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.

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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

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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.

Read Between The Lines Bikini Bottoms
Have em' read between the lines with bikini bottoms that stun. The bikini bottoms feature a low-rise waist, a high-cut front, contrasting trim, and a cheeky bottom. Complete look with the matching bikini top and sandals.

Shop Matching Bikini Top: Read Between The Lines Bikini Top

Fit & Features
- Low-rise waist
- High-cut front
- Contrasting trim
- Cheeky bottom
- Form hugging fit, moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0708

Category Name: Vacation Looks

Price: $5.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Read Between The Lines Bikini Top
Have em' read between the lines with a bikini top that stuns. The bikini top features a plunging V-neckline, supportive tank straps, contrasting trim, and a slide hook closure at the back. Complete your look with the matching bikini bottoms and sandals.

Shop Matching Bikini Bottoms: Read Between The Lines Bikini Bottoms

Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Contrasting trim
- Slide-hook fasten at the back
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0561

Category Name: Vacation Looks

Price: $5.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Fave Flowy V-Neck Midi Dress
This breezy lightweight midi dress will be your new casual fave for weekend plans. Designed with a sleeveless V-neck, low back, and mid-length flowy fit, style with a layered necklace and strappy sandals.

Fit & Features
- Gauze woven fabric, mini-length stretchy knit lining
- Sleeveless V-neckline
- Adjustable spaghetti straps, low back
- Hidden side pockets
- High side slit
- Midi-length flowy silhouette
- Runs true to size
Style Number/Barcode: 05102-000185

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sealed With Edge Jelly Sandals
These sandals are part glam, part edgy. The sandals feature a t-strap design with studded embellishments, a bow accent, an open almond toe, and composed of jelly material. Complete the look with a cute swimsuit and coverup.

Fit & Features
- Open almond toe
- T-strap design
- Studs
- Bow accent
- Jelly material
Style Number/Barcode: 07404-0684

Category Name: Vacation Looks

Price: $12.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Muse Tropical Floral Tie-Front Top
Serving island goddess energy with every step. This mesh tie-front top brings the vacay vibes with tropical floral drama and an ultra-cropped fit that moves with you from golden hour to after-party. Style with the matching maxi skirt for a look that slays.

Shop Matching Bottoms: Island Muse Tropical Floral Maxi Skirt

Fit & Features
- Sheer mesh fabric, high stretch
- Tropical floral print
- V-neckline
- Tie-front design
- Long bishop sleeves
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06202-000036

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet And Chic Ruffled Lace Romper
Keep it sweet and chic with a romper that brings pretty details. The romper features a sleeveless sweetheart neckline with a ruffled trim, tank-like shoulder straps, a lined lace body throughout, and wide-leg shorts with a cheeky fit. Complete look with wedges for a brunch ready look.

Fit & Features
- Sleeveless sweetheart neckline
- Ruffles
- Tank shoulder straps
- Lace body
- Wide leg shorts, cheeky fit
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06503-0098

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Stunner Tulip Pants
This spring season, bring those stunning bohemian vibes to your look with these chic tulip pants. They feature a high-rise waist with an elastic banded back, a flowy, wide-leg fit, and high front slits. The lightweight woven fabric has an all-over boho-inspired print that will pair perfectly with the matching top. Complete your look with strappy sandals.

Shop Matching Top: Bohemian Stunner Long Sleeve Crop Top

Fit & Features
- High-rise waist
- Elastic banded back
- Wide-leg fit
- High front slits
- Woven fabric with no stretch
- Boho-inspired print
- Runs true to size
Style Number/Barcode: 06302-0179

Category Name: Vacation Looks

Price: $16.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Stunner Long Sleeve Crop Top
This spring season, bring those stunning bohemian vibes to your look with this chic crop top. It features a deep V neckline, long loose sleeves with elastic cinched hems, and a cropped, form-hugging fit with an elastic banded back hem. The lightweight woven fabric has an all-over boho-inspired print that will pair perfectly with the matching pants. Complete your look with strappy sandals.

Shop Matching Bottoms: Bohemian Stunner Tulip Pants

Fit & Features
- V neckline
- Long loose sleeves with cinched hems
- Cropped, form-fitting style
- Elastic banded back hem
- Woven fabric with no stretch
- Boho-inspired print
- Runs true to size
Style Number/Barcode: 06003-1182

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Off The Shoulder Asymmetrical Midi Dress
Keep it fab in a floral midi dress that brings the romance to your outfit! The dress features an off the shoulder neckline, off the shoulder straps, a sweetheart bust with padded cups, a built-in no-slip strip, and a floral print. The relaxed fit bodice leads to a stunning asymmetrical midi length silhouette. Complete look with wedges.

Fit & Features
- Off the shoulder neckline
- Sweetheart bust, padded cups, gel no-slip strip
- Floral print
- Asymmetrical midi-length silhouette
- Lined smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0465

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Make A Splash Smocked Bikini Bottoms
Make a splash in chic bikini bottoms! The bikini bottoms feature a high-rise waist, dual O-ring accents at the hips, high cut, and a cheeky bottom. The swim bottoms are composed of a smocked fabric. Complete look with the matching bikini top and sunnies.

Shop Matching Bikini Top: Make A Splash Smocked Bikini Top

Fit & Features
- High rise waist
- Dual O-ring accents at the hips
- Smocked fabric
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0658

Category Name: Vacation Looks

Price: $2.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make A Splash Smocked Bikini Top
Make a splash in a chic bikini top! The bikini top features triangle cups, an O-ring accent at the center, tank-straps, and composed of a smocked fabric. Complete look with the matching bikini bottoms and sunnies.

Shop Matching Bikini Bottoms: Make A Splash Smocked Bikini Bottoms

Fit & Features
- Plunging V-neckline
- Tank straps
- O-ring accent
- Smocked fabric
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0509

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Edgy Glam Studded Jelly Sandals
These sandals are part glam, part edgy. The sandals feature a t-strap design with studded embellishments, a bow accent, an open almond toe, and composed of jelly material. Complete the look with a cute swimsuit and coverup.

Fit & Features
- Open almond toe
- T-strap design
- Studs
- Bow accent
- Jelly material
- Patent-like finish
Style Number/Barcode: 07404-0683

Category Name: Vacation Looks

Price: $12.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dreamy Stunner Boho Flare Pants
Showcase your stunning style in these dreamy boho-chic flare pants! They feature a high-rise elastic banded waist, form-fitting pant legs, and a flared-out hem. The stretchy knit fabric has an all-over paisley print that will pair perfectly with a basic crop top. Complete your look with strappy sandals.

Fit & Features
- High-rise elastic banded waist
- Form-fitting pant legs
- Flared hem
- Knit fabric with plenty of stretch
- Paisley print
- Runs true to size
Style Number/Barcode: 06502-0488

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Budding Romance Strapless Floral Jumpsuit
Get a romantic look for date night this spring in this stunning floral printed jumpsuit! It features a strapless square neckline, a high waist, and flowy pant legs. The sheer mesh fabric has a gorgeous all-over rose print and includes a full knit lining. Complete your outfit with wedges and new earrings.

Fit & Features
- Strapless square neckline with an elastic banded hem
- High waist
- Flowy pant legs
- Sheer mesh fabric with a full knit lining
- Rose print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0382

Category Name: Vacation Looks

Price: $18.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Essential Staple Denim Mini Skirt
Slay your look with an essential denim skirt that goes with everything! The skirt features a high-rise waist and a mini-length silhouette with a mini side slit. The skirt is composed of a denim fabric that offers a form-hugging fit. Complete look with a cami and clear mules for a girl-next-door look.

Fit & Features
- High rise waist
- Mini length silhouette
- Mini side slit
- Form hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0014

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Boho Babe Flowy Tie-Front Romper
You'll be a total boho babe in this flowy romper that is perf for the warmer months. It features an off-the-shoulder neckline that can also be worn on the shoulders, long wide bell sleeves, a tie-front belt, and flowy shorts. The lightweight gauze woven fabric has no stretch. Complete your look with statement earrings and strappy sandals.

