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.

  • Darling In Denim Mini Dress

    This darling denim mini is the new dress you need! It features a sleeveless, sweetheart neckline with a built-in padded bust, adjustable spaghetti straps, piping detailing down the front, and a short, curve-hugging fit. Complete the look in PVC strap mules.

    Fit & Features

    • Sleeveless, sweetheart neckline, built-in padded bust
    • Adjustable spaghetti straps
    • Back zipper closure
    • Piping detail down the front and back
    • Short, curve-hugging fit
    • Denim fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-0120

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flutter Sleeve Tie Front Top

    Look like a total babe in this swim pinstripe tie front top. Pair it with high waist denim, wedges and don’t forget a bag!

    Fits & Features

    • Short Flutter Sleeves
    • Pin Stripes
    • Tie Front Detail

    Style Number/Barcode: 06003-0923

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Blossoms Crop Top

    Add this pretty floral top to your collection. Pair it with high waist jeans and heels for a sweet feminine look.

     Fits & Features

    • Wrap Front Tie Waist Detail
    • ¾ Sleeves
    • Chiffon Fabric

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

    Style Number/Barcode: 06003-0797

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Side Floral Crop Top

    Sunny days are here, time to add more floral to your wardrobe! Style this crop top with denim shorts, heels and cute straw bag.

    Fits & Features

    • Wrap Front Tie Detail
    • Short Sleeves

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

    Style Number/Barcode: 06003-0867

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Polka Dot Smocked Top

    You'll look as pretty as ever in this polka dot crop! The top features sheer organza sleeves with elastic banded hems and a stretchy smocked top with a square neck and a sheer back. Garment offers plenty of stretch and a form hugging fit.

    Style Number/Barcode: 06003-0602

    Category Name: Vacation Looks

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Get A Cute 'Fit In Knit Cropped Tank

    Get a cute 'fit in this adorable knit cropped tank! Pair with some high waisted distressed denim and add some edgy booties for a look your whole squad will be lusting after.

    Fit & Features

    • Spaghetti straps
    • V neckline
    • Drawstring at hem to cinch
    • Cropped, merrow edge trim
    • Lightweight ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06002-0425

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye Daze Crop Top

    This crop top gets on the boho trend with an all-over tie-dye print that makes a trendy statement. This cute top is all you need to create a bohemian outfit. The top features a sleeveless square neckline and sleek bungee straps. Pair it with the matching tie-dye pants and white heels for a groovy look!

    Shop the Matching Bottoms: Tie Dye Daze Flare Pants

     Fits & Features

    • Thin bungee straps
    • Sleeveless square neckline
    • Tie-Dye print
    • Matching bottoms sold separately

     

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

    Style Number/Barcode: 06001-2431

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be Cool Tie Dye Wrap Crop Top

    Stay on-trend in this wrap tie-dye crop top. Keep it groovy in this timeless wrap crop top for a fun beach day or catching your favorite band's next show. This tie-dye top features a plunging wrap V-neckline to enhance curves, short sleeves, a tie waist strap at the hem to add a chic detail, and a cropped hem. The top is composed of a cotton-like fabric that offers a relaxed fit with a moderate stretch. Style it up with denim shorts and booties for an effortlessly cute look.

    Fits & Features

    • Wrap Front | Tie Waist
    • Short Sleeves
    • Tie-Dye Print

     

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

    Style Number/Barcode: 06001-2703

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet and Sassy Puff Sleeve Top

    A puff sleeve will take a basic top to the next level. Pair this top with denim and wedges and you’re ready for a fun summer day.

    Fits & Features

    • Puff Sleeves
    • Wrap V Neckline
    • Mid Length  

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

    Style Number/Barcode: 06001-2608

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dream On Tie Dye Crop Top

    This tie-dye crop top is perfect for a summer look. The top features a plunging V-neckline, spaghetti straps for a sleek statement, and a trendy tie-dye print to stay on-trend. Style the top with high waist denim shorts and white sandals.

    Fits & Features

    • Sleeveless bodice
    • Spaghetti straps
    • Wrap V-neckline
    • Tie-Dye Print
    • Cropped hem
    • Knit fabric

     

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

    Style Number/Barcode: 06001-2490

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getting My Way Coated Cropped Top

    Get things your way wearing this cropped top. No one will be able to say no to you when stepping out for a night out celebrating with the girls in this gorgeous top. The top features a sleeveless square neckline, bungee straps for sleek detail, and a smooth coated finish that slays. Don't forget to pick up the matching skirt though...it only works if you got the whole outfit.

    Shop Matching Skirt: Getting My Way Coated Mini Skirt

    Fit & Features

    • Square neckline
    • Bungee spaghetti straps
    • Cropped hemline
    • Form-fitting silhouette
    • Moderate stretch
    • Smooth-coated finish

     

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06001-2215

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Must Have Mesh Cropped Swim Cover Up

    This sheer mesh cropped swim cover up is a must have for sure! Pair with the matching bottoms over your trendiest bikini for a fire 'fit babe!

    Shop Matching Bottoms: Must Have Mesh Swim Cover Up Shorts

    Fit & Features

    • Wide rounded neckline
    • Long fitted sleeves
    • Ruched center front | Drawstring at hem
    • Cropped
    • Sheer mesh fabric | Plenty of stretch

    Style Number/Barcode: 06001-2720

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Vibes Bow Back Woven Crop Top

    This airy woven crop top will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric, it features a sweetheart neckline with ruching at the bust, thin tank shoulder straps, an alluring open back with the cutest tie-back bow design, and a cropped hem with a form-hugging fit for a snatched silhouette. Style with the matching midi skirt for a fabulous 'fit.

    Shop Matching Fuchsia Bottoms: Sunny Vibes Woven Wide-Leg Pants
    Shop Matching Orange Bottoms: Sunny Vibes High Slit Woven Midi Skirt

    Fit & Features

    • Woven fabric with front knit lining, minimal stretch
    • Sweetheart neckline, ruched bust
    • Thin tank straps
    • Open-back, tie-back bow design
    • Cropped hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2413

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hot for Summer Swim Top

    Sit pretty poolside in this red-hot bikini top. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Hot for Summer Swim Bottoms

    Fits & Features

    • O-Ring Front Detail
    • Adjustable Straps | Tie Back
    • 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: 07104-0436

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Polka Dot Ruffle Swim Top

    Ruffles and polka dots? We can’t think of a better combo. Pair this with the matching bottoms and a kimono and you will be pool party ready!

    Shop the Matching Bottoms: Polka Dot Ruffle Swim Bottoms

    Fits & Features

    • Ruffle Front Detail
    • Adjustable Straps
    • 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: 07104-0437

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let’s Get Away Swim Bottoms

    This tropical print bikini is just what you need for your next vacay! Pair it with the matching top and sunnies for the perfect beach look.

    Shop the Matching Top: Let’s Get Away Swim Top

    Fits & Features

    • Tie Sides
    • Tropical Print
    • Matching Top 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: 07105-0587

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling It Rainbow Bikini Top

    Add some fun color to your bikini collection! Don’t forget to puck up the matching bottoms to complete your fun summer look.

    Shop the Matching Bottoms: Feeling It Rainbow Bikini Bottoms

    Fits & Features

    • Tie Front & Back Detail
    • Adjustable Straps
    • Under Wire Molded Cups

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

    Style Number/Barcode: 07104-0435

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me to the Tropics Swim Top

    You’ll be ready to lay on a beach in paradise in this tropical bikini. Don’t forget to pick up the matching bottoms to complete the look.

    Shop Matching Bottoms: Take Me to the Tropics Swim Bottoms 

    Fits & Features

    • Ruffle Strap Detail
    • Criss Cross Tie Back
    • Tropical Print
    • Matching Bottoms Sold Separately 

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

    Style Number/Barcode: 07104-0434

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let’s Get Away Swim Top

    This tropical print bikini is just what you need for your next vacay! Pair it with the matching bottoms and sunnies for the perfect beach look.

    Shop the Matching Bottoms: Let’s get Away Swim Bottoms

    Fits & Features

    • Cutout Tie Front Detail
    • Adjustable Straps
    • 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: 07104-0439

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun in The Sun Swim Bottoms

    It’s time to have some fun in the sun and look good while doing it! Don’t forget to get the matching top to complete the look. 

    Shop Matching Top: Fun in the Sun Swim Top

    Fits & Features

    • Hight Waist
    • Scrunch Tie Side Detail
    • Floral Print
    • Matching Top 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: 07105-0581

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hot for Summer Swim Bottoms

    Sit pretty poolside in this red-hot bikini. Complete the look with the matching top.

    Shop the Matching Top: Hot for Summer Swim Top

    Fits & Features

    • O-Ring Sides Detail
    • Matching Top 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: 07105-0584

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling It Rainbow Bikini Bottoms

    Add some fun color to your bikini collection! Don’t forget to puck up the matching top to complete your fun summer look.

    Shop the Matching Top: Feeling It Rainbow Bikini Top

    Fits & Features

    • Tie Side Detail
    • Hipster Fit

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

    Style Number/Barcode: 07105-0583

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me to the Tropics Swim Bottoms

    You’ll be ready to lay on a beach in paradise in this tropical bikini. Don’t forget to pick up the matching top to complete the look.

    Shop Matching Top: Take me to the Tropics Swim Top

    Fits & Features

    • Ruffle Front Detail
    • Tie Sides
    • Tropical Print
    • Matching Top Sold Separately 

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

    Style Number/Barcode: 07105-0582

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just Enough Floral High Waist Pants

    Make a statement in these floral tie waist pants! Dress them up with a basic bodysuit and heels.

    Fits & Features

    • High waist fit
    • Tie waist accent
    • Straight leg
    • Featuring a pop of color floral print
    • Moderate stretch
    • Form fitting down to a relaxed hemline

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

    Style Number/Barcode: 06502-0372

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance