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

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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 Rise Fray Demin Shorts
You can never have too much denim. These denim shorts can be dressed up are down and are a wardrobe staple.

Fits & Features
- High Rise Waist
- Frayed Hem
- Slight destructed detailing on front and back
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06603-0110

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Day Dreamin’ Eyelet Mini Dress
Get ready for a sweet summer day in this eyelet dress. Pair it with wedges and a cute mini bag.

Fits & Features
- All Over Eyelet Pattern
- Puff Sleeves
- Lace Up Detailing
- Ruffle Hem
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0678

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bold New Look Corset Lace-Up Linen Skater Dress
Make a bold impression in this corset linen skater dress all season long! The sweetheart neckline with a bust tie and adjustable straps provides a flattering fit while the flexible boning supports your shape. The strappy lace-up back adds a touch of playfulness to the skater silhouette and short-length hem. Complete the look in wedge sandals and a handbag.

Fit & Features
- Linen blend fabric lined with stretchy knit
- Sweetheart neckline with bust tie
- Adjustable straps, side zipper and hook-eye closure
- Strappy lace-up back
- Flexible boning
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3256

Category Name: Vacation Looks

Price: $9.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Twist Of Fate Strapless Ruffled Maxi Dress
Because you didn’t plan to look this good... it just happened. Make your way in this breezy maxi dress designed with effortless, dreamy details from the twisted strapless bust to strappy open back and flowy ruffled silhouette.

Fit & Features
- Satin woven fabric, woven lining
- Strapless sweetheart neckline
- Twisted bust, keyhole cutout accent
- Strappy open back
- Ruffled silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000168

Category Name: Vacation Looks

Price: $9.97 $59.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Affair Tie Front Top
Stay sweet in this floral tie front top. Dress it up with heels and shorts for brunch with the girls!

Fits & Features
- All Over Floral Print
- Tie Front Detail
Style Number/Barcode: 06204-0388

Category Name: Vacation Looks

Price: $10.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Eyelet Dreams Romper
So dreamy! Pair this sweet romper with strappy sandals and gold jewelry for a cute spring look.

Fit & Features
- Off the shoulder neckline
- Short sleeves
- Tie waist
- Eyelet detail woven fabric
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06303-0092

Category Name: Vacation Looks

Price: $6.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Smocked Ruffle Mini Dress
This smocked and ruffled floral mini dress is a major yes. Add to cart and pair with some strappy heels for a nice daytime look!

Fit & Features
- Puff shoulders
- Long sleeves | Smocked detail | Ruffle hems
- Square neckline | Ruffle trim
- Stretchy smocked bodice
- Ruffle details
- Short tiered ruffle hem
- Floral print
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0649

Category Name: Vacation Looks

Price: $9.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Just Pretty Tie Front Top
Simply Pretty, you’re going to look bomb this bubble sleeve top. Team it up with denim shorts and sandals for a fresh summer look.

Fits & Features
- Bubble Sleeves
- Tie Front Detail
Style Number/Barcode: 06204-0005

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Brunch Babe Floral Mini Dress
We know you love to get cute for brunch with the girls! Style this smocked floral mini dress with white heels and gold accessories.

Fit & Features
- Tie front detail
- Front cut out
- Stretchy smocked body
- Short, form hugging fit
- Ditsy Floral print
- Adjustable Spaghetti Straps
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0744

Category Name: Vacation Looks

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Catch Me Poolside Swim Bottoms
You'll most def be chillin' poolside in these simple yet stylish swim bottoms! Pair with the matching top and you'll be a total sunkissed babe!

Shop Matching Top: Catch Me Poolside Swim Top

Fit & Features
- Mid rise waist
- Cheeky bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0540

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Catch Me Poolside Swim Top
You'll most def be chillin' poolside in this simple yet stylish swim top! Pair with the matching bottoms and you'll be a total sunkissed babe!

Shop Matching Bottoms: Catch Me Poolside Swim Bottoms

Fit & Features
- Thin tie shoulder straps
- Square neckline
- Back hook and bar closure
- No padding
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0391

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pretty Under The Palms Swim Bottoms
You'll be lounging pretty under the palms in these trendy bikini bottoms! Pair with the matching top and get ready to be vacay bound!

Shop the Matching Top: Pretty Under The Palms Tank Swim Top

Fit & Features
- All over palm leaf print
- Cheeky
- High Hip Fit
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07105-0617

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Pretty Under The Palms Tank Swim Top
You'll be lounging pretty under the palms in this trendy tank swim top! Pair with the matching bottoms and get ready to be vacay bound!

Shop Matching Bottoms: Pretty Under The Palms High Waist Swim Bottoms

Fit & Features
- Tank-like shoulder straps
- Square neck and back
- No padding
- Elastic banded hem
- All over palm leaf print
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07104-0464

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
At Ease Simple Clear Sandals
Keep the chill vibes going when you step out in these easy going sandals! Style with flowy pants, for that resort ready finish!
- Slide on fit
- Clear pink band over the toe
- Open almond toe
- Faux suede
Style Number/Barcode: 07404-0653

Category Name: Vacation Looks

Price: $10.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Jetsetter Cat Eye Sunglasses
You need these shades for next getaway! Style them with a crop top and denim shorts for an effortless look.
- Cat Eye Design
- Plastic Tortoise Frame
Style Number/Barcode: 07008-0758

Category Name: Vacation Looks

Price: $4.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Block Party Lace Up Sandals
These sandals are perfect for all your summer day parties! Style them with a denim mini skirt and an off the shoulder crop top.
- Block Heel
- Lace Up Ankle Tie
- Faux Suede
Style Number/Barcode: 07404-0595

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sea Salt Vibes Halter Crochet Midi Dress
Your next vacay is calling, and this crochet midi dress will set the vibes! Embrace the sand and sun in this stylish dress designed with a flattering high neckline and form-hugging fit.

Fit & Features
- Crochet knit fabric, stretchy knit lining
- High halter neckline, spaghetti strap ties
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000028

Category Name: Vacation Looks

Price: $18.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Always On The Go Clear Cork Mules
Even when you are always on the go, and busy, busy, busy you gotta have a good heel game! Easily style these heeled mules with work wear or dress down with cut off denim!
- Open almond toe
- Single band over the toe
- Double band mid-foot
- Cork designed sole
- Skinny clear lucite heel
Please be advised that this style runs 1/2 size small
Style Number/Barcode: 07401-2300

Category Name: Vacation Looks

Price: $11.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Perfect Collar Short Sleeve Mini Dress
There's nothing more perfect for warmer temps than this rib knit mini dress for an effortless athleisure vibe! This bodycon dress features a chic collar and short sleeves making it ideal for sunny days while the subtle side slit adds a flirty look.

Fit & Features
- Rib knit stretchy fabric
- Collar V-neckline
- Short sleeves
- Bodycon silhouette
- Side slit accent
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000127

Category Name: Vacation Looks

Price: $7.97 $39.90

On Sale: Yes

Availability: In Stock

Available Color: BLACK

Available Size: M/L
Product Badge:
- Sale
Sun's Out Oval Sunglasses
You’ll look effortlessly stylish when you add these sunnies to your outfit! They look perfect paired with distressed denim and a crop top.
- Oval Lenses
- Metal Frame
Style Number/Barcode: 07008-0764

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Island Gal Straw Floppy Hat
Look fine on your island vacay in this floppy hat! Pair it with your bikini and a kimono for a fun pool party look.
- Floppy Brim
- Straw Design
- Black Knit Band Detail
Style Number/Barcode: 07302-0206

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Extra Beaded Hoops
There’s nothing wrong with being extra! Add these beaded hoops to a casual outfit to make a statement.
- Ball Beaded Hoops
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0418

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Three Pack Charm Bead Bracelets
We love a little arm candy! Layer these bracelets with your fav gold watch.
- Set of 3 Bracelets
- Charm + Beaded Detailing
- Variety of Small + Medium Rings
Style Number/Barcode: 07003-0101

Category Name: Vacation Looks

Price: $5.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
It Girl Flat Top Sunglasses
Everyone will know you’re that girl when you step out in these sunnies! Pair them with a bodysuit, high waist denim and heels for a fashionable look.
- Flat Top Design
- Plastic Frame
Style Number/Barcode: 07008-0738

Category Name: Vacation Looks

Price: $4.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials