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

Discover Short Sleeve Dresses

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Get Eye-Catching Sandals For Women

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.

All The Chic Vibes Crop Top
Bring all the chic vibes to your look with this effortlessly trendy crop top. It features a collared V-neckline, long fitted sleeves with flared hems, and hook and eye front closures. The top is composed of a combination of crepe and sheer mesh fabric with a moderate stretch. Complete the 'fit with a faux leather mini skirt.

Fit & Features
- Collared V-neckline
- Long fitted sleeves, flared hems, slit details
- Hook and eye front closures
- Cropped, form-hugging fit
- Crepe and sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0225

Category Name: Vacation Looks

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In The Sun Long Mesh Swim Wrap
Look cute catching rays in this mesh swim wrap for hanging poolside! It features a long multi-wear design perfect for styling as a kimono or a skirt - the styling possibilities are endless! Complete the look in a trendy bikini.

Fit & Features
- Long multi-wear design
- Sheer mesh fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07305-0401

Category Name: Vacation Looks

Price: $15.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Desert Sun Lace Ruffle Mini Dress
Sway to the beat of your fave artist in this lace ruffle mini dress boasting a form-hugging fit and shark bite hem that pairs perfectly with boots!

Fit & Features
- Lace lined fabric
- Square neckline, bust tie
- Wide shoulder straps
- Form-hugging fit
- Shark bite ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000232

Category Name: Vacation Looks

Price: $39.90

Availability: In Stock

Available Color: RED, BLACK

Available Size: XXS, XS, S, M, L
Splish Splash Mesh Swim Wrap
The styling possibilities are endless with this sheer mesh swim wrap! It features a multi-wear design so you can style it your way. Wrap it around your waist to wear it as a skirt or style it as a shawl for a cute look out of the water. Complete the look in trendy sunglasses and a straw tote.

Fit & Features
- Sheer mesh fabric
- Multi-wear design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07305-0400

Category Name: Vacation Looks

Price: $8.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunshine Frills Hipster Bikini Bottoms
Soak up the sun! Stay cute catching rays in these bikini bottoms featuring a hipster style cut and scrunched side straps. Complete the look in the matching bikini top.

Shop The Matching Bikini Top: Sunshine Frill Ruffle Trim Bikini Top

Fit & Features
- Hipster style cut
- Scrunch side straps
- Very cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0806

Category Name: Vacation Looks

Price: $8.97 $20.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunshine Frill Ruffle Trim Bikini Top
Soak up the sun! Stay cute catching rays in this ruffle trim bikini top featuring a stylish tank-style bodice, front tie keyhole, and ruched cups. Complete the look in the matching bottoms.

Shop The Matching Bottoms: Sunshine Frills Hipster Bikini Bottoms

Fit & Features
- Tank-style bodice
- Ruffle trim straps and neckline
- Straps are removable
- Front tie keyhole
- Ruched cups
- Runs true to size
Style Number/Barcode: 07104-0659

Category Name: Vacation Looks

Price: $10.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Majorly Chic One-Piece Swimsuit
Elevated and chic, this one-piece swimsuit is a style above the rest! It features a sleeveless one-shoulder asymmetrical neckline with a single thin strap, a sultry front waist cutout, a lower back cutout, and a cheeky fit. Style this swimsuit with hoop earrings and oversized shades.

Fit & Features
- Sleeveless one-shoulder asymmetrical neckline
- Single thin shoulder strap
- Front waist cutout
- Back strap closure, lower back cutout
- Cheeky fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0296

Category Name: Vacation Looks

Price: $20.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Feelin' Flirty One-Piece Swimsuit
Feel oh-so-flirty in this adorable one-piece swimsuit! It features a plunging halter neckline, an open back, a high waist with a chic side tie accent, a cheeky bottom, and an all-over polka dot print. Style this swimsuit with a flowy mesh duster and cute shades for your next weekend getaway.

Fit & Features
- Sleeveless plunging halter neckline
- Open back
- High waist, side tie detail
- Cheeky fit
- Polka dot print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0294

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Special Price
Sleek Trendsetter Halter Midi Dress
Keep it sleek and stylish in this on-trend midi dress! It features a sleeveless halter neckline with tie-back spaghetti straps, ruching at the bust, and a mid-length, fitted silhouette. Complete the look with a faux leather jacket and clear mules.

Fit & Features
- Sleeveless halter neckline
- Tie-back spaghetti straps
- Center ruched detailing at the bust
- Mid-length, fitted silhouette
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1309

Category Name: Vacation Looks

Price: $19.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfectly Plaid Suspender Pants
Keep it poised in plaid! These suspender pants feature a high-rise fit, spaghetti straps, and skinny leg pants. The all-over plaid print easily mixes and matches with your favorite tops! The suspended pants are composed of a lined woven fabric that offers a form hugging fit with slight stretch stretch. Complete look with a ribbed bodysuit and lug boots.

Fit & Features
- High rise fit
- Spaghetti straps
- Plaid print
- Skinny pants
- Lined woven fabric
- Form hugging fit, slight stretch
- Runs true to size
Style Number/Barcode: 06502-0948

Category Name: Vacation Looks

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Ready To Roll Destructed Denim Jacket
Get ready to roll in a denim jacket that brings the edge to your look. The jacket features a collared neckline, a multi-button down front, two small chest pockets, long sleeves, heavy destruction throughout, and a cropped hem. The jacket is composed of a denim fabric that offers a relaxed fit with minimal stretch. Complete look with ankle booties and a short knit dress.

Fit & Features
- Collared neckline
- Button-down front
- Two small chest pockets
- Long sleeves
- Heavy destruction
- Denim fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06203-0227

Category Name: Vacation Looks

Price: $21.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Simply Elevated Tie-Front Trench
Layer on this chic trench for a simply elevated look. It features a lapel collar, long sleeves, a tie-front waist to stylishly cinch, and a short, relaxed fit. Layer this trench over a basic bodysuit and your favorite pair of denim.

Fit & Features
- Lapel collar
- Long sleeves
- Tie-front waist
- Side pockets
- Short, relaxed fit
- Lightweight woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1367

Category Name: Vacation Looks

Price: $14.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Reese High Rise Destructed Denim Shorts by Windsor Denim
Dare to go bold with denim shorts that show off your sassy side! The jean shorts by Windsor Denim feature a flattering high-rise waist, heavy destruction throughout, a light-medium wash with a rigid feel, and a cutoff hem. The shorts are composed of a cotton denim fabric that offers a relaxed fit with minimal stretch. Complete look with a crop top and sandals.

Fit & Features
- High rise waist
- Distressed accents on the front and back
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Light-medium wash rigid denim
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0223

Category Name: Vacation Looks

Price: $6.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Fierce And Fine Mesh Sarong
Look fierce and fine with this trendy sarong you can pair over your fave bikinis! It features a wrap design you can stylishly tie and an all-over leopard print pattern. Pair this sarong with oversized sunglasses for the perfect poolside 'fit.

Fit & Features
- Wrap design
- Leopard print
- Sheer mesh fabric
Style Number/Barcode: 07305-0376

Category Name: Vacation Looks

Price: $7.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wild One Leopard Hipster Bikini Bottoms
Fierce, fit, and fab! Show your spots in this leopard bikini bottom featuring a mid-rise waist and a hipster style cut. Complete the look in the matching bikini top.

Shop Matching Bikini Top: Wild One Leopard Halter Bikini Top

Fit & Features
- Mid-rise waist
- Hipster style cut
- Leopard pattern
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0807

Category Name: Vacation Looks

Price: $4.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Wild One Leopard Halter Bikini Top
Fierce, fit, and fab! Show your spots in this leopard halter bikini top featuring a plunge v-neckline, adjustable string tie strap, and triangle cups. Complete the look in the matching bottoms and a cover-up.

Shop Matching Bottoms: Wild One Leopard Hipster Bikini Bottoms

Fit & Features
- Triangle cups
- Removable padding
- Plunge V-neckline
- Adjustable string tie strap
- Leopard pattern
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0660

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Charmingly Perfect Floral A-Line Midi Dress
Step out in this charming and perfect floral midi dress to graduations, brunch, or shower celebrations! With adorable puff short sleeves, a flattering A-line silhouette, and a flirty front slit, you'll turn heads everywhere you go.

Fit & Features
- Floral print, woven fabric, stretchy knit lining
- Puff short sleeves
- Square neckline, bust tie
- Back zipper and hook-eye closure
- A-Line silhouette, front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-4067

Category Name: Vacation Looks

Price: $11.97 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Chic Statement Cross Rhinestone Earrings
Make a chic statement with earrings that bring the bling! The earring feature a large cross design, mini rhinestone embellishments, and a fishhook back. Complete look with a short corset dress and mules.

Fit & Features
- Large cross charm
- Mini rhinestones
- Fishhook back
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1177

Category Name: Vacation Looks

Price: $4.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Follow Your Heart Six Pack Studs
These stud earrings surely have won your heart! This six-pack set features a various rhinestone and solid styles each with post-back closure. Complete the look in a classy red dress for date night.

Fit & Features
- Six-pack set
- Various heart studs
- Rhinestone and solid styles
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1173

Category Name: Vacation Looks

Price: $4.97 $11.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Such A Snake Five-Pack Ring Set
This five-pack ring set brings the glitz to your outfit! It features various styles with rhinestone trim. Complete the look in an edgy moto jacket.

Fit & Features
- Five-pack set
- Rhinestone trim
- Various styles
Style Number/Barcode: 07004-0227

Category Name: Vacation Looks

Price: $5.97 $12.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Fresh Florals Chiffon Tie-Back Romper
This fresh-picked floral chiffon romper is perfect for wearing all-season long! It features peasant long sleeves, a square neck, draped waistline, and an open back with tie closure. Complete the look in wedges.

Fit & Features
- Peasant long sleeves
- Square neck
- Draped waistline
- Open-back with tie closure
- Floral print chiffon
- Lined, no stretch
- Fits true to size
Style Number/Barcode: 06403-0192

Category Name: Vacation Looks

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunkissed Vibes Lemon Bikini Bottoms
Chase those sunkissed vibes in bikini bottoms that channel those vibes. The bikini bottoms feature a low-rise hipster waist, a cute lemon print, and a cheeky bottom. Complete look with the matching bikini top.

Shop Matching Bikini Top: Sunkissed Vibes Lemon Bikini Top

Fit & Features
- Low-rise hipster waist
- Lemon print
- Cheeky bottom
- Form-hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0818

Category Name: Vacation Looks

Price: $8.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sunkissed Vibes Lemon Bikini Top
Chase those sunkissed vibes with a bikini top that channels those vibes. The bikini top features a bandeau-like styled bodice, a lemon print, removable padding, and adjustable spaghetti straps to give that customized fit.

Shop Matching Bikini Bottoms: Sunkissed Vibes Lemon Bikini Bottoms

Fit & Features
- Bandeau-styled bodice
- Lemon print
- Removable padding, flexible boning
- Adjustable spaghetti straps
- Smocking
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0671

Category Name: Vacation Looks

Price: $9.97 $18.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Figaro Rhinestone Snake Chain Layered Necklace
Stay on-trend in this layered necklace for dressing up your everyday fit'! It features a three-layer design with a figaro chain, snake chain, and rhinestone chain with lobster clasp closure. Complete the look in an edgy jacket.

Fit & Features
- Three-layer design
- Figaro chain
- Snake chain
- Rhinestone chain
- Lobster clasp closure
Style Number/Barcode: 07002-1018

Category Name: Vacation Looks

Price: $2.97 $12.90

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