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

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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.

Life's A Highway Aviator Sunglasses
Can't you imagine wearing these sleek aviator sunglasses on your next road trip or driving down by the beach? They feature a rose gold metal frame, rubber nose supports, a classic aviator design, and mirrored lenses. Complete the look in a graphic crop top and denim shorts!

Fit & Features
- Classic aviator design
- Sleek rose gold metal frame
- Rubber nose supports
- Mirrored lenses
Style Number/Barcode: 07008-1003

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stay Shady Woven Visor
Shade your eyes and look cute doing it with this woven visor featuring a classic wide brim and a velcro back closure. Complete the look in a basic tee and skort for exploring a beach city!

Fit & Features
- Classic wide brim
- Velcro back closure
- Woven material
Style Number/Barcode: 07302-1386

Category Name: Vacation Looks

Price: $1.97 $5.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Vacay Muse Tropical Print Halter Top
You'll be an alluring vacay muse in this tropical print halter top! It features a sleeveless sweetheart neckline, thin halter straps, and an ultra-cropped, fitted hem. Style with the matching maxi skirt for a dreamy look.

Shop Matching Bottoms: Vacay Muse Tropical Print Maxi Skirt

Fit & Features
- Sleeveless sweetheart neckline
- Thin halter straps
- Ultra-cropped, fitted hem
- Tropical print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4689

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Muse Tropical Print Maxi Skirt
You'll be an alluring vacay muse in this tropical print maxi skirt! It features a high-rise waist, ruching down the side, a maxi-length asymmetric hem creating a thigh-high side slit, and a curve-hugging fit. Style with the matching crop top for a dreamy look.

Shop Matching Top: Vacay Muse Tropical Print Halter Top

Fit & Features
- High-rise waist
- Side ruching
- Maxi-length asymmetric hem, high-side slit
- Form-hugging fit
- Tropical print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0785

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Throw It Back Low-Rise Micro Mini Skirt
Throw it back to the early 2000s with this trendy micro mini skirt! It features a low-rise waist, large front pockets, back pockets, and an ultra-mini-length hem with a frayed edge and the pocket lining peaking below. Style this form-hugging mini skirt with a crop top, sandals, and a cool pair of shades.

Fit & Features
- Low-rise waist, five belt loop accents
- Front button, hidden zipper closure
- Large front pockets, back flap pockets, button closures
- Micro mini-length hem, frayed edge, pocket lining
- Form-hugging fit
- Twill fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06301-0147

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Western Flair Faux Suede Crop Top
Show off a western flair in this trendy faux suede crop top! Featuring a sleeveless halter neckline with tie-back spaghetti straps, an open back, and a pointed, cropped hem with thin waist straps, this cute top is a summertime staple! Style with printed flare pants and strappy sandals.

Fit & Features
- Sleeveless halter neckline
- Tie-back spaghetti straps
- Open back
- Pointed, cropped hem
- Thin waist straps, tie closure
- Faux suede fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4192

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glitzy Bejeweled Thong Sandals
Keep it glitzy with these glamorous bejeweled sandals! They feature a round toe, a metallic thong strap design with clear PVC strap detailing, chain accents, stunning gemstone embellishments, and an open back for easy on-and-off styling. Pair with hoop earrings.

Fit & Features
- Round toe
- Metallic thong strap design
- Clear PVC straps, chain accents
- Gemstone embellishments
- Open back, slip-on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1133

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Festive Babe Crochet Fringe Top
Get ready for festival season babe! This boho crochet fringe top features a sleeveless halter neck with a tie closure, an open back, and a cropped length with cascading fringe down the front. Complete the look in distressed denim shorts and a ring set.

Fit & Features
- Sleeveless halter neck with tie closure
- Open back
- Cropped length
- Crochet design with front fringe
- Sweater knit fabric
- No stretch
- Runs true to size
Style Number/Barcode: 06005-1690

Category Name: Vacation Looks

Price: $11.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Dance All Day Crochet Halter Top
Get ready to dance at every festival looking so fire in this crochet halter top featuring a trendy open-back with tie closure and a V-neck atop an ultra-cropped hem. Complete the look in boho flare pants.

