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.

Make It Chic Cutout Mini Dress
Make it a chic moment with a stunning dress that draws all eyes on you! The dress features a plunging halter neck, tie-up neck ties, a cutout at the midriff, 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 wedges and hoops.

Fit & Features
- Plunging halter neck
- Tie-up neck ties
- Cutout at the midriff
- Mini-length silhouette
- Knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-3855

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casually Chic Espadrille Platform Wedges
Keep it casually chic with platform wedges that keep it lowkey! The platform wedges feature an open back, an adjustable ankle strap, a triple-row strap design, and an espadrille platform. Complete look with a cute matching top and skirt set.

Fit & Features
- Open back
- Adjustable ankle strap
- Triple-row strap design
- Espadrille platform
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0946

Category Name: Vacation Looks

Price: $7.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
La Vida Vodka Baseball Cap
Live your best life in this canvas baseball cap! It features a curved brim with an "Livin La Vida Vodka" embroidered script. Wear it with a bikini and cutoff denim shorts for your next beach day.

Fit & Features
- Traditional baseball cap design
- Embroidered script
Style Number/Barcode: 07302-0360

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Graffiti Glam Crossbody
Keep it part chic, part edgy with a crossbody that shows off your fierce style! The crossbody features a top handle, a rectangular body, a fold-over closure with turn-lock closure, a multi neon-hue, a graffiti design, a chunky chain link accent, and an adjustable shoulder strap. Complete look with a denim dress and mules.

Fit & Features
- Top handle
- Rectangular body
- Fold-over closure, turn-lock fasten
- Multi neon hue
- Graffiti design
- Chunky chain link accent, adjustable shoulder strap
- Faux leather material
Style Number/Barcode: 07203-0611

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bloom With A View Floral Mini Skirt
Wherever your travels take you, this floral mini skirt is here to make your view that much prettier! Designed to flatter, this skirt has a sleek mid-rise waist and bodycon silhouette that highlights your figure. Pair with the matching top to complete the look.

Fit & Features
- Floral print, mesh fabric, sewn-in knit lining, moderate stretch
- Mid-rise waist
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Shop The Matching Top: Bloom With A View Floral Tube Top
Style Number/Barcode: 06501-000048

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
No Hands Croc Embossed Fanny Pack Belt
Go totally hands-free babe with this fanny pack belt! It's designed with cross-embossed faux leather material, envelope-style front, and snap button closure. Wear with a romper for the ultimate music festival vibes.

Fit & Features
- Removable faux leather belt
- Envelope style front
- Snap-button closure
Style Number/Barcode: 07203-0809

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Miss Chic Faux Leather Purse
Show off your chic style with a purse that keeps your look all together! The purse features a top handle, a small rectangular-shaped body, contrast stitching, fold-over closure with a geometric-shaped metal accent. Complete look with a blazer and high waist jeans.

Fit & Features
- Top handle
- Small rectangular body
- Contrast stitching
- Fold-over closure
- Geometric-shaped metal accent
- Faux leather material
Style Number/Barcode: 07203-1016

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dainty Luxe Three Row Anklet
Bring the luxe with a dainty anklet that brings those chic details! The anklet features a three-row design, a dainty chain link, flat metal coins, and a rhinestone embellished cross charm. Includes a lobster clasp closure. Complete look with a white dress and wedges.

Fit & Features
- Three-row design
- Dainty chain link
- Flat metal coins
- Rhinestones
- Cross charm
- Lobster clasp closure
Style Number/Barcode: 07003-0249

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Chain Design Satin Scarf
This chic and sleek satin scarf can be styled in so many ways to elevate your look! The scarf features a cool chain design and is composed of a smooth, lightweight satin fabric. Style this scarf as a head wrap or a top and complete the look with hoop earrings for a trendy vibe.

Fit & Features
- Satin fabric
- Chain-link print
Style Number/Barcode: 07305-0303

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feelin' Flirty Butterfly Hoop Earrings
Showcase a fab and flirty look with these glam hoop earrings! They feature a large hoop design with detailed butterfly accents, two of the butterfly charms with rhinestone embellishment. Style these earrings with a dainty necklace.

Fit & Features
- Large hoop design
- Butterfly accents
- Rhinestone embellishment
- Omega closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0885

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Criss Cross Chic Faux Nubuck Sandals
Bring the chic factor to your look with sandals that are totally fab! The sandals feature a slip-on design, an open almond toe, and wide criss-cross straps over the toe. Complete look with a matching top and shorts set.

Fit & Features
- Slip-on design
- Open almond toe
- Wide criss-cross straps over the toe
- Faux nubuck
- Faux-leather sole
- Runs true to size
Style Number/Barcode: 07404-0888

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Living Large Faux Leather Wedges
Live it up with wedges that make your look feel so extra, babe! The wedges feature an open back, a wide clear PVC strap, a peep toe, and a platform wedge heel. Complete look with a ruffled mini dress and hoops.

Fit & Features
- Open back
- Wide clear PVC strap
- Peep toe
- Platform wedge heel
- Faux patent leather
- Runs true to size
Style Number/Barcode: 07406-0278

Category Name: Vacation Looks

Price: $12.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Major Glam Chainlink Sandals
Bring major glamour to your look with sandals that make major waves! The sandals feature an adjustable clear PVC strap, a chunky chain link accent, an open almond toe, and an ultra-low block heel. Complete look with a wrap dress and hoops.

