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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.

  • Heat Wave Bar Front Bandeau Swim Top

    Everyone's going to feel the heat as soon as you walk on by in this sizzling swim set! Obvi. don't forget to add the matching swim bottoms to cart 

    Shop Matching Bottoms: Heat Wave Bar Side Hipster Swim Bottoms

    Fits & Features

    • Bandeau-Style Swim Top 
    • Detachable Spaghetti Straps That Tie At The Nape
    • Lined With Removable Padded Bust 
    • Back Hook Closure
    • Heat Stone Embellishments & Bar Accents At Front 

     

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

    Style Number/Barcode: 07104-0350

    Category Name: Vacation Looks

    Price: $7.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Poolside Elegance Floppy Straw Hat

    Bring that poolside elegance with a floppy hat and some chic over-sized shades hunnayyy!

    • Medium size
    • Round top
    • Wide floppy brim
    • Woven straw with black woven detailing

    Style Number/Barcode: 07302-0166

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed Babe High Waist Swim Bottoms

    Bask under the sun like the sunkissed babe you are in these adorable swim bottoms! Pair with the matching swim top for the perf poolside lewk!

    Shop Matching Top: Sunkissed Babe Puff Sleeve Swim Top

    Fit & Features

    • High rise waist
    • High cut design
    • Cheeky bottom

     

    Model is 5'7" with a 34" 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: 07105-0453

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sherbet Rainbow Striped High Waist Bikini Bottoms

    Bring a pop of color to your summer vibes with a striped bikini! Don't forget to pick up the matching top to complete your summer fun look!

    Fit & Features

    • High waist fit
    • Strappy sides
    • Cheeky bottom
    • Rainbow stripe pattern

    Model is 5'6" with 33" bust, 26" waist and 36" hips. She is wearing a size small.  

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

    Style Number/Barcode: 07105-0525

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Only One For You Bandeau Swim Top

    This one shoulder bandeau swim top is obvi the only one for you! Grab your fave sunnies and bask in the sun pool side.

    Shop Matching Bottoms: Only One For You High Waist Swim Bottoms

    Fit & Features

    • One shoulder sweetheart neckline
    • Bandeau design
    • Center O-ring detail

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

    Style Number/Barcode: 07104-0318

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Outside The Box Acrylic Clutch
    You think outside the box and you've got nothing to hide—so you definitely need this covertable acrylic clutch! It has a 3-D rectangular construction, a short chain-link top handle, and gold-tone hardware including snap-shut closure.

    Style Number/Barcode: 07204-0053

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Only One For You High Waist Swim Bottoms

    These high waist swim bottoms are obvi the only ones for you! Grab your fave sunnies and bask in the sun pool side.

    Shop Matching Top: Only One For You Bandeau Swim Top

    Fit & Features

    • High rise elastic banded waist
    • High cut design
    • Cheeky bottom

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

    Style Number/Barcode: 07105-0474

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wide Brim Boater Hat
    With versatile style for all seasons this hat features a boater design, it has a wide brim and features a chain link belt! Hat is composed of a faux wool material.

    Style Number/Barcode: 07302-0012

    Category Name: Vacation Looks

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glisten And Glimmer Swim Bottoms

    Glisten & glimmer like the total goddess you are in these perf swim bottoms! Don't forget to purchase the matching top.

    Shop Matching Top: Glisten And Glimmer Swim Top

    Fit And Features

    • Hipster V design
    • Cheeky bottom
    • Shimmer knit fabric

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

    Style Number/Barcode: 07105-0560

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lasting Romance Strapless Lace Crop Top

    Romance yourself in this strapless lace crop top perfect for teaming with cute shorts!

    Fit & Features

    • Semi-lace lined fabric
    • Strapless sweetheart neckline
    • Twisted lined bust
    • Center split accent
    • Sheer bodice
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5722

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gold Moments Butterfly Clips

    Add a romantic finish to your look when you top it off with adorable butterfly clips! Style with a floral dress and strappy heels and captivate the room!

    • Set of two clips
    • Butterfly design
    • Gold finish

     

    Style Number/Barcode: 07006-0155

    Category Name: Vacation Looks

    Price: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss Americuh Bikini Swim Bottoms

    God bless america, and that fine bod' babe! Amen! Throw on this top for a 4th of July bbq with jean shorts and some boots, or pick up the matching bottoms for a pool partayy!

    Shop Matching Top: Miss Americuh Bikini Swim Top

    Fit & Features

    • Blue with white stars
    • Mid-rise fit
    • Lined
    • Tie hip strings
    • Moderate stretch

    Style Number/Barcode: 07105-0548

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clearly On Trend Box Clutch

    Clearly stay on trend with this must-have clutch! Pair this beauty with your favorite pieces to complete your look!

    • Clear Body
    • Rectangular Design
    • Metal Trim
    • Top Snap Closure
    • Detachable Chain Shoulder Strap

    Style Number/Barcode: 07203-0282

    Category Name: Vacation Looks

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunkissed Babe Puff Sleeve Swim Top

    Bask under the sun like the sunkissed babe you are in this adorable swim top! Pair with the matching swim bottoms for the perf poolside lewk!

    Shop Matching Bottoms: Sunkissed Babe High Waist Swim Bottoms

    Fit & Features

    • Off the shoulder neckline with short puff sleeves
    • Twist front detail
    • Unpadded
    • Back hook closure

     

    Model is 5'7" with a 34" 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: 07104-0297

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bling Bling Bby Rhinestone Sunglass Chain

    It's not just ur granny that can sport a glasses chain bae, show her up when you add a lil rhinestone in the mix!

    • Double row of rhinestones
    • Adjustable silicone attachment
    • Available in gold & iridescent

    Style Number/Barcode: 07002-0358

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sherbet Rainbow Striped Bikini Top

    Bring a pop of color to your summer vibes with a striped bikini! Don't forget to pick up the matching bottoms to complete your summer fun look!

    Fit & Features

    • Tie front detail
    • Halter neckline with tie strap 
    • Bar hook closure
    • Wired + padded
    • Rainbow stripe pattern

    Model is 5'6" with 33" bust, 26" waist and 36" hips. She is wearing a size small.

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

    Style Number/Barcode: 07104-0376

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild One Color Block Swim Bottoms

    You're a wild one when it comes to your style! These color block swim bottoms will give you a trendy vibe! Be sure to pair them with the matching top.

    Shop Matching Top: Wild One Tie Front Swim Top

    Fit & Features

    • V cut design
    • Cheeky bottom
    • Color block pattern
    • Leopard print

    Model is 5'6" with 33" bust, 26" waist and 36" hips. She is wearing a size small.

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

    Style Number/Barcode: 07105-0536

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cancun Vibes Wooden Beaded Mini Purse

    Get those total vacay vibes going when you top your look off with a neutral toned beaded mini purse! It only needs to hold one thing, that sun tan lotion!

    • Rectangular design
    • Light to dark coloring
    • Wooden beading
    • Double handles
    • Unlined
    • Removable chain link crossbody strap

    Style Number/Barcode: 07203-0219

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Extra Large Sleek Hoops

    These extra large hoop earrings are a must-have for your jewelry collection. With their sleek finish, they add the perfect amount of glam to any outfit. The omega closure is great for easy wear. Accessorize with them for a day date with your bae! Pair with a basic tee and your favorite mom jeans to elevate the look.

    Fit & Features

     

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

    Style Number/Barcode: 07001-0112

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Vibes Aviator Sunglasses

    You are givin' us major vibes in aviators hunny! Style with a graphic tee, sneakers, and a graphic tee for that effortlessly edgy finish.

    • Small aviator design
    • Skinny arms
    • Golden frame
    • 100% UV protection
    • Ombre lenses

    Style Number/Barcode: 07008-0710

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Find Me In Paradise Drawstring Swim Top

    Find yourself in paradise in the most flattering swim suit, with a drink in hand and sand between your toes. All you need is a curve flattering basic swimsuit to live in all vacay long! Don't forget to pick up the matching bottoms!

    Fit & Features

    • V-neckline
    • Adjustable spaghetti straps
    • Drawstring center
    • No padding
    • Matte nylon
    • Moderate stretch
    • Link to matching swim bottoms: 07105-0496

    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.   

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

    Style Number/Barcode: 07104-0345

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Flounce Off The Shoulder Swim Top

    Give off a flirty flair in this flounce detail off the shoulder swim top! Pair with the matching swim bottoms to complete your adorable look.

    Shop Matching Bottoms: Flirty Criss Cross High Waist Swim Bottoms

    Fit & Features

    • Off the shoulder neckline
    • Ruffle overlay
    • Removable padding
    • Lined
    Model is 5'7" with a 34" 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: 07104-0354

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Wave Bar Side Hipster Swim Bottoms

    Everyone's going to feel the heat as soon as you walk on by in this sizzling swim set! Obvi. don't forget to add the matching swim top to cart 

    Shop Matching Top: Heat Wave Bar Front Bandeau Swim Top

    Fits & Features

    • Hipster-Style Swim Bottoms 
    • Triple Bar Side Accents 
    • Cheeky Fit & Coverage
    • Lined With Heat Stone Embellishments At The Front 

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

    Style Number/Barcode: 07105-0501

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Energy High-Rise Midi Skirt

    Bring the energy to your destination getaway in this tropical midi skirt, designed with a sleek high-rise waist and form-hugging silhouette. Pair it with the matching top.

    Fit & Features

    • Tropical print, mesh fabric, soft knit stretchy lining
    • High-rise waist
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

     

    Shop The Matching Top: Tropical Energy Strapless Crop Top

    Style Number/Barcode: 06501-000010

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free