Fit & Features
- Off-the-shoulder neckline
- Long bell sleeves
- Elastic high waist
- Tie-front belt
- Flowy shorts
- Gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0106

Category Name: Vacation Looks

Price: $16.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Love At First Sight Mini Dress
With you in this adorable ditsy floral dress, it will be love at first sight. The dress features thin ruffle shoulder straps, a V neckline with subtle ruching, and a short, curve-hugging silhouette. The lightweight knit fabric offers plenty of stretch. Complete your look with a classic denim jacket and sneakers.

Fit & Features
- Thin ruffle shoulder straps
- V neckline with ruching
- Mini-length, form-hugging fit
- Knit fabric with plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-1429

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Retro Tie Dye Bodysuit
Channel a retro feel with a bodysuit that makes a colorful impression. The bodysuit features a sleeveless scoop neckline, tank shoulder straps, a tie-dye print, and a thong bottom with dual snap button closure. Complete look with a high waist mini skirt.

Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Tie-dye print
- Thong bottom with dual snap button closure
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3248

Category Name: Vacation Looks

Price: $11.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropic Time Halter Cutout Wide-Leg Jumpsuit
Bring on the summer weather in this tropical wide-leg jumpsuit for your next vacation or any weekend plans! This eye-catching jumpsuit features a flattering halter neckline and strategic cutouts that accentuate your curves.

Fit & Features
- Tropical print, stretchy knit fabric
- Halter neckline with spaghetti strap ties
- Cutout bodice
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06502-000013

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Stripes Strapless Romper
Stun with a striped romper that channels those stylish vibes! The romper features a strapless square neckline, a tie-waist belt, and striped wide-leg shorts. Complete your cute brunch outfit with a pair of wedges and sleek hoops.

Fit & Features
- Strapless square neckline
- Tie-waist belt
- Striped wide-leg shorts
- Elastic banded back hem
- Form-hugging fit
- Knit top with a moderate stretch
- Lightweight woven shorts with a knit lining
- Runs true to size
Style Number/Barcode: 06303-0107

Category Name: Vacation Looks

Price: $16.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Day In The Sun Bikini Top
Spend a day in the sun to catch those golden rays in this cute bikini top. The bikini top features a plunging sweetheart neckline, supportive underwire, adjustable spaghetti straps, and a slide-hook fasten closure. Complete your vacay outfit with the matching bikini bottoms and sunnies for that cabana-ready look.

Shop Matching Bikini Bottoms: Day In The Sun Bikini Bottoms

Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Slide-hook fasten closure
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0558

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ruffled Romance Ditsy Floral Mini Skirt
Bring the romance with a mini skirt that is perfect for when you want to feel extra girly. The skirt features a high-rise waist, a ditsy floral print, an asymmetrical wrap with ruffled trim, and a mini-length silhouette with ruffled trim. The skirt is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with a cami and mules.

Fit & Features
- High rise waist
- Ditsy floral print
- Asymmetrical wrap design
- Ruffled
- Mini length silhouette
- Lined lightweight woven fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 06401-0303

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ditsy Floral Asymmetrical Mini Skirt
Bring the charm with a mini skirt that is perfect for when you want to feel extra girly. The skirt features a high-rise waist, a ditsy floral print, an asymmetrical wrap with ruffled trim, and a mini-length silhouette with ruffled trim. The skirt is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with a cami and mules.

Fit & Features
- High rise waist
- Ditsy floral print
- Asymmetrical wrap design
- Ruffled
- Mini length silhouette
- Lined lightweight woven fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 06401-0304

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Glam Oversized Square Sunglasses
Keep your look so glam with sunglasses that are the perfect accent to your look. The sunglasses feature an oversized square-shaped frame, a metal trim, and sleek arms. Complete look with matching separates.

Fit & Features
- Oversized
- Square-shaped frame
- Metal trim
- Sleek arms
- 100% UV protection
Style Number/Barcode: 07008-0834

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials