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.

Spring Break Vibes Bandeau Swim Top
Bring the spring break vibes to your look with this bold swim top! It features a strapless bandeau design with a subtle sweetheart neckline and a trendy all-over swirl print. Style with the matching swim bottoms and sarong for the perf poolside 'fit!

Shop Matching Bottoms: Spring Break Vibes Swim Bottoms

Shop Matching Sarong: Spring Break Vibes Sarong

Fit & Features
- Strapless bandeau design
- Sweetheart neckline
- Back strap, bar closure
- Swirl print
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0647

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
So Luxe Lurex Bikini Top
Bring the luxe to your next getaway with a bikini top that reveals glamour! The bikini top features demi-shaped cups with underwire, adjustable spaghetti straps, and a slide-hook closure at the back. Complete look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: So Luxe Lurex Bikini Bottoms

Fit & Features
- Demi-cups
- Underwire
- Adjustable spaghetti straps
- Slide-hook closure at back
- Lined lurex fabric
- Form hugging fit
- Runs true to size
Style Number/Barcode: 07104-0645

Category Name: Vacation Looks

Price: $4.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
It Girl Cat Eye Sunglasses
Step out in trendy sunglasses that put you front and center! The sunglasses feature a cat-eye frame, dark lenses, and offer 100% UV protection. Complete look with a sundress and sandals.

Fit & Features
- Cat-eye frame
- Dark lenses
- 100% UV protection
Style Number/Barcode: 07008-0926

Category Name: Vacation Looks

Price: $4.97 $10.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
So Luxe Lurex Swim Sarong
Wrap yourself in a luxe sarong to elevate your beachwear! This must-have sarong features a high-rise waist with a twist knot accent and a wrap silhouette. The sarong is composed of a lined lurex fabric that offers a form hugging fit with a moderate stretch. Complete look with a pair of sunnies.

Fit & Features
- High rise waist
- Twist knot accent
- Wrap silhouette
- Lined lurex fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07305-0370

Category Name: Vacation Looks

Price: $5.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pretty Lady Floral Chiffon Romper
Check you out, pretty lady! Flaunt this flirty floral chiffon romper all over town. It features short puff sleeves, a ruched square neckline, a fitted bodice, and flowy shorts. Complete the look in sparkly hoop earrings.

Fit & Features
- Short puff sleeves, elastic cinched hems
- Ruched square neckline
- Fitted bodice, stretchy smocked back detail
- Flowy shorts
- Floral chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0200

Category Name: Vacation Looks

Price: $8.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Happy Flower V-Neck Crochet Romper
You'll be one happy flower in this adorable V-neck romper featuring a sleeveless bodice, adjustable spaghetti straps, and a sheer crochet waist atop flowy shorts on floral printed chiffon fabric. Complete the look in sandals for the perf spring outfit.

Fit & Features
- Sleeveless, V-neck, adjustable spaghetti straps
- Sheer crochet waist
- Back zipper, hook and eye closure
- Flowy shorts
- Floral chiffon fabric, knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0209

Category Name: Vacation Looks

Price: $6.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Level Up High-Rise Denim Shorts
Elevate your casual style with shorts that are perf for a day out! The shorts feature a high-rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, heavy destruction, and cutoff hem. Complete look with a crop top and slides.

Fit & Features
- High-rise waist
- Cutoff hem, heavy destruction
- Five-pocket and belt loop design
- Front button and hidden zipper closure
- Medium wash denim fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0296

Category Name: Vacation Looks

Price: $9.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Bring The Heat Printed Midi Skirt
Bring the heat to your vacay look with this sultry midi skirt! It features a high-rise waist, chic ruched detailing down the sides, a midi-length, curve-hugging fit, and an all-over tropical palm leaf print. Style with the matching tube top and strappy mules.

Shop Matching Top: Bring The Heat Printed Tube Top

Fit & Features
- High-rise elasticized waist
- Ruching down the sides
- Midi-length, form-fitting silhouette
- Tropical palm leaf print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0541

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Tropical Dream Maxi Skirt
Let this maxi skirt transport you to an island paradise! The skirt features a pretty tropical print, a high-side slit, and a maxi-length silhouette. The skirt is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching tube top.

Shop Matching Tube Top: Tropical Dream Tube Top

Fit & Features
- Elastic high-rise waist
- Tropical palm leaf print
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0537

Category Name: Vacation Looks

Price: $12.97 $31.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chill Out Smocked Joggers
Chill out in joggers that are perf to dress down in but still look cute! The joggers feature a high-rise smocked waist, a drawstring, hidden side pockets, and a straight leg with a smocked tapered leg. Complete look with a ribbed bodysuit and sandals.

Fit & Features
- High-rise smocked waist
- Drawstring
- Hidden side pockets, back pockets
- Straight leg, smocked tapered leg
- Woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0643

Category Name: Vacation Looks

Price: $29.90

Availability: Out of Stock
Product Badge:
- Clearance
Ditsy Blooms Lace-Up Crop Top
Ditsy and cute, this crop top is in full bloom for spring! It features short puff sleeves, a square neck, and an open back with a lace-up closure. Composed of a brushed knit with a moderate stretch. Style with the matching bottoms.

Shop Matching Bottoms: Ditsy Blooms Ruched Mini Skirt

Fit & Features
- Short puff sleeves, elasticized hems
- Square neck
- Cropped hem
- Open-back, lace-up closure
- Ditsy floral pattern
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3839

Category Name: Vacation Looks

Price: $6.97 $21.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ditsy Blooms Ruched Mini Skirt
Ditsy and cute, this mini skirt is in full bloom for spring! It features a high-rise waist, a side ruched seam that accentuates your curves on the form-fitting silhouette. Composed of a brushed knit with a moderate stretch. Style with the matching top.

Shop Matching Top: Ditsy Blooms Lace-Up Crop Top

Fit & Features
- High-rise waist
- Side ruched seam
- Form-fitting silhouette
- Mini-length hem
- Ditsy floral pattern
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0556

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ruffle and Ready Chiffon Halter Maxi Dress
Love to make an entrance? Nail it with this chiffon maxi dress! With cascading ruffles, sultry cutouts, and a leggy slit, this chiffon maxi brings the drama every time.

Fit & Features
- Chiffon fabric, lined with stretchy knit
- Sweetheart halter neckline with tie straps, padded bra cups
- Cutout back and sides
- Cascading ruffle trims
- Flowy silhouette, front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000198

Category Name: Vacation Looks

Price: $59.90

Availability: In Stock

Available Color: BROWN

Available Size: XS, S, M, L
Rhinestone Fringe Skirt Belt
Bring the fringe to your festival outfits with this fab skirt belt! The belt features a triple-row design of mini rhinestones, a cascading fringe design, and an adjustable lobster clasp closure. Complete look with a bikini and boots.

Fit & Features
- Triple-row design
- Mini rhinestones
- Cascading fringe
- Lobster clasp closure
- One size fits most
Style Number/Barcode: 07301-0428

Category Name: Vacation Looks

Price: $35.90

Availability: Out of Stock
Product Badge:
- Sale
Easy Breezy Eyelet Skater Dress
Easy, breezy, and flirty! This eyelet skater dress is perfect for your next spring fling. It features a sleeveless, square neck, spaghetti straps, high waist seam, and a trendy open-back with twist detail on the flared short silhouette. The dress is composed of a lined lightweight woven knit fabric that offers a flattering form hugging fit with a moderate stretch. Complete the look in espadrille sandals.

Fit & Features
- Sleeveless, square neck, spaghetti straps
- High waist seam
- Open-back with twist detail
- Flared short silhouette
- Eyelet pattern
- Lined lightweight woven knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4415

Category Name: Vacation Looks

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Daydream With Me Satin Floral Skirt
Look like a total daydream in this satin floral mini skirt featuring a high-rise waist, a fitted silhouette, a flirty front slit accent, and a back zipper closure. Complete the look in a boho-style top for brunch.

Fit & Features
- High-rise waist
- Fitted silhouette
- Front slit accent
- Back zipper closure
- Mini-length hem
- Floral satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06401-0446

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Go With It Cropped Denim Jacket
Go with the flow in a cropped denim jacket that is perf to layer over your casual outfits! The jacket features a collared neckline, a multi-button down front, two chest pockets with a single button closure, long sleeves, and an elastic cropped hem. The jacket is composed of denim fabric that offers a relaxed oversized fit with a minimal stretch. Complete look with a midi dress and mules.

Fit & Features
- Collared neckline
- Multi-button down front
- Two chest pockets
- Long sleeves
- Elastic cropped hem
- Denim fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06203-0200

Category Name: Vacation Looks

Price: $39.90

Availability: Out of Stock
Product Badge:
- Sale
Girl's Trip Boho Slit Maxi Skirt
Grab the girls, book the flight, and pack this cute boho maxi skirt! It features a high-rise waist, a front slit, and a long hem. Complete the look in the matching top.

Shop Matching Top: Girl's Trip Boho Tie-Front Top

Fit & Features
- High-rise waist
- Front slit
- Long hem
- Boho pattern
- Runs true to size
Style Number/Barcode: 06301-0104

Category Name: Vacation Looks

Price: $13.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Girl's Trip Boho Tie-Front Top
Grab the girls, book the flight, and pack this cute boho tie-front top! It features a sleeveless V-neck, spaghetti straps, and a smocked back. Complete the look in the matching skirt.

Shop Matching Skirt: Girl's Trip Boho Slit Maxi Skirt

Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Tie-front detail
- Smocked back
- Cropped hem
- Boho pattern
- Runs true to size
Style Number/Barcode: 06003-1569

Category Name: Vacation Looks

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Seashore Stroll Drawstring Linen Joggers
These drawstring linen joggers are perfect for your daily strolls by the seashore! They feature a high-rise elasticized waist with a front tie closure, a four-pocket design, a slim-fit leg, and elasticized cuffs. Complete the look in a basic bodysuit and sandals.

Fit & Features
- High-rise elasticized waist
- Drawstring front tie-closure
- Four-pocket design
- Slim-fit leg
- Elasticized cuffs
- Linen fabric
- Fits true to size
Style Number/Barcode: 06302-0640

Category Name: Vacation Looks

Price: $12.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Faux Suede Fringe Mini Skirt
Get fab in a fringe skirt that adds that extra detail to your look! The skirt features an elastic high-rise waist, an asymmetrical high side slit with fringe trim, and a mini-length hem. The skirt is composed of a lined faux suede fabric that offers a form hugging fit with a moderate stretch. Complete look with a crochet top and boots.

Fit & Features
- Elastic high rise waist
- Asymmetrical high side slit
- Fringe trim
- Mini length hem
- Faux suede fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0657

Category Name: Vacation Looks

Price: $10.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Like It Or Dot Puff Sleeve Crop Top
Like it or not, this polka dot crop top will surely be your fav! It features short puff sleeves, a sweetheart neckline, and a tie-front closure. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete the look in the matching shorts.

Shop Matching Shorts: Like It Or Dot High Rise Shorts

Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Tie-front closure
- Cropped hem
- Polka dot pattern
- Lightweight woven fabric
- Runs true to size
Style Number/Barcode: 06001-4103

Category Name: Vacation Looks

Price: $6.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Like It Or Dot High Rise Shorts
Like it or not, these polka dot shorts will surely be your fav! It features a high-rise waist and a flowy silhouette. The shorts are composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete the look in the matching top.

Shop Matching Top: Like It Or Dot Puff Sleeve Crop Top

Fit & Features
- High-rise waist
- Flowy silhouette
- Polka dot pattern
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06503-0961

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Beachside Brunch Swim Coverup Dress
Strut down the pier looking so fab in this maxi coverup dress featuring a sleeveless V-neckline, tank straps, and a form-fitting silhouette with a sultry front slit. The coverup dress is composed of an unlined semi-sheer knit fabric that offers a form-hugging fit. Perf for layering over your bikinis, complete the look in sandals.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Sleeveless V-neckline, tank straps
- Surplice accent
- Form-fitting silhouette
- Front slit
- Maxi-length hem
- Unlined, semi-sheer sweater-knit fabric, no stretch
- Runs true to size
Style Number/Barcode: 06005-1250

Category Name: Vacation Looks

Price: $7.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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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