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.

Feelin' Like A Dream Chiffon Skater Dress
Look and feel like a dream in this chiffon skater dress perfect for baby showers or birthdays! It features an off-the-shoulder, ruffle trim sweetheart neckline, sheer peasant long sleeves with elastic cuffs, a lightly padded bust, and a flowy tiered ruffled short-length hem. Complete the look in cute mules.

Fit & Features
- Off-the-shoulder, smocked back
- Ruffle trim sweetheart neck, lightly padded bust
- Sheer peasant long sleeves, elastic cuffs
- Fit and flare skater silhouette
- Flowy tiered ruffled short-length hem
- Chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2113

Category Name: Vacation Looks

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Break Vibes Wide-Leg Pants
This trendy retro print pant radiates spring break vibes! It features a high-rise waist, wide-leg silhouette, and an all-over eye-catching marble print pattern. The pleated chiffon fabric has a full knit lining. Style with the matching tops.

Shop Matching Tops: Spring Break Vibes Pleated Bra Top, Spring Break Vibes Pleated Button-Down Top

Fit & Features
- High-rise waist
- Back zipper, hook and eye closure
- Wide-leg silhouette
- Marble print pattern
- Pleated chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06402-0557

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spring Break Vibes Pleated Bra Top
This trendy retro print bra top radiates spring break vibes! It features a sleeveless V-neckline, a padded bust, adjustable spaghetti straps, a fitted cropped hem, and an all-over eye-catching marble print pattern. The pleated chiffon fabric has a full knit lining. Style with the matching button-down top.

Shop Matching Top and Pants: Spring Break Vibes Pleated Button-Down Top, Spring Break Vibes Wide-Leg Pants

Fit & Features
- Sleeveless V-neckline, padded bust
- Adjustable spaghetti straps
- Back elastic strap with hook and eye closures
- Fitted cropped hem
- Marble print pattern
- Pleated chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-2063

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Delight Bow Flat Sandals
Perfect for the beach or any casual plans, these flat sandals will delight with a charming bow strap and comfortable footbed.

Fit & Features
- Square toe
- H-shaped band with bow
- Cushioned insole
- Faux leather material
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1288

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Break Vibes Pleated Button-Down Top
This trendy retro print button-down top radiates spring break vibes! It features a collared neckline, long sleeves with a single button detail, a complete button-down front, a mid-length hem with a relaxed fit, and an all-over eye-catching marble print pattern. The pleated chiffon fabric is semi-sheer with a lightweight feel. Style with the matching bra top.

Shop Matching Top And Pants: Spring Break Vibes Pleated Bra Top, Spring Break Vibes Wide-Leg Pants

Fit & Features
- Collared neckline
- Long sleeves, single button detail
- Button-down front
- Mid-length hem, relaxed fit
- Marble print pattern
- Pleated chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-2064

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Match My Mood Six-Pack Earrings Set
Match your mood with any of the earrings in this six-pack set! Features one pair of faux pearl studs and huggies, one pair of sleek metal ball studs and huggies, and one pair of rhinestone studs with sleek metal huggies. Complete the look in a matching set for day or night plans!

Fit & Features
- Six-pack earrings set
- One pair of metal ball studs and huggies
- One pair of faux pearl studs and huggies
- One pair of rhinestone studs and sleek metal huggies
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1480

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Good Angle Mid Rise Wide-Leg Denim Jeans
These denim jeans capture your best angles! They feature a flattering mid-rise waist, front and back distressed accents, and a wide-leg silhouette, and are crafted from premium non-stretch denim fabric. Style with a cute graphic tee to complete the look!

Fit & Features
- Mid-rise waist
- Front and back distressed accents
- Wide-leg silhouette
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium non-stretch denim fabric
- Runs true to size
Style Number/Barcode: 06602-0435

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Trendy Ribbed Knit Cropped Tank
Elevate your casual summer 'fits with this trendy cropped tank! It features a sleeveless scoop neckline with a notched front design, tank shoulder straps, a center cutout at the hem, and a cropped, form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch. Style this tank with distressed denim shorts.

Fit & Features
- Sleeveless scoop neckline
- Notched front design
- Tank shoulder straps
- Center cutout at the hem
- Cropped, form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1531

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Desert Dreamer Swirl Print Crop Top
Embrace the dreamy retro vibes this festival season with this swirl print crop top! It features a plunging neckline with an alluring center cutout under the bust, long bishop sleeves, a lower back cutout with a tie-back design, and a fitted cropped hem. The trendy swirl print pattern will capture everyone's attention. Style with faux leather shorts and strappy mules.

