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

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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.

Shady Baby Floppy Straw Hat
Catch those rays, but don't forget to grab shade! The perfect poolside partner for your lazy sun-daze
- Large Size
- Round Top
- Wide Floppy Brim
- Woven Straw Hat With Contrast Band
Style Number/Barcode: 07302-0214

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ava Formal Floral Pleated Dress
Special Occasion

Bloom into the season in charming florals as you make a dreamy impression in our Ava formal floral dress! Her florals and pleats are bring a sweet attention to detail that we love for a bridal shower or spring wedding. Complete Ava with a pair of clear heels to let the print really standout!

Fit & Features
- V-Neckline
- Ruffled Should Straps
- Open Back
- Floral Print
- Pleated A-Line Silhouette
- Lined Chiffon Fabric
- Relaxed Fit
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05002-1033

Category Name: Vacation Looks

Price: $14.97 $79.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Floral Bell Sleeve Top
Look just as sweet as can be in this adorable floral bell sleeve top! Pair with some high rise white denim cut off shorts or jeans and strappy heels for the perf fresh spring time vibe.

Fit & Features
- Long bell sleeves
- V neckline
- Tie front detail
- Cropped
- All over floral print
- Polyester woven fabric
Style Number/Barcode: 06204-0561

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylishly Sweet Smocked Tube Skater Dress
Stylishly sweet, this smocked tube skater dress is perfect for weekend brunch! It features a strapless straight neckline, a V-shaped waist, and a short A-line silhouette for that flirty flair.

Fit & Features
- Poplin cotton-blend woven fabric, stretchy knit lining
- Strapless straight-across neckline
- Stretchy smocked bodice
- V-shaped waist
- Pleating
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000049

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Take Me To The Tropics Scarf
You'll be totally ready for the tropics in this gorg printed lightweight scarf! Pair over your fave bikini and with strappy sandals and you'll be ready to lounge poolside.

Fit & Features
- All over palm leaf print
- Lightweight woven fabric
Style Number/Barcode: 07305-0083

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dangle Dangle Tassel Fringe Earrings
Dangle dangle babay, show off that perfect style with a pair of dangling fringe earrings. Spring ready, and perfectly paired with a flowing maxi dress, or a lace mini!
- Dangling design
- Tassel fringe detail
- Gold hammered finish
- Post back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-0572

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bring The Heat One Shoulder Swimsuit
Bring the heat in this chic one shoulder one piece! You'll look sizzlin' and stylish as you lounge poolside!

Fit & Features
- Asymmetric one shoulder neckline | Thin shoulder strap
- Sweetheart neckline | Removable padding
- Back hook and bar closure
- Front waist cut out
- Cheeky bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0183

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Step Out On The Scene Low Clear Heels
Ya'll know me when I step out on the scene with the cutest clear heelzzz!
- Open almond toe
- Single clear band over the toe
- Sling back ankle strap
- Adjustable pin buckle closure
- Low clear heel
- Faux leather lining
Style Number/Barcode: 07401-0908

Category Name: Vacation Looks

Price: $24.97 $31.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make The Cut Swimsuit
This sultry one piece swimsuit will most def make the cut! Pair with some oversize sunnies and get that chic and sexy poolside lewk!

Fit & Features
- Tank-like shoulder straps
- Scoop neckline
- Low V back
- Front keyhole cut out
- Sheer mesh paneling
- High waist
- Cheeky bottom
Style Number/Barcode: 07109-0212

Category Name: Vacation Looks

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Heatin' Up High Hip One Piece Swim
Suns out, swimsuit's on! Stay lookin' poolside with this dare-to-bare swimsuit!

Fits & Features
- One Piece Swimsuit
- Tank Shoulder Straps I Scoop Neckline
- Cut Out At Back
- Sheer Mesh Inset Throughout
- Metal Clasp Closure At Back
- Cheeky Bottoms I High Hip
- Moderate Stretch
Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0211

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Head In The Clouds Tie-Dye Swim Tank
We got our head in the clouds, dreaming of days in a cute swimsuit by the pool with a frozen marg in hand!

Shop Matching Bottoms: Head In The Clouds Tie-Dye Swim Bottoms

Fit & Features
- Low scoop neckline
- Tank straps
- Banded hemline
- Moderate stretch
- Lined | Not padded
- Tie-dye pattern
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: 07104-0385

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Radiant Ruffled Floral Swimsuit
Showcase your radiance as you bask in the sun in this adorable ruffled floral swimsuit! Pair with a flowy kimono cover up and some strappy sandals for the perf summer look!

Fit & Features
- Adjsutable spaghetti straps
- V neckline | Tie front accent
- Removable padding
- Front waist cut out | Ruffle trim
- Lace up back detail | Back cut out
- High waist | Cheeky bottom
- All over tropical floral print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0177

Category Name: Vacation Looks

Price: $15.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Busy Days Quilted Faux Leather Sneakers
We all need our go to sneaks for a busy day! Walk a mile in these babies and look fresh doing so! Easily styled with denim, or a cute floral mini dress!
- Round toe
- Slip on fit
- Quilted design
- Faux leather
- Padded cushion insole
Style Number/Barcode: 07405-0028

Category Name: Vacation Looks

Price: $12.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Call It Complete Espadrille Flats
Throw on a summer dress and call yourself complete when you finish your look with the cutest espadrille flats!
- Closed round toe
- Espadrille sole
- Ankle strap
- Pin buckle closure
- Faux suede
Style Number/Barcode: 07405-0022

Category Name: Vacation Looks

Price: $11.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Especially Espadrille Cork Wedges
Take on the weekend in these especially cute Espadrille platform wedges! Style with a summer matching set, or your go-to flowy dress!
- Open almond toe
- Single band over the toe
- Wrap around ankle strap
- Adjustable o-ring pin buckle closure
- Faux leather trim
- Cork wedge
- Espadrille sole
Style Number/Barcode: 07406-0051

Category Name: Vacation Looks

Price: $22.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Head In The Clouds Tie-Dye Swim Bottoms
We got our head in the clouds, dreaming of days in a cute swimsuit by the pool with a frozen marg in hand!

Shop Matching Top: Head In The Clouds Tie-Dye Swim Tank

Fit & Features
- High waist fit
- Narrow design | Hipster
- Cheeky bottom
- Tie-dye pattern
- 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: 07105-0534

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Heat Wave Bar Front Bandeau Swim Top
Everyone's going to feel the heat as soon as you walk on by in this sizzling swim set! Obvi. don't forget to add the matching swim bottoms to cart

Shop Matching Bottoms: Heat Wave Bar Side Hipster Swim Bottoms

Fits & Features
- Bandeau-Style Swim Top
- Detachable Spaghetti Straps That Tie At The Nape
- Lined With Removable Padded Bust
- Back Hook Closure
- Heat Stone Embellishments & Bar Accents At Front
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0351

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunny State Mid-Rise Distressed Denim Shorts
Grab your besties and make plans to rock these mid-rise denim shorts for fun under the sun! The mid-rise waist and form-hugging fit flatter your curves, while the distressed accents and cut-off hem add a touch of edge. Complete the look in a cute bodysuit and platform sneakers!

Fit & Features
- Denim fabric, minimal stretch
- Mid-rise waist
- Distressed accents, cut-off hem
- Form-hugging
- Front button and hidden zipper closure, five-pockets
- Runs true to size
Style Number/Barcode: 06603-0388

Category Name: Vacation Looks

Price: $13.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Heat Wave Bar Side Hipster Swim Bottoms
Everyone's going to feel the heat as soon as you walk on by in this sizzling swim set! Obvi. don't forget to add the matching swim top to cart

Shop Matching Top: Heat Wave Bar Front Bandeau Swim Top

Fits & Features
- Hipster-Style Swim Bottoms
- Triple Bar Side Accents
- Cheeky Fit & Coverage
- Lined With Heat Stone Embellishments At The Front
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0502

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Neon Basic Bandeau
Brighten up your look with a pop of neon! Wear this bandeau alone or layer it with your fav pieces!

Fit & Features
- Straight Strapless Neckline
- Ribbed Hem
- Lined Knit Fabric
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 07107-0440

Category Name: Vacation Looks

Price: $2.97 $3.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Neon Basic Bandeau
Brighten up your look with a pop of neon! Wear this bandeau alone or layer it with your fav pieces!

Fit & Features
- Straight Strapless Neckline
- Ribbed Hem
- Lined Knit Fabric
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 07107-0441

Category Name: Vacation Looks

Price: $2.97 $3.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Neon Basic Bandeau
Brighten up your look with a pop of neon! Wear this bandeau alone or layer it with your fav pieces!

Fit & Features
- Straight Strapless Neckline
- Ribbed Hem
- Lined Knit Fabric
- Relaxed Fit
- Moderate Stretch
Style Number/Barcode: 07107-0439

Category Name: Vacation Looks

Price: $2.97 $3.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Lady Lace Bandeau
She's a lovely vision in lace! This essential piece is a must-have for every wardrobe. Dress up with high waist biker shorts, and an over-sized blazer, or dress down when you wear under your fav over-sized tee!

Fits & Features
- Lace Composition
- Partially Lined
- Unlined At The Back
- Merrow Edge Trim
- Ample Stretch
Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics and lingerie are considered final sale merchandise FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 07107-0363

Category Name: Vacation Looks

Price: $5.97 $6.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Inspire To Shine Sheer Glitter Scarf
Bring the glitter you fab babe! Run around with your arms in the air and live your best life when you top off your look with a glittering sheer statement piece! Easily paired over a black bodysuit and high waist shorts!
- Long sheer design
- Silver glitter reflects
- Ruffled trim
- Offers stretch
Style Number/Barcode: 07305-0082

Category Name: Vacation Looks

Price: $6.97 $14.90

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