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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.

  • Go Diva Oversized Sunglasses

    These sunglasses were made just for you diva! Style them with all your hot summer looks.

    • Oversized Ombre Tinted Lenses
    • Metal Frame
    • Square Lenses

    Style Number/Barcode: 07008-0777

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Girl Square Sunglasses

    Add some glam to your look with these sunnies! Rock them with a bikini or a crop top and denim for a chill summer day.

    • Plastic Frame
    • Think Arms
    • Square Lenses

    Style Number/Barcode: 07008-0782

    Category Name: Vacation Looks

    Price: $4.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Days Straw Panama Hat

    Block out the sun and look good while doing it in this panama hat! Pair it with a cute bikini and sandals on your next beach day.

    • Panama Design
    • Frayed Edge
    • Belt Detail

    Style Number/Barcode: 07302-0197

    Category Name: Vacation Looks

    Price: $10.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cruisin’ Round Sunglasses

    Sunny days are here, and you need this pair of round shades in your collection!

    • Round Design
    • Gold Frame

    Style Number/Barcode: 07008-0766

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • No Shade Cat Eye Sunglasses

    You won’t have time to throw shade when you’re busy looking bomb in these sunnies!

    • Cat Eye Design
    • Plastic Frame

    Style Number/Barcode: 07008-0786

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Is My Season Straw Panama Hat

    If summer is your season, then a straw panama hat is an essential for you babe! Style with a linen set, or a floral mini dress!

    • Panama design
    • Black knit belt detail
    • Wide brim with fringe edges
    • Tan straw

    Style Number/Barcode: 07302-0221

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Here To Be Loved V-Neck Eyelet Skater Mini Dress

    Layered or worn solo, this stunning skater dress features a forever flattering mini-length silhouette and an adorable eyelet pattern for the perfect femme finish.

    Fit & Features

    • Eyelet woven fabric, stretchy knit lining
    • V-neckline, bust tie
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Skater silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3950

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feel The Breeze Straw Boater Hat

    Feel the ocean breeze, and stay vacay ready in the cutest straw boater hat! Style with your swim suit & cover up, or even with a summer mini dress!

    • Flat top
    • Straw woven design
    • Floppy brim
    • Thick black knit belt

    Style Number/Barcode: 07302-0223

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feel The Breeze Straw Tan Boater Hat

    Feel the ocean breeze, and stay vacay ready in the cutest straw boater hat! Style with your swim suit & cover up, or even with a summer mini dress!

    • Flat top
    • Straw woven design
    • Floppy brim
    • Thick black knit belt
    • Tan

    Style Number/Barcode: 07302-0222

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Addiction Mid-Rise Fray Denim Shorts

    Upgrade your denim collection with these mid-rise denim shorts with a trendy frayed hem and perfect vintage-inspired look and feel!

    Fit & Features

    • Medium wash denim
    • Front button and zipper closure, belt loops
    • Five-pocket styling
    • Frayed hem
    • Runs true to size

    Style Number/Barcode: 06603-0508

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take A Dip O-Ring One Piece Swim

    Take a dip in a sexy one piece! Designed with the perfect amount of sexy!

    Fit & Features

    • Straight neckline
    • Adjustable spaghetti straps
    • Deep plunging front cut out
    • O-ring detail down the center
    • Removable padding
    • Lined | Cheeky bottom

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

    Style Number/Barcode: 07109-0187

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Dream Tie Front Top

    Look like a total dream in this boho chic tie front top! Pair with a trendy bralette underneath and some high waisted denim shorts for that desert wanderer vibe!

    Fit & Features

    • Cap sleeves
    • V neckline
    • Tie front
    • Cropped
    • Sheer lightweight gauze fabric
    • No stretch

    Style Number/Barcode: 06204-0536

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Romance Floral Kimono

    Add a twist of romance to your look with a flowing floral kimono! Style with high waist denim, and a light colored tank or bodysuit and watch your look pop!

    Fit & Features

    • Open front
    • High low design
    • 3/4 Sleeves
    • Flowing chiffon 
    • Relaxed fit
    • Romantic floral pattern

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

    Style Number/Barcode: 06204-0386

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortlessly Pretty Tie Front Top

    Look so effortlessly pretty in this tie front top that you can easily pair over your fave bodysuit or bikini!

