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.

Spread The Fun Butterfly Thong Sandals
Spread your wings and have fun with your fashion in these flat sandals featuring a jeweled butterfly charm, round toe with a thong-style strap, and dual foot straps on faux leather material. Complete the look with a ring set.

Fit & Features
- Round toe
- Jeweled butterfly charm
- Thong-style toe strap
- Dual foot straps
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1134

Category Name: Vacation Looks

Price: $6.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spring Into Style Espadrille Platform Heels
Spring into these stylish espadrille heels for the warmer season ahead! They feature an almond toe, wide toe strap, chunky platform sole, a block heel, and an ankle strap with buckle closure. Complete the look with a trendy handbag.

Fit & Features
- Almond toe
- Wide toe strap
- Chunky platform sole
- Block heel
- Ankle strap with buckle closure
- Espadrille material
- Runs true to size
Style Number/Barcode: 07401-4206

Category Name: Vacation Looks

Price: $9.97 $43.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Happily In Love Scoop Neck Mini Dress
You'll be happily in love with how stunning you look in this sleeveless mini dress for a graduation or birthday brunch! It features a scoop neck with a flirty bust tie, spaghetti straps, and a bodycon silhouette on rib knit fabric with a stretchy knit lining. Complete the look in trendy wedges.

Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Bust tie
- Bodycon silhouette
- Mini-length hem
- Rib knit, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4754

Category Name: Vacation Looks

Price: $19.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Must-Have Buckle-Strap Sandals
These buckle-strap sandals are a trendy must-have for the spring and summer seasons! They feature a round toe, a two-strap design with adjustable buckles, an open back for easy on-and-off styling, and a flat sole. Style with hoop earrings and a layered necklace.

Fit & Features
- Open round toe
- Two-strap design
- Adjustable buckles
- Open back
- Flat sole
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07404-1132

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Meli Mid-Rise Cuffed Shorts By Windsor Denim
Take your daily walk around town in the Meli shorts by Windsor Denim perfect for adding to your closet! They feature a classic mid-rise waist, distressed accents, and a cuffed hem on white denim fabric. Complete the look in a cute crop top for a backyard bbq or festival!

Fit & Features
- Mid-rise waist
- Distressed accents
- Cuffed hem
- Front button closure
- Five-pocket styling, belt loop accents
- Premium white denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0307

Category Name: Vacation Looks

Price: $6.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fabulous Vibes Platform Mules
Give off fabulous vibes in these of-the-moment platform mules! They feature an open almond-shaped toe, a wide banded toe strap, an open back for easy on-and-off styling, a platform sole, and a thick block heel. Pair with a quilted handbag.

Fit & Features
- Open almond-shaped toe
- Wide banded toe strap
- Open back
- Platform sole
- Thick block heel
- Faux leather material, subtle cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4161

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All Eyes on You Knit Striped Mini Dress
Turn heads without even trying. This tube striped dress hugs you just right with a twist-front that brings the drama.

Fit & Features
- Striped pattern, stretchy knit fabric
- Strapless tube sweetheart neckline
- Twist bust
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000044

Category Name: Vacation Looks

Price: $7.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Leave An Impression Halter Sweater Mini Dress
Leave an impression in this sweater mini dress for dates or weekend getaways! The rib knit dress features a sleeveless halter neckline, a partially open back, a bodycon silhouette, and a mini-length hem with a flirty slit. Complete the look in heeled sandals.

Fit & Features
- Sleeveless halter neckline
- Partially open back
- Bodycon silhouette
- Mini-length hem, slit accent
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1424

Category Name: Vacation Looks

Price: $6.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Chrome Cutie Slide Sandals
Slip into these cute and effortless chrome slide sandals perfect for your everyday occasions! They feature an almond toe, a wide single strap, and a flat sole on faux leather material. Complete the look in a trendy denim jacket.