Fit & Features
- Plunging neckline
- Center cutout under the bust
- Long bishop sleeves, cinched hems
- Lower back cutout, tie-back design
- Fitted cropped hem
- Swirl print pattern, knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4682

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Breeze In Style Ruffled Skater Romper
Breeze into the party in this skater romper for a flirty allure everywhere you go! It features peasant long sleeves, a plunge V-neckline, a cutout waist with a tie-back design, and a layered ruffle skort bottom. Complete the look in strappy sandals.

Fit & Features
- Peasant long sleeves
- Plunge V-neckline
- Cutout waist, tie-back design
- Back zipper and hook-eye closure
- Layered, ruffle skort bottom
- Gauze woven fabric, sewn-in lining, no stretch
- Runs true to size
Style Number/Barcode: 06303-0154

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Casual Glam Rhinestone Bow Sandals
Go for these adorable bow sandals to add some casual glamour to your look! They feature an open square toe, a dual clear strap design with metallic straps and rhinestone bow accents, an open back for easy on-and-off styling, a flat sole, and a metallic sheen. Pair with sparkly stud earrings.

Fit & Features
- Open square toe
- Dual clear strap design
- Metallic straps, rhinestone-adorned bow accents
- Open back, on-and-off styling
- Flat sole
- Metallic sheen
- Runs true to size
Style Number/Barcode: 07404-1124

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Elevated Side Slit Skort
Create an elevated 'fit with this chic of-the-moment skort! It features a high-rise elasticized waist, fitted shorts, and a mini-length front overlay with a side seam leading to a slit accent. The ponte knit fabric offers a moderate stretch. Style with the matching cropped bustier for a seamless look!

Shop Matching Top: So Elevated Ponte Crop Bustier

Fit & Features
- High-rise elasticized waist
- Fitted shorts
- Mini-length front overlay
- Side seam leading to slit
- Ponte knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1030

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Elevated Ponte Crop Bustier
Create an elevated 'fit with this chic of-the-moment crop bustier! It features a sleeveless sweetheart neck, wide shoulder straps, bust seam detailing, and a fitted crop hem. The ponte knit fabric offers a moderate stretch. Style with the matching skort for a seamless look!

Shop Matching Bottoms: So Elevated Side Slit Skort

Fit & Features
- Sleeveless sweetheart neck
- Wide shoulder straps
- Bust seam detailing
- Fitted crop hem
- Ponte knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4717

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Island Time Floral Wide-Leg Pants
You'll be on total island time in these bold floral pants! They feature a high-rise banded waist, a wide-leg silhouette, a relaxed fit, and an abstract floral print pattern that will draw everyone's attention to your chic look. Style with the matching tube top for a vacay-ready 'fit.

Shop Matching Top: Island Time Floral Cropped Tube Top

Fit & Features
- High-rise banded waist
- Wide-leg silhouette
- Relaxed fit
- Abstract floral print
- Knit fabric
- Runs true to size
Style Number/Barcode: 06502-2239

Category Name: Vacation Looks

Price: $15.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Muse Floral Satin Pants
When it comes to your fashion style, you're a major muse for sure. These floral satin pants are perf for you. It features a high-rise waist, side pockets, and a wide-leg silhouette. The silky-smooth satin fabric features a chic all-over floral print pattern. Complete the look with the matching button-down top and bra.

Shop Matching Tops: Major Muse Floral Satin Bra Top, Major Muse Floral Satin Button-Down Top

Fit & Features
- High-rise waist
- Side pockets
- Wide-leg silhouette
- Floral print
- Satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-1318

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major Muse Floral Satin Button-Down Top
When it comes to your fashion style, you're a major muse for sure. This floral satin button-down top is perf for you. It features a collared neckline, long sleeves with dual button details, a complete button-down front, and a relaxed fit. The silky-smooth satin fabric features a chic all-over floral print pattern. Complete the look with the matching bra top and wide-leg pants.

Shop Matching Top: Major Muse Floral Satin Bra Top

Shop Matching Bottoms: Major Muse Floral Satin Pants

Fit & Features
- Collared neckline
- Long sleeves, dual button details
- Button-down front
- Relaxed fit
- Floral print
- Satin woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-2199

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Higher Love Twill Wrap Denim Skort
You'll have a high love for this twill denim skort perfect for your weekend plans! It features a high-rise waist with a side metal hoop inset and a strap belt accent, a front wrap, and a cheeky short bottom. The skort is composed of a twill denim woven fabric with no stretch. Complete the look in strappy sandals.

Fit & Features
- High-rise waist
- Side metal hoop, strap belt accent
- Side zipper closure
- Front wrap design
- Cheeky short bottom
- Twill denim woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0229

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Too Glam To Care Oversized Braid Sunglasses
These oversized sunglasses with braided arms bring instant luxe vibes. Whether you’re blocking out the sun or the shade, they’ve got your back in style.

Fit & Features
- Oversized sleek frames
- Braided detail on the arms
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000061

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ready For Brunch Cork Espadrille Wedges
These adorable cork espadrille wedges will have you ready for weekend brunch! They feature an open almond toe with a toe strap, an adjustable ankle strap with a back criss-cross design, a sturdy cork wedge heel, and a braided espadrille trim. Complete your look with a chic handbag.

Fit & Features
- Open almond toe, faux leather toe strap
- Faux leather adjustable ankle strap, back criss-cross design
- Metal buckle detail
- Cork wedge heel
- Espadrille trim
- Faux leather cushioned insole
- Runs true to size
Style Number/Barcode: 07406-0319

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cute And Dainty Butterfly Charm Necklace
You'll adore the cute and dainty details of this butterfly charm necklace! It features a single-row chain-link design with small clear butterfly-beaded charms. Includes an adjustable chain with a lobster clasp closure. Style with rhinestone stud earrings.

Fit & Features
- Single-row dainty chain-link design
- Small clear butterfly-beaded charms
- Adjustable chain, lobster clasp closure
Style Number/Barcode: 07002-1480

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Glam Babe Charm Necklace Set
Give off trendy glam babe energy in this embellished charm necklace set! It features two necklaces, including a single snake chain necklace, and a five-row layered necklace with dainty chains, mini rhinestones, and small charms featuring butterfly, star, sun, moon, and cross designs. Style this set with sleek hoop earrings.

Fit & Features
- Set of two necklaces
- Single snake chain necklace
- Five-row layered necklace
- Dainty chains, mini rhinestones, small charms
- Butterfly, star, sun, moon, and cross designs
- Adjustable chains, lobster clasp closures
Style Number/Barcode: 07002-1475

Category Name: Vacation Looks

Price: $2.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fresh 'Fit Long Sleeve Denim Romper
Show off a fresh 'fit in this trendy denim romper! It features a collared neckline, a partial button-down front, chest pockets, long loose sleeves with cinched hems, a high waist silhouette with belt loops, fitted shorts, and a form-hugging fit. Style with cowboy boots for a cool western vibe.

Fit & Features
- Collared neckline, partial button-down front, chest pockets
- Long loose sleeves, cinched hems
- High waist, belt loops, button-front closure
- Fitted shorts, back pockets
- Form-hugging fit
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0309

Category Name: Vacation Looks

Price: $20.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Major Muse Floral Satin Bra Top
When it comes to your fashion style, you're a major muse for sure. This floral satin bra top is perf for you. It features a sleeveless V-neckline with a twist-front design at the bust, adjustable spaghetti straps, a stretchy smocked back panel, and a fitted cropped hem. The silky-smooth satin fabric features a chic all-over floral print pattern. Complete the look with the matching button-down top and wide-leg pants.

Shop Matching Top: Major Muse Floral Satin Button-Down Top

Shop Matching Bottoms: Major Muse Floral Satin Pants

Fit & Features
- Sleeveless V-neckline, twist-front design
- Adjustable spaghetti straps
- Stretchy smocked back panel
- Fitted cropped hem
- Floral print
- Satin woven fabric, knit lining at the bust
- Runs true to size
Style Number/Barcode: 06003-2198

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flowy Feels Paisley Maxi Dress
You'll love the flowy fit of this paisley maxi dress, perfect for the warmer months! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem, and a thigh-high front slit. The smooth and stretchy knit fabric features a trendy paisley print pattern. Complete the look with strappy sandals.

Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Maxi-length hem, high front slit
- Flowy silhouette
- Paisley print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4967

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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Vacation Looks

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Now Trending

STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials