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.

Edgy Fab High Waist Denim Shorts
These denim shorts are all you need to nail an edgy fab vibe! These bold must-haves feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, heavy destruction, and a raw edge hem. The denim shorts offer a form hugging fit with slight stretch. Complete look with a fringe vest and boots!

Fit & Features
- High rise waist
- Heavy destruction
- Raw-edge hem
- Single-button with zipper closure
- Traditional five-pocket belt loop design
- Form hugging fit, slight stretch, runs true to size
Style Number/Barcode: 06603-0293

Category Name: Vacation Looks

Price: $10.97 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cute Essential Cropped Halter Top
This lightweight knit crop top is such a cute essential! It features a sleeveless halter neckline with thin bungee straps and a cropped, form-hugging fit. The ribbed knit fabric offers plenty of stretch. Keep it casual with high-rise denim, or elevate the look with a curve-hugging mini skirt.

Fit & Features
- Sleeveless halter neckline
- Thin bungee straps
- Cropped, form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1226

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vintage Glam Burnout Tie Front Top
Channel a vintage look with this sophisticated tie front top that features a baroque-inspired burnout pattern, a plunging V-neckline, long sleeves, and a cropped hem with a tie-front accent. The top is composed of an unlined mesh fabric that offers a form hugging fit with minimal stretch. Complete look with high waist jeans and mules.

Fit & Features
- Baroque-inspired burnout pattern
- V-neckline
- Long sleeves
- Tie-front accent, cropped hem
- Unlined mesh fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1242

Category Name: Vacation Looks

Price: $14.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Walk Away Lace-Up Crop Top
Walk away and catch all the stares in this fierce crop top featuring an eye-catching lace-up back design with tie-closure. Complete the look in high-rise jeans and sandals.

Fit & Features
- Sleeveless, spaghetti straps, square neck
- Cropped hem
- Lace-up back, tie-closure
- Sleek knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4161

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Distressed Cut-Off Denim Shorts
This trendy pair of denim shorts will be a style staple of the season! They feature a high-rise waist, front distressed detailing, and a frayed, cut-off hem. The denim fabric offers a rigid fit with no stretch. Style with a cropped graphic tee and sneakers.

Fit & Features
- High-rise waist
- Front distressing
- Frayed, cut-off hem
- Five-pocket and belt loop design
- Front button and hidden zipper closure
- Denim fabric, rigid fit, no stretch
- Runs true to size
Style Number/Barcode: 06603-0292

Category Name: Vacation Looks

Price: $10.97 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Let's Get Together Twist Crop Top
You and this crop top must get together soon! Start prepping for brunch under the sun in this sleeveless top featuring spaghetti straps, a twisted V-neck, and a cutout bodice with strap detail. Complete the look with the matching maxi skirt.

Shop Matching Bottoms: Let's Get Together Tiered Maxi Skirt

Fit & Features
- Sleeveless, spaghetti straps
- Twisted V-neckline
- Cutout bodice, strap detail
- Back longline hem
- Knit fabric
- Runs true to size
Style Number/Barcode: 06001-3919

Category Name: Vacation Looks

Price: $11.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Let's Get Together Tiered Maxi Skirt
You and this maxi skirt must get together soon! Start prepping for brunch under the sun in this maxi skirt featuring a high-rise waist, tiered design, and a flowy silhouette. Complete the look in the matching top.

Shop Matching Top: Let's Get Together Twist Crop Top

Fit & Features
- High-rise waist
- Tiered design
- Flowy silhouette
- Pull-on/off styling
- Gauze woven fabric
- Runs true to size
Style Number/Barcode: 06501-0572

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sway With Me Floral Chiffon Dress
Sashay and sway in this adorable floral chiffon dress featuring a sleeveless, scoop neck, adjustable spaghetti straps, smocked back panel, and a flowy, ruffled tiered short hem. Complete the look in trendy sandals for your next getaway.