Fit & Features
- Almond toe
- Wide single strap
- Faux leather material
- Chrome design
- Slide-on and off styling
- Runs true to size
Style Number/Barcode: 07404-1085

Category Name: Vacation Looks

Price: $6.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Alluring Wide-Leg Pants
Entice them all with your alluring look in these bold wide-leg pants! They feature a high-rise banded waist, a hip-hugging fit, and a flowy, relaxed, wide-leg silhouette. The textured knit fabric offers plenty of stretch. Style these chic pants with the matching crop top!

Shop Matching Top: Always Alluring Halter Crop Top

Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Flowy, wide-leg silhouette
- Textured knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-2244

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sweetest Of All Paisley Crop Top
A paisley crop top that adds boho sweetness to your favorite bottoms!

Fit & Features
- Paisley graphic print, stretchy knit fabric
- Scoop neckline
- Adjustable spaghetti straps
- Fitted pointy crop hem
- Runs true to size
Style Number/Barcode: 06002-000055

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Alluring Halter Crop Top
Entice them all with your alluring look in this bold halter crop top! It features a high halter neckline, spaghetti straps that lead to a cross-back lace-up design, a fitted, cropped hem, and spaghetti straps at the waist that tie in the back. The textured knit fabric offers plenty of stretch. Style this chic top with the matching wide-leg pants!

Shop Matching Bottoms: Always Alluring Wide-Leg Pants

Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, cross-back lace-up design, tie closure
- Fitted, cropped hem
- Waist spaghetti straps, tie-back closure
- Textured knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4694

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bri High-Rise Split Hem Flare Jeans by Windsor Denim
Elevate your everyday outfits with a fab retro vibe with the Bri split hem flare jeans by Windsor Denim. They feature a high-rise waist, a hip-hugging fit that continues throughout the legs, and a flared hem with a front split hem accent. Style with a crop top and platform heels.

Fit & Features
- High-rise waist
- Hip-hugging fit
- Form-hugging fit throughout the legs
- Flared hem, front split hem
- Front button closure, five-pocket and belt loop design
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0405

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Effortless Style Sleeveless Romper
Get that effortless style that's perf for warmer months in this casual and cute sleeveless romper. It features tank shoulder straps, a deep V-neck and back, a high waist with smocked detailing, trendy side cutouts, and flowy shorts. Pair this gauze romper with strappy sandals and hoop earrings.

Fit & Features
- Tank shoulder straps
- Deep V-neck and back
- High waist, smocked detailing
- Side cutouts
- Flowy shorts
- Gauze fabric
- Runs true to size
Style Number/Barcode: 06303-0221

Category Name: Vacation Looks

Price: $14.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortless Spring Style Floral Romper
Show off an effortless spring style with this adorable chiffon romper. It features short puff sleeves, a subtle sweetheart neckline with a ruched bust, a smocked back design, dual high waist seams, and flowy shorts with a cute fit and flare silhouette. The airy chiffon fabric features a dainty floral print pattern. Complete the look with braided sandals.

Fit & Features
- Short puff sleeves, elastic cinched hems
- Sweetheart neckline, ruched bust
- Smocked back design
- Dual high waist seams, flowy shorts, fit and flare silhouette
- Dainty floral print
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0251

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Gal Floral Boho Flare Pants
You'll be the trendiest gal at the festival or concert in these boho flare pants! They feature a flattering high-rise elastic waist, a hip-hugging fit, and a flared hem. The pants are designed with a floral striped print on stretchy brushed knit fabric. Complete the look in a crochet top and a hat.

Fit & Features
- High-rise elastic waist
- Hip-hugging fit
- Flared hem
- Floral striped print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06502-0910

Category Name: Vacation Looks

Price: $11.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
In For Romance Short Skater Dress
You'll be in for the romantic vibes of this short skater dress perfect for bridal showers or day dates! It features three-quarter-length puff sleeves, a sweetheart neck, a tie-front, and a fit and flare silhouette. The dress is composed of a swiss dot pattern cotton fabric with a smooth woven lining. Complete the look in simple block heels.

