casually Chic Ribbed Knit Cropped Jacket

Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Short, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-1492

Category Name: Vacation Looks

Price: $19.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty Vibes Linen Mini Dress
Channel those flirty vibes with a mini dress that brings those girly details! The dress features an off-the-shoulder neckline, a tiered ruffle popover, a smocked waist, and an A-Line silhouette. The dress is composed of a linen knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops.

Fit & Features
- Off the shoulder neckline
- Tiered ruffle popover
- Smocked waist
- Mini length silhouette
- A-Line
- Linen knit fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1058

Category Name: Vacation Looks

Price: $22.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Alluring Tropical Floral Maxi Dress
Create a stylish and alluring look for your next vacay in this gorgeous maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a lace-up back design, a high waist, a floor-length hem with a chic side slit, and a flowy, relaxed fit. The knit fabric has an all-over tropical floral print, making this dress a perf pick for summer. Complete the outfit with strappy sandals.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Lace-up back design
- High waist
- Floor-length hem, side slit, relaxed fit
- Knit fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-0195

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Carefree Style Tie-Dye Mini Dress
Showcase an effortless and carefree style this summer with this tie-dye mini dress! It features a sleeveless square neckline, spaghetti straps, side ruching with drawstrings at the hem, and a mini-length, curve-hugging silhouette. The soft brushed knit fabric offers a moderate stretch. Complete the look with casual sneakers.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side ruching, drawstrings at the hem
- Short, form-hugging fit
- Brushed knit fabric, moderate stretch
- Tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4057

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Edge Of Fringe High Waist Denim Shorts
Take your look to the edge with high waist shorts that channel that glamour punk vibe! The shorts feature a high-rise waist, a single button with zipper closure, destruction, a traditional five-pocket with belt loop design, and a cutoff hem with rhinestone fringe. Complete look with a crop top and moto jacket.

Fit & Features
- High-rise waist
- Single-button with hidden zipper closure
- Destructed detailing
- Traditional five-pocket with belt loop design
- Cutoff hem with rhinestone fringe
- Denim fabric, form-hugging fit, no stretch
- Runs true to size
Style Number/Barcode: 06603-0200

Category Name: Vacation Looks

Price: $31.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Down For It Mid-Rise Cutoff Denim Shorts
These mid-rise denim shorts will have you down for a good time! Designed with a form-hugging fit and a trendy cutoff hem, these shorts are perfect for any summer outfit.

Fit & Features
- Medium wash denim fabric, some stretch
- Mid-rise waist, button front and zipper closure, belt loops
- Form-hugging fit
- Front and back pockets
- Cutoff hem
- Runs true to size
Style Number/Barcode: 06603-000006

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: In Stock

Available Color: MED, DENIM

Available Size: S, M, XL
Product Badge:
- Sale
Flawless In Florals Scuba Skater Dress
A stunning floral print makes this an eye-catching dress! We're loving the flowy skater skirt that makes you want to keep spinning!

Fits & Features
- Spaghetti Straps
- V Neckline I Zippered Lace Back
- Mini Length I Skater Style Skirt
- Smooth Scuba Fabric
- Moderate Stretch
Style Number/Barcode: 05101-0504

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Major Appeal High Slit Maxi Dress
Create major appeal with a maxi dress that wows from all your best angles! The dress features a sleeveless V-neckline, spaghetti straps, and a maxi length silhouette accented with a high side slit. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with heels.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0525

Category Name: Vacation Looks

Price: $5.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ready To Glow Glitter Mini Dress
Get ready to glow with a mini dress that brings the shine to your outfit! The dress features a sleeveless square neckline, sleek spaghetti straps, a sultry backless design, and side ruching with dual drawstrings. The dress is composed of a glitter knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with heels.

Fit & Features
- Sleeveless square neckline, spaghetti straps
- Adhesive bra recommended
- Backless design
- Side ruching, dual drawstrings
- Mini-length bodycon silhouette
- Glitter knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-0397

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Classic Style Linen Jumpsuit
Showcase a classic style this season in this chic linen jumpsuit. It features a sleeveless V-neckline with a small front cutout and tie-front detail, adjustable spaghetti straps that lead to a cross-back design, a high waist, and wide pant legs with a relaxed fit. Complete your look with sleek hoop earrings and a faux leather crossbody purse.

Fit & Features
- Sleeveless V-neckline
- Small front cutout, tie-front detail
- Adjustable spaghetti straps, cross-back design
- High waist
- Wide pant legs, relaxed fit
- Linen fabric
- Runs true to size
Style Number/Barcode: 06302-0188

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Locked In Style Chunky Chain Link Sandals
Lock in a chic look with sandals that impress! The sandals feature a slip-on design, an open square toe, a wide strap with a chunky chain-link accent, and a faux leather body. Complete look with a romper and sunglasses.

Fit & Features
- Slip-on design
- Open square toe
- Chunky chain accent
- Clear version features PVC strap
- Faux leather body
Style Number/Barcode: 07404-0741

Category Name: Vacation Looks

Price: $14.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Whisked Away Halter Crop Top
Get whisked away in a crop top that will have you channeling those vacay vibes! The top features a halter neck with a sweetheart bust, neck tie, back ties, and a cropped hem. Complete look with the matching high waist pants and wedges.

