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.

  • Boho Feels Tie Front Top

    Get all those boho feels in this flowy tie front top! Wear as a cute top or over your fave swimsuit poolside!

    Fit & Features

    • Flowy three quarter length sleeves
    • V neckline
    • Tie front
    • Cropped
    • Striped
    • Lighweight, textured crepe fabric
    • No stretch

    Style Number/Barcode: 06204-0482

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Color Splash Tie Dye Tie Front Kimono

    Make a splash in your outfit with this gorge kimono! Layer it on for a trendy lewk on the beach 

    Fits & Features

    • Drape Open Front
    • Kimono Sleeves 
    • Slits At The Sides 
    • Woven Gauze Fabric I Tie Dye Print I Fringe Trim
    • Relaxed Fit
    • Minimal Stretch 

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

    Style Number/Barcode: 06204-0433

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Vibes Denim Jacket

    Fall back on basics to complete your look! A denim jacket is a must-have for this season! Pair with your favorite pastel pieces for a Spring ready look! 

    Fit & Features 

    • Collard Neckline
    • Button-Down Front 
    • Long Sleeves | Single Button Cuff
    • Side Pockets
    • Light Medium Wash Denim Fabric
    • Relaxed Fit 
    • Minimal Stretch 

     

    Model is 5'4" with a 32" bust, 23" waist and 38" hips. She is wearing a size small. 


    Style Number/Barcode: 06203-0042

    Category Name: Vacation Looks

    Price: $11.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Cropped Tube Top

    Stick to the basics with this classic crop top!

    Fit & Features

    • Straight, strapless neckline
    • Flattering slim fit
    • Heathered knit
    • Plenty of stretch for comfort

    Style Number/Barcode: 06002-5398

    Category Name: Vacation Looks

    Price: $6.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Fling Tie Front Top

    We love a good spring time lewk! Pair this adorable tie front crop top with your fave satin midi skirt and some chic heels.

    Fit & Features

    • Long puff sleeves | Smocked arms
    • Tie front detail
    • Cropped
    • Lightweight, cotton blend fabric
    • No stretch

    Style Number/Barcode: 06204-0591

    Category Name: Vacation Looks

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denim Sweetheart Lace Up Crop Top

    Hey babe! You'll look like a total sweetheart in this adorable denim lace up crop top, perf paired with some white shorts and matching white booties!

    Fit & Features

    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Lace up front
    • Exposed back zipper closure
    • Cropped
    • Denim fabric
    • Relaxed 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: 06003-0520

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer-Coded Crochet Halter Mini Dress

    Serve all the summer vibes in this crochet knit mini dress designed with a halter V-neck with a beaded trim on the straps. Style with espadrille wedges for sunset happy hour.

    Fit & Features

    • Sheer crochet knit fabric with knit lining, moderate stretch
    • Sleeveless V-neckline
    • Tie-back halter straps, beaded trim
    • Partially open back
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6114

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Dream Kimono Sleeve Top

    Look like a total dream in this gorgeous floral kimono sleeve top! Pair with some high rise denim cutoffs for the perf spring vibe.

    Fit & Features

    • Three quarter length flowy kimono sleeves
    • V neckline
    • Tie front detail
    • Cropped
    • All over floral print
    • Polyester woven fabric

    Style Number/Barcode: 06204-0558

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Why Knot Flutter Sleeve Chambray Tie Front Top

    Perfect for sunny days and adding a sultry touch to your look. Tie up your look with this adorbs flutter sleeve top! 

    Fits & Features

    • Adjustable Center Front Tie
    • Plunging V Neckline
    • Short, Flutter Sleeves
    • Crop Hemline 
    • Chambray Fabric  

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

    Style Number/Barcode: 06204-0462

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Vibes Tie Front Top

    Give off some seriously chic vibes in this fab tie front top that will keep you on trend babe! Pair this tie front top with your fav high waist denim and strappy sandal or fun wedge heel!

    Fit & Features

    • Tie Front Bodice 
    • Quarter Length Sleeves
    • Puff Sleeves
    • Cropped Hem 
    • Floral Print
    • Lightweight Woven Fabric 

     

     


    Style Number/Barcode: 06204-0549

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tied Down Flutter Sleeve Tie Front Top

    Get tied down to this cute top! Perfectly paired with denim skinnies or cut-offs, feel chic and fresh with this outfit topper! 

    Fits & Features

    • Plunging V Neckline
    • Center Tie Front 
    • Double Layer, Short Flutter Sleeves
    • Woven Lightweight Gauze Fabric 
    • Cropped Hem

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

    Style Number/Barcode: 06204-0499

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dream State Chiffon Floral High Low Duster

    "I must be dreaming". Hit 'em with an entrance in this dreamy and romantic duster! A perfect layering piece over your bikini set, you can also work your charm by pairing it over a tube top and some denim cut-offs!