Fit & Features
- Slingback strap
- Clear PVC straps
- Chunky chain link accent
- Open almond toe
- Ultra-low block heel
- Runs true to size
Style Number/Barcode: 07404-0962

Category Name: Vacation Looks

Price: $7.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
It's Casual Nubuck Slip On Sandals
Kick back and keep it casual in this pair of sandals! They feature a slip-on design, a thick strap, and an open toe. Wear them with all your breezy sundresses for a summery vibe!

Fit & Features
- Slip-on design
- Nubuck fabrication
- Open toe
- Thick strap
- Runs true to size
Style Number/Barcode: 07404-0886

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On The Edge Bow Studded Jelly Sandals
Keep your style on the edge in this pair of super chic jelly sandals! They feature clear PVC straps, studded embellishments, and a bow detail. Wear them with an oversized straw hat to soak up the sun in the park.

Fit & Features
- PVC straps
- Studded embellishments
- Bow detail
- Open toe
- Runs true to size
Style Number/Barcode: 07404-0891

Category Name: Vacation Looks

Price: $8.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
'90s Babe Jelly Square Toe Mule
Show off those throwback vibes with this '90s chic pair of mules! They feature a thick jelly strap, open square toe, and low block heel. Pair with a flirty sundress and thin choker for the ultimate retro-inspired look.

Fit & Features
- Open square toe
- Low block heel
- Thick jelly strap
- Runs true to size
Style Number/Barcode: 07401-3213

Category Name: Vacation Looks

Price: $7.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Oh-So-Fab Tie-Dye Maxi Dress
Keep your look trendy and fab in this curve-hugging tie-dye maxi dress. It features a sleeveless asymmetrical one-shoulder neckline, a single spaghetti strap, a flattering high waist seam, and a form-fitting maxi-length silhouette with a sultry thigh-high side slit. Complete the outfit with clear heels.

Fit & Features
- Sleeveless asymmetrical one-shoulder neckline
- Single spaghetti strap
- High waist seam
- Maxi-length silhouette, form-hugging fit
- High side slit, ruched detailing
- Knit fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4277

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feelin' Wild Sleeveless Slip Dress
Showcase a chic wild style in this sleeveless slip dress! It features a lined V-neckline, spaghetti straps, a cute tie-back detail, and a flirty short silhouette with a subtle flared-out hem. The lightweight woven fabric has a trendy all-over animal print. Complete the look with strappy mules.

Fit & Features
- Sleeveless lined V-neckline
- Spaghetti straps
- Tie-back detail
- Mini-length silhouette
- Woven fabric, no stretch, animal print
- Runs true to size
Style Number/Barcode: 05102-4245

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Summer Glow-Up Watercolor Woven Tube Top
Show off a summer glow-up in this watercolor-printed woven tube top designed with a strapless sweetheart neckline, tie-front, and fitted ultra-cropped hem. Style with the matching shorts for a chic vibe.

Shop Matching Bottoms: Summer Glow-Up Watercolor Woven Shorts

Fit & Features
- Linen-like woven fabric, watercolor print
- Strapless sweetheart neckline
- Tie-front design
- Stretchy smocked back
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06003-000034

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Make It Bold High Waist Palazzo Pants
Create a bold and trendy look for a night out with these chic palazzo pants. They feature a high-rise waist, pleating, and a flared wide-leg hem. Style these pants with the matching crop top and cute mules.

Shop Matching Top: Make It Bold Cutout Crop Top

Fit & Features
- High-rise waist, elastic waistband
- Pleating
- Wide-leg hem
- Lightweight knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0669

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fab And Fierce Chain Link Jelly Mules
Keep it fab and fierce with mules that bring the heat to your look! The mules feature an open back, an open square toe, a wide strap over the toe with a chainlink accent, and a low block heel. The mules are composed of a jelly material Complete look with a matching top and skirt set.

Fit & Features
- Open back
- Open square toe
- Wide strap over the toe
- Chainlink
- Low block heel
- Jelly material
- Runs true to size
Style Number/Barcode: 07401-3212

Category Name: Vacation Looks

Price: $7.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Staple Denim Jacket
Layer this stylish staple over your favorite dresses and jumpsuits for a day out! The jacket features a collared neckline, a multi-button down front, chest pockets, side pockets, and long sleeves. The jacket is composed of a denim fabric that offers a relaxed fit with slight stretch.

Fit & Features
- Collared neckline
- Multi-button down front
- Chest pockets, side pockets
- Long sleeves
- Denim fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06203-0184

Category Name: Vacation Looks

Price: $23.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Buckled Up Denim Square Toe Block Heels
Channel retro babe vibes in this pair of block heels! They're designed with an open square toe, fun buckle detail and denim fabrication. Wear them with a jumpsuit to dance the night away.

Fit & Features
- Open square toe
- Block heel
- U-shaped buckle accent
- Denim material
- Runs true to size
Style Number/Barcode: 07401-2792

Category Name: Vacation Looks

Price: $7.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In The Mix Criss Cross Platform Block Heels
Stunt on them on your next night out in this pair of block heels! They're designed with a platform wedge, block heel and criss cross straps.

Fit & Features
- Open almond toe
- Criss cross ankle straps
- Block heel
- Platform
Style Number/Barcode: 07401-3309

Category Name: Vacation Looks

Price: $7.97 $28.90

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