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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.

  • Vacay Bound Tassel Hoop Earrings

    You'll be totally ready for your next tropical vacay in these boho tassel hoop earrings! Pair with your fave floral maxi dress and strappy sandals and get ready to bask under the sun!

    • Hammered metal hoop
    • Fanned out tassel detailing
    • Omega closure

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0577

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Chic Tassel Fan Earrings

    Amp up your trendy look with these boho chic tassel earrings! Perf for pairing with your fave spring time 'fit!

    • Metal geometric earring | Hammered detailing
    • Tassel accent in a fanned out design

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0573

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Can't Take My Eyes Off U Frameless Sunglasses

    Make a statement with your sunnies hunnayyy! These pink ombre shades are a summer must have! Style with a deep v bodysuit and fringe shorts!

    • Over-sized 
    • Square flat top design
    • Frameless
    • Dainty arms
    • Light pink ombre lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0775

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Don't Bother Me White Square Sunglasses

    Don't bother her when she has her sunnies on, and shes laying out, because she is full relaxation mode!

    • Square design
    • White frame
    • Dark lenses
    • UV Protection

    Style Number/Barcode: 07008-0760

    Category Name: Vacation Looks

    Price: $4.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Kewl Ombre Cat Eye Sunglasses

    Hunny you are kewl, calm, and collected in these ombre shadez! They are a definite closet staple as they pair with everything!

    • Medium size
    • Cat eye design
    • Ombre lenses
    • Skinny arms

    Style Number/Barcode: 07008-0755

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful View Halter Crochet Crop Top

    Enjoy stylish bliss in this crochet top on your next getaway or weekend outing! The top offers a flattering halter neckline with a spaghetti strap tie and a fitted crop hem. Complete the look with the matching midi skirt.

    Shop Matching Bottoms: Blissful View Crochet Knit Midi Skirt

    Fit & Features

    • Crochet knit fabric, geometric pattern, knit lining
    • Halter neckline with spaghetti strap tie
    • Cropped length
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2271

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Looks Can Slay Faux Wool Panama Hat

    Serve some looks when you top off your 'fit with this faux wool panama hat! It features a faux leather belt detail to add a chic touch. It would be perfectly styled with a faux leather jacket and booties.

    Fit & Features

    • Panama design
    • Faux leather belt detail
    • Faux wool material
    • Wide brim

    Style Number/Barcode: 07302-0145

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Minimalist Moves Faux Leather Flip Flops

    Make it cute when you step out in a simple pair of sandals! Easily styled with high waist shorts, bathing suits, or a summer dress!

    • Open round toe
    • Slip on fit
    • Faux leather ,material
    • Thong design

    Style Number/Barcode: 07404-0163

    Category Name: Vacation Looks

    Price: $9.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Breeze Strapless Wide-Leg Jumpsuit

    Feel the breeze in this cute tropical jumpsuit while on vacation! It showcases a sleek strapless neckline and flattering wide-leg silhouette perfect for layering over a swimsuit.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Strapless neckline
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000002

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lil Miss Sunshine Smocked Ditsy Mini Skirt

    Nothing but good vibes in our Lil Miss Sunshine set! Brighten up any room as you walk in bringing the fun! 

    Shop Matching Top: Lil Miss Sunshine Smocked Tube Top 

    Fits & Features

    • High Rise Elastic Waist
    • Ruffle-Trim Hem
    • Woven Gauze Fabric I Smocking
    • Ditsy Floral Print 

    Style Number/Barcode: 06301-0038

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Belted Bell Beauty Top
    Here's looking at you beauty! The taupe top features a plunging V neckline with knotted bodice, long bell sleeves, a cropped hem and a tie waist belt accent. Top is composed of woven knit fabric that offers a relaxed fit with minimal stretch.

    Model is 5'7" with 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06001-1359

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Taste Of Crochet Bodysuit
    Get a little taste of crochet with this sweet bodysuit! It has a flattering V neckline with a wide crochet trim paired with narrow shoulder straps and a thong bottom that includes a snap button closure. The garment is composed of wide ribbed knit that offers plenty of stretch.

    Style Number/Barcode: 06001-9937

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flowy Flutter Sleeve Tie Front Top

    Flutter some hearts in this adorable flowy sleeve tie front top! The sheer, lightweight chiffon fabric makes it a perf layering piece.

    Fit & Features

    • Three quarter length flutter sleeves | Tiered ruffle hems
    • V neckline
    • Tie front detail
    • Sheer chiffon fabric | No stretch

    Style Number/Barcode: 06204-0484

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Sweetheart Ruched Crop Top

    Refresh your wardrobe with this spring-inspired top! Don't forget to add some shine to your look by adding some sparkling earrings. 

    Fits & Features

    • Sweetheart Neckline 
    • Sheer, Roomy Long Sleeves | Elastic Cuffs
    • Ruching At Front Bodice
    • Smocked Back 
    • Crop Hemline 
    • Woven Gauze Fabric | Fully Lined At Front Bodice
    • Form Hugging Fit | Ample Stretch

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0594

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wildflower Floral Belted Kimono

    Add a touch of femme to your look with a floral kimono! Style with denim and a satin top or wear over your swim attire!

    Fit & Features

    • Long sleeve
    • Open front 
    • Belt accent
    • Floral pattern
    • Relaxed fit

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small. 

    Style Number/Barcode: 06204-0435

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Issa Vibe High Waist Shorts

    Oasis by Eunina

    You're all about the good vibes and that drama-free life girl! Kick back with a pair of high waist shorts and a cute crop to keep your look on point! 

    Fit & Features 

    • High Rise Waist 
    • Single Button and Zipper Closure 
    • Traditional Five Pocket and Belt Loop Design 
    • Cut Off Fringe Hem 
    • Denim Fabric 
    • Form Hugging Fit 
    • Moderate Stretch 

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.

     


    Style Number/Barcode: 06603-0032

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Waist Button Down Denim Shorts

    Keep it light and fresh when you step out in denim!  Perfect for a sunny day, these high waist babies literally go with everything!

    Fit & Features

    • High waist fit
    • Button closures down the center
    • Raw hemline
    • Traditional pockets
    • Denim fabric

    White: Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.  

    Style Number/Barcode: 06603-0076

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On A Tropical Getaway Mesh Duster

    Don't forget to pack ur tropical duster because every bronzed vacay goddess needs one! Style as a bathing suit cover up, or dress it up with heels and your go-to high waist shorts!

    Fit & Features

    • Open front design
    • Long sleeve | Long hemline
    • Mesh material | Moderate stretch
    • Tropical palm leaf neutral print

     Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.  

    Style Number/Barcode: 06202-0051

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Twist Front Knit Crop Top

    Amp up your everyday basic tee with this trendy twist front knit crop top! Pair with some dressy tie waist pants and strappy mules to pull the look together!

    Fit & Features

    • High rounded neckline
    • Long fitted sleeves
    • Twist front detail
    • Majorly cropped hem
    • Jersey knit fabric | Semi-sheer

    Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06001-2485

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blousant Sleeve Tie Front Top

    The perf layering addition to all your looks! Easily pair this tie front top over you bikini set for a cute AF poolside addition! 

    Fits & Features

    • V Neckline
    • Tie Front Design
    • Roomy Blousant Drop Shoulder Long Sleeves I Elastic Cuffs
    • Crop Hemline 
    • Lightweight Woven Gauze Fabric
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 06204-0429

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wanderlust Beauty Lace Kimono

    You're just a wanderlust beauty, always looking for a cute new 'fit! Layer on this perf lace kimono for that instant boho babe look!

    Fit & Features

    • Three quarter length sleeves
    • Drape open front
    • High how hem
    • Flowy, relaxed, and comfortable fit
    • Sheer lace mesh fabric | Moderate stretch

    Style Number/Barcode: 06204-0409

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortlessly Embroidered Floral Crop Top

    Showcase that effortless beauty in this embroidered floral crop top! Pair with a bralette underneath for a fab spring time look.

    Fit & Features

    • Half length puff sleeves
    • Wrap front V neckline
    • Tie front detail
    • Cropped
    • Sheer floral embroidered woven fabric
    • Undergarment not included

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0542

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Impressive Style Strappy Sandals

    Step out in impressive style in these flat sandals showcasing a strappy design with trendy inserts for the cutest look.

    Fit & Features

    • Square toe
    • Strappy design with inserts
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1282

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Rise Destructed Cut Off Shorts

    Your new fave black denim shorts of the season. This high rise destructed cut off pair will go with any of your trendy 'fits.

    Fit & Features

    • High rise waist
    • Two front and back pockets
    • Belt loops
    • Front button closure
    • Distressed detailing
    • Frayed, cut off hem

    Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06603-0027

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale