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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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.

Multi Slaying In Paradise Swimsuit
You'll be slaying in a tropical paradise with this one piece swimsuit! This piece is a monokini-style with a plunging neckline, a low-cut back with adjustable straps, and a high cut bottom with partial coverage. Does not include padding.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 07105-0252

Category Name: Vacation Looks

Price: $30.00 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Palm Paradise Swim Bottom
All you need are those cabana vibes to channel a laid back feel! These swim bottoms features a multi hued color, a high rise waist with brief cut and a cheeky bottom coverage. The all over palm leaf print features a pretty green color to contrast with a black background. Be sure to pick up the matching top!
Model is 5'6" with a 34" 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: 07105-0071

Category Name: Vacation Looks

Price: $20.87 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glow Up High Waist Swim Bottoms
Glow up in these summer approved swim bottoms! They feature a high rise waist with a cheeky fit and a bright orange hue. Don't forget to purchase the matching swim top!
Model is 5'6" with a 34" 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: 07105-0007

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Lace Up Caged Bikini Top
Lace up in this pretty swim top to catch some sun this season! It features a vibrant fuchsia pink hue, a neck tie strap, a multi strap caged design, triangle cups and removable padded cups. Be sure to pick up the matching bottoms to complete your look!
Model is 5'6" with a 34" 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: 07105-0056

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mesh Me Much Swim Bottom
They'll be missing you long after the pool party in this sexy neon pink swim bottom! It features a high waist with mesh detailing, front cut outs, and a full coverage bottom. Don't forget the matching swim top!
Model is 5'6" with a 34" 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: 07105-0018

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hint Of Romance Lace Trim Mini Skort
They know you've got it. Add a romantic vibe in this lace trim mini skort perfect for any plans.

Fit & Features
- Ponte knit fabric
- High-rise waist
- Bodycon fit
- Lace trim mini-length hem
- Shorts lining
- Runs true to size
Style Number/Barcode: 06503-000003

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Locked In Swim Bottoms
Get locked in for this sizzling look! These black swim bottoms feature a high rise waist, lace up side accents and a brief cut with cheeky bottom. Be sure to pick up the matching swim top to complete your look!
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07105-0052

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sassy Straps Bandeau Swim Bottoms
Stay sassy as you soak up the sun in this chic swim bottom! It features a neon pink hue, a high rise waist, mini strap insets on the side seams and a cheeky bottom.

Be sure to pick up the matching top! Model is 5'6" with a 34" 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: 07105-0013

Category Name: Vacation Looks

Price: $17.87 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glow On Swim Bottoms
Glow on bby in this bold neon swim bottom! It features a high rise waist, knot accents and a cheeky bottom. Be sure to pick up the matching top to complete your look!
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07105-0015

Category Name: Vacation Looks

Price: $8.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sassy Straps High Waist Swim Bottom
Stay sassy as you soak up the sun in this chic swim bottom! It features a black hue, a high rise waist, mini strap insets on the side seams and a cheeky bottom. Be sure to pick up the matching top!
Model is 5'6" with a 34" 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: 07105-0014

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pucker Up Lemon Bikini Top
Pucker up in this zesty inspired bikini top! It features a cute lemon print, halter neck ties, push-up cups with supportive underwire, a mini tie front accent and a bar strap fasten. Be sure to pick up the matching bottoms to complete your beach side look!
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.

Style Number/Barcode: 07104-0234

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Brighter Days Striped Swim Top
Soak up some rays in this sassy striped swim top! It features a neon pink color, a mock neck, a zippered down front and cap sleeves. Get those sporty vibes with the athletic tape accents along the shoulder. Be sure to pick up the matching bikini bottoms to complete your look!
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'6" with a 34" bust, 26.5" waist and 38" hips. Bra Size: 32D. She is wearing a size small.

Style Number/Barcode: 07104-0238

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stylish And Strappy Swim Top
Have fun in the sun with your squad in this stylish and strappy royal blue swim top! It features neon yellow spaghetti straps, a square neckline, a front cut out under the bust with a strap accent, and a cross over detail in the back. Don't forget to purchase the matching swim bottoms!
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07104-0266

Category Name: Vacation Looks

Price: $7.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Americana Swim Top
Rock some stars and stripes to show off your patriotic pride! This red swim top features a scoop neckline and tank straps! The striped pattern features red and white hues. Be sure to pick up the matching bottom to fully represent the USA!
Model is 5'6" with a 34" 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: 07104-0260

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hot Wrap Ruffle Swim Top
Bring on the heat in this flirty mustard yellow swim top! It features a wrap design with long ties that wrap around the torso and ruffle details for an extra fun look! Don't forget the matching bottoms to complete your look!
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07104-0253

Category Name: Vacation Looks

Price: $10.44 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Rainbow Bright Swim Top
Be bold and be bright in this one of a kind swim top! It features a scoop neck, long sleeves, an under bust slit and a colorful array of colors. Don't forget the matching bikini bottoms!
Model is 5'7" with a 34" bust, 24." waist and 36" hips. She is wearing a size small.

RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07104-0250

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mesh Me Much Swim Top
They'll be missing you long after the pool party in this sexy neon pink swim top! It features triangle cups, a caged chest with mesh insets, and a halter neck. Swim top closes with hook closures at the neck and back. Don't forget the matching swim bottom!
Model is 5'6" with a 34" 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: 07104-0032

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mesh Bandeau Bikini Top
Get the ultimate beach babe look with this black bandeau bikini top! It features a strapless neckline, a sheer mesh panel in the center of the bust, and a slim fit. Matching bottoms available.
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: 07104-0197

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Oh My Triangle Swim Top
Make jaws drop baby girl! This super sexy taupe bikini top features classic triangle cups, string ties and no padding. Don't forget the matching bottoms!
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07104-0204

Category Name: Vacation Looks

Price: $18.90

Availability: Out of Stock
Product Badge:
- Ships Free
Perfect Match High-Rise Lace Mini Skirt
You in this lace mini skirt plus your weekend plans equals the perfect match! Pair the skirt with the matching top.

Fit & Features
- Lace fabric lined with sewn-in knit
- High-rise waist
- Adjustable side ties
- Bodycon fit
- Ruffled mini-length hem
- Runs true to size
Shop The Matching Top: Perfect Match Long Sleeve Lace Crop Top
Style Number/Barcode: 06501-1128

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hei Tiare Bikini Top
Step into the most gorgeous tropical paradise in this floral bikini top! It has triangle cups that tie at the front and a vibrant tropical print. Bikini top is composed of a smooth fabric with a moderate stretch. Bust is not padded. Pair with matching bottoms to complete your tropical look!
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: 07104-0151

Category Name: Vacation Looks

Price: $27.90

Availability: Out of Stock
Product Badge:
- Ships Free
Strappy And Sultry Swim Top
This swim top gives off major strappy and sultry vibes! It features a halter neckline with thin adjustable shoulder straps, a V neckline with structured cups and strap detailing, and a trendy lattice back. Don't forget the matching swim bottoms!
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: 07104-0203

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Cream Floral Animation Bikini Top
This fun floral bikini top brings in some rustic and retro vibes! It has triangle cups that tie at the front and a bold floral print. Bikini top is composed of a smooth fabric with a moderate stretch. Bust is not padded. Pair with matching bottoms to complete your beach babe look!
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: 07104-0149

Category Name: Vacation Looks

Price: $27.90

Availability: Out of Stock
Product Badge:
- Ships Free
Strap On Bikini Top
Make a strappy statement with this black bikini top! It features a deep square neckline, narrow shoulder straps, and an under bust strap with a narrow cut out. Matching bottoms available.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

Style Number/Barcode: 07104-0191

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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Vacation Looks