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.

Properly Posh Rhinestone Door Knocker Earrings
Get those posh vibes going when you add in rhinestone door knocker earrings! We love these because not only do they pair well with your evening looks but even those casual lookz too!
- Door knocker design
- Leafy rhinestone outline
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0350

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ready For Vacay Square Toe Wedges
Get vacay ready in a sweet pair of wedges! With the perfect heel height for comfort, and a unique square toe, they pair perfectly with a flowy midi dress!
- Square toe
- Single band over the toe
- Narrow fit
- Stacked wooden wedge heel
- Adjustable pin buckle closure
- Ankle strap
- Composed of faux suede
Style Number/Barcode: 07406-0049

Category Name: Vacation Looks

Price: $18.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chiffon Flow Skater Dress
Go with the flow in a skater dress that is party-ready! The dress features a flattering wrap v-neckline, adjustable spaghetti straps for a customized fit, and a high waist fit that leads to a flowy layered skater skirt that beautifully cascades silhouette. Complete your brunch-ready look with a dainty necklace and clear heels.

Fits & Features
- Wrap bodice with deep v neckline
- Adjustable spaghetti straps
- Exposed back zipper closure
- High waist seam
- Wrapped and layered skater skirt
- Fully lined, chiffon fabric
- No stretch
Mauve Dress: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Navy Dress: Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-7908

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Leopard Love Lace Up Front Mini Dress
We've all got love for leopard print in our wardrobe! Make your presence be known in this fierce mini dress!

Fits & Features
- Sheer Roomy Long Sleeves
- Ruffle-Trim At Sweetheart Neckline & Shoulders
- Lace-Up Front
- Back Zipper With Hook & Eye Closure
- Mini Length Hemline I Adjustable Dual Drawstrings At The Front
- Woven Lined Fabric
- Minimal Stretch
Style Number/Barcode: 05101-0768

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Flower Of Love Scuba Mini Dress
Brighten up your wardrobe with bold and beautiful floral prints! It's the perf dress for your wedding guest attire!

Fits & Features
- Wire V Neckline I Vertical Darts At The Bust
- High Waist Seam
- Mini Length Silhouette
- Smooth Scuba Fabric
- Form Hugging Fit I Moderate Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0191

Category Name: Vacation Looks

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stylishly Glam Strappy Rhinestone Pearl Sandals
Strappy and stylish, these sandals are designed with glam rhinestones and faux pearl trims that elevate every look.

Fit & Features
- Square toe
- Strappy design
- Rhinestone and faux pearl trims
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1281

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Don't Underestimate Me Low Rise Swim Bottoms
Don't underestimate a simple swimsuit babe! Dress it up with a gold chain belt and some stunner shades! Don't forge to pick up your matching swim top!

Fit & Features
- Low-rise fit
- High hip design
- Cheeky bottom
- Moderate stretch
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0562

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunny Skies Ahead Swimsuit
Get sunkissed in this simply sexy one piece!

Fit & Features
- Spaghetti straps
- Scoop neckline
- Deep scoop back
- Open sides
- Removable padding
- Fully lined
- Ribbed fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0143

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In The Spotlight Heat Stone Mesh One Piece Swimsuit
Show off those curves and let them stare because you in this swimsuit...you'll always be in the spotlight!

Fits & Features
- One Piece Swimsuit
- High Round Sheer Mesh Neckline I Plunging V
- Heat Stone Embellishments At The Front
- Removable Padded Bust
- Sheer Mesh Insets At The Side
- Low Open Back I Cheeky Bottoms
Model is 5'4" with a 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0198

Category Name: Vacation Looks

Price: $9.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Show Your Shimmer Scoop Back Swimsuit
Soak up the sun and show off that shimmer in this fabulous swimsuit!

Fits & Features
- Narrow Spaghetti Straps
- Plunging V Neckline I Low Scoop Back
- Low Open Sides
- Fully lined
- No padding
- Cheeky Coverage & Fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0142

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Thank You Next Swimsuit
Thank you, next. Our new life motto. Wear it proud on this super cute pink monokini! It features a scoop neckline, spaghetti straps, an open back, and high cut bottom with a semi-cheeky fit.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07109-0108

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bold And Beaded Woven Tunic
Can this beaded tunic be more festival ready?! Layer on this bold piece for a majorly trendy vibe.

Fit & Features
- Rounded neckline
- Spaghetti straps
- Beaded and woven sheer fabric
- Short fit
- No stretch
Style Number/Barcode: 06005-0631

Category Name: Vacation Looks

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Button Down Tie Front Midi Dress
A casual midi dress with chic details! Slip into some mules and you're all set for those daytime festivities with your girls!

Fits & Features
- Bust Tie & Faux Button Front Design
- Short Sleeves I Elastic Cuffs & Shoulders
- Midi Length Silhouette
- Rib Knit Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0720

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Flirty and Frilly Skater Lace Dress
Keep it flirty and fab in this twirl-worthy skater dress! Pair this must-have dress with pumps and dainty pieces to complete your look!

Fit & Features
- Sweetheart Neckline
- Floral Lace Bodice
- Adjustable Spaghetti Straps
- Lattice Back
- Skater Silhouette
- Lined Crepe Fabric
- Relaxed Fit | Moderate Stretch
Style Number/Barcode: 05101-0738

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Two Pack Heart Charm And Rhinestone Anklet
Make sure to accessorize from head to toe with this adorable layered datinty anklet!
- Two dainty chain layers
- Heart charm
- Mini rhinestone detailing
- Adjustable lobster clasp closure
Style Number/Barcode: 07003-0099

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Two Pack Rhinestone Cross And Beaded Anklet Set
Accessorize with this set of dainty anklets to make your look gorg from head to toe!
- Two pack
- Dainty chains
- Rhinestone cross charm
- Beaded details
- Adjustable lobster clasp closures
Style Number/Barcode: 07003-0098

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Criss Cross High Waist Swim Bottoms
Give off a flirty flair in these criss cross detailed high waist swim bottoms! Pair with the matching swim top to complete your adorable look.

Shop Matching Top: Flirty Flounce Off The Shoulder Swim Top

Fit & Features
- High rise waist
- Criss cross detail down the sides with open cut outs
- Covered bottom
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0505

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Poolside Princess Swimsuit
You'll be slaying it poolside with this sexy swimsuit! (You're just missing the marg )
- Adjustable Spaghetti Straps
- Low, Open Back
- Lattice Design At Center Front
- Full Coverage Bottoms
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0157

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry And Sheer Mesh Waist Swimsuit
Look totally fab sitting poolside in this sultry and sheer mesh waist one piece!

Fit & Features
- Adjustable spaghetti straps
- Plunging V neckline
- Back tie closure followed by a lower back cut out
- Sheer mesh overlay at the waist
- Cheeky bottom with side cut outs
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0167

Category Name: Vacation Looks

Price: $17.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Summer Icon Striped Crochet Halter Top
You'll be a cool summer icon in this striped crochet crop top featuring a plunging V-neckline with tie-back halter straps and a fitted, cropped hem. Style with cutoff denim shorts!

Fit & Features
- Crochet knit fabric, moderate stretch
- Striped pattern
- Sleeveless plunge V-neckline
- Tie-back halter straps, partially open back
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06005-000070

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Find Me In Paradise High Waist Swim Bottoms
Find yourself in paradise in the most flattering swim suit, with a drink in hand and sand between your toes. All you need is a curve flattering basic swimsuit to live in all vacay long! Don't forget to pick up the matching top!

Fit & Features
- High waist fit
- Drawstring hip detailing
- Matte nylon
- Moderate stretch
- Link to matching swim top: 07104-0345
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0496

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flutter Sleeve Floral Chiffon Skater Romper
Make hearts flutter in this flirty floral chiffon skater romper! Perf for spring with its light pastel hue, pair it with sleek gold hoops and strappy mules.

Fit & Features
- Short flutter sleeves
- Wrap front V neckline
- Back hidden zipper | Hook and eye closure
- High waist band | Back tie closure
- Flowy skater skirt covering shorts
- All over floral print
- Woven fabric | No stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06403-0057

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Free Spirit Fan Tassel Earrings
Show off your free spirit when you add in a little bohemian flare to your look! Style with your swimsuit looks, or a flowy dress!
- Gold hammered post
- Fan tassel design
- Fish hook closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0391

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Rainbow Shimmer Iridescent One Piece Swimsuit
Shimmer and shine as you lay out poolside in the most perf swimsuit! Pair with some oversize sunnies and you'll be ready for spring break bby!

Fit & Features
- Adjustable spaghetti straps
- V neckline
- Scoop back
- Removable padding
- Cheeky bottom
- Shimmer rainbow hued iridescent fabric
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0154

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