Vacation Looks

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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.

  • Casual Cutie Linen Skater Dress

    Get a casual cute look in this lightweight linen skater dress. It features adjustable spaghetti straps, a lined crochet bodice with a V neckline, an open back with a tie closure, and a flowy, skater silhouette. The gauze and linen fabric has a knit lining. Complete your outfit with adorable wedges and a chic shoulder bag.

    Fit & Features

    • Adjustable spaghetti straps
    • Lined crochet bodice with a V neckline
    • Open back with a tie closure
    • Short skater silhouette
    • Gauze and linen fabric with no stretch
    • Knit lining
    • Runs true to size

    Style Number/Barcode: 05102-0233

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Classic Tie Back Bikini Top

    Classic tie-back bikini tops are always in style! Fall back on this bikini top that features triangle cups, neck-ties, and tie-back straps for a secure fit. Complete look with the matching bikini bottoms, matching dress, and sunnies. 

    Shop Matching Bikini Bottoms: The Classic Low Rise Bikini Bottoms

    Shop Matching Coverup: Drawn To You Mesh Cover Up

    Fit & Features

    • Triangle cups
    • Removable padding
    • Sleek neck ties
    • Tie-back straps
    • Form hugging fit
    • Runs true to size

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0544

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drawn To You Mesh Cover Up

    Get drawn in with this chic coverup that brings sheer appeal! The coverup features a crew neckline, a ruched drawstring at the side, and a mini-length silhouette. The coverup is composed of a sheer unlined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching bikini set, sunnies, and sandals! 

    Shop Matching Bikini Top: The Classic Tie Back Bikini Top

    Shop Matching Bikini Bottoms: The Classic Low Rise Bikini Bottoms

    Fit & Features

    • Crew neck
    • Sleeveless
    • Ruched drawstring at the side
    • Mini length silhouette
    • Unlined mesh fabric 
    • Form hugging fit 

    Style Number/Barcode: 06001-3135

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cinched and Chic Mesh Swim Coverup

    Keep it chic under the cabana in a cinched skirt coverup! The skirt features a high-rise waist, a cinched side seam, and an asymmetrical hem. The skirt coverup is composed of a sheer unlined mesh fabric that offers a form-hugging fit. Complete your look with the matching headwrap, a cute two-piece swimsuit, and sunnies.

    Shop Matching Headwrap: Chic Vibes Mesh Headwrap

    Fit & Features

    • High-rise waist
    • Ruched side drawstring
    • Asymmetrical hem
    • Mini-length silhouette
    • Sheer unlined mesh fabric
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-0374

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crochet Beauty Lattice Back Top

    You'll look like a total boho beauty in this trendy crochet top. It features short cap sleeves, a scoop neckline, a lattice back design with a tie detail, and a form-hugging fit. The sheer crochet fabric has no stretch. Pair an adorable bralette under this top and style with denim shorts.

    Fit & Features

    • Short cap sleeves
    • Scoop neckline
    • Lattice back design
    • Tie closure with tassel details
    • Form-fitting style
    • Sheer crochet fabric with no stretch
    • Runs true to size

    Style Number/Barcode: 06005-0883

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You're The Zest Lemon Print Bikini Bottoms

    These bikini bottoms will have you looking your best this season with a too-cute lemon print! The bikini bottoms feature a mid-rise waist, a lemon print, and a cheeky bottom. Complete look with the matching bikini top and sunnies. 

    Shop Matching Bikini Top: You're The Zest Lemon Print Bikini Top

    Fit & Features

    • Mid-rise 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: 07105-0645

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You're The Zest Lemon Print Bikini Top

    This bikini top will have you looking your best this season with a too-cute lemon print! The bikini top features a sleeveless scoop neckline, a smocked bodice, a lemon print, removable padding, and adjustable spaghetti straps. Complete look with the matching bikini bottoms and a pair of stylish sunnies. 

