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.

Cool Effect Utility Woven Crop Jacket
A versatile woven jacket that brings a cool effect to every outfit! Layer on this twill jacket with slouchy long sleeves and elasticized cuffs to keep you warm, a collar neckline with button closure, and a front button-up design. With flap pockets and an adjustable drawstring crop hem, you'll have both function and fashion. Complete the look with trendy boots for casual plans!

Fit & Features
- Twill cotton woven fabric
- Flap pockets
- Button-up front closures
- Adjustable drawstring crop hem
- Runs true to size
Style Number/Barcode: 06204-1709

Category Name: Vacation Looks

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pretty Darling Sleeveless Smocked Crop Top
You'll adore styling this crop top with your favorite bottoms for any casual summer plans! The top is made from a woven fabric adorned with a square neckline, flirty ruffled shoulder straps, and a stretchy smocked bodice with a cropped hem for flaunting your figure. Complete the look in women's best-selling bottoms for the cutest outfit!

Fit & Features
- Woven fabric
- Ruffled shoulder straps
- Square neckline
- Stretchy smocked bodice
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2509

Category Name: Vacation Looks

Price: $22.90

Availability: Out of Stock
Product Badge:
- Ships Free
Bloom Baby Flower Claw Clip Set
Hair game = bloomin’ cute. These floral claw clips bring the vibe, whether you're going for soft girl sweet or Y2K realness—just clip and go.

Fit & Features
- Durable material with a glossy finish
- Bold floral design with petal detail
- Claw grip closure
Style Number/Barcode: 07006-000105

Category Name: Vacation Looks

Price: $10.90

Availability: In Stock

Available Color: GOLD

Available Size: NS
Good Times Bodycon Abstract Print Mini Dress
A mini dress that calls for good times only at casual parties or weekend plans! Designed with an alluring abstract print on mesh fabric, this dress is both chic and versatile. The sleeveless crew neckline and bodycon silhouette highlight your curves, while the side ruched seams flatter your figure. Complete the look with a mini shoulder bag and heels.

Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Side ruched seams
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5606

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Lovely In Eyelet A-Line Mini Dress
Make a lovely impression in this eyelet A-line mini dress at bridal showers or brunch with the girls!

Fit & Features
- Eyelet lace fabric, stretchy knit lining
- Strapless neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5997

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sittin Pretty Tie Waist Wide-Leg Palazzo Pants
Sit pretty in these high-rise palazzo pants to elevate your workwear or weekend wear! The chic pants offer a tie-waist design to snatch your waistline and a flattering wide-leg silhouette on breezy woven fabric. Complete the look in a bodysuit and mules.

Fit & Features
- Woven fabric
- Tie-waist design
- Back zipper closure
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1384

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Effortless Ribbed Knit Bodycon Midi Dress
This bodycon midi dress is the perfect blend of effortless and chic! Designed with a stretchy ribbed knit fabric for that comfortable fit, this mid-length dress features a trendy sleeveless square neck and back design with thin tank shoulder straps. The ribbed design on the body-hugging silhouette will flaunt your gorgeous figure. Layer on a faux leather jacket and pair with ankle booties for a night out!

Fit & Features
- Stretchy ribbed knit fabric
- Sleeveless square neck and back
- Tank straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5585

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Note To Self Ribbed Knit A-Line Mini Dress
Note to self, this sleeveless mini dress is a must-have for every day! Perfect for any occasion, this stretchy ribbed knit dress will surely become a staple in your wardrobe. It features a crew neckline with tank straps and a flattering A-line silhouette with a flirty front slit on the mini-length hem. Complete the look with an oversized blazer and a sleek necklace.

Fit & Features
- Soft and stretchy ribbed knit fabric
- Crew neckline
- Tank shoulder straps
- Front slit
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5632

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Looking Chic Belted Trouser Shorts With Linen
You'll be looking chic for the season in these lightweight linen-blend trouser shorts with a belted waist design. Style with the matching blazer for an elevated weekend vibe!

Shop Matching Blazer: Looking Chic Blazer With Linen

Fit & Features
- Linen-blend woven fabric, smooth woven lining, no stretch
- High-rise waist, belted design
- Dual front pockets
- Pleating
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06303-0299

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hidden Treasure Lace-Up Shell Accent Midi Dress
Discover your new signature look with this irresistible midi dress featuring a unique shell accent neckline, lace-up back offers undeniable allure, and a sultry side slit creates movement.

Fit & Features
- Texture knit fabric, moderate stretch, stretchy knit lining
- V-neckline with shell accent trim
- Spaghetti straps
- Lace-up back
- Side slit
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6119

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Summer Love Eyelet Knit Mini Dress
You'll fall in love with the effortless summer vibes of this eyelet knit mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, a form-hugging fit, and a pretty floral eyelet pattern. The lined knit fabric offers plenty of stretch for comfortable wear. Style with strappy sandals.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length hem
- Form-hugging fit
- Floral eyelet pattern, knit fabric, knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5113

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Art Of Patchwork Crop Denim Jacket
Layer on this retro-fab denim jacket for springtime fun! Showcasing a 60s-inspired patchwork design, this jacket offers a modern crop silhouette, slouchy long sleeves with button cuffs, a classic collar neckline, faux flap pockets, and button-down front closures for multiple styling options. Complete the look in a denim midi skirt to rock a denim-on-denim outfit!

Fit & Features
- Patchwork design
- Non-stretch denim fabric
- Button-down front
- Faux flap pockets
- Cropped hem
- Runs true to size
Style Number/Barcode: 06203-0521

Category Name: Vacation Looks

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vintage Charm Gingham Slit Peasant Maxi Skirt
Vintage charm is yours with this gingham peasant maxi skirt showcasing a modern high front slit for effortless movement!

Fit & Features
- Gingham print, woven fabric
- High-rise elasticized waist
- High front slit
- Flowy ruffled maxi-length silhouette
- Runs true to size
Style Number/Barcode: 06301-000002

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Breezy Sheer Lace Tie-Front Top
Cute and breezy, this sheer floral lace top features a V-neck with a tie-front design and long fitted sleeves with flared hems. Style with denim shorts and sandals for a casual summer look.

Fit & Features
- Sheer textured floral lace fabric
- V-neckline
- Tie-front design
- Long fitted sleeves, flared hems
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06202-000029

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tea Time Ruffled Short Skater Dress
It's time for afternoon tea and this skater dress will make an adorable entrance! Get ready to sashay in this dress featuring a ruffle trim square neckline and tiered ruffled short-length hem to add a playful touch to the skater silhouette. And with adjustable spaghetti straps and a stretchy smocked bodice, you'll be comfortable all day. Complete the look in chic wedges and a flouncy hat.

Fit & Features
- Woven fabric lined with woven fabric
- Ruffle trim neckline
- Adjustable spaghetti straps
- Stretchy smocked bodice
- Tiered ruffled short-length hem
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3059

Category Name: Vacation Looks

Price: $6.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunshine And Good Time V-Neck Mermaid Maxi Dress
This mermaid maxi dress is here for sunshine and good times! Made from textured mesh fabric, this dress will have you feeling so cute. Features a flattering V-neckline, dual spaghetti straps, a crisscross back, and a bust cutout. The mermaid silhouette and high front slit accentuate your curves, while the maxi-length hem adds a touch of chicness. Complete the look with sandals and sunglasses!

Fit & Features
- Textured mesh fabric, stretchy knit lining
- Dual spaghetti straps
- V-neckline
- High front slit
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5690

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Real Babe High-Rise Denim Skort
Bring real babe energy in this high-rise denim skort perfect for casual, everyday styling! With a bodycon fit and shorts bottom for coverage, this skort will be the one you reach for.

Fit & Features
- Dark wash denim
- High-rise waist
- Front button and hidden zipper closure
- Bodycon silhouette
- Mini-length hem
- Shorts bottom
- Runs true to size
Style Number/Barcode: 06603-0443

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
My Main Chic V-Neck Ruched Midi Dress
Ultra-flattering and soft, this sleeveless midi dress will be your main chic style! The knee-length dress is designed with a classic V-neckline, spaghetti straps, side ruched seams, and a bodycon silhouette that shows off your curves on smooth-lined knit fabric. Complete the look with stiletto heels for a birthday brunch or bridal shower!

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Side ruched seams, bodycon silhouette
- Midi-length hem
- Lined smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5479

Category Name: Vacation Looks

Price: $6.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glittery Vibes High Slit Maxi Skirt
Bring on the glittery vibes for your next girl's night in this high slit maxi skirt! Designed with a glitzy glitter knit fabric that has a mini-length lining, this long skirt is glam perfection. It features a high waist, a hip-hugging fit to flaunt your figure, a maxi-length hem with a high-cut back slit for an alluring detail, and an overall form-fitting silhouette for a sultry slay. Complete your going-out look with the matching crop top and clear heels!

Shop Matching Top: Glittery Vibes Ruched Spaghetti Strap Crop Top

Fit & Features
- Textured glitter knit fabric with mini-length knit lining
- Plenty of stretch
- High waist
- Maxi-length hem
- Back slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-0932

Category Name: Vacation Looks

Price: $14.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In My Sweet Era Cowl Neck Eyelet Lace Romper
Enter your sweet era with this eyelet lace romper for the ultimate romantic aura at brunch, birthdays, or showers! The flowy and breezy sleeveless rompers feature a flattering cowl neckline with spaghetti straps and an adorable fit and flare silhouette for all-day twirls. Complete the look in wedges.

Fit & Features
- Eyelet lace knit fabric, shorts lining, moderate stretch
- Spaghetti straps, cowl neckline
- Fit and flare silhouette
- Runs true to size
Style Number/Barcode: 06503-1128

Category Name: Vacation Looks

Price: $15.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Breezy Mood Collared Linen Crop Top
This breezy linen crop top is a sunny day staple! Designed with a lightweight linen-blend fabric, this top is perfect for your summer weekend plans. It features a collared V-neckline with a partial button-down front, a single chest pocket, cap sleeves, a twist-front cropped hem, and a relaxed fit. Style with wide-leg pants and sandals.

Fit & Features
- Linen-blend fabric
- Collared V-neckline
- Chest pocket, button-down front
- Cap sleeves
- Side zipper closure
- Twist-front cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06003-2431

Category Name: Vacation Looks

Price: $30.90

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek Glam Large Hollow Hoop Earrings
You'll love the sleek glamour these large brass hollow hoop earrings add to your everyday looks. Perfect for the girlies with sensitive skin, these hoops are hypoallergenic.

Fit & Features
- Genuine brass
- Hollow hoop
- Hypoallergenic
- Large hoop design
- Omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000074

Category Name: Vacation Looks

Price: $2.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Darling Twirl Crepe Ruffle Skater Dress
Delight with your darling twirls in this crepe skater dress perfect for family parties or brunch! It features adorable puff short sleeves, a V-neckline, and a ruffled layered short-length hem with a fit-and-flare silhouette. Complete the look in this skater dress with sleek hoop earrings.

Fit & Features
- Puff short sleeves
- V-neckline
- Back zipper and hook-eye closure
- Skater silhouette
- Ruffled layered short-length hem
- Crepe fabric, partial stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5064

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Instant Staple Double-Slit Mini Skort
This chic double-slit mini skort will be an instant staple you'll love to style up. It features a high-rise elasticized waist, fitted shorts, and a mini-length front overlay with a double-slit design. The ponte knit fabric offers a moderate stretch. Complete the look with a form-hugging bodysuit and strappy mules.

Fit & Features
- High-rise elasticized waist
- Fitted shorts
- Mini-length front overlay, double-slit design
- Ponte knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1074

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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