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.

Polished Strut Faux Pearl Straw Stiletto Pumps
Indulge in the ultimate polished pumps for a poised summer style! These closed pointed toe pumps feature a stunning faux pearl accent that adds a touch of chic to any outfit, while the stiletto heel elevates the look.

Fit & Features
- Stiletto heel
- Closed pointed-toe, faux pearl accent
- Adjustable ankle strap with buckle closure
- Straw material
- Runs true to size
Style Number/Barcode: 07401-000080

Category Name: Vacation Looks

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sheer And Sultry One Shoulder One Piece Swimsuit
Make a splash in a swimsuit that brings sheer and sultry appeal. The one-piece swimsuit features a one-shoulder neckline, a combination of sheer mesh panels and cutout accents to create a wrap-around design, and a cheeky fit. Complete look with sunglasses and sandals for a pool-side ready look.

Fit & Features
- One-shoulder neckline
- Sheer mesh panels
- Cutout design
- Wrap around pattern
- Cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0224

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Classic Glamour Greek Key Bikini Bottoms
Keep it classically glam with bikini bottoms that are perfect for your next getaway! The bikini bottoms feature a high rise waist, greek key trim, and a cheeky fit. Complete your look with the matching bikini top.

Shop Matching Bikini Top: Classic Glamour Bandeau Bikini Top

Fit & Features
- High rise waist
- Greek key trim
- Cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0651

Category Name: Vacation Looks

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Classic Glamour Bandeau Bikini Top
Keep it classically glam with a bikini top that is perfect for your next getaway! The bikini top features a bandeau neckline with a sweetheart bust, a twisted-front detail, and molded cups. Includes adjustable spaghetti straps that can be removed and a slide hook fasten closure.

Shop Matching Bikini Bottoms: Classic Glamour Greek Key Bikini Bottoms

Fit & Features
- Bandeau neckline
- Sweetheart bust
- Twisted-front
- Molded cups
- Removable adjustable spaghetti straps
- Slide hook fasten closure
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0503

Category Name: Vacation Looks

Price: $5.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Heat Things Up High Waist Swim Bottoms
Heat things up a little bit with some heat stone details! We are obsessing over these high waist briefs that are pool party ready!

Shop Matching Top: Heat Things Up Triangle Swim Top

Fit & Features
- Mid-rise fit
- Black rhinestone detailing
- Cheeky bottom
- Moderate stretch
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0493

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Heat Things Up Triangle Swim Top
Heat things up a little bit with some heat stone details! We are obsessing over this pool ready set, don't forget to pick up the matching bottoms!

Shop Matching Bottoms: Heat Things Up High Waist Swim Bottoms

Fit & Features
- Triangle design
- Tie closures
- Rhinestone detailing
- Moderate stretch
- Removable padding
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0342

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chic Trends Cropped Corset Top
Keep it chic with a crop top that is totally trend-worthy! The top features an elastic off-the-shoulder neckline, long sleeves with an elastic cuff, corset-like seams on the bodice, and a cropped hem. The top is composed of stretchy lightweight woven fabric that offers a form-hugging fit. Complete your look with a high waist skirt.

Fit & Features
- Elastic off-the-shoulder neckline
- Long sleeves with an elastic cuff
- Corset-like seams
- Cropped hem
- Lightweight woven fabric, form-hugging fit, moderate stretch
- Hidden zipper closure
- Runs true to size
Style Number/Barcode: 06003-1185

Category Name: Vacation Looks

Price: $6.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweet Intentions Floral Ruffled Duster
Show off your sweet side with a floral duster that is too gorge to resist! The duster features a draped open front with a tie front, short sleeves, a floral print, a long flowy length, and a ruffled trim. The duster is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with a cami and high waist jeans.

Fit & Features
- Draped open front
- Tie-front
- Short sleeves
- Floral print
- Long flowy length
- Ruffled trim
- Lightweight woven fabric, relaxed fit, minimal stretch
Style Number/Barcode: 06204-0585

Category Name: Vacation Looks

Price: $14.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sultry Appeal V-Neck One Piece Swimsuit
Take the plunge with this sultry swimsuit that showcases curves in all the right places. The swimsuit features a plunging V-neckline, a sexy open back design adorned with cross straps, and a tie waist belt that cinches at the lower back. Complete look with sleek sandals and a floppy hat.

Fit & Features
- Sleeveless V-neckline
- Open back with cross straps
- Tie waist belt
- Cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0227

Category Name: Vacation Looks

Price: $18.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Make The Cut One-Piece Swimsuit
This sultry-chic one-piece swimsuit will definitely make the cut and into your closet! It features a one-shoulder neckline, two wrap-around cutouts with sheer mesh inserts, and a semi-cheeky fit. Complete your poolside look with a flowy duster and trendy sunnies.

Fit & Features
- One-shoulder neckline
- Two wrap-around cutouts
- Sheer mesh inserts
- Semi-cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0223

Category Name: Vacation Looks

Price: $19.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Raising Standards Clear PVC Mules
Raise your style standards with these mules that complement all your favorite outfits. The mules feature an open back, a clear PVC strap, an almond toe with a clear strap over the toe, and a clear narrow lucite block heel. Complete look with a ruched mini dress and a bucket bag for a brunch ready look.

Fit & Features
- Open back
- Clear PVC strap
- Almond toe
- Clear strap over the toe
- Clear lucite thin block heel
Style Number/Barcode: 07401-2684

Category Name: Vacation Looks

Price: $12.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Passion Long Knit Duster
Showcase your sweet side with this charming floral duster. The duster features a draped open front, a floral print, long sleeves, and a long length. The duster is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with a ribbed knit mini dress.

Fit & Features
- Draped open front
- Floral print
- Long sleeves
- Long length
- Brushed knit fabric
- Relaxed fit
- Moderate stretch
Style Number/Barcode: 06202-0098

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Bold Boho Vibes Flared Pants
Bring those bold bohemian vibes to your everyday look with these printed flared pants. They feature a high rise banded waist and a form-hugging fit with a trendy flared out hem. The knit fabric showcases an all-over medallion print to achieve that perf boho-chic look. Pair these pants with the matching crop top and cute sandals.

Shop Matching Crop Top: Bold Boho Vibes Tie Front Top

Fit & Features
- High rise banded waist
- Form-hugging fit
- Flared hem
- Knit fabric
- Medallion print
- Brushed knit fabric
- Runs true to size
Style Number/Barcode: 06502-0480

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Dreaming Of Paradise Swim Top
You'll be dreaming of paradise as you relax poolside in this adorable swim top! It features a wrap front neckline with halter straps that tie at the back, removable padding, a sexy keyhole cut-out, a back gold metal bar closure, and an all-over tropical floral print for those pretty vacay vibes. Pair this swim top with the matching swim bottoms and a long flowy duster.

Shop Matching Swim Bottoms: Dreaming Of Paradise Swim Bottoms

Fit & Features
- Wrap front neckline
- Halter straps
- Removable padding
- Keyhole cut-out
- Back gold metal bar closure
- Tropical floral print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0549

Category Name: Vacation Looks

Price: $11.97 $25.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Cute But Chill A-Line Mini Dress
Looks like a serve, feels like a chill day 'fit. This nylon mini dress comes through with a flattering silhouette and hidden shorts, so you can dance, lounge, or do your thing without a second thought.

Fit & Features
- Smooth nylon fabric, moderate stretch
- Sleeveless square neckline
- Spaghetti straps
- Short front slit
- Mini-length hem, hidden shorts
- Fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000031

Category Name: Vacation Looks

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Tropical Paradise Ruffled Bikini Top
Transport to an island paradise with this pretty bikini top! The bikini top features a tropical floral print, an off the shoulder neckline with a ruffled popover detail, and a cropped hem. Complete your vacation outfit with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Tropical Paradise High Waist Bikini Bottoms

Fit & Features
- Off the shoulder neckline
- Tropical floral print
- Ruffled popover detail
- Cropped hem
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0505

Category Name: Vacation Looks

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Laced Up In Denim Dress
Lace-up in this trendy denim dress to make a stylish statement! This dress features a sleeveless, plunge v-neck, adjustable spaghetti straps, a trendy lace-up front detail, and a curve hugging, midi silhouette. Complete the look with simple block heels.

Fit & Features
- Sleeveless, plunge v-neck
- Adjustable spaghetti straps
- Back zipper closure
- Lace-up front
- Curve-hugging silhouette
- Midi-length hem
- Denim fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-0291

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Taking The Plunge Bikini Top
Take the plunge in this sexy bikini top for your next Insta-worthy post! The bikini top features a plunging V-neckline, demi-cups, adjustable spaghetti straps, and underwire for support. Complete your look with the matching bikini bottoms.

Shop Matching Bikini Bottoms: Taking The Plunge Bikini Bottoms

Fit & Features
- Plunging V-neckline
- Adjustable spaghetti straps
- Demi-cups
- Underwire
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0495

Category Name: Vacation Looks

Price: $10.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Taking The Plunge Bikini Bottoms
Take the plunge in these sexy bikini bottoms for your next Insta-worthy post! The bikini bottoms feature a low-rise waist, a sexy side twist design at the hip, and a cheeky bottom. Complete your look with the matching bikini top.

Shop Matching Bikini Top: Taking The Plunge Bikini Top

Fit & Features
- Low-rise waist
- Side twist design at the hip
- Cheeky fit
- Matching bikini top sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0643

Category Name: Vacation Looks

Price: $9.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Feelin' Flirty Ditsy Floral Crop Top
Give your casual everyday look a spring upgrade in this flirty ditsy floral top! It features an off the shoulder neckline, long bishop sleeves with elastic banded hems, and a stretchy smocked bodice with a cropped, form-hugging fit. Pair this top with denim shorts and cute sandals.

Fit & Features
- Off the shoulder neckline
- Long bishop sleeves with elastic banded hems
- Stretchy smocked bodice
- Cropped, form-fitting style
- Ditsy floral print
- Lightweight woven gauze fabric
- Runs to true
Style Number/Barcode: 06003-1209

Category Name: Vacation Looks

Price: $6.97 $26.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Vintage Glam Oversized Denim Jacket
Create a vintage glam moment with an oversized denim jacket that adds a layer of style to your look. The jacket features a collared neckline, long sleeves, big pockets, a multi-button down front, and a cropped hem. The denim jacket offers a relaxed fit with minimal stretch. Complete look a crop top and a mini skirt.

Fit & Features
- Collared neckline
- Long sleeves
- Big Pockets
- Multi-button down front
- Cropped hem
- Light distressing
- Relaxed fit, minimal stretch
Style Number/Barcode: 06203-0117

Category Name: Vacation Looks

Price: $19.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Lovin' Lace Crochet Crop Top
Lace-up in this charming crop top that creates a sweet impression. The crop top features an off the shoulder neckline, a square neck bust with a cute tie-front, unlined long sleeves with elastic hem, and a cropped hem with lace trim. The top is composed of a lined crochet lace fabric that offers a relaxed fit with a slight stretch. Complete your look with cut off shorts and knee-high boots.

Fit & Features
- Off the shoulder neckline
- Square neck with tie front
- Unlined long sleeves
- Crochet lace bodice
- Cropped hem
- Relaxed fit, slight stretch
- Back zipper closure
Style Number/Barcode: 06001-3113

Category Name: Vacation Looks

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Trendy Destructed Oversized Denim Jacket
Layer on this trendy denim jacket for an effortlessly edgy vibe! It features a collared neckline, long sleeves with buttons, a complete button-down front, buttoned chest pockets, lower front pockets, distressed detailing, and a relaxed, oversized fit. Pair this denim jacket with a graphic tee and your fave pair of shorts.

Fit & Features
- Collared neckline
- Long sleeves with buttons
- Button-down front
- Buttoned chest pockets
- Lower front pockets
- Destructed denim fabric
- Oversized fit
Style Number/Barcode: 06203-0116

Category Name: Vacation Looks

Price: $14.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Chasing The Sun Bikini Top
Chase those warmer days with a cute bikini top that is vacay ready! The bikini top features a padded square neck, cute tie shoulder straps, and cropped hem. Complete your fit' with the matching bikini bottoms and sunglasses.

Shop Matching Bikini Bottoms: Chasing The Sun Bikini Bottoms

Fit & Features
- Sleeveless square neck
- Padded
- Tie-shoulder straps
- Cropped hem
- Matching bikini bottoms sold separately
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0356

Category Name: Vacation Looks

Price: $9.97 $16.90

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