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.

Bohemian Dreams Paisley Print Bikini Top
Channel those wanderlust vibes with this dreamy bikini top! The bikini top features a paisley print, halter neck ties, traditional triangle cups, and ties at the back. Complete look with the matching bikini bottoms, swim coverup, and or duster!

Shop Matching Bikini Bottoms: Bohemian Dreams Paisley Print Bikini Bottoms

Shop Matching Swim Coverup: Bohemian Dreams Ruched Paisley Print Swim Coverup

Shop Matching Duster: Bohemian Dreams Paisley Print Duster

Fit & Features
- Paisley print
- Halter neck ties
- Triangle cups
- Ties at the back
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0577

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Dreams Ruched Mini Skirt
Channel those wanderlust vibes with this dreamy mini skirt. The skirt features a high-rise waist, a ruched side seam with drawstring, a mini-length silhouette, and a paisley print. Complete look with the matching bikini top and bikini bottoms.

Shop Matching Bikini Top: Bohemian Dreams Paisley Print Bikini Top

Shop Matching Bikini Bottoms: Bohemian Dreams Paisley Print Bikini Bottoms

Fit & Features
- High rise waist
- Ruched side seam
- Drawstring
- Paisley print
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0430

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Own the Bloom Floral Strappy Halter Maxi
Bloom like you mean it. This floral maxi dress turns heads with a plunge strappy neckline, open back, and form-hugging fit that was made to steal the spotlight.

Fit & Features
- Floral print, mesh-lined fabric
- Strappy plunge halter neckline, tie straps
- Open back
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000034

Category Name: Vacation Looks

Price: $11.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All My Love Ditsy Floral Mini Dress
Keep it lovely and gorge with a mini dress that shows off your sweet side! The dress features a ditsy floral print, a sleeveless square neckline, spaghetti straps, a lower back keyhole with tie-back straps, and a skater silhouette with a ruffled hem. Complete look with chunky sneakers.

Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lower back keyhole
- Tie-back straps
- Skater silhouette, ruffled hem
- Lightweight woven fabric, ditsy floral print
- Relaxed fit, no stretch
- Runs true to size
Style Number/Barcode: 05102-4147

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Good Vibes Paisley Flare Pants
Channel those good vibes with flared pants that keep it effortlessly stylish! The pants feature a high-rise waist, a paisley print, and a straight leg with a flared hem. Complete the look with the matching crop top.

Shop Matching Crop Top: Good Vibes Paisley Crop Top

Fit & Features
- High-rise waist
- Paisley print
- Straight leg fit, flared hem
- Form-hugging fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-0580

Category Name: Vacation Looks

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Vibes Crochet Knit Maxi Dress
Channel those vacay vibes with a maxi dress that brings those resort vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a lower back keyhole with tie-back straps, and a maxi length silhouette. The dress is composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Lower back keyhole with tie-back straps
- Maxi length silhouette
- Lined gauze knit fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-0297

Category Name: Vacation Looks

Price: $6.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Mesmerizing Beauty Puff Sleeve Eyelet Skater Dress
Mesmerize with a skater dress that is perf for your next photoshoot! The dress features a square neckline, short puff sleeves, an eyelet pattern, and a skater silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

Fit & Features
- Square neckline
- Short puff sleeves
- Eyelet pattern
- Skater silhouette
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4073

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Let Beauty Bloom Floral Midi Dress
Let your beauty bloom with a midi dress that is perf for the season! The dress features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back, a tropical floral print, ruching, and a midi-length silhouette with an asymmetrical hem. Complete look with wedges.

Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Cross-back
- Tropical floral print
- Midi length silhouette
- Asymmetrical hem
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0328

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Glow On Rhinestone Thong Strap Kitten Heels
Bring the glow with kitten heels that add that sparkling touch to your outfit. The heels feature an open back, an open almond toe, a rhinestone embellished thong strap, and a stiletto heel. Complete look with a bodycon and clutch for your next date night.

Fit & Features
- Open back
- Open almond toe
- Rhinestones
- Thong strap
- Stiletto heel
- Faux leather material
Style Number/Barcode: 07401-3049

Category Name: Vacation Looks

Price: $17.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Attitude Cat-Eye Sunglasses
Bring that chic and stylish attitude with these adorable sunnies! The sunglasses feature a geometric pointed cat-eye design, a plastic frame, and tinted lenses. Complete your look with a fab clutch.

Fit & Features
- Geometric pointed cat-eye design
- Plastic frame
- Tinted lenses
Style Number/Barcode: 07008-0838

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Stunner Cat-Eye Sunglasses
Showcase your stunningly chic style with these trendy cat-eye shades. They feature a small cat-eye design with a plastic frame and tinted lenses. Complete your outfit with a cute crossbody purse.

Fit & Features
- Small cat-eye design
- Plastic frame
- Tinted lenses
- 100% UV Protection
Style Number/Barcode: 07008-0851

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Fab Cat-Eye Sunglasses
You'll look oh-so-fab in these chic cat-eye sunglasses. They feature an oversized angled cat-eye design, metal accents on the sides, and tinted lenses. Style these sunnies with a casual dress and mules.

Fit & Features
- Oversized cat-eye design
- Metal accents
- Tinted lenses
Style Number/Barcode: 07008-0837

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep it Cute Basic Block Heels
It's warming up, so it’s time to add some color to your shoe collection! These faux suede basic heels feature an open almond toe, a single toe strap and an adjustable ankle strap. Style them with a crop top and a flirty mini skirt.

Fit & Features
- Block heel
- Adjustable ankle strap
- Faux suede material
- Runs true to size
Style Number/Barcode: 07401-3031

Category Name: Vacation Looks

Price: $12.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feel the Vibe Tie-Dye Platform Heels
Spice up a summer outfit wit these fun cork heels. These heels feature an open almond toe, tie-dye lace up straps, a wide platform and a cork heel. Pair them with a basic bodysuit and denim shorts.

Fit & Features
- Tie-Dye lace up straps
- Platform
- Cork heel
- Open almond tie
- Runs true to size
Style Number/Barcode: 07401-2970

Category Name: Vacation Looks

Price: $7.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Center of Attention Snake Block Heels
All eyes will be on you when you step out in these heels! The heels feature an open toe, a PU snake material, a lace up detail around the ankle and a block heel. Style them with a white mini dress and a matching bag.

Fit & Features
- PU snake material
- Block heel
- Lace-up straps
- Runs true to size
Style Number/Barcode: 07401-2957

Category Name: Vacation Looks

Price: $16.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vacay Vibes Cork Wedges
Your summer wardrobe isn’t complete without a pair of cork wedges! These wedges feature an open toe with a single strap and an ankle buckle closure. Style them with a maxi dress and a floppy hat.

Fit & Features
- Open toe
- Adjustable ankle strap
- Faux nubuck material
- Cork wedge heel
- Runs true to size
Style Number/Barcode: 07406-0252

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
90s Icon Platform Block Heel Mules
Strut like a '90s icon in these statement mules designed with a platform sole and block heel to elevate your favorite looks!

Fit & Features
- Block heel
- Square toe
- Wide foot strap
- Platform sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07401-000274

Category Name: Vacation Looks

Price: $9.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sleek And Stylish Aviator Sunglasses
These sleek aviator sunnies will give your outfit major stylish vibes. They feature a traditional aviator design, a metal trim and metal arms, and tinted lenses. Complete your look with a chic crossbody purse.

Fit & Features
- Traditional aviator design
- Metal trim and metal arms
- Tinted lenses
Style Number/Barcode: 07008-0873

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Status Chain Detail Sunglasses
Elevate your chic status when you accessorize with these trendy sunglasses. They feature a square-shaped design, a plastic frame with chain detailing on the arms, and tinted lenses. Complete your look with a stylish shoulder bag.

Fit & Features
- Square-shaped design
- Plastic frame
- Chain detailing on the arms
- Tinted lenses
Style Number/Barcode: 07008-0843

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Make It Fierce Snake Print Headwrap
Create a fierce impression with a snake print headwrap that is all the rage! The headwrap is composed of mesh fabric and has an oversized-fit wrap-around design. Complete the look with the matching swim cover-up, bikini top, and bikini bottoms.

Shop Matching Bikini Top: Make It Fierce Snake Print Bikini Top

Shop Matching Bikini Bottoms: Make It Fierce Snake Print Bikini Bottoms

Fit & Features
- Wrap-around design
- Snake print
- Mesh material
- Moderate stretch
Style Number/Barcode: 07305-0302

Category Name: Vacation Looks

Price: $3.97 $8.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Make It Fierce Ruched Mini Skirt
Create a fierce impression with a snake print mini skirt that is all the rage! The skirt features a high-rise waist, a ruched side seam with a drawstring, a mini-length silhouette, and a snake print. Complete look with the matching bikini top and bikini bottoms.

Shop Matching Bikini Top: Make It Fierce Snake Print Bikini Top

Shop Matching Bikini Bottoms: Make It Fierce Snake Print Bikini Bottoms

Fit & Features
- High-rise elastic banded waist
- Ruched side seam with a drawstring
- Snake print
- Mini-length silhouette, form-hugging fit
- Mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0431

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Make It Fierce Ruched Snake Print Swim Coverup
Create a fierce impression with a snake print swim coverup that is all the rage! The coverup features a sleeveless crew neckline, a snake print, a ruched drawstring, and a mini-length silhouette. The coverup is composed of a sheer mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with a bikini and slides.

Shop Matching Bikini Top: Make It Fierce Snake Print Bikini Top

Shop Matching Bikini Bottoms: Make It Fierce Snake Print Bikini Bottoms

Shop Matching Headwrap: Make It Fierce Snake Print Headwrap

Fit & Features
- Sleeveless crew neckline
- Snake print
- Ruched drawstring
- Mini-length silhouette
- Unlined mesh fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3417

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pretty In Paradise Crop Top
You'll look so pretty on your next getaway in this tropical floral printed top! It features long dramatic kimono-style sleeves, a V-neckline, a tie detail that can be worn in the front or back, and a cropped fit. Dress up the look with statement earrings and a trendy ring set.

Fit & Features
- Long kimono-style sleeves
- V-neckline
- Tie detail that can be worn in the front or back
- Cropped fit
- Gauze fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 06003-1315

Category Name: Vacation Looks

Price: $7.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunny Vibe Cutout Strappy Slide Sandals
The perfect cutout strappy slide sandal for sun-soaked days!

Fit & Features
- Round toe
- Strappy cutout design
- Adjustable strap
- Flat sole
- Slide on-and-off styling
- Runs true to size
Style Number/Barcode: 07404-1276

Category Name: Vacation Looks

Price: $9.97 $25.90

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