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 Flared High Waist Pants
Channel those wanderlust vibes with these dreamy pants. The pants feature a high-rise waist, paisley print, and a wide-leg hem. The pants are composed of a sheer unlined mesh fabric that offers a form-hugging fit with a moderate stretch. 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
- Paisley print
- Flared wide-leg hem
- Unlined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0583

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Diva Moment Leopard Print Sunglasses
Create a diva moment with sunnies that bring the drama! The sunglasses feature a leopard print, an oversize square-shaped frame, and sleek arms. Complete look with a maxi dresses and faux leather sandals.

Fit & Features
- Leopard print
- Oversized square-shaped frame
- Sleek arms
Style Number/Barcode: 07008-0800

Category Name: Vacation Looks

Price: $4.97 $9.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Butterfly Beauty Mesh Swim Wrap
Effortless and trendy, this swim wrap is a must-have for the summer! It features a sheer mesh fabric with a beautiful all-over butterfly print. Style this wrap across your hips as a swim cover-up, as a scarf top over your fave bikini, or as a pretty head wrap.

Fit & Features
- Sheer mesh fabric
- Butterfly print
- Versatile ways to wear
Style Number/Barcode: 07305-0295

Category Name: Vacation Looks

Price: $10.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Weekend Vibes Espadrille Wedges
You'll be totally ready for your weekend plans with these adorable espadrille wedges! They feature an open round toe, a thin strappy design with an adjustable ankle strap, and a trendy espadrille wedge heel. Style these wedges with a floral dress and chic shades.

Fit & Features
- Open round toe
- Thin strappy design, faux leather material
- Adjustable ankle strap, buckle detail
- Espadrille wedge heel
- Faux leather straps
- Runs true to size
Style Number/Barcode: 07406-0259

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Keep It Trendy Zebra Print Sandals
Keep your summer look trendy and on point with these fab slide-on sandals! They feature an open square toe, a wide toe strap, a flat sole, and a fun zebra print design. Style these sandals with a casual dress and hoop earrings.

Fit & Features
- Open square toe
- Wide toe strap
- Flat sole
- Zebra print
- Runs true to size
Style Number/Barcode: 07404-0789

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Always Chic Croc-Embossed Sandals
Your look will always be chic with these stylish slide-on sandals. They feature an open square toe, a wide toe strap, a flat sole, and a trendy croc-embossed print. Pair these sandals with boyfriend jeans.

Fit & Features
- Open square toe
- Wide toe strap
- Flat sole
- Croc-embossed print
- Runs true to size
Style Number/Barcode: 07404-0791

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On Vacation Straw Block Heels
You’ll be vacay ready in these straw heels! They feature an open almond toe, a single toe strap, a block heel and a back zipper closure. Style them with a printed romper and matching straw bag.

Fit & Features
- Open almond toe
- Straw material
- Block heel
- Runs true to size
Style Number/Barcode: 07401-2895

Category Name: Vacation Looks

Price: $15.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Keep it Simple Clear Sandals
Keep it simple and chic in these minimal PVC sandals. They feature a single thick clear strap, and open round toe and a flat footbed. Pair them with a floral dress and gold jewelry for a sweet summer look.

Fit & Features
- Open round toe
- PVC strap
- Runs true to size
Style Number/Barcode: 07404-0760

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Single Band Netted Slides
Time to upgrade your sandal collection with these netted slides! They feature an single band with a net design and an open square toe. Style them with a cute sundress and a crossbody bag.

Fit & Features
- Open square toe
- Netted design
- Runs true to size
Style Number/Barcode: 07404-0856

Category Name: Vacation Looks

Price: $12.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sleek And Basic Espadrille Sandals
Keep it sleek and basic with sandals that go with everything! The sandals feature an around the ankle strap, an off-center T-strap, an open almond toe, and an espadrille sole. Complete look with a matching crop top and skirt set.

Fit & Features
- Around the ankle strap
- Off-center T-strap
- Open almond toe
- Espadrille sole
- Triangle-shaped metal accents
- Faux leather material
Style Number/Barcode: 07404-0820

Category Name: Vacation Looks

Price: $7.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Stunner Ribbed Knit Midi Dress
Stun on them with a stylish midi dress that makes a head-turning impression! The dress features a sleeveless V-neckline, spaghetti straps, an open back with an O-ring accent, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with clear mules.

Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Open back, O-ring accent
- Midi-length
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4071

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Trendsetting Babe Panama Hat
You're such a trendsetting babe, and this adorable straw Panama hat was made for you. It features a floppy brim and a fab leopard print band. Style this hat with cool shades and chic earrings.

Fit & Features
- Floppy brim
- Faux leather leopard print band
- Straw material
Style Number/Barcode: 07302-0342

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfect Symphony Floral Tube Top
This floral tube top brings perfect tropical vibes to your weekend plans or vacation! Pair with the matching skirt to complete the look.

Shop Matching Bottoms: Perfect Symphony Floral Maxi Skirt

Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Tie-back detail, stretchy smocked panel
- Strapless tube neckline
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06003-000053

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bohemian Dreams Ruched Paisley Print Swim Coverup
Keep it dreamy with a swim coverup that channels those wanderlust vibes! The coverup features a paisley print, sleeveless crew neckline, 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 the matching bikini top, bikini bottoms, and headwrap.

