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.

High Waist Linen Shorts
Fall back on basic shorts with a stylish twist! These shorts are ready for warmer days with a high-rise waist, a tie-waist belt, a wide leg hem, and a back zipper closure for a secure fit. Complete look with a floral bodysuit and wedges for the perfect brunch outfit with the squad!

Fit & Features
- High-rise waist
- Tie-waist belt
- Wide leg hem
- Back zipper closure
- Lined linen fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06303-0150

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Tropical Day Dream Tie-Front Crop Top
Look like a tropical day dream in this crop top while on vacation! The flowy long sleeves with banded cuffs ensure a comfortable fit, while the tie-front closure and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching pants and skirt.

Shop Matching Pants: Tropical Day Dream High-Rise Wide Leg Pants
Shop Matching Skirt: Tropical Day Dream High-Rise Wrap Mini Skirt

Fit & Features
- Tropical print, stretchy knit fabric
- Flowy long sleeves, banded cuffs
- Tie-front closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-0451

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stripe With It Halter Ribbed Knit Crop Top
Own this striped knit crop top all season! It's perfect for flaunting your figure with a square halter neckline and fitted crop hem. The striped pattern on the ribbed knit fabric gives it a trendy vibe. Complete the look in denim shorts for a summer fair or BBQ.

Fit & Features
- Striped pattern
- Stretchy ribbed knit fabric
- Halter square neckline, tie closure
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06005-1994

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Laced-Up Masterpiece Floral Slit Maxi Dress
Elevate your style with this stunning floral maxi dress that commands attention. The striking lace-up back adds an alluring touch, while the front slit reveals some skin along the form-hugging silhouette.

Fit & Features
- Floral print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Back lace-up
- Front slit
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4143

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Parisian Beauty Wool Beret
Look and feel like a Parisian beauty accessorizing with this wool beret perfect for styling with a sleek crop blazer for a city-girl look.

Fit & Features
- Classic beret style
- Wool material
Style Number/Barcode: 07302-1347

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cozy Fall Vibes Belted Plaid Shacket
Layer on this trendy plaid flannel shacket for all the cozy fall vibes! It features a collared neckline, long sleeves, a complete button-down front, pockets, a tie-front belt to stylishly cinch your waist, and a relaxed fit. Pair with a basic bodysuit and a knit midi skirt.

Fit & Features
- Collared neckline, long sleeves, single button details
- Button-down front
- Buttoned chest pockets, faux side pockets
- Tie-front belt
- Relaxed fit
- Plaid print, woven flannel fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1447

Category Name: Vacation Looks

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Soft Serve Floral Ruffle Tie-Front Top
Serving soft with a wink. This sheer floral mesh top brings the flirt with ruffled edges, lace trim, and a tie-front that keeps things just bold enough. Perfect for date nights or casual slays.

Shop Matching Skirt: Soft Serve Floral High Slit Maxi Skirt

Fit & Features
- Sheer mesh fabric, high stretch
- Floral print
- V-neckline with lace trim
- Ruffled tie-front design
- Long fitted sleeves
- Mid-length hem
- Runs true to size
Style Number/Barcode: 06202-000037

Category Name: Vacation Looks

Price: $29.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Product Badge:
- Part of a Set
Cute Retreat Straw Envelope Clutch Crossbody Bag
A straw clutch crossbody bag features a detachable wristlet strap, a front flap with snap-button closure, and a detachable shoulder strap for multiple styling options. Perfect for vacation retreats or summer styling.

Fit & Features
- Detachable wristlet strap
- Front flap with snap-button closure
- Detachable shoulder strap
- Straw material
Style Number/Barcode: 07203-2071

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortlessly Chic Over-The-Knee Boots
These fitted over-the-knee boots are so effortlessly chic. They feature an almond-shaped toe, a block heel, and an inner zipper closure. The boots are composed of a half faux suede and half stretchy knit composition. Style with a sweater dress and a trendy boater hat.

Fit & Features
- Over-the-knee fitted design
- Almond-shaped toe
- Block heel
- Partial inner zipper closure
- Half faux suede and half stretchy knit composition
- Runs true to size
Style Number/Barcode: 07402-0812

Category Name: Vacation Looks

Price: $12.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feelin' Sweet Chiffon Halter Babydoll Dress
You'll be feelin' sweet and chic in this airy chiffon mini dress featuring a halter cutout neckline and flowy babydoll silhouette. Perfect for pairing with pearl earrings.

