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.

Tropical Allure Mesh Crop Top
Let those tropical vibes allure you in with this cute crop top! The crop features a sleeveless square neckline, bungee spaghetti straps, a tropical palm leaf print, and a cropped hem. Complete look with the matching mini skirt and wedges that will have you vacay ready.

Shop Matching Mini Skirt: Tropical Allure Ruched Mini Skirt

Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Tropical palm leaf print
- Cropped hem
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3251

Category Name: Vacation Looks

Price: $6.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Glam Trendsetter Floppy Boater Hat
Top off your summer look with this boater hat for a trendy glam vibe! It features a floppy brim, a thin rhinestone band with a tie-back detail, and is made of a straw-like material. Style this hat with a boho-chic crop top and denim shorts for festival season.

Fit & Features
- Floppy brim
- Rhinestone trim band, tie-back detail
- Straw-like material
Style Number/Barcode: 07302-0319

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Shimmering Beauty Mesh Fringe Wrap
Layer on this shimmering mesh fringe wrap for a stunning summertime look! It features a sheer mesh fabric with a trendy fringe hem and embroidered sequins in a pretty floral design. Style this wrap as a chic cover-up over your fave bikinis.

Fit & Features
- Sheer mesh fabric, fringe hem
- Embroidered sequins in a floral design
Style Number/Barcode: 07305-0272

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flawlessly Fab Crochet Crop Top
Keep it flawless with a crochet top that brings the glam to your look! The crop top features a boat neckline, long sleeves, a crochet knit bodice, and a cropped hem. The crop top can be styled with an adhesive bra or as a swim coverup.

Fit & Features
- Boat neckline
- Long sleeves
- Crochet knit bodice
- Cropped hem
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 06005-0672

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fashionably Frayed Cutoff Denim Shorts
These fashionably frayed denim shorts will be your go-to pair of denim this summer! They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button closure, and a cutoff frayed hem. Pair these shorts with your fave crop top and sandals.

Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button closure
- Cutoff frayed hem
- Denim fabric
- Runs true to size
Style Number/Barcode: 06603-0169

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Stunning Beauty Tropical Maxi Dress
Showcase your stunning beauty in this tropical maxi dress on your next weekend getaway! It features a sleeveless V neckline, spaghetti straps that lead to an open back with a strappy design, a high waist, and a floor-length hem with a relaxed fit. The knit fabric has an all-over palm leaf print to bring the vacay vibes. Complete the look with strappy sandals.

Fit & Features
- Sleeveless V neckline
- Spaghetti straps
- Open back, strappy design
- High waist
- Floor-length hem, relaxed fit
- Knit fabric, palm leaf print
- Runs true to size
Style Number/Barcode: 05102-0525

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cutie Vibe Gingham Print Thong Strap Sandals
You'll love the cute vibe these thong strap sandals bring to your weekend 'fits! The adorable gingham print is a spring and summer staple.

Fit & Features
- Faux leather material
- Gingham print
- Almond-shaped toe
- Thong strap design
- Open back, on-and-off styling
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1249

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: In Stock

Available Color: PINK, RED, BLUE

Available Size: 5.5, 6.5, 7, 7.5, 6, 9, 8
Product Badge:
- Sale
Vacay Bound Tropical Mini Dress
Don't forget to pack this gorgeous mini dress for your summer vacay! It features a sleeveless square neckline, adjustable spaghetti straps, a back zipper closure, all-over ruching, and a mini-length, curve-hugging silhouette. The knit fabric has an all-over tropical floral print that will pair perfectly with a flowy sheer duster. Complete the look with mules.

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper closure
- Ruching
- Short, form-hugging fit
- Knit fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 05103-3839

Category Name: Vacation Looks

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Basic And Chic Bikini Bottoms
Keep it basic and chic with bikini bottoms that will have you vacay-ready to bask in the sun! The bikini bottoms feature a high-rise waist, side ties, and a thong bottom. Complete look with the matching bikini top and a floppy hat.

Shop Matching Bikini Top: Basic And Chic Bikini Top

Fit & Features
- High rise waist
- Side ties
- Thong bottom
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0514

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Basic And Chic Bikini Top
Keep it basic and chic with a bikini top that will have you vacay-ready to bask in the sun! The bikini features triangle cups, halter neck ties, and back ties. Complete look with the matching bikini bottoms and a floppy hat.

Shop Matching Bikini Bottoms: Basic And Chic Bikini Bottoms

Fit & Features
- Triangle cups
- Halter neck ties
- Back ties
- Form hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0364

Category Name: Vacation Looks

Price: $9.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Lovestruck Butterfly Print Smocked Mini Dress
Get lovestruck with this pretty butterfly print mini dress that brings the charm! The mini dress features a sleeveless sweetheart neckline with a cute tie-front accent, a cutout at the midriff, adjustable spaghetti straps, a smocked back, and a mini-length silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules!

Fit & Features
- Sleeveless sweetheart neckline
- Tie-front accent
- Adjustable spaghetti straps
- Cutout at the midriff
- Smocked back
- Gauze knit fabric, mini length silhouette
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1230

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pop Of Floral Mesh Maxi Dress
Add a pop of floral to your summer look with this gorgeous maxi dress. It features a sleeveless wrap-front V neckline, spaghetti straps, a cross-back design with a tie closure, a fitted high waist, and a floor-length skirt with dual front slits and a flowy silhouette. This dress is perfect for attending a summer wedding styled with basic heels and stud earrings.

Fit & Features
- Wrap-front V neckline
- Spaghetti straps
- Cross-back design, tie closure
- Fitted high waist
- Floor-length skirt, dual front slits, flowy silhouette
- Floral printed sheer mesh fabric, short lining
- Runs true to size
Style Number/Barcode: 05101-0544

Category Name: Vacation Looks

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Sleek Basic Band Sandals
Keep it so sleek with basic sandals that perf for beach days and brunch! The sandals feature a slip-on design and open almond toe with a wide strap over the toe and a faux leather insole. Complete look with a bikini top and cutoff shorts.

Fit & Features
- Slip-on design
- Open almond toe
- Wide strap over the toe
- Faux leather insole
Style Number/Barcode: 07404-0687

Category Name: Vacation Looks

Price: $12.97 $15.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Two Strap Buckle Sandals
Step out in style in these trendy sandals that are perf for casual brunch dates! They feature a round open toe, a dual strap design with double buckle detailing, and a slide-on fit. Pair these sandals with your favorite casual dress and a classic denim jacket.

Fit & Features
- Round open toe
- Dual strap design
- Double buckle detailing
- Slide-on fit
- Cork sole
Style Number/Barcode: 07404-0685

Category Name: Vacation Looks

Price: $12.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wanderlust Beauty Tie Front Top
You're a total wanderlust beauty, and this tie-front top is a must-have style for you. The top features a plunging V-neckline, a tie-front, short sleeves, and a bohemian-inspired paisley print. Complete your look with the matching pants and sandals for the perf warm-weather outfit.

Shop Matching Pants: Wanderlust Beauty Flared Pants

Fit & Features
- V-neckline
- Tie-front accent
- Short sleeves
- Bohemian-inspired paisley print
- Cropped hem
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06202-0184

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Brunch-Ready Floral Midi Dress
Style this adorable floral midi dress for weekend brunch with the girls! It features a sleeveless square neckline, spaghetti straps, a high waist, ruching, and a mid-length, curve-hugging silhouette. The knit fabric includes a knit lining and offers plenty of stretch. Complete the look with cute sunglasses and chic mules.

Fit & Features
- Square neckline
- Spaghetti straps
- High waist
- Ruching
- Mid-length, form-hugging fit
- Lined knit fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-1045

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Shot Queen Tequila Script Cap
Let this cap say it all, tequila queen! The cap features a traditional baseball brim and a script that reads: "Tequila, Salt & Lime". Complete the look with a white tee and cutoff shorts.

Fit & Features
- Traditional baseball brim
- Script reads" "Tequila, Salt & Lime"
Style Number/Barcode: 07302-0336

Category Name: Vacation Looks

Price: $6.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish And Chic Clear Sandals
Get a stylish and chic vibe when you add these clear sandals to your look! They feature a round open toe, a clear PVC wide strap, and a slide-on design. Pair these sandals with a floral mini dress for a casual day-time date.

Fit & Features
- Round open toe
- Clear PVC wide strap
- Slide-on design
- Patent PU flat sole
Style Number/Barcode: 07404-0686

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Chic Criss-Cross Faux Suede Sandals
Keep it so chic with sandals that elevate your look. The sandals feature a slip-on design, an open almond toe, criss-cross straps, and composed of a faux suede material. Complete look with a matching crop top and shorts set.

Fit & Features
- Slip-on design
- Open almond toe
- Criss-cross straps
- Faux suede material
Style Number/Barcode: 07404-0722

Category Name: Vacation Looks

Price: $12.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Leopard Pyramid Stud Jelly Thong Sandals
Keep it fierce and chic with jelly sandals that let your inner diva show! The sandals feature a jelly body, a leopard print, pyramid-shaped studs, a bow accent, and an open almond toe with a thong strap. Complete look with cutoff shorts and a crop top.

Fit & Features
- Jelly body
- Leopard print
- Pyramid-shaped studs
- Bow accent
- Open almond toe
- Thong strap
Style Number/Barcode: 07404-0726

Category Name: Vacation Looks

Price: $12.97 $14.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Main Squeeze Ribbed Knit Halter Top
She’s cute, confident, and totally crush-worthy. This ribbed halter top brings the heat with a flirty hanky hem and body-hugging fit—perfect for rooftop sunsets, flings, and everything in between.

Fit & Features
- Ribbed knit fabric, plenty of stretch
- Sleeveless halter neckline
- Partially open back
- Angled hanky hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000042

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Here For The Drama Sunglasses
Accessorize your summer look with these oversized sunglasses for a dramatic and chic vibe. They feature a square-shaped design with a plastic frame and tinted lenses. Style these shades with a casual dress and mules.

Fit & Features
- Oversized square-shaped design
- Plastic frame
- Tinted lenses
Style Number/Barcode: 07008-0850

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flowy And Chic Woven Kimono
Layer on this lightweight, airy kimono to add a chic style to your poolside look. It features kimono-style sleeves, an open front, side slits, and a flowy silhouette. The woven fabric has a pretty lace insert on the back and a cute all-over trim detail. Pair this kimono with your fave bikini and complete the look with strappy sandals.

Fit & Features
- Kimono-style sleeves
- Open front
- Side slits
- Flowy silhouette, relaxed fit
- Woven fabric, back lace insert, trim detail
Style Number/Barcode: 06204-0915

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Major Boho Vibes Tie-Front Top
Get those major boho vibes you've been seeing all over your feed with this tie-front top! It features long flared sleeves, a V neckline, a tie-front, and a cropped, form-hugging fit. Style this top with cutoff denim shorts and strappy sandals.

Fit & Features
- Long flared sleeves
- V neckline
- Tie-front
- Cropped, form-hugging fit
- Faux suede fabric
- Runs true to size
Style Number/Barcode: 06204-0924

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