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.

Set On The Tropics Handkerchief Top
Set your sights on the tropics with a top that is perf for that cabana life! The top features a sleeveless square neckline, a handkerchief bodice, spaghetti straps, a tie-back accent, and a tropical print. Complete look with high waist shorts.

Fit & Features
- Sleeveless square neckline
- Handkerchief bodice
- Spaghetti straps
- Tie-back accent
- Cropped hem
- Tropical print
- Form hugging fit runs true to size
Style Number/Barcode: 06003-1287

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Floral Passion Sleeveless Mini Dress
Channel the romance with a floral mini dress that brings charm to your look. The dress features a sleeveless V-neckline, tie-front, spaghetti straps, ditsy floral print, and mini-length silhouette. Complete look with mules and a charm necklace.

Fit & Features
- Sleeveless V-neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2692

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Headed To The Tropics Mini Dress
Get ready to head to the tropics with this mini dress! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, tropical palm leaf print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0480

Category Name: Vacation Looks

Price: $9.97 $33.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Pleated And Striped Shorts
Keep it trendy with shorts that are all the rage! The shorts feature a high-rise waist, a trendy striped pattern, pleats, and a cheeky fit. Complete the look with the matching tube top.

Shop Matching Tube Top: Trendy Pleated And Striped Tube Top

Fit & Features
- High-rise waist
- Striped pattern
- Pleats
- Cheeky fit
- Form-hugging fit, moderate stretch
- Lightweight knit fabric
- Runs true to size
Style Number/Barcode: 06503-0251

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Pleated And Striped Tube Top
Keep it trendy with a tube top that is all the rage! The top features a trendy striped pattern, a sleeveless sweetheart neckline, and surplice ties that can be used to create a halter neck or tie front. Complete the look with the matching shorts.

Shop Matching Shorts: Trendy Pleated And Striped Shorts

Fit & Features
- Sleeveless sweetheart neckline
- Striped pattern
- Surplice ties
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3750

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Darling Gingham Print Mini Dress
Stay on trend with a pretty mini dress that is perf for brunch with the squad! The dress features a sleeveless square neckline, spaghetti straps, gingham print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Gingham print
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4074

Category Name: Vacation Looks

Price: $19.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Glitz Rhinestone Butterfly Charm Choker
Keep it so glam with a butterfly charm choker that brings a luxe touch to your outfit! The choker features a chunky chain link with a single row of rhinestone embellished butterfly charms and a lobster clasp closure. Complete look with a matching floral top and shorts set.

Fit & Features
- Chunky chain link
- Single row of butterfly charms
- Rhinestones
- Lobster clasp closure
Style Number/Barcode: 07002-0744

Category Name: Vacation Looks

Price: $5.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wanderlust Moment Crochet Crop Top
Create a wanderlust moment with a crochet top to nail that dream vacay outfit. The crop top features a halter neck with adjustable neck ties, a mini-lattice accent at the center of the bodice, a matching lattice accent at the back, and a cropped hem. The top is composed of an unlined crochet knit fabric that offers a relaxed fit with minimal stretch. Complete look with gel pasties and flared pants.

Fit & Features
- Halter neck
- Adjustable neck ties
- Mini lattice accent at front and back
- Cropped hem
- Crochet knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-0900

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spotlight On Me Tiered Skater Dress
Dazzle in the spotlight with a skater dress that brings all eyes on you! The dress features a sleeveless V-neckline, a sheer waist inset with a cross-bar design, and a tiered skater silhouette. The dress is composed of a scuba knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a dainty rhinestone necklace.

Fit & Features
- Sleeveless V-neckline
- Sheer waist
- Cross-bar design at the waist
- Tiered skater silhouette
- Scuba knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0667

Category Name: Vacation Looks

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Paradise Paisley Print Bikini Top
Transport to paradise with this cute bikini top! The bikini features a gorge paisley print, halter neck strap, traditional triangle cups with removable padding, and wrap-around straps at the hem. Complete the look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Bohemian Paradise Paisley Print Bikini Bottoms

Fit & Features
- Paisley print
- Halter neck strap
- Triangle cups
- Removable padding
- Wrap around straps at hem
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0588

Category Name: Vacation Looks

Price: $5.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Days High Rise Cutoff Denim Shorts
Make your day a stylish one with cutoff shorts that keep you on-trend! The shorts feature a high-rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, moderate destruction, and a cutoff hem. Complete the look with a crop top and sneakers.

Fit & Features
- High rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Moderate destruction
- Cutoff hem
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0177

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Remarkable Energy Abstract Striped Wide-Leg Jumpsuit
This abstract striped jumpsuit will never fail to impress! The cutout bodice adds a sassy allure while the hidden side pockets along the flattering wide-leg silhouette provide trendy convenience!

Fit & Features
- Abstract striped print, woven fabric
- Sweetheart neckline, spaghetti straps
- Stretchy smocked back
- Cutout bodice
- Hidden side pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-000001

Category Name: Vacation Looks

Price: $9.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Crochet Knit Handkerchief Crop Top
Keep it cute and chic with a crochet crop top! The top features a halter neckline, a handkerchief-styled bodice, neck ties, and back ties. The top is composed of a crochet knit fabric that offers a relaxed fit with a moderate stretch. Complete look with adhesive pasties.

Fit & Features
- Halter neckline
- Handkerchief-style bodice
- Neck ties
- Back ties
- Crochet knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0965

Category Name: Vacation Looks

Price: $11.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho-Chic Convertible Tube Top
This convertible tube top will give you those boho-chic vibes you've been seeing all over social media! It features a strapless neckline, a cropped, form-hugging fit, and can be worn as a halter, tie-front, or with the ties in the back. Style this versatile top with the matching pants for the perf vacay outfit.

Shop Matching Bottoms: Boho-Chic Wide-Leg Pants

Fit & Features
- Strapless neckline
- Cropped, form-hugging fit
- Versatile styling
- Knit fabric
- Runs true to size
Style Number/Barcode: 06001-3375

Category Name: Vacation Looks

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho-Chic Wide-Leg Pants
These wide-leg pants will give you those boho-chic vibes you've been seeing all over social media! They feature a high-rise banded waist, pleated detailing, and a wide-leg, relaxed fit. Style these cute pants with the matching top for the perf vacay outfit.

Shop Matching Top: Boho-Chic Convertible Crop Top

Fit & Features
- High-rise elastic banded waist
- Pleated detailing
- Wide-leg, relaxed fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-0577

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Casual Day Crochet Knit Midi Dress
Keep it casual with a midi dress that will have you channeling your bohemian side. The dress features a sleeveless V-neckline, spaghetti straps, a tie waist belt, and a midi length silhouette, The dress is composed of a crochet knit fabric that offers a relaxed fit with a slight stretch. Complete look with wedges.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-waist belt
- Midi length silhouette
- Crochet knit fabric
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 06005-0921

Category Name: Vacation Looks

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Clearly on Trend Box Crossbody
Stay on trend with a cute clear crossbody that keeps all your essentials close to you! The crossbody features a box design, a clear body, a top fasten closure, and a chain shoulder strap. Complete look with a bodysuit and joggers.

Fit & Features
- Clear body
- Box design
- Top fasten closure
- Chain shoulder strap
Style Number/Barcode: 07203-0463

Category Name: Vacation Looks

Price: $8.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stunning Boho Vibes Woven Shorts
Showcase those stunning boho vibes in these on-trend woven shorts! They feature a high-rise waist, a relaxed fit, and an all-over chic paisley pattern. Style these shorts with the matching top and strappy sandals for the perf everyday summer look.

Shop Matching Top: Stunning Boho Vibes Tie-Front Top

Fit & Features
- High-rise waist
- Relaxed fit
- Woven fabric, paisley pattern
- Runs true to size
Style Number/Barcode: 06303-0121

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flirty In Floral Off-The-Shoulder Romper
Get a cute and flirty look for a casual summer date in this floral printed romper! It features an off-the-shoulder neckline, short puff sleeves, a high waist with a tie-front accent, and relaxed-fitting shorts. Style this romper with hoop earrings and strappy sandals.

Fit & Features
- Off-the-shoulder neckline
- Short puff sleeves
- High waist, tie-front
- Relaxed-fitting shorts
- Woven fabric, floral print
- Runs true to size
Style Number/Barcode: 06403-0153

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stunning Boho Vibes Tie-Front Top
Showcase those stunning boho vibes in this on-trend top! It features short flutter sleeves, a V-neckline, a tie-front detail, a cropped, relaxed fit, and an all-over chic paisley pattern. Style this top with the matching shorts and strappy sandals for the perf everyday summer look.

Shop Matching Bottoms: Stunning Boho Vibes Woven Shorts

Fit & Features
- Short flutter sleeves
- V-neckline
- Tie-front
- Cropped, relaxed fit
- Woven fabric, paisley pattern
- Runs true to size
Style Number/Barcode: 06204-0994

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ready For Paradise Smocked Tube Top
You'll be totally ready for your vacay to paradise in this tropical floral tube top! It features a strapless neckline, a cropped, form-hugging fit, and a smocked woven fabric. Style it with the matching mini skirt and complete the look with a chic floppy hat.

Shop Matching Bottoms: Ready For Paradise Smocked Mini Skirt

Fit & Features
- Strapless neckline
- Cropped, form-hugging fit
- Smocked woven fabric
- Tropical floral print
- Runs true to size
Style Number/Barcode: 06003-0705

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Candid Chic Faux Suede Crop Top
Keep it candidly chic with a crop top that slays! The crop top features a plunging V-neckline, spaghetti straps that lead to a cross-strap back, and a cropped hem. The top is composed of faux suede material that offers a form-hugging fit with minimal stretch. Complete look with a high waist skirt.

Fit & Features
- Sleeveless sweetheart neckline, padded cups
- Spaghetti straps
- Cross-back, hook and eye closure at back
- Cropped hem
- Faux suede fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1276

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ready For Paradise Smocked Mini Skirt
You'll be totally ready for your vacay to paradise in this tropical floral mini skirt! It features a high-rise waist, a mini-length, curve-hugging silhouette with a ruffled hem, and a smocked woven fabric. Style it with the matching tube top and complete the look with a chic floppy hat.

Shop Matching Top: Ready For Paradise Smocked Tube Top

Fit & Features
- High-rise waist
- Short, form-hugging fit
- Ruffled hem
- Smocked woven fabric
- Tropical floral print
- Runs true to size
Style Number/Barcode: 06301-0061

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay On My Mind Tropical Print Kimono
You'll be ready for a vacay in this cute kimono that brings those island vibes! The kimono features a drape open front, tropical palm leaf print, kimono sleeves. and an above the knee length. Complete look with the matching crop top and shorts.

Shop Matching Crop Top: Vacay On My Mind Tropical Print Crop Top

Shop Matching Shorts: Vacay On My Mind Tropical Print Shorts

Fit & Features
- Draped open front
- Tropical palm leaf print
- Kimono sleeves
- Above the knee length
- Chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0772

Category Name: Vacation Looks

Price: $9.97 $26.90

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