    Shop Matching Bikini Bottoms: You're The Zest Lemon Print Bikini Bottoms

    Fit & Features

    • Sleeveless scoop neckline
    • Lemon print
    • Smocked bodice
    • Removable padding 
    • Adjustable spaghetti straps
    • Form hugging fit, moderate stretch 
    • Runs true to size

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0497

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Drama Cutout One Piece Swimsuit

    Let this one-piece swimsuit make a dramatic splash for your beachside look! The sexy one-piece swimsuit features a sleeveless square neckline with spaghetti straps, a sexy cutout at the midriff, an asymmetrical strap, and a high cut bottom with a thong bottom. Complete look with sunnies. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cutout
    • Asymmetrical strap 
    • High cut bottom
    • Thong bottom 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 07109-0246

    Category Name: Vacation Looks

    Price: $4.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • East Coast Graphic Tee

    Rep the east coast in style with this trendy graphic tee! It features a crew neckline, short sleeves, a mid-length, form-hugging fit, and a center graphic that reads "East Coast." Complete your look with biker shorts and cute sneaks.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Mid-length hem
    • Center graphic that reads "East Coast"
    • Jersey knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-0758

    Category Name: Vacation Looks

    Price: $5.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On-Trend Destructed Denim Mini Skirt

    Keep your everyday style on-trend for spring in this adorable denim mini skirt! It features a high-rise waist, a traditional five-pocket and belt loop design, a front button and hidden zipper closure, distressed details, a short raw cut hem, and a form-hugging silhouette. Pair this skirt with a floral crop top and strappy sandals.

    Fit & Features

    • High-rise waist
    • Traditional five-pocket and belt loop design
    • Front button and hidden zipper closure
    • Destructed details and a raw cut hem
    • Mini-length, form-hugging fit
    • Light wash denim fabric with minimal stretch
    • Runs true to size

    Style Number/Barcode: 06601-0038

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrap Me In Glam Mesh Maxi Skirt

    Wrap yourself in a chic mesh coverup skirt that makes a sheer impression. The skirt features an elastic high-rise waist, a high side slit, and a maxi-length silhouette. The skirt is composed of a sheer unlined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching crop top and sunnies.

    Shop Matching Crop Top: Wrap Me In Glam Mesh Maxi Skirt

    Fit & Features

    • Elastic high-rise waist
    • High side slit
    • Maxi-length silhouette
    • Unlined mesh fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0260

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunkissed Beauty One-Piece Swimsuit

    You'll look like a sunkissed beauty in this stunning one-piece swimsuit! It features halter straps, a low scoop neckline, a backless design with tie-back straps, side cutouts at the waist with a criss-cross design, and a semi-cheeky fit. The all-over tropical floral print is perf for the warmer weather. Complete your look with strappy sandals.

    Fit & Features

    • Halter straps
    • Low scoop neckline
    • Backless design
    • Tie-back straps
    • Side cutouts with a criss-cross design
    • Semi-cheeky fit
    • Tropical floral print
    • Runs true to size


    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07109-0242

    Category Name: Vacation Looks

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fierce And Flirty Swim Top

    Bring a fierce and flirty vibe to your poolside look with this on-trend swim top! It features a one-shoulder neckline, a center cutout above the bust, and a cutout at the hem that goes from the front to the back. Pair this swim top with the matching swim bottoms and some chic sunglasses.

    Shop Matching Bottoms: Fierce And Flirty Swim Bottoms

    Fit & Features

    • One-shoulder neckline
    • Center cutout above the bust
    • Cutout at the hem
    • Runs true to size


    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0530

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brunch At Noon Off-The-Shoulder Floral Romper

    Step out for brunch in this floral off-the-shoulder romper with a flirty tie-waist and ruffled hem for a playful look.

    Fit & Features

    • Floral print, chiffon fabric, woven shorts lining
    • Off-the-shoulder neckline, ruffled short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Tie-waist
    • Flowy ruffled short hem
    • Runs true to size

    Style Number/Barcode: 06403-1093

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Headturner Cutout Mesh One Piece Swimsuit

    Cause a head-turning moment with a swimsuit that is boldly fab! The one-piece swimsuit features a plunging sweetheart neckline, sleek spaghetti straps, a caged detail, sexy cutouts at the midriff and waist, a sheer mesh panel, and a cheeky bottom. Complete look with jelly sandals and sunnies. 

    Fit & Features

    • Sleeveless sweetheart neckline, spaghetti straps
    • Caged design 
    • Removable padded cups
    • Cutouts at the midriff and waist
    • Mesh panel 
    • Double row of slide hook closures
    • High cut with a cheeky bottom 

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07109-0256

    Category Name: Vacation Looks

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get Sprung Floral Bikini Bottoms

    Get spring on these cute bikini bottoms! The bottoms feature a high-rise waist, a floral print, a cute tie-waist belt, and a cheeky bottom. Complete the look with the matching bikini top and sandals. 

    Shop Matching Bikini Top: Get Sprung Floral Bikini Top

    Fit & Features

    • High rise waist
    • Floral print
    • Tie-waist belt 
    • Cheeky fit
    • Form hugging fit
    • Runs true to size

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0674

    Category Name: Vacation Looks

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get Sprung Floral Bikini Top

    Get sprung on this cute bikini top! The top features a plunging sweetheart neckline, molded cups, a  floral print, adjustable spaghetti straps, and a slide-hook closure. Complete the look with the matching bikini bottoms and jelly sandals. 

    Shop Matching Bikini Bottoms: Get Sprung Floral Bikini Bottoms

    Fit & Features

    • Sleeveless sweetheart neckline
    • Molded cups
    • Adjustable spaghetti straps
    • Floral print
    • Slide-hook closure 
    • Form hugging fit
    • Runs true to size

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0526

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Palm Paradise Bikini Top

    Keep it pretty underneath the palm trees with bikini bottoms that take you to paradise. The bikini top features an off-the-shoulder neckline, a sweetheart bust, off-the-shoulder straps, and a palm tree print. Complete your look with the matching bikini bottoms and jelly sandals. 

    Shop Matching Bikini Bottoms: Pretty Palm Paradise Bikini Bottoms

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust
    • Palm tree print
    • Form hugging fit
    • Runs true to size

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0525

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Palm Paradise Bikini Bottoms

    Keep it pretty underneath the palm trees with a bikini top that takes you to paradise. The bikini bottoms feature a low-rise hipster, a palm tree print, bar strap cutouts at the waist, and a cheeky fit. Complete your look with the matching bikini top and jelly sandals. 

    Shop Matching Bikini Top: Pretty Palm Paradise Bikini Top

    Fit & Features

    • Low-rise waist
    • Palm tree print
    • Bar strap cutouts at the waist
    • Cheeky fit
    • Form hugging fit
    • Runs true to size

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0673

    Category Name: Vacation Looks

    Price: $1.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babygirl Rhinestone Baseball Cap

    Dazzle on baby girl with a cap that is part sporty, part glam. The cap features a traditional baseball cap design and a rhinestone embellished scrip that reads "Babygirl". 
    Complete the look with a crop top and cutoff jeans. 

    Fit & Features

    • Baseball cap design 
    • Rhinestones
    • Script that reads "Babygirl"

    Style Number/Barcode: 07302-0293

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Beauty Floral Chiffon Tie-Front Top

    Let your stunning beauty radiate in this breezy chiffon top! It features long blouson sleeves with elastic banded hems, a V neckline leading to a tie-front closure, and a cropped, form-hugging fit. The sheer chiffon fabric showcases a pretty floral print that will pair perfectly with light-wash denim. Accessorize with sleek hoop earrings for a stylish look.

    Fit & Features

    • Long blouson sleeves with elastic banded hems
    • V neckline
    • Tie-front closure
    • Cropped, form-fitting style
    • Sheer floral chiffon fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06204-0808

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed Tropical Bandeau Bikini Top

    Channel a sunkissed look with a bikini top that will have you beach-ready! The top features a bandeau-style, a tropical print, a tortoise-hued O-ring at the center, supportive flexible boning at the sides, and removable padding. Complete look with the matching bikini bottoms and t-strap sandals. 

    Shop Matching Bikini Bottoms: Sunkissed Tropical High Waist Bikini Bottoms

    Fit & Features

    • Bandeau-style
    • Tropical print
    • Removable padding
    • Tortoise-hued O-ring at the center
    • Flexible boning
    • Form hugging fit, moderate stretch 
    • Runs true to size

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0535

    Category Name: Vacation Looks

    Price: $5.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed Tropical High Waist Bikini Bottoms

    Channel a sunkissed look with bikini bottoms that will have you beach-ready! The bottoms feature a high-rise waist, a tropical print, and a cheeky bottom. Complete look with the matching bikini top and t-strap sandals. 

    Shop Matching Bikini Top: Sunkissed Tropical Bandeau Bikini Top

    Fit & Features

    • High rise waist
    • Tropical print
    • High cut
    • 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: 07105-0683

    Category Name: Vacation Looks

    Price: $4.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Cinched One Piece Swimsuit

    Channel a chic and cinched look with a swimsuit that shows curves off in all the right places. The swimsuit features a sleeveless square neckline, adjustable spaghetti straps, removable padding, dual drawstrings, and a high cut with a cheeky bottom. The swimsuit is composed of a lined textured waffle-knit fabric that offers a form-hugging fit. Complete look with sunnies.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Removable padding
    • Dual drawstrings
    • High cut
    • 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: 07109-0263

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free