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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.

  • Effortless Ease Raw Hem Gauze Shorts

    Not sure what to wear? This cute co-ord set just needs your personal touches and you'll be owning this look with effortless ease! Just make sure you add the matching top to cart before you check out! 

    Shop Matching Top: Effortless Ease Twist Front Gauze Crop Top 

    Fits & Features

    • Elastic Drawstring Waistband 
    • High Rise Waist 
    • Slant Hand Pockets
    • Wide Leg Shorts 
    • Gauze Cotton Fabric I Fully Lined 
    • Moderate Stretch
    • Matching Top Sold Separately  

    Style Number/Barcode: 06303-0062

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • First In Class Strapless Jumpsuit

    Elevate your jumpsuit game in this chic jumpsuit! Pair with sleek hoops and power platforms for a head-turning look!

    Fit & Features

    • Strapless Neckline | Wired V-Neck Inset
    • No-Slip Strip 
    • Tie Front Accent 
    • Straight Leg 
    • Lined Lightweight Woven Fabric | Knit Shorts Lining
    • Relaxed Fit 
    • Minimal Stretch 


    Style Number/Barcode: 06402-0174

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For My Close Up Textured Mini Skirt

    Look refreshed and lovely in this striking set! The best part? You can mix and match the top and bottom to recreate other cute outfits! Just don't forget to pick up the matching crop top 

    Shop Matching Top: Ready For My Close Up Textured Crop Top

    Fits & Features

    • High RIse Waistband
    • Mini Length Silhouette  
    • Textured Knit Fabric I Fully Lined
    • Form Hugging Fit I Plenty Of Stretch 
    • Matching Crop Top Sold Separately 

    Style Number/Barcode: 06501-0273

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take A Cue Tapered Eyelet Pants

    Take a cue from the season and freshen up your look with a spring-fling set bb girl! Just make sure you add the matching bottoms to cart 

    Shop Matching Top: Take A Cue Eyelet Crop Top 

    Fits & Features

    • High Rise Waist I Belt Loops
    • Bar Hook Closure At Waist I Zipper Fly 
    • Slant Hand Pockets
    • Tapered Pant Legs I Built-In Lined Shorts
    • Woven Fabric I All Over Eyelet Design 
    • Relax Fit I Minimal Stretch 

    Style Number/Barcode: 06302-0133

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take A Cue Eyelet Crop Top

    Take a cue from the season and freshen up your look with a spring-fling set bb girl! Just make sure you add the matching bottoms to cart 

    Shop Matching Bottoms: Take A Cue Tapered Eyelet Pants

    Fits & Features

    • Fixed Shoulder Straps 
    • Square Neckline & Back 
    • Hidden Front Zipper 
    • Crop Hemline 
    • Fully Lined Woven Fabric I Eyelet Design All Over
    • Minimal Stretch 

    Style Number/Barcode: 06003-0889

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feels Like Summer Smocked Crop Top

    Get those summer vibes in this adorable smocked crop top! Make it a complete 'fit with the matching shorts.

    Shop Matching Shorts: Feels Like Summer Smocked Shorts

    Fit & Features

    • Off the shoulder sweetheart neckline
    • Long puff sleeves | Elastic banded cuffs
    • Stretchy smocked bodice
    • Cropped | Drawstring at hem
    • Small floral print

    Style Number/Barcode: 06003-0892

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Which Way To The Beach Large Straw Tote

    Excuse me miss, which way to the beach? and where did you get that straw tote from? and that sweet summer style? 

    • Large over-sized U-shape structure
    • Double O-ring handles
    • Woven straw design
    • Cotton lining 
    • Drawstring closure

    Style Number/Barcode: 07203-0286

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Leafy Mini Rhinestone Hoop Earrings

    You are a goddess! Show them what you are capable of when you top your look off with ethereal leafy mini hoops!