Fit & Features
- Sleeveless, scoop neck, adjustable spaghetti straps
- Smocked back panel
- Flowy, tiered short hem
- Floral pattern
- Chiffon-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 05102-4495

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Free Spirit Crochet Waist Jumpsuit
A free spirit like you is in need of this effortless boho jumpsuit featuring a sleeveless, plunge v-neck, halter tie-closure, open-back, a crochet waist, and a flowy wide-leg silhouette. Complete the look in wedges for a day date.

Fit & Features
- Sleeveless, plunge v-neck
- Halter tie closure
- Open-back
- Crochet waist accent
- Flowy, wide-leg silhouette
- Gauze woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0624

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
So Trendy Ruched Halter Top
Make your trendy status known in this adorable ruched crop top! It features a sleeveless halter neckline with tie-back straps, ruched detailing at the bust, and a cropped, form-hugging fit. Style this top with light wash mom jeans and cute mules.

Fit & Features
- Sleeveless halter neckline
- Tie-back straps
- Ruching at the bust
- Cropped, form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4076

Category Name: Vacation Looks

Price: $16.90

Availability: Out of Stock
Product Badge:
- Sale
Twist and Slay Crochet Mini Dress
Serving looks front to back—literally. This crochet mini dress hugs in all the right places with a twist-back moment that’s made to be seen. Perfect for summer parties, day-to-night vibes, or when you just wanna turn heads.

Fit & Features
- Sheer crochet knit fabric with lining, moderate stretch
- Sleeveless scoop neckline
- Spaghetti straps
- Dual twist-back strap design
- Back cutouts
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000046

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Coastal Chic Striped Mesh Tunic
Create chic beachside looks with this on-trend mesh tunic. It features a V-neckline, long fitted sleeves with flared hems, center ruched detailing, and a short, curve-hugging fit. Style this striped tunic as a cover-up over your fave bikini.

Fit & Features
- V-neckline
- Long fitted sleeves, flared hems
- Center ruching, adjustable drawstring
- Mini-length, form-fitting silhouette
- Striped pattern
- Semi-sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4195

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Perfect Day High Waist Denim Shorts
These denim shorts are all you need for the perfect day! These cute must-haves feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, moderate destruction, and a raw edge hem. The light wash denim shorts offer a form-hugging fit with slight stretch. Complete look with a fringe vest and boots!

Fit & Features
- High-rise waist
- Moderate destruction
- Form-hugging fit, raw-edge hem
- Single-button with zipper closure
- Traditional five-pocket belt loop design
- Light wash denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0295

Category Name: Vacation Looks

Price: $10.97 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Reese High Waist Button Denim Shorts by Windsor Denim
Take on the day in shorts by Windsor Denim that will quickly become your fav staple piece! The shorts feature a high-rise waist, a multi-button down front, a traditional five-pocket with belt loop design, and a raw edge cut-off hem. The shorts are composed of an acid wash denim fabric that offers a form hugging fit with minimal stretch. Complete look with a bodysuit and sandals.

Fit & Features
- High rise waist
- Distressed accents
- Raw cut off hem
- Multi-button down front
- Traditional five-pocket with belt loop design
- Acid wash denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0229

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Forever Femme Cold Shoulder Corset
Show off your femme figure in this cold shoulder corset to create a dreamy, timeless style! Featuring adjustable spaghetti straps, short-sleeve cuffs, a sweetheart neckline with built-in padded bust and underwire, a fitted bodice with flexible boning, and hook-eye back closures. Complete the look in ponte pants and heels.

Fit & Features
- Cold shoulder, short-sleeve cuffs
- Adjustable spaghetti straps
- Sweetheart neck, built-in padded bust, underwire
- Flexible boning, crop hem
- Hook-eye back closures
- Rayon woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1737

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stylish Basics Nubuck Slide Sandals
Keep your look stylish in these nubuck slide sandals perfect for dressing up or down. They feature an almond toe, a wide strap, and a slide-on/off styling. Complete the look in a cute sundress for a coffee date.

Fit & Features
- Almond toe
- Wide strap
- Flat silhouette
- Slide-on/off styling
- Nubuck material
- Runs true to size
Style Number/Barcode: 07404-0988

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Stunner Striped Halter Short Dress
Keep it stylish in a short sweater dress that wows and keeps it effortless. The dress features a halter neck with an adjustable neck tie, a striped pattern, and a short-length hem. The dress is composed of an unlined knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with wedges.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Halter neck
- Adjustable neck ties
- Striped pattern
- Short-length hem
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1231

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sun's Out Round Sunglasses
Sun's out and shades on! Sheild your eyes while keeping stylish in these round frame sunglasses with a slight gradient lens. Complete the look in a cute bikini for a beach day.

Fit & Features
- Round plastic frames
- Slight gradient lens
- Supportive arms
Style Number/Barcode: 07008-0935

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Style Stunner Faux Leather Block Heels
Step out in style with block heels that elevate your look! The heels feature a closed zippered back, a wrap-around ankle strap, an open almond toe with strap over the toe, and a block heel. The heels are composed of a faux leather material. Complete look with a bodysuit and mini skirt.

Fit & Features
- Zippered back
- Wrap around ankle strap
- Open almond toe, strap over toe
- Block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3936

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Cutest Look Floral Mini Skirt
Get the cutest look for spring dates in this adorable mini skirt. It features a high-rise waist, smocked detailing throughout, a mini-length ruffled hem, and an all-over dainty ditsy floral print. Style with the matching crop top and a pair of mules.

Shop Matching Top: The Cutest Look Floral Crop Top

Fit & Features
- High-rise elasticized waist
- Smocked detailing
- Mini-length ruffled hem
- Form-hugging fit
- Ditsy floral print
- Textured crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06301-0122

Category Name: Vacation Looks

Price: $4.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
The Cutest Look Floral Crop Top
Get the cutest look for spring dates in this adorable crop top. It features long sleeves with puff shoulders and smocked detailing, a V-neckline with a tie-front design, a majorly cropped fit, and an all-over dainty ditsy floral print. Style with the matching mini skirt and a pair of mules.

Shop Matching Bottoms: The Cutest Look Floral Mini Skirt

Fit & Features
- Long sleeves, puff shoulders, smocked detailing
- V-neckline
- Tie-front
- Cropped
- Ditsy floral print
- Textured crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06003-1793

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Toucan Strapless Jumpsuit
Slip on this tropical mesh jumpsuit for instant island vibes! It features a strapless straight across neckline, chic ruched detailing down the sides of the top, a fitted high waist seam, straight pant legs with a flowy fit, and a palm leaf print on sheer mesh knit fabric with a moderate stretch. Complete the look with strappy sandals and oversized sunglasses.

Shop Matching Top: Tropical Toucan Mesh Crop Top

Shop Matching Bottoms: Tropical Toucan Ruched Mini Skirt

Shop Matching Duster: Tropical Toucan Long Mesh Duster

Fit & Features
- Strapless straight across elasticized neckline
- Ruching down the sides of the top
- Fitted high waist elasticized seam
- Straight pant legs, flowy fit
- Palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0779

Category Name: Vacation Looks

Price: $20.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Classic Thong Sandals
These classic thong sandals are the perfect pair for the spring and summer seasons. They feature an open curved toe, thong-style faux leather straps, and a soft foam flat sole. Pair these sandals with a sheer flowy duster.

Fit & Features
- Open curved toe
- Thong-style faux leather straps
- Soft comfort fit
- Runs true to size
Style Number/Barcode: 07404-1064

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Pop Tie-Dye Stripe Halter Jumpsuit
Add a pop of summer's favorite print to your closet! This trendy tie-dye stripe halter jumpsuit features a sleeveless, plunge v-neck, dual tie-back closures on an alluring open-back, and a fitted empire waist with side pockets and a jogger style leg. Complete the look with a cute handbag.

Fit & Features
- Sleeveless, plunge halter v-neck
- Open-back, dual tie-back closures
- Fitted empire waist, side pockets
- Jogger style legs
- Tie-dye striped pattern
- Partial satin-lining, no stretch
- Fits true to size
Style Number/Barcode: 06302-0201

Category Name: Vacation Looks

Price: $18.97 $44.90

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