Shop Matching Pants: Whisked Away High Waist Pants

Fit & Features
- Halter neck, sweetheart bust
- Neck ties
- Back ties
- Cropped hem
- Lightweight linen knit
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1258

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Good Vibes Paisley Flared Pants
Channel those vibes with flared pants that are perf for festival! The pants feature a high-rise waist, a paisley print, and a straight leg fit with a flared hem. Complete look with a cute crop top and platforms.

Fit & Features
- High rise waist
- Paisley print
- Straight leg fit
- Flared hem
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0579

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Heart Of Glam Platform Straw Heels
Keep it glam with platform heels that will have you ready for brunch with the squad! The heels feature an adjustable ankle strap, an open almond toe with a strap over the toe, a faux suede material, a straw platform, and a block heel. Complete the look with a jumpsuit and a dainty necklace.

Fit & Features
- Adjustable ankle strap
- Open almond toe, strap over the toe
- Faux suede body
- Straw platform
- Straw block heel
Style Number/Barcode: 07401-2913

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Looped In Style Faux Leather Sandals
Get looped in with these cute sandals to stay on trend this season! The sandals feature an open almond toe, a strap over the toe with a toe loop accent, and a flat footbed. The sandals are composed of a faux leather material. Complete look with a romper and a dainty choker.

Fit & Features
- Open almond toe
- Slip-on design
- Strap over the toe, toe loop
- Flat footbed
- Faux leather material
Style Number/Barcode: 07404-0824

Category Name: Vacation Looks

Price: $12.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sealed With Glam Faux Leather Wedges
Seal your look with cute wedges that step up your style game! The heels feature an adjustable ankle strap, an open almond toe with a knot accent, and a wood patterned wedge heel. Complete look with a mini dress and butterfly necklace.

Fit & Features
- Open back
- Adjustable ankle strap
- Open almond toe
- Strap over the toe with knot accent
- Wood patterned wedge heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-0262

Category Name: Vacation Looks

Price: $7.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Faux Leather Quilted Studded Sandals
Slip on these glam sandals that bring a luxe vibe to your look! The sandals feature a slip-on design, an open square toe, a wide strap embellished with nailhead accents, and composed of faux leather material. Complete look with a crop and mini skirt.

Fit & Features
- Slip-on design
- Open square toe
- Nailhead accents
- Faux leather material
Style Number/Barcode: 07404-0718

Category Name: Vacation Looks

Price: $11.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Eyes On You Lace-Up Slit Maxi Dress
Not just a dress—this is the moment. From date nights to rooftop dinner parties, this linen maxi dress boasts a cutout bodice and leg-baring slit that does all the flirting for you!

Fit & Features
- Gauze linen-blend woven fabric, stretchy knit lining
- Halter neckline, spaghetti strap ties
- Lace-up back
- Cutout accents
- High front slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000053

Category Name: Vacation Looks

Price: $19.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Beauty Wide-Leg Pants
Showcase your beauty in these trendy boho-inspired pants! They feature a high-rise waist, a back zipper closure, and flowy wide pant legs. The lightweight floral printed gauze fabric has no stretch. Complete the look with a crochet bralette and strappy sandals.

Fit & Features
- High-rise waist
- Back zipper closure
- Flowy wide pant legs
- Gauze fabric, no stretch
- Floral print
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06302-0181

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Faux Leather Basket Weave Sandals
Stay on trend with sandals that bring pretty details! The sandals feature an open square toe, a wide basket-weave pattern toe strap, and composed of a faux leather material. Complete look with a crop top and shorts.

Fit & Features
- Open square toe
- Basket-weave pattern
- Faux leather material
Style Number/Barcode: 07404-0826

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunshine Weather Floral Chiffon Romper
Bare your shoulders on sun-soaked days in this floral chiffon romper at brunch, parties, or shower celebrations! Designed with flattering drop waist seam to accentuate your figure and a flowy short hem.

Fit & Features
- Floral print, chiffon fabric, sewn-in knit lining
- Strapless neckline
- Stretchy smocked bodice
- Drop waist seam
- Flowy short hem
- Runs true to size
Style Number/Barcode: 06403-1101

Category Name: Vacation Looks

Price: $9.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mesmerizing Beauty Floral Mini Dress
Showcase your mesmerizing beauty in this chic floral mini dress. It features a sleeveless wrap-front V-neckline, spaghetti straps, a wrap skirt with an asymmetric hem, and a curve-hugging silhouette. Style this dress with clear heels and a sleek clutch for a summer date night.

Fit & Features
- Sleeveless wrap-front V-neckline
- Spaghetti straps
- Wrap skirt, asymmetric hem
- Form-hugging fit
- Floral printed knit fabric
- Runs true to size
Style Number/Barcode: 05102-0567

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Falling For Rhinestone Fringe Earrings
Fall for these fringe earrings that bring the glitz to your outfit! The earrings features a rhinestone stud that leads to a draping U-shaped metal fringe. Complete look with an LBD and heels for your next date night with bae!

Fit & Features
- Rhinestone stud
- U-shaped metal fringe
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0838

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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