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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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.

Chasing The Sun Bikini Bottoms
Chose those warmer days with cute bikini bottoms that are vacay ready! The bikini bottoms feature a high rise waist and a cheeky fit. Complete your fit' with the matching bikini top and sunglasses.

Shop Matching Bikini Top: Chasing The Sun Bikini Top

Fit & Features
- High rise waist
- High cut
- Cheeky fit
- Matching bikini top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0508

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Moment Oversized Cropped Denim Jacket
Create a trendy moment with an oversized denim jacket that adds a layer of style to your look. The jacket features a collared neckline, long sleeves, big pockets, a multi-button down front, and a cropped hem. The denim jacket offers a relaxed fit with minimal stretch. Complete look a crop top and a mini skirt.

Fit & Features
- Collared neckline
- Long sleeves
- Big Pockets
- Multi-button down front
- Cropped hem
- Light distressing
- Relaxed fit, minimal stretch
Style Number/Barcode: 06203-0118

Category Name: Vacation Looks

Price: $13.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glamorous Vibes Rhinestone Trim Sunglasses
These fabulous sunglasses will give you major gorgeous and glam vibes! They feature an oversized design with tinted lenses and a stylish rhinestone trim. Pair these sunnies with a rhinestone choker necklace to really bring the bling.

Fit & Features
- Oversized design
- Plastic frame
- Tinted lenses
- Rhinestone trim
Style Number/Barcode: 07008-0805

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Flirt Ditsy Floral Mini Dress
Capture hearts in this flirty ditsy floral printed mini dress that is perfect for spring! It features short puff sleeves, a sweetheart neckline with a tie-front detail, and a mini-length, curve-hugging silhouette. The dress is composed of a lightweight, stretchy knit fabric with no lining. Style this floral dress with cute wedges for brunch with the girls.

Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Tie-front at the bust
- Short, form-hugging fit
- Ditsy floral print
- Stretchy unlined knit fabric
- Runs true to size
Style Number/Barcode: 05102-1078

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortless Chic Tie-Front Crop Top
Effortless for vacay or weekend fun, this chic top is designed with flowy short sleeves and a tie-front perfect for styling alone or layering!

Fit & Features
- Cotton woven fabric
- Flowy short sleeves
- V-neckline
- Tie-front
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-000017

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Dreamer Lace Corset Crop Top
Get a dreamy boho-inspired look in this sheer lace crop top! It features tank-like shoulder straps, a corset design with hook and eye front closures, a stretchy smocked back, and a cropped, form-hugging fit. Pair this top with high rise distressed jean shorts and some strappy sandals.

Fit & Features
- Tank-like shoulder straps
- Corset design
- Hook and eye front closures
- Stretchy smocked back
- Cropped
- Form-fitting
- Sheer lace fabric with moderate stretch
Style Number/Barcode: 06001-3013

Category Name: Vacation Looks

Price: $11.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Forever Fierce Micro Swim Top
Feel forever fierce as you relax poolside in this adorable micro swim top! It features a triangle design with halter spaghetti straps, a padded bust, lower thin straps that tie at the back, and a trendy leopard print. Pair this swim top with the matching swim bottoms and a flowy sheer mesh duster.

Shop Matching Swim Bottoms: Forever Fierce Micro Swim Bottoms

Fit & Features
- Triangle design
- Halter spaghetti straps
- Padded bust
- Thin straps that tie at the back
- Leopard print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0496

Category Name: Vacation Looks

Price: $9.97 $23.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Forever Fierce Micro Swim Bottoms
Feel forever fierce as you relax poolside in these adorable micro swim bottoms! They feature a high-cut cheeky fit, thin side straps, and a trendy leopard print. Pair these swim bottoms with the matching swim top and a flowy sheer mesh duster.

Shop Matching Swim Top: Forever Fierce Micro Swim Top

Fit & Features
- High-cut cheeky fit
- Thin side straps
- Leopard print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0644

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylishly Studded Flat-Top Sunglasses
Accessorize your trendy look and get a cool, chic vibe with these sunglasses! They feature a flat-top design, a center cut-out, and tinted lenses with small stud detailing on each side. Pair these shades with a graphic tee and distressed denim.

Fit & Features
- Flat-top design
- Center cut-out
- Tinted lenses
- Small stud detailing
- Plastic frame and arms
Style Number/Barcode: 07008-0819

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Greek Key Choker Necklace
Accessorize your everyday 'fit with this chic choker necklace! It features a trendy greek key design with small chain links and an adjustable lobster clasp closure. Pair this necklace with a graphic tee for a cool vibe.

Fit & Features
- Greek key design
- Small chain links
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0643

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Effortlessly Chic Cat Eye Sunglasses
Show off your effortlessly chic style when you accessorize your 'fit with these sunglasses! They feature a cat eye design with a tortoise-shell hued plastic frame and tinted lenses. Pair these sunnies with your fave loungewear set to elevate the look.

Fit & Features
- Cat eye design
- Tortoise-shell hued plastic frame and arms
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0821

Category Name: Vacation Looks

Price: $3.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Luxe Layered Three-Pack Necklace Set
Add some luxe and trendy layers to your everyday 'fit with this necklace set! It features three necklaces, the shortest layer a thick round chain design, the middle layer a thick chain link design with mini rhinestone details, and the longest layer a dainty chain with a center lock charm. Pair this necklace set with a cool graphic tee.

Fit & Features
- Three-pack necklace set
- Adjustable lobster clasp closures
Style Number/Barcode: 07002-0633

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic On-Trend Two-Pack Necklace Set
Layer on this chic necklace set to keep your look fab and on-trend! It features two necklaces, the shorter layer with a twisted chain and the longer layer showcasing a dainty chain with a center butterfly detailed tag charm. Pair this set with a basic tee and a classic denim jacket.

Fit & Features
- Two-pack necklace set
- Twisted chain
- Dainty chain
- Center butterfly tag charm
- Adjustable lobster clasp closures
Style Number/Barcode: 07002-0644

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Falling For Florals Puff Sleeve Crop Top
Fall for a floral crop top that brings on those charming feels! The crop top features a sweetheart neckline, a ruched bodice, long puff sleeves with cinched ruffled hems, a gorge floral print, a stretchy smocked back, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with a mini skirt and clear heels.

Fit & Features
- Sweetheart neckline
- Ruched bodice
- Long puff sleeves with cinched ruffled hems
- Floral print
- Stretchy smocked back, cropped hem
- Lightweight woven fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1159

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wanderlust Beauty Flared Pants
You're a total wanderlust beauty, and these boho-chic flared pants are a must-have style for you. They feature a high-rise elastic banded waist, a form-hugging fit, and a flared-out hem. The stretchy knit fabric showcases an all-over paisley pattern for a trendy vibe. Complete your look with a crop top and sandals for the perf warm-weather outfit.

Shop Matching Smock Top: Wanderlust Beauty Smocked Tube Top

Shop Matching Tie-Front Top: Wanderlust Beauty Tie Front Top

Shop Matching Lace-Up Top: Wanderlust Beauty Lace-Up Top

Fit & Features
- High-rise elastic banded waist
- Form-fitting style
- Flared hem
- Knit fabric with plenty of stretch
- Paisley print
- Runs true to size
Style Number/Barcode: 06502-0613

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Strike A Pose Cat Eye Sunglasses
Strike a pose in chic sunglasses to relax poolside! The sunnies feature an oversized cat eye frame, a sleek metal nose bridge, and a trendy print. Complete the look with a cute monokini and sandals.

Fit & Features
- Oversized cat-eye frame
- Metal nose bridge
- Trendy print
Style Number/Barcode: 07008-0806

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Instant Classic Cat Eye Sunglasses
Create an instantly classic look with these sunglasses that are simply stunning! The sunglasses feature a cat-eye frame, dark lenses, and sleek arms. Complete the look with a ribbed mini dress and mules for the perfect outfit to grab your favorite iced coffee!

Fit & Features
- Cat-eye frame
- Dark lenses
- Sleek arms
Style Number/Barcode: 07008-0807

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Textured Hoop Earrings
Add a gorgeous glam vibe to your look with these trendy hoop earrings! They feature a large thick hoop with a textured wrap design and an omega closure. Pair these earrings with your fave chic catsuit and strappy heels.

Fit & Features
- Thick hoop
- Textured wrap design
- Omega closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0498

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Give Trendy Vibes High-Rise Button Mini Skort
Stroll around in this adorable mini skort with button accents along a flattering high-rise waist and a flirty ruffled hem.

Fit & Features
- Woven fabric, shorts lining
- High-rise waist
- Side button accents
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 06303-000012

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: In Stock

Available Color: YELLOW

Available Size: L
Product Badge:
- Sale
Golden Glow Chandelier Earrings
Get a gorgeous golden glow when you accessorize your fancy 'fit with these chandelier earrings! They feature an intricately detailed tiered design with dangling diamond-shaped charms and a fish hook closure. Pair these stunning statement earrings with a classic little black dress to add a glam factor to your look.

Fit & Features
- Chandelier tiered design
- Diamond-shaped charms
- Fish hook closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0500

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish Floral Flair Crop Top
You'll have that stylish floral flair in this adorable crop top that is perfect for spring! It features a sleeveless bodice with tie shoulder straps, a round neckline, hook and eye front closures, ruched detailing, and a cropped, form-hugging fit. The top is composed of a floral printed woven fabric with a woven lining and has no stretch. Complete your look with denim shorts and gold hoop earrings.

Fit & Features
- Tie shoulder straps
- Round neckline
- Hook and eye front closures
- Ruched detailing
- Cropped, form-fitting style
- Lined woven fabric with no stretch
- Floral print
Style Number/Barcode: 06003-1157

Category Name: Vacation Looks

Price: $6.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Poised Paper Bag Ponte Shorts
Keep it poised in paper bag shorts that are totally on-trend! The shorts feature a high rise paper bag waist, a tie waist belt with belt loops, side pockets, and a wide-leg fit. The shorts are composed of a curve-hugging Ponte-knit fabric that offers a moderate stretch. Complete look with a lace crop top.

Fit & Features
- High rise paper bag waist
- Tie-waist belt with belt loops
- Side pockets
- Wide-leg fit
- Ponte-knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06503-0206

Category Name: Vacation Looks

Price: $13.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty and Fluttery Butterfly Charm Necklace
Keep it flirty with a charming butterfly necklace that showcases your sweet side. The necklace features a dainty chain link and a butterfly charm pendant composed of baguette gemstones and rhinestone stones. Complete look with a floral dress and wedges.

Fit & Features
- Dainty chain link
- Butterfly charm
- Rhinestones
- Baguette gemstones
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0665

Category Name: Vacation Looks

Price: $5.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Florals Ruffled Chiffon Mini Dress
Bring the charm in a ruffled mini dress that makes a sweet impression! The dress features a plunging V-neckline, adjustable cross-straps, a floral print, tiered ruffles, and a mini-length silhouette. The dress is composed of a sheer lined chiffon fabric that offers a form-hugging fit that offers a minimal stretch. Complete your look with wedges and a floppy hat for a brunch-worthy outfit.

Fit & Features
- Sleeveless V-neckline
- Adjustable cross-straps
- Floral print, back zipper closure
- Tiered ruffles
- Mini length silhouette
- Chiffon fabric, knit lining
- Fits true to size
Style Number/Barcode: 05101-0463

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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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