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.

Resort Worthy Espadrille Flat Sandals
Give your feet a vacation from heels in these trendy sandals that give off resort vibes! They feature an almond toe, nubuck toe and wrap-around ankle strap with buckle closure, and an espadrille trim along the flat sole. Complete the look with a stylish crossbody bag.

Fit & Features
- Almond toe
- Nubuck toe and wrap-around ankle strap
- Buckle closure
- Espadrille trim along flat sole
- Runs true to size
Style Number/Barcode: 07404-1079

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Blinged-Out Rhinestone Straight-Leg Jeans
Love a blinged-out look? Style up these rhinestone embellished straight-leg jeans for a fab 'fit. Perfect for festival season, they feature a high-rise waist, a straight-leg silhouette, and mini rhinestone embellishments in curved designs for a cool illusion. The light wash rigid denim fabric has a trendy vintage-inspired look with no stretch. Pair with a crop top and mules.

Fit & Features
- High-rise waist
- Straight-leg silhouette
- Mini rhinestones, curved embellished designs
- Belt loops, dual front and back pockets
- Front button, hidden zipper closure
- Light wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06602-0431

Category Name: Vacation Looks

Price: $9.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Retro Diva Denim Catsuit
This curve-hugging denim catsuit will make you a fab retro diva! It features an asymmetric one-shoulder neckline, a single adjustable spaghetti strap, a partially open back, a fitted high waist seam, and form-fitting pant legs. Style with sleek hoops and clear heels.

Fit & Features
- Asymmetric one-shoulder neckline
- Single and adjustable spaghetti strap
- Partially open back, zipper and hook-eye closure
- Fitted high waist seam
- Form-fitting pant legs
- Denim fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06602-0421

Category Name: Vacation Looks

Price: $19.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Remy High-Rise Distressed Shorts By Windsor Denim
Super flattering and fab! The Remy shorts by Windsor denim are perfect for refreshing your closet. They feature a high-rise waist, distressed accents, and a cut-off hem. The shorts are composed of premium denim fabric with minimal stretch. Complete the look with caged flat sandals for a weekend festival!

Fit & Features
- High-rise waist
- Distressed accents
- Cut-off hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0311

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Can't Stop This Shine Metallic Bow Sandals
Shimmer and shine with each step in these sandals featuring a square toe, metallic bow strap, faux leather sole, and slide-on-and-off styling. Complete the look in a trendy crop jacket for a date night.

Fit & Features
- Square toe
- Metallic bow strap
- Faux leather sole
- Slide-on-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1120

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Trendy Mood Sheer Mesh Crop Top
Get in a trendy mood with this alluring and edgy sheer mesh crop top! It features a crew neckline, loose short sleeves, a cropped hem, a relaxed fit, and a completely sheer mesh fabric. Create the perfect festival 'fit with the matching shorts and a pair of fab cowboy boots!

Shop Matching Bottoms: Trendy Mood Sheer Mesh Shorts

Fit & Features
- Crew neckline
- Loose short sleeves
- Cropped hem
- Relaxed fit
- Sheer mesh fabric
- Runs true to size
- Bra not included
Style Number/Barcode: 07103-0868

Category Name: Vacation Looks

Price: $8.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Mood Sheer Mesh Shorts
Get in a trendy mood with these alluring and edgy sheer mesh shorts! They feature a high-rise waist with a faux front drawstring, a fitted silhouette, and a completely sheer mesh fabric. Create the perfect festival 'fit with the matching crop top and a pair of fab cowboy boots!

Shop Matching Top: Trendy Mood Sheer Mesh Crop Top

Fit & Features
- High-rise elasticized waist
- Faux front drawstring
- Fitted silhouette
- Sheer mesh fabric, plenty of stretch
- Runs true to size
- Undergarment not included
Style Number/Barcode: 07103-0870

Category Name: Vacation Looks

Price: $9.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Twirl All Day Linen Skater Dress
You'll be twirling all day in this linen skater dress perfect for a day date or Sunday brunch! It features a sleeveless, square neck, adjustable spaghetti straps, fitted bust, open-back with an elasticized band, and a flowy short hem. Complete the look in PVC strap heels.

Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- Fitted bust
- Open-back, elasticized band
- Flowy skater silhouette
- Short length hem
- Linen woven fabric, knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-1667

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Bring The Heat Printed Wide-Leg Pants
Bring the heat to your spring break look with these trendy pants that will get everyone's attention! They feature a high-rise waist, pleating, an exaggerated wide-leg silhouette with a relaxed fit, and a sassy abstract printed design. Style with the matching crop top to be vacay-ready!

Shop Matching Top: Bring The Heat Printed Crop Top

Fit & Features
- High-rise waist, back elastic band
- Pleating
- Wide-leg silhouette, relaxed fit
- Abstract printed design
- Satin woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-0536

Category Name: Vacation Looks

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendsetting Vibe Lace-Up Denim Shorts
Show off a trendsetting vibe in these mid-rise denim shorts for festival season! The lace-up side design adds the perfect edge to your casual 'fits.

Fit & Features
- Denim fabric, moderate stretch
- Mid-rise waist, belt loops
- Front button and hidden zipper closure
- Lace-up side design
- Fitted
- Runs true to size
Style Number/Barcode: 06603-0472

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: In Stock

Available Color: OLIVE

Available Size: XL
Product Badge:
- Sale
Bring The Heat Printed Crop Top
Bring the heat to your spring break look with this trendy crop top that will get everyone's attention! It features a sleeveless sweetheart neckline with a padded bust, thin halter straps with multiple ways to style, a stretchy smocked back, an ultra-cropped hem, and a sassy abstract printed design. Style with the matching wide-leg pants to be vacay-ready!

Shop Matching Bottoms: Bring The Heat Printed Wide-Leg Pants

Fit & Features
- Sleeveless sweetheart neckline, padded bust
- Thin halter straps, multiple ways to style
- Smocked back design
- Ultra-cropped hem
- Abstract printed design
- Satin woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-2061

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pretty Deets Crepe Lace-Up Midi Dress
This crepe midi dress has the pretty deets you're looking for! The dress features a sleeveless square neck, spaghetti straps, an open lace-up back with tie closure, a ruched bust, and a bodycon silhouette. Complete the look in chic flat sandals.

Fit & Features
- Sleeveless square neck, spaghetti straps
- Open lace-up back, tie closure
- Ruched bust
- Bodycon silhouette
- Midi-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4891

Category Name: Vacation Looks

Price: $19.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Diva Oversized Sunglasses
Bring the diva energy with these fabulous oversized sunglasses. They feature a square-shaped frame with a chic gold trim and tinted lenses. Style with hoop earrings.

Fit & Features
- Oversized design
- Square-shaped plastic frame
- Top gold trim
- Tinted lenses
Style Number/Barcode: 07008-0981

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On Your Radar Mirrored Aviator Sunglasses
These trendy aviator sunglasses definitely need to be on your radar! They feature an aviator design with a thin metal frame, thin metal arms, and mirrored lenses. Style with a graphic tee for an edgy-chic look.

Fit & Features
- Aviator design
- Thin metal frame, metal arms
- Mirrored lenses
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-0983

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sent You A Text Square Neck Mini Dress
You might want to reply back to your new favorite casual mini dress for weekend outings or day dates! It features a sleeveless square neck, tank-style straps, and a bodycon silhouette, and is composed of a textured fabric with a stretch knit lining. Style with a denim jacket and sandals.

Fit & Features
- Sleeveless square neck
- Tank-style straps
- Bodycon silhouette
- Mini-length hem
- Textured fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4860

Category Name: Vacation Looks

Price: $5.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Such A Cutie Flower Drop Earrings
Create the cutest everyday look with these adorable flower drop earrings! They feature a fish hook design connected to a thin metal flower-shaped outline. Style with a floral dress and strappy sandals for a pretty vibe.

Fit & Features
- Fish hook design
- Thin metal flower-shaped outline
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1471

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
A Boost Of Cute Two Pack Flower Clips
Every outfit could use a boost of these cute flower hair clips! They feature double-sided flower designs with a claw clip closure. Complete the look with a trendy shoulder bag.

Fit & Features
- Two pack hair clip set
- Double-sided flower designs
- Claw clip closure
Style Number/Barcode: 07006-0375

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Got The Edgy Look Oversized Sunglasses
Get an edgy look to shade your eyes from the rays in these oversized sunglasses featuring a flat top design, tortoise plastic frames, and tinted lenses. Complete the look in a cool faux leather jacket.

Fit & Features
- Oversized design
- Flat top
- Tortoise plastic frames
- Tinted lenses
Style Number/Barcode: 07008-0990

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Happy Girl Smiley Face Belly Chain
If you're happy and you know it, just wear it! Show your mood in this smiley happy face belly chain with an adjustable chain lobster clasp closure. Complete the look in a crop top and bottoms matching set!

Fit & Features
- Smiley happy face charms
- Chain with adjustable lobster clasp closure
Style Number/Barcode: 07002-1478

Category Name: Vacation Looks

Price: $2.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Boho Flair Lace-Up Sandals
Let festival season inspire your spring wardrobe with these on-trend sandals that bring a boho flair. They feature an open almond-shaped toe with a toe strap, a thin, asymmetric, strappy design across the foot, a thicker heel strap, a matching thin strappy design that wraps around the leg, and a flat sole. Style with a flowy midi dress and statement earrings.

Fit & Features
- Open almond-shaped toe, toe strap
- Thin, asymmetric, strappy design across the foot
- Heel strap
- Thin strappy wrap-around design
- Flat comfort sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1119

Category Name: Vacation Looks

Price: $5.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Simply Fab Pearl Detail Crossbody Bag
Simply fab, this quilted faux leather crossbody bag is a chic staple! It features an oval shape with a top zipper closure, faux pearl, rhinestone, and chain strap accents, and a thin chain-link shoulder strap. Style with your fave mules.

Fit & Features
- Oval shape
- Top zipper closure
- Faux pearl, rhinestone, and chain strap accents
- Thin chain-link shoulder strap
- Diamond quilted pattern
- Faux leather material
Style Number/Barcode: 07203-1189

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casually Glam Rhinestone Chrome Sandals
Amp up your everyday looks with these casually glam chrome sandals! They feature a square toe, an asymmetrical strappy design with sparkly rhinestone accents, an open back for easy on-and-off styling, and a fab metallic sheen. Pair these sandals with a clear handbag.

Fit & Features
- Square toe
- Asymmetrical strappy design, rhinestone embellishments
- Open back
- Flat sole
- Chrome sheen
- Faux leather cushioned insole
- Runs true to size
Style Number/Barcode: 07404-1088

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Always Glam Pearl And Rhinestone Sandals
You're always glam, even when it comes to your casual 'fits! These faux leather sandals are a perfect match for you. They feature a square toe, a dual clear strap design with faux pearl and mini rhinestone accents, and an open back for easy on-and-off styling. Pair with dainty stud earrings.

Fit & Features
- Square toe
- Dual clear strap design
- Faux pearls, mini rhinestones
- Open back
- Flat sole
- Faux leather insole
- Runs true to size
Style Number/Barcode: 07404-1081

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Getaway Vibe Tropical Print Tie-Front Top
This airy mesh top gives off getaway vibes with its trendy tropical print and effortless tie-front design. Style with denim shorts and sandals.

Fit & Features
- Sheer mesh fabric, high stretch
- Tropical print
- V-neckline
- Tie-front design
- Long bell sleeves
- Cropped hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06202-000005

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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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