    • Mini hoop design
    • Rhinestone leafy detailing
    • Pin & snap closure

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

    Style Number/Barcode: 07001-0392

    Category Name: Vacation Looks

    Price: $5.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek And Sultry Maxi Skirt

    Sleek and sultry will be your total vibe in this wrap front maxi skirt. Pair with a chic crop top and some clear mules to amp up your lewk!

    Fit & Features

    • High rise elastic banded waist
    • Ruched detailing
    • Wrap front design | Front slit
    • Maxi length
    • Form hugging fit
    • Stretchy knit fabric

    Style Number/Barcode: 06501-0230

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Draw Me In Crop Top

    Get drawn into this cute crop as you draw them all in! Pair this beauty with high waist shorts and stand out wedges to complete your look! 

    Fit & Features 

    • Off The Shoulder Neckline
    • Smocked Bodice | Front Tie Accent
    • Bell Sleeves
    • Cropped Hem 
    • Gauze and Smocked Fabric 
    • Relaxed Fit Moderate Stretch 

     

    Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small


    Style Number/Barcode: 06003-0519

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • That Summer Feeling Woven Tote

    Get in those summer feelings when you sub out your regular purse for a straw tote, throw on some sandals and a flowy dress and you are ready!

    • Large square structure
    • Bamboo handles
    • Woven straw design
    • Linen lining
    • Zipper closure

    Style Number/Barcode: 07203-0283

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Hot to Handle Halter Knit Mini Dress

    This halter mini dress hugs you with a bodycon fit and a side sash that brings the drama and accentuates your curves. Pair with sandals for brunch by the beach or vacay!

    Fit & Features

    • Texture knit stretchy fabric, stretchy knit lining
    • Halter neckline with hardware trim, spaghetti strap tie
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Front wrap sash design
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000115

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Top Handle Wallet Cross Body Purse

    Convenient and oh so stylish, this wallet cross body purse is a total must!

    • Rectangular fold over design
    • Snap button closure
    • Interior pouch and multiple card slots
    • Top handle
    • Smooth faux leather fabric
    • Faux leather and chain link shoulder strap

    Style Number/Barcode: 07201-0014

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Groovy Baby Tie Dye Mesh Mini Dress

    Show them how you groove in this tie-dye mini! We'd love to see you step out in this with a white pair of booties bb girl! 

    Fits & Features 

    • Spaghetti Straps Cross & Tie At Back 
    • V Neckline 
    • Mini Length Silhouette 
    • Fully Lined Mesh Fabric I Tie Dye Print 
    • Ruching Throughout
    • Form Hugging Fit I Plenty Of Stretch 

    Style Number/Barcode: 05102-0466

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lace Up & Ready Swimsuit

    Curves for days. You are looking SO ready for that poolside appearance! 

    Fits & Features

    • Adjustable Ribbed Spaghetti Straps With Halter Neckline Design I Cross Back 
    • Molded & Padded Bust
    • Metal Eyelets & Lace Up Detail At Center Bodice
    • Rib Knit Construction I Moderate Stretch
    • Semi-Cheeky Coverage Bottoms 

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

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

    Style Number/Barcode: 07109-0148

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Essential Bandeau

    Keep it effortlessly basic in a bandeau to layer with your favorite tops, sweaters and/or jackets, or simply to wear on its own. The essential bandeau features elastic hemlines to prevent slippage and a soft knit that offers plenty of stretch for the perfect fit. Complete your casually chic look with high waist denim and chunky sneakers.

    Fit & Features

    • Straight sleeveless neckline
    • Elastic hemlines
    • Soft knit fabric
    • Plenty of stretch 
    • One size fits most

    Style Number/Barcode: 07107-0190

    Category Name: Vacation Looks

    Price: $3.97 $5.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Feels Like Summer Smocked Shorts

    Get those summer vibes in these adorable smocked shorts! Make it a complete 'fit with the matching top.

    Shop Matching Top: Feels Like Summer Smocked Crop Top

    Fit & Features

    • High rise elastic banded waist
    • Stretchy smocked waist
    • Short, ruffle hem
    • Small floral print

    Style Number/Barcode: 06303-0079

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For My Close Up Textured Crop Top

    Look refreshed and lovely in this striking set! The best part? You can mix and match the top and bottom to recreate other cute outfits! Just don't forget to pick up the matching bottoms 

    Shop Matching Bottoms: Ready For My Close Up Textured Crop Top 

    Fits & Features

    • Off Shoulder, Ruffle Trim Neckline & Short Sleeves 
    • No-Slip Interior Strip 
    • Keyhole Opening & Tie Front At Center 
    • Crop Hemline 
    • Textured Knit Fabric 
    • Form Hugging Fit I Plenty Of Stretch 
    • Matching Bottoms Sold Separately 

    Style Number/Barcode: 06001-2643

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Ease Twist Front Gauze Crop Top

    Not sure what to wear? This cute co-ord set just needs your personal touches and you'll be owning this look with effortless ease! Just make sure you add the matching bottoms to cart before you check out! 

    Shop Matching Bottoms: Effortless Ease Raw Hem Gauze Shorts

    Fits & Features

    • Collared 
    • Button Down Front
    • Short Sleeves
    • Crop Hemline I Decorative Twist Front Design 
    • Lightweight Gauze Cotton Fabric 
    • Boxy Silhouette I Minimal Stretch 
    • Matching Bottoms Sold Separately 

    Style Number/Barcode: 06003-0813

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle Tease Smocked Crop Top

    Show off those ruffles in this sweet and flirty crop top! Top this off on a pair of denim shorts and sneakers. 

    Fits & Features

    • Ruffle-Trim Sweetheart Neckline
    • Gathering Detail At Center Bust 
    • Layered Ruffles At The Sheer Roomy Long Sleeves I Elastic Cuffs
    • Smocked Bodice I Crop Hemline
    • Woven Fabric With Glitter Lurex 
    • Form Hugging Fit I Plenty Of Stretch 

    Style Number/Barcode: 06003-0798

    Category Name: Vacation Looks

    Price: $14.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off Balance Asymmetrical Hem Romper

    The best things in life aren't always linear. Strut it in this chic and comfy romper! It's the ideal lewk for that brunch you got planned with your gals 

    Fits & Features

    • Spaghetti Straps
    • Surplice V Neckline
    • Back Zipper 
    • Asymmetrical Wrap Front Design I Fitted Shorts
    • Crepe Fabric I Moderate Stretch 

    Style Number/Barcode: 06503-0107

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In My Element Convertible Crop Top

    Keep them guessing with how you wear this! Style it as a sexy tie halter top or a  crossover bandage halter top...there are versatile ways to create a cute look! Don't forget to pick up the matching bottom for a put-together 'fit! 

    Shop Matching Bottoms: In My Element Wide Leg Pants 

    Fits & Features

    • Strapless & Sleeveless 
    • Crop Hemline
    • Smooth Cotton Blend Fabric 
    • Minimal Stretch 
    • Can Be Worn Multiple Ways 
    • Matching Bottoms Sold Separately 

    Style Number/Barcode: 06003-0878

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blissful In Lace Maxi Dress

    This gorge lace maxi dress will have you looking and feeling blissful! Don't forget to pair this dress with a fab mini purse and block heels!

    Fits & Features

    • Crew Neckline I Button Nape & Keyhole Opening At Back
    • Sheer Fitted Long Sleeves I Smocked Cuffs 
    • Sheer Partially Lined Bodice 
    • Maxi Length Hem 
    • Lace Fabric I Mini-Length Lining 
    • Form Hugging Fit I Plenty Of Stretch 

    Style Number/Barcode: 05101-0760

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Waves Of Color Beaded Mini Purse

    Add a subtle touch of color to your summer time attire! We think this would look so cute with a neutral linen dress or mini skirt set!

    • Mini square structure
    • Multi-colored wooden beaded detailing
    • Straw O-ring handles
    • Linen lining

    Style Number/Barcode: 07203-0284

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale