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.

Color Me Pretty Satin Abstract Crop Top
Color you pretty in this satin crop top to brighten up this new season! It features a sleeveless plunge halter neckline, a center hardware insert, and an ultra-cropped hem on smooth satin with an abstract print. Complete the look with the matching bottoms for a vacation!

Shop Matching Bottoms: Color Me Pretty Satin Abstract Wide-Leg Pants

Fit & Features
- Sleeveless plunge halter neckline
- Front hardware insert
- Ultra-cropped hem
- Abstract print
- Smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-2286

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make A Statement Strappy Open Back Jumpsuit
Make a statement in this head turning jumpsuit featuring a flattering cowl neckline and show-stopping beaded back detail with strappy open design and a straight leg silhouette creates a sleek, elongated look.

Fit & Features
- Texture knit fabric, partial knit lining
- Cowl neckline, bungee spaghetti straps
- Strappy beaded open back
- Straight-leg fit
- Runs true to size
Style Number/Barcode: 06502-000023

Category Name: Vacation Looks

Price: $64.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Totally Heart Flat Sandals
Fall in love with these heart sandals perfect for everyday styling!

Fit & Features
- Almond toe
- Wide band with heart
- Flat faux leather insole
- Trim accents
- Runs true to size
Style Number/Barcode: 07405-0228

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Sleek Cross Concho Chain Belt
Sleek and trendy, this cross concho chain belt radiates boho-chic vibes. Style over a lace skirt with knee-high boots.

Fit & Features
- Cross and concho textured metal design
- Center stone embellishments
- Back adjustable chain, lobster clasp closure
Style Number/Barcode: 07301-000045

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Daydream Tie-Dye Bodycon Mini Dress
You'll be lookin' like a daydream in this trendy tie-dye bodycon mini dress! Designed with an asymmetric tie-dye pattern on the airy mesh fabric, it features a sleeveless square neckline, bungee spaghetti straps, ruching down the side seams, a mini-length hem, and a bodycon silhouette to accentuate your curves. The sheer mesh fabric includes a full-length knit lining. Style this short dress with platform heels.

Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched side seams
- Mini-length hem, bodycon fit
- Asymmetric tie-dye pattern
- Sheer mesh fabric, full-length sewn-in knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5481

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Deets Cap Sleeve Open Twist Back Midi Dress
This crew neck midi dress may look basic from the front but the open back reveals sultry deets! Featuring classic cap sleeves and a twisted open back design to flaunt some skin, and a bodycon silhouette that hugs your curves. Complete the look with a clutch for a dinner party!

Fit & Features
- Brushed knit fabric lined with stretchy knit
- Crew neckline
- Twisted open back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5754

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Laid-Back Chic High Waist Shorts
Give off a laid-back chic look for your weekend plans in these cute high waist shorts! Designed from a cozy ribbed sweater knit fabric, they feature a high-rise banded waist, a short-length hem, and a form-hugging fit. Style with the matching cropped sweater for the perf lounge vibe!

Shop Matching Top: Laid-Back Chic Collared Cropped Sweater

Fit & Features
- High-rise banded waist
- Short-length hem
- Form-hugging fit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1114

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Statement Platform Under-The-Knee Boots
These of-the-moment platform boots will make a trendy statement this season! They feature an under-the-knee height with a simple pull-on design, a classic round toe, a chunky platform lug sole, and a short block heel. The boots are composed of a smooth matte jelly-like rubber material. Complete your cold-weather look with a plaid shacket!

Fit & Features
- Under-the-knee height
- Pull-on design
- Round toe
- Platform lug sole
- Short block heel
- Matte rubber material
- Runs true to size
Style Number/Barcode: 07402-0986

Category Name: Vacation Looks

Price: $4.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Desert Princess Halter Maxi Dress With Pockets
Experience the effortless beauty of this boho maxi dress! The sleeveless halter neckline and spaghetti strap tie create a flowy silhouette, while the hidden side pockets add functionality. The front slit and ruffled maxi-length hem in a chic bohemian print will make you feel like a true desert princess! Complete the look in sandals and sunnies.