Fit & Features
- Sleeveless, halter V-neck, tie closure
- Open-back
- Crochet design, unlined sweater knit fabric
- No stretch
- Runs true to size
Style Number/Barcode: 06005-1694

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cherish Me Eyelet Lace Skater Dress
All eyes on you in this lovely eyelet lace skater dress as the bride-to-be or graduate! The dress features a sleeveless sweetheart neck with flirty ruffle trim, adjustable spaghetti straps, a front bust tie and button accents, and a tiered fit and flare silhouette with a ruffled short hem. Complete the look in platform sandals.

Fit & Features
- Sleeveless sweetheart neck with ruffle trim
- Adjustable spaghetti straps
- Front bust tie, button accents
- Tiered, skater silhouette
- Ruffled short-length hem
- Eyelet lace cotton fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4907

Category Name: Vacation Looks

Price: $5.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Hint Of Radiance Rhinestone Flat Sandals
Treat your feet to a hint of radiance with these flat sandals - perfect for brides, graduates, or dressy parties! They feature a square toe, a twisted toe strap with rhinestone embellishments, and an ankle strap with buckle closure on faux leather material. Complete the look with a glam ring set.

Fit & Features
- Square toe
- Twisted toe strap with rhinestones
- Ankle strap with buckle closure
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1091

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Can't Go Wrong Crochet Knit Shorts
You can't go wrong with these crochet knit shorts perfect for a sunny day out on a weekend or vacation!

Fit & Features
- Crochet knit fabric, sheer design
- Low-rise drawstring waist
- Fitted hem
- Runs true to size
Style Number/Barcode: 06503-000026

Category Name: Vacation Looks

Price: $26.90

Availability: In Stock

Available Color: BLACK

Available Size: L
Product Badge:
- Part of a Set
Dainty Leaf Fringe Hoop Earrings
These dainty detailed hoops will bring that boho-chic glam! They feature a textured hoop with leaf-shaped charms in a dangling fringe design. Style with a layered necklace set.

Fit & Features
- Textured hoop
- Leaf-shaped charms, fringe design
- Rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1560

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Impressed Satin Pleated Maxi Skirt
You'll always be dressed to impress in this satin pleated maxi skirt featuring an elasticized high-rise waist, slim bodycon silhouette, and a center front side ruched seam atop a flirty slit. Style with the matching top for a night of dinner and dancing!

Shop Matching Top: Always Impressed Satin Pleated Crop Top

Fit & Features
- High-rise elasticized waist
- Slim, bodycon silhouette
- Center front side ruched seam, high slit
- Maxi-length hem
- Satin pleated fabric, backside lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06501-0793

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Always Impressed Satin Pleated Crop Top
You'll always be dressed to impress in this satin pleated top featuring a sleeveless V-neck, wide straps, a center-ruched bust seam, and a fitted crop hem. Style with the matching skirt for a night of dinner and dancing!

Shop Matching Bottoms: Always Impressed Satin Pleated Maxi Skirt

Fit & Features
- Sleeveless V-neck
- Wide straps
- Center-ruched bust seam
- Fitted crop hem
- Satin pleated fabric, bust lining
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4716

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Mixing It Up Twist Sweater Top
Mix up your everyday style in this flirty sweater crop top featuring a sleeveless, sweetheart neck, tank-style straps, and a twisted bodice on stretchy and soft rib-knit fabric. Complete the look in high-rise skinny jeans for a brunch.

Fit & Features
- Sleeveless, sweetheart neck, tank-style straps
- Twisted bodice
- Cropped hem
- Soft and stretchy
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1310

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Totally In Fringe Rhinestone Denim Shorts
You can be found in these denim shorts all season long! They feature a flattering high-rise waist, cascading rhinestone fringe along the front, and a cut-off style hem on premium non-stretch denim fabric. Complete the look in a flirty crop top and cowboy boots for a festival!

Fit & Features
- High-rise waist
- Cascading front rhinestone fringe
- Cut-off style hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium non-stretch denim fabric
- Runs true to size
Style Number/Barcode: 06603-0346

Category Name: Vacation Looks

Price: $6.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On The Verge Chiffon A-Line Midi Dress
You'll be on the verge of a stylish breakthrough with the addition of this chiffon midi dress to your fashion closet! Effortless and breezy, this dress features a sleeveless v-neckline, halter spaghetti straps, a lace-up open back that lets you customize the fit, and an asymmetrical hem with a flirty slit. Complete the look with stiletto heels and a bracelet!

Fit & Features
- Sleeveless v-neckline
- Halter spaghetti straps
- Lace-up open back
- A-line silhouette
- Asymmetrical midi-length hem, slit accent
- Chiffon fabric, stretchy knit lining
- Fits true to size
Style Number/Barcode: 05102-4905

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Trendy Diva Rhinestone Denim Block Heels
You'll be a total trendy diva with these sparkly rhinestone denim heels! They feature an open square-shaped toe, a wide toe strap, a thin adjustable ankle strap, a closed back, a block heel, and all-over rhinestones on the denim material. Style with a mini handbag.

Fit & Features
- Open square-shaped toe
- Wide toe strap
- Thin adjustable ankle strap, buckle detail, closed back
- Block heel
- Rhinestone embellishments
- Denim material
- Runs true to size
Style Number/Barcode: 07401-4163

Category Name: Vacation Looks

Price: $14.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Weekend Festivities Chunky Platform Heels
These bold platform heels were made for fun weekend festivities! They feature an open almond-shaped toe, dual braided straps, a chunky platform sole, and an ultra-tall block heel that will level up your look. Style with a sleek clutch for drinks with the girls!

Fit & Features
- Open almond-shaped toe
- Dual braided straps
- Open back
- Chunky platform sole
- Ultra-tall block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4286

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glam Rhinestone Buckle-Strap Sandals
Casual with a glam touch, these buckle-strap sandals are a trendy style for the summer season. They feature a round toe, a two-strap design with adjustable buckles, sparkling rhinestone embellishments, an open back for easy on-and-off styling, and a flat sole. Pair with hoop earrings.

Fit & Features
- Round toe
- Two-strap design, adjustable buckles
- Mini rhinestones
- Open back
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1137

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cross Paths Strappy Slide Sandals
Let these faux leather sandals cross your path! Perfect for casual days out or somewhere by the water, these sandals feature an on-trend square toe, asymmetrical thin strappy design, a flat sole, and a slide-on-and-off styling. Complete the look with chic jewelry.

Fit & Features
- Square toe
- Asymmetrical thin strappy design
- Flat sole
- Slide-on-and-off styling
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1090

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
You Better Work Lace-Up Crop Top
Work it out girl with a crop top that slays! The crop top features a sleeveless square neckline, tank shoulder straps, a lace-up back, and a cropped hem. The top is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with high waist shorts and mules.

Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Lace-up back
- Cropped hem
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1684

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Robyn High-Rise Crop Flare Jeans By Windsor Denim
Kick up your style in the must-have Robyn jeans by Windsor denim perfect for adding to your spring-to-summer lineup! They feature a flattering high-rise waist, hip-hugging fit, distressed knee accent, and a flare crop raw hem on premium white denim with a moderate stretch. Complete the look in a trendy crop top and wedges for a pool party!

Fit & Features
- High-rise waist, hip-hugging fit
- Distressed knee accent
- Flare cropped raw hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium white denim, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0413

Category Name: Vacation Looks

Price: $9.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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Vacation Looks

HomeVacation Looks

Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials