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.

Worth It Linen Wide-Leg Pants
These linen pants are worth taking on your next weekend adventure! They feature a high-rise waist, back zipper closure, side pockets, and a wide-leg silhouette. Complete the look with the matching top.

Shop Matching Top: Worth It Linen Tube Top

Fit & Features
- High-rise waist
- Back zipper closure
- Side pockets
- Wide-leg silhouette
- Linen fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06302-0726

Category Name: Vacation Looks

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Worth It Linen Tube Top
This linen-blend tube top is worth taking on your next weekend adventure! It features a sleeveless bodice, a convertible design so you can style it multiple ways, and a cropped hem. Complete the look with the matching bottoms.

Shop Matching Bottoms: Worth It Linen Wide-Leg Pants

Fit & Features
- Sleeveless bodice
- Convertible design
- Multiple ways to style
- Cropped hem
- Linen-blend fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06003-2167

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Remy High-Rise Destructed Frayed Shorts by Windsor Denim
Take your everyday 'fit up a notch with the Remy destructed frayed shorts by Windsor Denim. They feature a high-rise waist, on-trend destructed detailing, and a majorly frayed cut-off hem. The light-wash denim fabric has a rigid fit with no stretch. Style with a graphic tee and sneakers.

Fit & Features
- High-rise waist
- Destructed accents
- Frayed cut-off hem
- Front button-down closure
- Five-pocket and belt loop design
- Light wash denim fabric, rigid fit, no stretch
- Runs true to size
Style Number/Barcode: 06603-0247

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Retro Upgrade Sleek Rectangle Sunglasses
Upgrade your look with these retro-cool sunglasses featuring sleek rectangular tinted lenses and clear plastic arms. Style with a casual mini dress for a pool party!

Fit & Features
- Sleek rectangular tinted lenses
- Clear plastic arms
- 100% UV protection
Style Number/Barcode: 07008-0999

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Outer Limits Silver Racer Sunglasses
Your style will look out of this world in these retro-fab silver sunglasses featuring a geometric style plastic frame, tinted lenses, and a sleek design. Complete the look in lug booties.

Fit & Features
- Silver geometric style plastic frame
- Sleek design
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0997

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Attitude Round Metal Frame Sunglasses
Serve major attitude in these on-trend round sunglasses featuring a sleek metal frame, brown tinted lenses, rubber nose, and arm supports. Complete the look in sassy sandals for a day out with friends!

Fit & Features
- Sleek metal round frame
- Brown tinted lenses
- Rubber nose and arm supports
- 100% UV protection
Style Number/Barcode: 07008-1001

Category Name: Vacation Looks

Price: $2.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Strides Chain-Detail Jelly Sandals
Make trendy strides in these of-the-moment jelly sandals. They feature a square toe, a dual strap design with chunky chain-link accents, an open back for easy on-and-off styling, and a flat sole. Style with a casual dress and a mini handbag.

Fit & Features
- Square-shaped toe
- Dual strap design
- Chunky chain-link accents
- Open back
- Flat sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-1130

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stand Out Mid-Rise Denim Hot Shorts
Designed to stand out, these mid-rise denim hot shorts are everything for the next concert or festival!

Fit & Features
- Denim fabric with color wash tint effect
- Mid-rise waist
- Hidden front hook-eye and zipper closure
- Seam detailing
- Fitted cheeky fit
- Runs true to size
Style Number/Barcode: 06603-0445

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: In Stock

Available Color: DENIM

Available Size: S, L
Product Badge:
- Sale
Can't Help It Jelly Bejeweled Flat Sandals
You can't help but flaunt your glam in these clear jelly sandals featuring a square toe, a wide strap with statement rhinestone jewels, and a flat sole. Style with a chic handbag for a daytime soiree!

Fit & Features
- Square toe
- Wide strap
- Rhinestone jewels
- Flat sole
- Clear jelly material
- Runs true to size
Style Number/Barcode: 07404-1128

Category Name: Vacation Looks

Price: $5.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Little Princess Jeweled Thong Sandals
Grace everyone with your princess energy in these stunning thong sandals to bring the glamour to sitting poolside in a private cabana with the girls! They feature a square toe, colored gemstones with rhinestone trim on thin PVC clear straps, a flat sole, a metallic footbed, and a colored rhinestone ankle chain strap with a lobster clasp closure. Complete the look in a chic duster kimono to layer over your swimsuit!

Fit & Features
- Square toe
- Colored gemstones, rhinestone trim
- PVC clear thong straps
- Flat sole, metallic footbed
- Colored rhinestone ankle chain strap
- Lobster clasp closure
- Runs true to size
Style Number/Barcode: 07404-1138

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreamy In Floral Satin Midi Dress
Create a dreamy look in this floral satin midi dress for brunch or bridal showers! It features a sleeveless cowl neckline, adjustable spaghetti straps, a curve-hugging slim silhouette, and a flirty side slit accent. Complete the look in heeled mules.

Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Curve-hugging, slim silhouette
- Side slit accent
- Midi-length hem
- Floral print, silky satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4985

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Favorite Pick Ruched Slit Midi Dress
Your new favorite midi dress for looking stylish and cute! It features a sleeveless square neck, sleek bungee spaghetti straps, a bodycon silhouette, and a side slit with a ruched drawstring that lets you customize the fit. The midi dress is composed of a rib-knit fabric with lining and plenty of stretch. Complete the look in trendy flat sandals for a bridal shower or brunch!

Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Bodycon silhouette
- Side slit, ruched adjustable drawstring
- Midi-length hem
- Rib knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5034

Category Name: Vacation Looks

Price: $5.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bohemian Dreamer Sweater Knit Halter Top
Create a dreamy bohemian-inspired look with this sweater knit crop top. It features a sleeveless halter neckline with spaghetti straps, an open back with cross-back straps and a lower lace-up strappy design, and a fitted, cropped hem with a dainty eyelet pattern. Style with a printed maxi skirt and strappy sandals.

Fit & Features
- Sleeveless halter neckline
- Spaghetti straps
- Open back, cross-back straps
- Lower lace-up strappy design, tie closure
- Fitted, cropped hem, eyelet pattern
- Ribbed sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1445

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Girl Era Chunky Platform Mules
You'll be in your trendy girl era with these fabulous chunky platform mules! They feature an open almond-shaped toe, a wide banded toe strap, an open back for easy on-and-off styling, a chunky platform with a lug sole, and a tall block heel. Style with a flirty floral dress.

Fit & Features
- Open almond-shaped toe
- Wide banded toe strap
- Open back
- Chunky platform, lug sole
- Tall block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4200

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Total Glam Vibe Rhinestone Lace-Up Sandals
Give off a total glam vibe in these rhinestone lace-up sandals that will add a trendy sparkle! They feature an almond-shaped toe with a strap, an asymmetric strappy design that laces up the leg with mini rhinestone embellishments, and a comfortable flat sole. Style with a graphic tee and distressed denim shorts for an edgy look.

Fit & Features
- Almond-shaped toe, toe strap
- Asymmetric strappy lace-up design, tie closure
- Mini rhinestones
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1135

Category Name: Vacation Looks

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Country Style Western Denim Booties
Amp up your looks for festival season or every day with this trendy pair of western denim booties! They feature a mid-calf height with loops on each side for easy on-and-off styling, an inner zipper closure, a pointed toe, a comfortable stacked block heel, and cute western-inspired stitching with a side pocket detail. Style with a casual dress and hoop earrings!

Fit & Features
- Mid-calf height
- Loop accents, inner zipper closure
- Pointed toe
- Stacked block heel
- Denim fabric
- Western-inspired stitching, side pocket detail
- Runs true to size
Style Number/Barcode: 07403-1636

Category Name: Vacation Looks

Price: $18.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Diva Alert Denim Platform Block Heels
These diva-worthy denim platform block heels will level up all of your fab 'fits! They feature an open almond-shaped toe with a strap, a thin adjustable ankle strap, a bold platform sole, and an ultra-tall block heel. Style with a trendy shoulder bag.

Fit & Features
- Open almond-shaped toe
- Toe strap
- Thin adjustable ankle strap, buckle detail
- Platform sole
- Ultra-tall block heel
- Denim material
- Runs true to size
Style Number/Barcode: 07401-4279

Category Name: Vacation Looks

Price: $12.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic Ribbed Knit Crop Top
Keep it stylish in basics! This versatile crop top features a sleeveless square neckline, bungee spaghetti straps, and a cropped hem. The top is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with high waist shorts and a floppy hat.

Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Cropped hem
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0976

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Glam Rhinestone Chrome Sandals
You'll absolutely adore the casual glam style of these rhinestone chrome sandals! They feature a square-shaped toe, a triple strap design with mini rhinestone embellishments, an open back for easy on-and-off styling, and a metallic flat sole for comfortable wear. Pair with rhinestone stud earrings.

Fit & Features
- Square-shaped toe
- Triple strap design
- Mini rhinestones
- Slip-on-and-off styling
- Metallic flat sole
- Runs true to size
Style Number/Barcode: 07404-1092

Category Name: Vacation Looks

Price: $12.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Weekend Mood High-Rise Denim Mom Shorts
These cute and casual denim mom shorts will have you in the mood for fun weekend plans! They feature a high-rise waist, front button closures, and a frayed, raw-cut hem. The medium-wash denim fabric has a rigid fit with no stretch. Style with a graphic tee and sandals.

Fit & Features
- High-rise waist
- Front button closures
- Five belt loops
- Two front and back pockets
- Frayed, raw-cut hem
- Medium-wash denim fabric, rigid fit, no stretch
- Runs true to size
Style Number/Barcode: 06603-0350

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Playful In Denim Lace-Up Romper
Play up your style in this fun and flirty denim romper perfect for visiting a beach town or a casual hang with friends! It features a sleeveless square neck, spaghetti straps that create the lace-up open-back design, back pockets, and a fitted short-length hem. Complete the look in cute flat sandals.

Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Lace-up open-back design
- Back pockets, zipper and hook-eye closure
- Fitted short-length hem
- Medium wash denim, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0321

Category Name: Vacation Looks

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fierce And Flirty Leopard Floral Maxi Skirt
Show up fierce and flirty in this leopard floral maxi skirt! The flattering high waist accentuates your curves while the daring side slit adds movement and drama to every step. Pair with the matching tie-front top.

Shop Matching Top: Fierce And Flirty Leopard Floral Tie-Front Top

Fit & Features
- Leopard floral print, mesh fabric, stretchy knit lining
- High-rise waist
- High side slit
- Curve-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000054

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sultry Summer Style Cutout Denim Romper
Show off a sultry summer style with this alluring denim romper! It features a sleeveless V-neckline, a center bust cutout with a tie-front design, a bold waist cutout, adjustable spaghetti straps, fitted shorts with a high waist silhouette, and a form-hugging fit. Complete the look with sleek hoop earrings and strappy mules.

Fit & Features
- Sleeveless V-neckline, center bust cutout, tie-front detail
- Waist cutout, back zipper and hook-eye closure
- Adjustable spaghetti straps, back zipper closure
- Fitted shorts, high waist silhouette
- Form-hugging fit
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0248

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Coveted Cool Girl Square Gold Trim Sunglasses
Covet that cool girl style in these sleek square sunglasses featuring a plastic frame with gold trim sides, quilted-pattern arms, and tinted lenses. Complete the look in a faux leather blazer.

Fit & Features
- Square plastic frame
- Gold trim sides
- Quilted-pattern arms
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0996

Category Name: Vacation Looks

Price: $2.97 $10.90

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