    Fit & Features

    • Three quarter length kimono sleeves
    • V neckline
    • Tie front detail
    • Lightweight rayon fabric | No stretch

    Style Number/Barcode: 06204-0483

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked Tie Front Tube Top

    The perf top to wear with all of your spring 'fits! Make sure to get them in all the colors!

    Fit & Features

    • Strapless sweetheart neckline 
    • Tie front detail
    • Stretchy smocked fabric
    • Cropped

    Mauve: Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.

    Light Blue and White: Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06001-2505

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Waist Linen Shorts

    These high waist linen shorts can so easily be taken from day with a cute tank to night with a chic chiffon blouse! A must for your wardobe.

    Fit & Features

    • High rise waist
    • Tie front woven belt
    • Front button | Hidden zipper closure
    • Slanted front pockets
    • Faux back pockets
    • Short, form-fitting style
    • Linen fabric | No stretch

    Style Number/Barcode: 06303-0061

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Taking Chances Cropped Skinny Jeans

    Take a risk girl in these dangerously bold jeans! Pair these edgy pants with a crop or a sassy graphic tee! 

    Fit & Features 

    • High Rise Waist 
    • Single Button and Zipper Closure 
    • Traditional Five Pocket Design 
    • Heavy Destructed Detailing 
    • Medium Wash Fabric 
    • Skinny Leg Fit 
    • Form Hugging Fit | Moderate Stretch 

     


    Style Number/Barcode: 06602-0103

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Brushed Knit Wrap Front Crop Top

    An elevated basic everyone needs in thier life, this wrap front crop top is a must have.

    Fit & Features

    • Long fitted sleeves
    • Wrap front V neckline
    • Cross tie straps at the hem
    • Cropped
    • Soft brushed knit fabric
    • Form hugging fit | Plenty of stretch

    Style Number/Barcode: 06001-2632

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rise Up Distressed Skinny Jeans

    Rise up in style with this edgy distressed skinny jeans! Pair these staple jeans with a sassy graphic tee to slay on! 

    Fit & Features 

    • Super High Rise Waist
    • Single Button and Zipper Closure 
    • Traditional Five Pocket and Belt Loop Design 
    • Skinny Leg
    • Heavy Distressed Detailing | Raw Edge Hem 
    • Medium Wash Denim Fabric 
    • Form Hugging Fit | Moderate Stretch  

     

    Style Number/Barcode: 06602-0105

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Waist Acid Wash Jean Shorts

    Yes girl, these acid wash jean shorts are a total must. Def don't miss out - add to cart!

    Fit & Features

    • High rise waist
    • Traditional five pocket and belt loop design
    • Front button up closure
    • Major distressed detailing
    • Frayed hem
    • Acid wash denim fabric | No stretch

    Style Number/Barcode: 06603-0075

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Time To Chill Faux Suede Sandals

    Time to chill and lay back, because summer is right around the corner! First stop, finding the best sandals! Style these cuties with flowy pants, or even a flowy mini dress!

    • Open round toe
    • Thick band over the toe
    • Closed heel
    • Flat sole
    • Composed of faux suede

    Style Number/Barcode: 07404-0575

    Category Name: Vacation Looks

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Fierce Cover Up

    Complete your sexy pool party look with this fierce leopard cover up!

    Fit & Features

    • All over leopard print
    • Lightweight woven fabric

    Style Number/Barcode: 07305-0081

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Off Snake Swim Top

    Show off at the beach in this sexy bikini. Rock it with the matching bottoms and a mesh kimono.

    Shop the Matching Bottoms : Show Off Snake Swim Bottoms

    Fits & Features

    • Adjustable Straps
    • Snake Print
    • Matching Bottoms Sold Separately

    Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

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

    Style Number/Barcode: 07104-0470

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time For Vacay Tie Front Tropical Crop Top

    This tropical tie front crop top is ready for your next vacay! Features fluttery short sleeves and a tie front cropped hem for a flattering fit. The palm print on lined knit fabric adds a touch of paradise to any outfit. Complete the look with the matching pants.

    Shop Matching Bottoms: Time For Vacay High Rise Tropical Palazzo Pants

    Fit & Features

    • Palm print, lined stretchy knit fabric
    • High rise waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06202-0458

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free