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.

Top Style Ombre Aviators
Be on top of the style game in these aviator sunglasses featuring a stylish ombre lens, metal trim, and sturdy arms. Complete the look in an edgy graphic top.

Fit & Features
- Ombre gradient lens
- Metal trim
- Sturdy arms
Style Number/Barcode: 07008-0915

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cheer Squad Ponte Pleated Mini Skirt
The crowd will cheer for you in this cute pleated mini skirt featuring a high-rise waist and an A-line silhouette. Composed of a Ponte knit fabric with an inner shorts lining. Finish the look in a crop top and sneakers.

Fit & Features
- High-rise waist
- Pleat detailing
- A-line silhouette
- Mini-length hem
- Ponte knit fabric, inner shorts lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0658

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Simplicity is Bliss Layered Choker
Add the perfect finishing touch with this choker featuring four layers of various chain styles with a lobster clasp closure. Complete your fit in a cropped jacket.

Fit & Features
- Four-layered design
- Various styles of chains
- Lobster clasp closure
Style Number/Barcode: 07002-1126

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Work Of Art Filigree Hoops
These hoops are works of art! They feature a filigree design with an omega-back closure. Complete the look in a chic casual dress.

Fit & Features
- Filigree design
- Omega-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-1163

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunny Days Hipster Bikini Bottoms
Bask in the sun with bikini bottoms that are perf for your next getaway! The bottoms feature a hipster-styled waist and a cheeky bottom. Complete look with the matching bikini top.

Shop Matching Bikini Top: Sunny Days Bikini Top

Fit & Features
- Hipster waist
- Cheeky bottom coverage
- Form-hugging fit
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0811

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunny Days Bikini Top
Bask in the sun with a bikini top that is perf for your next getaway! The bikini top features a bandeau-style bodice, a wired V inset, adjustable tank shoulder straps, and removable padding. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Sunny Days Hipster Bikini Bottoms

Fit & Features
- Bandeau styled bodice
- Wired V inset
- Adjustable tank shoulder straps
- Removable padding
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0664

Category Name: Vacation Looks

Price: $8.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Dramatica Script Baseball Cap
Bring the drama with a cap that says it all! The hat features a traditional baseball cap design and an embroidered "Dramatica" script. This hat would go perf with all your casual OOTDs!

Fit & Features
- Traditional baseball cap design
- Embroidered "Dramatica" script
- Adjustable fasten
Style Number/Barcode: 07302-0542

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
Rise And Glam Oval Bead Hoops
It's time to rise and get the glam girl! These hoops feature oval metal beads with rhinestone insets and an omega-back closure. Complete the look in a sultry bustier.

Fit & Features
- Oval metal beads
- Rhinestone insets
- Omega-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1160

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Purrfect Cateye Trim Sunglasses
The purrfect cat-eye sunnies are here and they require no practice! The sunglasses feature oversized frames with a metal top trim, sturdy plastic arms, and nose brim. Complete the look in a chic jumpsuit.

Fit & Features
- Oversized frame
- Cat-eye style lens
- Metal top trim
- Sturdy plastic arms and nose brim
Style Number/Barcode: 07008-0912

Category Name: Vacation Looks

Price: $3.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Beach Side Button-Front Linen Shirt
This button-front linen shirt is beach-bound! It features long sleeves with button cuffs, a collared neckline, front flap pockets, a button-down front closure, and a round hem. Complete the look in denim shorts and sandals.

Fit & Features
- Long sleeves, button cuffs
- Collared neckline
- Front flap pockets
- Button-down front closures
- Round hem
- Woven linen fabric
- Fits true to size, no stretch
Style Number/Barcode: 06003-1859

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Time To Stun One Piece Swimsuit
Babe, stun it out in a one-piece swimsuit that will have you vacay-ready! The must-have swimsuit features a plunging V-neckline, removable padding, adjustable spaghetti straps, sheer unlined mesh bodice, and a full coverage bottom. Complete look with sunglasses and sandals.

Fit & Features
- Sleeveless V-neckline
- Removable padding
- Adjustable spaghetti straps
- Sheer unlined mesh bodice
- Full coverage bottom
- Slide hook closure at the back
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0275

Category Name: Vacation Looks

Price: $4.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Just Add Water Caged One-Piece Swimsuit
Just add water! Make a splash in this sultry one-piece swimsuit featuring a V-neck, adjustable spaghetti straps with tie-back closure, a built-in padded bust, front O-ring, and a cutout center with attached cheeky fit bottoms. Complete the look in oversized sunglasses.

Fit & Features
- V-neck, built-in padded bust
- Adjustable spaghetti straps, tie-back closure
- Front O-ring inset, cutout center
- Attached cheeky fit bottoms
- Caged detail, O-ring insets on hips
- Runs true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0276

Category Name: Vacation Looks

Price: $4.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sweet Like That Floral Lace Mini Dress
Giving soft girl glam with a flirty twist—this floral lace strapless mini dress brings all the charm. Perfect for brunch, birthdays, or shower celebrations!

Fit & Features
- Floral print lace fabric lined with stretch knit
- Strapless neckline
- Ruched fitted bodice
- Tiered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000270

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On Cloud Nine Low Rise Bikini Bottoms
You'll totally fall for this cloud tie-dye bikini top perfect for a beach day! It features adjustable side ties, a low-rise waist, and a cheeky bottom. Complete the look with the matching bikini top.

Shop The Matching Bikini Top: On Cloud Nine Triangle Bikini Top

Fit & Features
- Adjustable side ties
- Low-rise waist
- Cheeky-cut bottom
- Cloud tie-dye pattern
- Fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0759

Category Name: Vacation Looks

Price: $8.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
On Cloud Nine Triangle Bikini Top
You'll totally fall for this cloud tie-dye bikini top perfect for a beach day! It features a string tie v-neck, padded triangle cups, and a drawstring hem with tie-back closure. Complete the look with the matching bikini bottoms.

Shop The Matching Bikini Bottoms: On Cloud Nine Low Rise Bikini Bottoms

Fit & Features
- String tie v-neck
- Padded triangle cups
- Drawstring hem, tie-back closure
- Cloud tie-dye pattern
- Fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0612

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
New Classic Metal Aviator Sunglasses
Elevate your hip style in these aviator sunglasses featuring a gradient lens, metal trim throughout, rubber nose supports, and sturdy metal arms. Complete the look in a trendy denim jacket.

Fit & Features
- Aviator style
- Gradient lens
- Metal trim throughout
- Rubber nose supports
- Sturdy metal arms
Style Number/Barcode: 07008-0910

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spotted On Trend Low Rise Bikini Bottoms
Get spotted on-trend with bikini bottoms that keep your look so fierce! The bikini bottoms feature a leopard print, a low-rise waist, side ties, and a cheeky bottom. Complete look with the matching bikini top.

Shop Matching Bikini Top: Spotted On Trend Bandeau Bikini Top

Fit & Features
- Leopard print
- Low-rise waist
- Side ties
- Cheeky bottom
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0757

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Spotted On Trend Bandeau Bikini Top
Get spotted on-trend with a bikini top that keeps your look so fierce! The bikini top features a leopard print, a bandeau-styled bodice, cutout at the center, halter ties, and removable padding. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Spotted On Trend Low Rise Bikini Bottoms

Fit & Features
- Leopard print
- Bandeau-styled bodice
- Cutout at the center
- Halter ties
- Removable padding
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0610

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Moment Flat Top Sunglasses
Have a trendy moment in these bold shades. They feature a flat top design with a sheer plastic frame and tinted lenses. Style these sunglasses with a distressed denim jacket.

Fit & Features
- Flat top design
- Sheer plastic frame
- Tinted lenses, dual stud accents
- 100% UV Protection
Style Number/Barcode: 07008-0914

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glowing Paradise O-Ring Bikini Bottoms
Transport to paradise with these bikini bottoms that will have you vacay-ready! The bikini bottoms feature a low-rise waist, dual acrylic O-rings at the waist, side ties, and a thong bottom. Complete look with the matching bikini top.

Shop Matching Bikini Top: Glowing Paradise O-Ring Bikini Top

Fit & Features
- Low-rise waist
- Dual acrylic O-rings at the waist
- Side ties
- Thong bottom
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0758

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glowing Paradise O-Ring Bikini Top
Transport to paradise with this bikini top that will have you vacay-ready! The bikini top features triangle-shaped cups with removable padding, halter neck ties, an acrylic O-ring at the center, and crisscross ties at the midriff. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Glowing Paradise O-Ring Bikini Bottoms

Fit & Features
- Triangle cups
- Removable padding
- Halter neck ties
- Acrylic O-ring
- Criss-cross ties at the midriff
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0611

Category Name: Vacation Looks

Price: $9.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Attitude Round Sunglasses
Bring that chic and stylish attitude with these adorable sunnies! They feature round tinted lenses with a plastic frame and sleek gold-hued arms. Style these sunglasses with your fave Panama hat.

Fit & Features
- Round tinted lenses
- Plastic frame
- Gold-hued arms
- 100% UV Protection
Style Number/Barcode: 07008-0916

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make A Splash One-Piece Swimsuit
Have a splash looking so cute in this one-piece swimsuit perfect for a pool party! It features an adjustable halter strap, a square neck with a sultry cutout, padded cups, and an open back with tie closure, and semi-cheeky bottoms. Complete the look in chic sunnies.

Fit & Features
- Adjustable halter strap
- Squareneck, cutout accent, padded cups
- Open-back, tie back closure
- Semi-cheeky bottoms
- Ribbed knit fabric
- Runs true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0274

Category Name: Vacation Looks

Price: $16.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
On Cloud Nine Mesh Ruched Cover-Up
You'll totally fall for this cloud tie-dye cover-up perfect for a beach day! It features long sleeves, a plunge neckline, and a ruched front so you can adjust the fit. Composed of a sheer mesh fabric with some stretch. Complete the look in the matching bikini top and bottom.

Fit & Features
- Long sleeves
- Plunge neckline
- Adjustable ruched front design
- Cloud tie-dye pattern
- Sheer mesh fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06001-3881

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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