    Fits & Features

    • Short Flutter Sleeves 
    • Plunging V Neckline I Empire Waist With Triple Button Closure 
    • High-Low Hem 
    • Sheer Chiffon Fabric 
    • Floral Prints Throughout 

     

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

    Style Number/Barcode: 06204-0387

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In My Feels Scoop Neck Bra Top

    Whether you're on vacay or sitting poolside, this scoop neck bra top will have you feeling yourself! Pair with the matching skirt.

    Fit & Features

    • Stretchy knit fabric
    • Spaghetti straps
    • Scoop neckline
    • Ultra-cropped hem
    • Runs true to size

     

    Shop The Matching Skirt: In My Feels High-Rise Midi Skirt

    Style Number/Barcode: 06005-2257

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Flirt Ruffle Detail Romper

    Give off major flirty vibes in this adorable ruffle detail romper! With a tie front accent and on trend mint hue, this romper will have you totally spring ready.

    Fit & Features

    • Off the shoulder sweetheart neckline | Spaghetti straps
    • Sheer flowy short sleeves
    • Ruffle overlay
    • High waist | Side tie detail
    • Flowy shorts
    • Dainty trim detail

    Style Number/Barcode: 06403-0096

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sassy Smocked Ruffle Detail Crop Top

    Sassy and smocked, this ruffle detail crop top is a must-have for this spring season! Pair it with some trendy light wash denim shorts for the perf warm weather look.

    Fit & Features

    • Strapless square neckline
    • Smocked knit fabric
    • Ruffle detail trim
    • Cropped

    Style Number/Barcode: 06001-2735

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Living Fine in Rhinestones Sandals

    Show off your affinity for that luxe life in these dazzling rhinestone sandals that easily dress up your most casual lewks!

    • Mid-Calf Length Wrap Around Strap 
    • Rhinestone Embellished and Beaded Strap 
    • Flat Sole 
    • Faux Leather Material 


    Style Number/Barcode: 07404-0638

    Category Name: Vacation Looks

    Price: $12.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Carry On Vibrant Snake Mini Purse
    Keep doin' you boo-boo! Add a pop of color and hold all your essentials in this trendy mini purse. Make room for your newest addition bb!
    • Rectangular Design 
    • Top Handle 
    • Snap Button Closure 
    • Detachable And Adjustable Nylon Shoulder Strap
    • Multi Vibrant Textured Snake Print 

    Style Number/Barcode: 07203-0334

    Category Name: Vacation Looks

    Price: $11.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hips Don't Lie Cubic Zirconia Dainty Chain Belt

    Accentuate those hips a little when you add a little body jewelry in the mix! This stunning hip chain is the perfect way to level up that swim look! 

    • Cubic zirconia rhinestones
    • Adjustable lobster clasp closure
    • Chain link design
    • Dainty

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

    Style Number/Barcode: 07002-0446

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Move Double Band Platform Sandals

    Babe you are about to be on the move real soon and why not make sure you have the cutest sandals on hand! Pair with high waist shorts, or even a linen midi skirt!

    • Open round toe
    • Double band design
    • Cork detailing
    • Sport platform sole

    Style Number/Barcode: 07404-0657

    Category Name: Vacation Looks

    Price: $14.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Affair Puff Sleeve Crop Top

    Style yourself with spring in mind! This ever so floral cropped top is a sunny day essential. Pair with white high waist denim, or even a mini skirt!

    Fit & Features

    • Sweetheart neckline
    • Quarter puff sleeves
    • Form fitting
    • Tie front detail
    • Smocked back
    • Smooth knit

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

    Style Number/Barcode: 06003-0576

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set The Tone Halter A-Line Floral Midi Dress

    Set the tone for spring dressing in this halter floral midi dress designed in a statement A-line silhouette perfect for brunch, garden parties, and day dates!

    Fit & Features

    • Floral print, woven fabric, woven lining
    • Sweetheart halter neckline, tie-back design
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Flowy midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3969

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Gem Vintage Bohemian Ring 5 Pack

    Add a vintage touch to your look when you style in some stunning boho rings! It's the little things that make your look come to life!

    • Set of five rings
    • Vintage boho design
    • Gemstone detailing
    • Gold rustic finish

    Style Number/Barcode: 07004-0074

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Perfect Touch Gold Cuff Bracelet

    We have the perfect touch for your look! Adding in an arm cuff to your sleeveless dress gives it a fun twist!

    • Four rows
    • Open ended
    • Simple rhinestone detailing
    • Available in silver

    Style Number/Barcode: 07003-0102

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Time Straw Fringe Clutch

    Girl, we know you're on that out-of-office, do not disturb, runnin' on island time mood when you bust out this clutch! Pairs perfectly with a marg and that vacay set you got packed!

    • Long Rectangular Structure
    • Snap Button Closure
    • Main Compartment With Interior Pocket Sleeve
    • Straw Composition I Fringe Detail 


    Style Number/Barcode: 07203-0324

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free