Shop Matching Bikini Top: Bohemian Dreams Paisley Print Bikini Top

Shop Matching Bikini Bottoms: Bohemian Dreams Paisley Print Bikini Bottoms

Shop Matching Headwrap: Bohemian Dreams Paisley Print Headwrap

Fit & Features
- Sleeveless crew neckline
- Paisley print
- Ruched drawstring
- Mini-lengh silhouette
- Unlined mesh fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3415

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
So Unforgettable Destructed Denim Shorts
Make an unforgettable impression with these trendy denim shorts. The shorts feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, a frayed hem, and a V-shaped hem on the left leg. Complete the look with a graphic tee and chunky sneakers.

Fit & Features
- High-rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Frayed hem
- V-shaped hem
- Denim fabric, no stretch, form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0152

Category Name: Vacation Looks

Price: $4.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Let’s Getaway Espadrille Platform Sandals
These sandals are a must have for your next tropical getaway! The sandals feature a thick toe strap, an adjustable ankle strap and a platform espadrille sole. Style them with denim cutoffs and a crop top.

Fit & Features
- Open almond toe
- Platform espadrille sole
- PU material
- Adjustable ankle strap
- Runs true to size
Style Number/Barcode: 07404-0837

Category Name: Vacation Looks

Price: $7.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Take a Trip Straw Platform Heels
You’ll be vacay ready with these platform heels! The heels feature an open almond toe, a platform with a braided straw detail, an adjustable ankle strap and a block heel. Pair them with a printed romper and a floppy hat.

Fit & Features
- Open almond toe
- Braided straw platform
- Block heel
- PU material
- Adjustable ankle strap
- Runs true to size
Style Number/Barcode: 07401-3075

Category Name: Vacation Looks

Price: $16.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Stylish Vibes Striped Wide-Leg Pants
Showcase stylish vibes in these chic striped wide-leg pants. They feature a high-rise waist, a tie-front accent, wide pant legs, and a relaxed fit. Complete the look with a basic crop top and cute mules for an effortless summer outfit.

Fit & Features
- High-rise waist
- Tie-front
- Wide pant legs
- Relaxed fit
- Woven fabric, striped pattern
- Runs true to size
Style Number/Barcode: 06302-0197

Category Name: Vacation Looks

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fun in the Sun Single Band Sandals
These simple slide on sandals are perfect for a casual fun summer day! They feature a thick single band, hardware trim detail and a flat footbed. Style them with denim shorts and a graphic tee.

Fit & Features
- Open almond toe
- Slip-on design
- Hardware trim
- Flat footbed
- Runs true to size
Style Number/Barcode: 07404-0730

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
All You Need PVC Strappy Sandals
These simple yet chic sandals are a summer necessity! They feature an open almond toe, clear dainty straps and a flat footbed. Style them with a sundress and mini bag for a cute brunch look.

Fit & Features
- Open almond toe
- Slip on design
- Flat footbed
- PVC straps
- Runs true to size
Style Number/Barcode: 07404-0744

Category Name: Vacation Looks

Price: $9.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Meant To Be Ruffled Mini Dress
You and this dress are totally meant to be! The dress features a sleeveless V-neckline, spaghetti straps, lace-up back, a mini-length silhouette with a faux-wrap overlay, and ruffles. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete the look with platform wedges and a butterfly necklace.

Fit & Features
- Sleeveless V-neckline
- Lace-up back
- Mini length silhouette
- Faux-wrap overlay
- Ruffles
- Lined mesh fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0758

Category Name: Vacation Looks

Price: $38.90

Availability: Out of Stock
Product Badge:
- Ships Free
Trendy Vibes Rhinestone Belly Chain
Get those trendy vibes when you accessorize with this glam belly chain! It features a dainty chain with rhinestone detailing, an adjustable lobster clasp closure, and a cross charm accent. Style this belly chain with your fave bikini and chic shades.

Fit & Features
- Dainty chain
- Rhinestone detailing
- Adjustable lobster clasp closure
- Cross charm
Style Number/Barcode: 07002-0733

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic And Edgy Ring Set
Bring the chic and edgy vibes to your look with this stylish ring set! It features eight varying rings with chain-link designs and glam rhinestone detailing. Style this set with stud earrings and cool sunglasses.

Fit & Features
- Set of eight rings
- Chain-link designs
- Rhinestone detailing
Style Number/Barcode: 07004-0202

Category Name: Vacation Looks

Price: $6.97 $13.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Dainty Butterfly Charm Anklet
Accessorize your summer 'fits with this adorable anklet! It features three rows of dainty chains, the longest layer with trendy butterfly charms. Style this anklet with a cute pair of mules.

Fit & Features
- Three rows of dainty chains
- Butterfly charms
- Adjustable lobster clasp closure
Style Number/Barcode: 07003-0247

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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Vacation Looks

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STYLE SPOTLIGHT

Vacation Dresses & Outfits for Effortless Getaways

Easy, Packable Styles

Day-to-Night Versatility

Resort & Beach Essentials