Fit & Features
- Bohemian print, woven fabric, no stretch
- Halter neckline, spaghetti strap tie
- Hidden side pockets
- Flowy ruffled silhouette
- Runs true to size
Style Number/Barcode: 05102-5804

Category Name: Vacation Looks

Price: $16.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Golden Nights Halter Ruffle Romper
Perfect for any occasion when you want to shine, this halter romper features a flattering form-hugging fit and playful ruffles that create movement with every step. Style with lace-up heels.

Fit & Features
- Smooth knit stretchy fabric, shorts lining
- Halter plunge neckline, tie closure
- Form-hugging fit
- Ruffled mini hem
- Runs true to size
Style Number/Barcode: 06503-000062

Category Name: Vacation Looks

Price: $44.90

Availability: In Stock

Available Color: BLACK

Available Size: S, M, L
Product Badge:
- Back In Stock
Trendy Match Chevron Knit Tube Top
Trend right with this chevron knit tube top for weekend fun or vacation! Pair with the matching skirt to complete the look.

Fit & Features
- Chevron pattern, stretchy knit lined fabric
- Strapless neckline
- Fitted crop hem
- Runs true to size
Shop The Matching Skirt: Trendy Match Chevron Knit Midi Skirt
Style Number/Barcode: 06005-2254

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek And Sophisticated Satin Wide-Leg Pants
Sleek and sophisticated, these satin wide-leg pants will stylishly elevate your look. They feature a high-rise waist, front pleating, a wide-leg silhouette, and a relaxed fit. The satin woven fabric has minimal stretch. Pair with a basic bodysuit and strappy mules.

Fit & Features
- High-rise waist, elasticized back waistband
- Front pleated detailing
- Wide-leg silhouette
- Relaxed fit
- Satin woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06402-1327

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Paradise Bound Braided Striped Straw Tote Bag
Step off the plane into paradise carrying this must-have straw tote bag! It's designed with convenient top handles and a trendy multi-hued braided striped pattern.

Fit & Features
- Faux leather top handles
- Multi-hued braided stripe design
- Large square-shaped body
- Straw material
Style Number/Barcode: 07203-2116

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simply Sophisticated Faux Leather Block Heels
Step into these faux leather block heels for a simply sophisticated look for any occasion! These almond-toe heels feature a comfortable block heel and a closed-ankle style. The adjustable ankle strap with buckle closure secures the style. Complete the look with a trendy handbag.

Fit & Features
- Block Heel
- Almond toe
- Closed ankle, adjustable ankle buckle strap
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4856

Category Name: Vacation Looks

Price: $9.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Beachy Sheer Woven Palazzo Pants
These beachy sheer woven palazzo pants feature an adjustable tie-front drawstring and a wide-leg silhouette for a relaxed fit. Style as a cover-up over your fave bikini!

Fit & Features
- Sheer textured woven fabric, minimal stretch
- High-rise elasticized waist
- Adjustable tie-front drawstring
- Wide-leg silhouette
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06302-000003

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Oh-So-Cute Puff Sleeve Lace-Up Gingham Mini Dress
Oh-so-cute and sweet! This gingham mini dress is sure to charm at brunch and picnics. You'll have comfort and style, made from a gauze woven fabric boasting a cheery gingham print line with a stretchy knit. With puff sleeves and a V-neckline, this bodycon dress flatters your figure and adds a fun touch with its lace-up back. The mini-length hem and playful gingham print make it perfect for any spring-to-summer event. Complete the look in sandals and sunnies!

Fit & Features
- Gingham print, gauze woven fabric lined with stretchy knit
- V-neckline
- Lace-up, back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5438

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cool Girl Era Wedge Heels
Enter your cool girl era and style up these sleek faux leather wedge heels to elevate your fave 'fits. Pair with your everyday shoulder bag.