Fit & Features
- Sheer chiffon fabric with woven lining, no stretch
- Sleeveless halter neckline, V-cut bust
- Adjustable spaghetti straps, partially open back
- Flowy babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4035

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Always In Plaid Woven Crop Shacket
Don't be surprised if you find yourself wearing this plaid crop shacket on repeat! It features long sleeves with button cuffs, a collar neckline, a button-down placket, pockets, and a boyfriend silhouette. Complete the look in knee-high boots for a chic autumn outfit!

Fit & Features
- Long sleeves with button cuffs
- Collar neckline
- Button-down placket, pockets
- Boyfriend silhouette
- Cropped hem
- Plaid pattern, flannel woven fabric
- Fits true to size
Style Number/Barcode: 06204-1454

Category Name: Vacation Looks

Price: $21.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
Vacay Attitude V-Neck Floral Tropical Maxi Dress
Book those tickets and pack a bag cause vacation is calling and this floral tropical maxi dress is ready to answer! Made from an airy floral tropical printed chiffon fabric with a short woven lining, this dress is perfect for summer days. Featuring spaghetti strap tassel ties and V-neckline, cutout sides add a touch of flirty fun, while the flowy maxi-length silhouette and front slit provide style. Complete the look with a straw tote bag and sandals!

Fit & Features
- Tropical floral print, chiffon fabric, short woven lining
- Spaghetti strap tassel ties
- V-neckline
- Cutout sides
- Front slit
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3446

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep It On Check Plaid Crop Jacket
Keep your fall look in check in this plaid crop jacket perf for the cozy season! It features long sleeves, a collar neckline, snap-button front closures, flap pockets, and a pull tab hem with button closure. Complete the look in trendy boots.

Fit & Features
- Long sleeves, collar neckline
- Snap-button front closures
- Flap pockets
- Pull tab hem with button closure
- Cropped length
- Plaid pattern, woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1421

Category Name: Vacation Looks

Price: $18.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Enticing Flirty Sleeveless Lace-Up Denim Romper
Entice them all with your flirtiness in this denim romper perfect for festivals, concerts, or casual plans! Featuring a square neckline and adjustable thin tank straps, this romper hugs your curves and offers a flirty lace-up front. Perfect for a casual day out, and with a short-length hem, it's the ultimate summer must-have. Complete the look in trendy cowboy boots.

Fit & Features
- Dark wash cotton-blend denim fabric, moderate stretch
- Square neckline
- Adjustable tank straps
- Back zipper with hook and eye closure
- Lace-up
- Form-hugging
- Runs true to size
Style Number/Barcode: 06603-0380

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Love For Fall Plaid Cropped Shacket
Showcase your love for this cozy season with this on-trend cropped shacket. It features a collared neckline, long sleeves, a multi-button down front, and a cropped, cinched back hem. The flannel woven fabric features an all-over plaid print, perfect for the fall time. Layer over a bodysuit with faux leather pants for an elevated look.

Fit & Features
- Collared neckline
- Long sleeves, button details
- Multi-button down front
- Buttoned chest pockets
- Cropped hem with a cinched back
- Plaid print, flannel woven fabric
- Runs true to size
Style Number/Barcode: 06204-1450

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Weekend Chic Linen Tie-Front Corset Romper
Show up looking casual-chic for your weekend plans in this adorable tie-front corset romper! Designed with a lightweight linen woven fabric, it features a sleeveless square neckline with adjustable spaghetti straps offering a customized fit leading to a back zipper closure. The corset bodice will create that cinched silhouette, followed by a tie-front belt for a cute touch. Style with espadrille wedges.

Fit & Features
- Linen woven fabric
- Square neckline
- Adjustable spaghetti straps, back zipper and hook-eye closure
- Corset bodice, flexible boning
- Tie-front belt, side pockets
- Runs true to size
Style Number/Barcode: 06303-0251

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vibe Of Summer Tie Front Eyelet Crop Top
This gorgeous eyelet crop top will bring you the vibe of summer vacations and parties! The sweetheart neckline flatters your look while the tie front design and spaghetti straps add a playful touch to the cropped hem on breezy eyelet fabric. Complete the look with the matching maxi skirt.

Shop Matching Bottoms: Vibe Of Summer High Rise Eyelet Maxi Skirt

Fit & Features
- Eyelet fabric, moderate stretch
- Spaghetti straps
- Sweetheart neckline
- Tie front
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5358

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Get Like Me Cutout Wide-Leg Jumpsuit
Make a striking impression in this bold strapless jumpsuit on vacay or a summer night out! With O-ring inserts, a cutout bodice, and a flattering wide-leg fit, this jumpsuit will turn heads everywhere you go.

Fit & Features
- Smooth knit stretchy fabric, full knit lining
- Strapless neckline
- O-ring inserts, cutout bodice
- Wide-leg fit
- Runs true to size
Style Number/Barcode: 06502-000036

Category Name: Vacation Looks

Price: $9.97 $45.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK

Available Size: M, L
Product Badge:
- Sale
Festival Vibes Halter Crop Top
Showcase trendy festival vibes all season with this alluring crop top! It features a sleeveless halter neckline with spaghetti straps in a cross-front design and a cropped, form-hugging fit. Style with the matching wide-leg pants and retro shades.

Shop Matching Bottoms: Festival Vibes Wide-Leg Pants

Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, cross-front design, tie at the back of the neck
- Cropped, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06001-4029

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Minimalistic Chic Faux Leather Belt
Add the perfect touch of chic to your look with this faux leather belt featuring a sleek metal buckle accent, dual bands with perforated holes, and a pull-through design. Complete the look in a form-fitting jumpsuit and heels.

Fit & Features
- Sleek metal buckle accent
- Dual faux leather bands
- Perforated holes
- Pull-through design
Style Number/Barcode: 07301-0468

Category Name: Vacation Looks

Price: $3.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stay Forever Chic Faux Wool Hat
You'll stay forever chic with this of-the-moment faux wool hat! It features a structured top with a wide flat brim and a sleek faux leather trim. Style with a mock neck bodysuit and your fave pair of denim.

Fit & Features
- Structured top
- Wide flat brim
- Thin faux leather trim, adjustable buckle detail
- Faux wool material
Style Number/Barcode: 07302-1394

Category Name: Vacation Looks

Price: $7.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Flirty Fun V-Neck Tie Striped Knit Crop Top
Give your vacay style a dynamic upgrade in this flirty knit crop top perfect for a getaway or weekend fun! The top boasts a sultry V-neckline, dual tie-back design, and an ultra-cropped hem on pointelle knit fabric showcasing a trendy striped pattern. Complete the look with the matching skirt.

Shop Matching Skirt: Flirty Fun High Rise Striped Knit Midi Skirt

Fit & Features
- Pointelle knit fabric, striped pattern
- V-Neck
- Dual tie-back design
- Ultra-cropped length hem
- Runs true to size
Style Number/Barcode: 06005-1970

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cutie In A Lug Bootie
Hey, there cutie rocking these lug sole booties! They feature a round toe, chunky block heel, and rib-knit upper design on faux leather material. Complete the look in a flannel shacket for cold-weather vibes.

Fit & Features
- Almond toe
- Lug sole
- Chunky block heel
- Rib-knit upper design
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1584

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charming Vibe Tie-Back Flowy Floral Woven Maxi Dress
Give off a charming vibe at summer parties in this simply stunning floral woven maxi dress! The breezy lightweight woven fabric is detailed with a gorgeous floral print pattern and includes a mini-length lining for coverage. The sleeveless bodice is shaped with a sweetheart neckline, a dainty tie-front bust design for a cute detail, and spaghetti straps leading to an open back with a cross-back strappy design and a customized tie closure. The fitted high waist flows out to a maxi-length hem with an effortlessly chic A-line silhouette. Style with hoop earrings and slip-on sandals.

Fit & Features
- Floral print
- Lightweight woven fabric, mini-length woven lining, no stretch
- Sweetheart neckline with tie-front bust, spaghetti straps
- Open back, cross-back strappy design, tie closure
- High waist seam
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3048

Category Name: Vacation Looks

Price: $9.97 $59.90

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