Fit & Features
- Three-quarter-length puff sleeves
- Square neck, tie-front
- Skater silhouette
- Short-length hem
- Swiss dot pattern, smooth woven lining
- No stretch
- Runs true to size
Style Number/Barcode: 05102-4902

Category Name: Vacation Looks

Price: $5.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wild Blooms Floral Short Dress
Tame your wild side and showcase this flirtatious floral short dress perfect for a casual picnic date! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a cutout back accent. Complete the look in wedges.

Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Bodycon silhouette
- Cutout back accent
- Short-length hem
- Floral print knit fabric, knit lining at the bust, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4579

Category Name: Vacation Looks

Price: $5.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spring In Full Swing Floral Skater Dress
With spring in full swing, this floral skater dress is an adorable must-have for the season! It features a V-neckline and a matching V-back design with a tie closure, sheer long balloon sleeves, dual high waist seams, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The airy chiffon fabric features a blooming floral print pattern. Style with strappy mules for weekend brunch!

Fit & Features
- V-neckline, V-back design, tie closure
- Sheer long balloon sleeves, elastic cinched hems
- Dual high waist seams, smocked back
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Floral print, sheer chiffon fabric, partial woven lining
- Runs true to size
Style Number/Barcode: 05101-2140

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
That 70s Chick Retro Print Mini Dress
Inspired by the groovy era, you'll look like a cute chick in this retro mini dress perfect for parties! It features a sleeveless square neck, spaghetti straps, side ruched seams that hug your figure, a bodycon silhouette, and a geometric-retro print design. Complete the look with bold earrings.

Fit & Features
- Sleeveless square neck, spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Geometric-retro print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5005

Category Name: Vacation Looks

Price: $19.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Gorgeous Blooms Puff Sleeve Crop Top
Dress up your weekend brunch 'fits with this gorgeous blooming floral crop top. It features short puff sleeves, a subtle sweetheart neckline, front hook-eye closure, trendy lattice side detailing, and a cropped hem. Style with a form-hugging mini skirt and mules.

Fit & Features
- Short puff sleeves, elasticized hems
- Sweetheart neckline
- Flexible boning, front hook-eye closures
- Stretchy side lattice straps
- Cropped hem
- Floral print pattern
- Smooth woven fabric, lined, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1864

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Flirty Ways Halter Lace Trim Crop Top
With this flirty crop top for celebrations or date night, you'll stun in the plunge halter V-neckline with a dainty lace trim and partially open back. Pair with the matching skirt to complete the look.

Shop Matching Bottoms: Flirty Ways Ruched High Slit Midi Skirt

Fit & Features
- Double-lined stretchy knit fabric
- Plunge halter V-neckline, lace trim, tie closure
- Partially open back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-000094

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sporty Babe Skater Skort
Channel a sporty babe vibe with this adorable skater skort! It features a high-rise waist with a flattering V-shaped design, fitted shorts, and a short skater skirt overlay. The smooth jersey knit fabric offers plenty of stretch. Style with a crop top and sneakers.

Fit & Features
- High-rise waist, V-shaped design
- Fitted shorts
- Short skater skirt overlay
- Jersey knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06503-1065

Category Name: Vacation Looks

Price: $11.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cabo Calling Boho Tulip Pants
Answer the call! Look fab on vacay in this boho tube top featuring an eye-catching tie-front, halter neckline, a smocked back, and a cute boho-inspired print on lined woven fabric with no stretch. Complete the look in matching pants and sandals.

Shop The Matching Top: Cabo Calling Boho Tube Top

Fit & Features
- Elasticized high-rise waist
- Front tulip-cut slits
- Boho-inspired print
- Woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0616

Category Name: Vacation Looks

Price: $9.97 $36.90

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