Fit & Features
- Wedge heel
- Faux leather material
- Open almond-shaped toe
- Wide toe strap
- Thin adjustable ankle and heel straps, buckle detail
- Cushioned insole
- Runs true to size
Style Number/Barcode: 07406-000007

Category Name: Vacation Looks

Price: $28.90

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Feelings Sleeveless Ditsy Floral Mini Dress
Give yourself a sweet feeling in this ditsy floral mesh mini dress perfect for spring and summer soirees! With a sweetheart neckline, padded bra cups, and adjustable spaghetti straps you;ll feel confident and comfortable. The side ruched seams accentuate your curves along the bodycon fit for a playful touch. Complete the look with a choker necklace.

Fit & Features
- Ditsy floral print, mesh fabric, sewn-in knit lining, stretchy
- Adjustable spaghetti straps
- Sweetheart neckline, padded bra cups
- Back zipper and hook-eye closure
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5550

Category Name: Vacation Looks

Price: $9.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Spice Corset Lace-Up Floral Midi Dress
Sweet and spice combine on this floral midi dress designed with a stylish lace-up back, corset bodice, and a flirty front slit for movement. Complete the look with mules.

Fit & Features
- Ditsy floral print, smooth woven fabric, woven lining
- Sleeveless sweetheart neckline with tie
- Shoulder straps, side zipper and hook-eye closure
- Lace-up back design
- Underwire bust, corset bodice
- Front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-3819

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Delicate Essence Puff Sleeve Corset Lace Mini Dress
The delicate essence of this lace mini dress will have you looking so cute at a bridal shower, as the birthday girl or graduate! Featuring sheer puff sleeves, an underwire bust for support, and flexible boning for a flattering bodycon fit. The front ruched seam adds a touch of sophistication to this playful mini-length dress. Complete the look in cute sandals and a purse!

Fit & Features
- Lace fabric lined with stretchy knit
- Back zipper and hook-eye closure
- Sweetheart neckline, underwire bust
- Flexible boning
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3226

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirt And Twirl Puff Sleeve Tie-Back Skater Dress
Flirt and twirl in this cute skater dress at parties and day dates! The puff short sleeves and square neckline add a touch of charm, while the tie-back design and skater silhouette create a flattering fit. Complete the look with hoop earrings.

Fit & Features
- Crepe woven fabric, stretchy knit lining
- Square neckline
- Tie-back detail
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3243

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glimmer Game Strong Layered Belly Chain
Double the chains, double the compliments. This layered belly chain is all about sparkle with a flirty twist—perfect for beach days, rooftop nights, and every crop top moment in between.

Fit & Features
- Dainty textured chain, high-shine finish
- Two-row layered design
- Hanging diamond-shaped charms, stone embellishments
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-000097

Category Name: Vacation Looks

Price: $14.90

Availability: In Stock

Available Color: GOLD

Available Size: NS
Love's In The Air Floral Chiffon A-Line Dress
Slip into romance! This dainty floral chiffon short dress features a sweetheart neckline and bust tie to accentuate your figure while the wide shoulder straps and underwire bust provide support. The corset-trim bodice and back lace-up design add a touch of romance along the flattering A-line silhouette and short-length hem. Complete the look with a ring set and sandals for a date or brunch!

Fit & Features
- Sleeveless sweetheart neckline
- Wide shoulder straps
- Underwire bust, tie front, side zipper and hook-eye closure
- Corset-trim bodice, lace-up back design
- A-line silhouette, short-length hem
- Dainty floral print, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3007

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fresh Vibe High-Rise Destructed Straight-Leg Jeans by Windsor Denim
These trendy destructed straight-leg jeans by Windsor Denim will give you that fresh vibe you crave for the summer season. Made with a stretchy cotton-blend denim fabric, they feature a high-rise waist and a straight-leg fit with destructed detailing for an effortlessly cool look. Include a five-pocket and belt loop design with a front button and hidden zipper closure. Style these jeans with a graphic tee and ankle booties.

Fit & Features
- Cotton-blend denim fabric with moderate stretch
- High-rise waist
- Straight-leg fit
- Destructed detailing
- Five-pocket and belt loop design
- Front button, zipper closure
- Runs true to size
Style Number/Barcode: 06602-0492

Category Name: Vacation Looks

Price: $6.97 $48.90

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