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.

  • Blooming Beauty Satin Tie Front Top

    Add some floral flair to your look with the Blooming Beauty tie front top! Wear it with your fave high waisted jeans or some faux leather pants! 

    Fits & Features

    • Long Sleeves With Elastic Banded Cuffs
    • Plunging V Neckline 
    • Tie Front Detail 
    • Crop Hemline 
    • Satin-Like Fabric | Floral Prints Throughout
    • Minimal Stretch 

    Style Number/Barcode: 06204-0437

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Rise Destructed Straight Leg Jeans

    Everyone needs a good pair of destructed denim in their wardrobe! These high rise straight leg jeans are the perf pair!

    Fit & Features

    • High rise waist
    • Traditional five pocket and belt loop design
    • Front button down closure
    • Destructed detailing at thigh, knee, and ankles
    • Straight leg fit | Frayed hem
    • Denim fabric | Minimal stretch

    Style Number/Barcode: 06602-0093

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tobi Super High Rise Destructed Mom Jeans

    Oasis by Eunina

    You need a pair of our Tobi super high rise mom jeans! With their trendy fit and destructed detailing, they're a definite add to cart item.

    Fit & Features

    • Super high rise waist
    • Traditional five pocket and belt loop design
    • Front button | Hidden zipper closure
    • Destructed detailing down the front
    • Ankle cut hem
    • Denim fabric | Moderate stretch

    Style Number/Barcode: 06602-0109

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Denim Doll Distressed Overall Shorts

    Rock a retro look in these short denim overalls! Go for a laidback look by styling an off-shoulder top and a wide brim hat. Level up your OOTD by pairing it with a sheer long sleeve top and some heels! 

    Fits & Features

    • Racerback Straps With Snap Buckle Closure
    • Front Bib Pocket 
    • Traditional 5-Pocket Styling 
    • Belt Loops I Zipper At The Side Seam 
    • Distressing Throughout I Fringe & Frayed Hem
    • Sturdy Denim Composition I Minimal Stretch 

    Model is 5'6" with a 31" bust, 26" waist and 36" hips. She is wearing a size small. 

      Style Number/Barcode: 06603-0085

      Category Name: Vacation Looks

      Price: $6.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Spring Has Sprung Floral Romper

      Spring forward in this adorable floral romper! Pair with some chic clear mules and your fave handbag and you'll be ready for lunch with the girls!

      Fit & Features

      • Short puff sleeves
      • Sweetheart neckline
      • Tie front detail | Small keyhole cut out
      • Elastic banded high waist seam
      • Flowy shorts
      • Ditsy floral print
      • Knit fabric | Plenty of stretch

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

      Style Number/Barcode: 06503-0104

      Category Name: Vacation Looks

      Price: $6.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Baby Just Ask Tie Front Knit Mini Dress

      Babe, prepare yourself, because they will all be asking where you copped this knit mini dress! Style with heels, or do what we are loving right now and throw on some sneaks and a scrunchy for an effortless cool!

      Fit & Features

      • Off shoulder neckline
      • Eyelet lattice tie front detail
      • Long sleeves that puff at the wrist
      • Form fitting silhouette0
      • Mini hemline
      • Ribbed knit material
      • Moderate stretch

      Style Number/Barcode: 06005-0541

      Category Name: Vacation Looks

      Price: $6.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Girly Gingham Print Ruffled Mini Dress

      You love all things girly, so this adorable gingham print mini dress is perfect for you. The all-over smocked design adds stretch, while the ruffled neck and hem bring the cutesy vibe.

      Fit & Features

      • Smocked cotton fabric, high stretch
      • Gingham print
      • Sleeveless sweetheart neckline, ruffled trim, small bow detail
      • Adjustable spaghetti straps
      • Mini-length ruffled hem
      • Form-hugging fit
      • Runs true to size

      Style Number/Barcode: 05102-000160

      Category Name: Vacation Looks

      Price: $19.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Lovely In Linen Smocked Mini Dress

      Look oh so lovely in linen in this perf springtime mini! The smocked detailing make it all the more flattering!

      Fit & Features

      • Long sleeves | Smocked cuffs
      • Square neck | Eyelet trim detail
      • Front tie | Keyhole cut out
      • Stretchy smocked skirt
      • Short, ruffle hem
      • Linen fabric

      Style Number/Barcode: 05102-0681

      Category Name: Vacation Looks

      Price: $9.97 $46.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Poised In Petals Floral Chiffon Bodysuit

      Look pretty and poised in this flowy bodysuit! Team the look up with a pair of denim skinny jeans or a mini skirt!

      Fits & Features

      • Surplice Plunging V Neckline With Single Snap Button Closure
      • Roomy Sheer Long Sleeves I Elastic Cuffs
      • Thong Bottom With Dual Snap Button Closure 
      • Chiffon Fabric I Lined At The Front Bodice 
      • Relax Fit I Minimal Stretch 

      Style Number/Barcode: 06003-0575

      Category Name: Vacation Looks

      Price: $6.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Leopard Purrfection Satin Midi Dress

      Tap into your instincts with this fiercely-inspired print! This midi dress only needs a pair of booties and dainty pieces to complete the look!

      Fit & Features 

      • V-Neckline
      • Spaghetti Straps 
      • Leopard Print
      • Side Slit 
      • Lined Satin Fabric 
      • Relaxed Fit 
      • Minimal Stretch 

       


      Style Number/Barcode: 05101-0599

      Category Name: Vacation Looks

      Price: $9.97 $46.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Float On Balloon Sleeve Mesh Crop Top

      Breeze through any occasion looking oh-so-stylish and chic in this mesh crop top! Pair with some skinny jeans and a cute pair of heels! 

      Fits & Features

      • V Neckline
      • Sheer Balloon Sleeves I Elastic Shoulders 
      • Drawstring Front I Ruching Along The Back 
      • Crop Hemline 
      • Mesh Fabric With Knit Lined Bodice 
      • Form Hugging Fit I Moderate Stretch 

      Style Number/Barcode: 06001-2448

      Category Name: Vacation Looks

      Price: $9.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • In Bloom Floral Crop Top

      Your beauty is blooming! Catch the floral fever and flaunt a springtime look in this cute top! 

      Fits & Features

      • Sheer Back & Ruched Short Sleeves
      • Plunging V Neckline
      • Crop Hemline I Decorative Button-Front 
      • Mesh Floral Printed Fabric I Lined At The Front Bodice 
      • Form Hugging Fit I Moderate Stretch

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

      Style Number/Barcode: 06003-0724

      Category Name: Vacation Looks

      Price: $9.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Kara High Rise Denim Shorts

      Every babe needs a staple pair of high rise denim shorts in her life for those warmer days! Style with an over-sized tee or even a pretty cropped blouse!

      Fit & Features

      • High rise fit
      • Destructed detailing
      • Zipper + button closure
      • Cuffed hemline
      • Light-wash denim
      • Slight stretch

      Model is 5'9" with 32" bust, 23" waist and 36" hips. She is wearing a size small.    

      Style Number/Barcode: 06603-0029

      Category Name: Vacation Looks

      Price: $6.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Ditsy Floral Daze Mini Dress

      Ditsy florals are the trendy print of the season! This floral printed dress features a sleeveless square neckline with ruffle spaghetti straps, ruched detailing down the side, and a mini-length, curve-hugging silhouette. Pair this adorable dress with some cute strappy sandals for the perf daytime 'fit!

      Fit & Features

      • Ruffle spaghetti straps
      • Square neck and back
      • Ruched side detailing, adjustable drawstring at hem
      • Short, form-hugging fit
      • Ditsy floral print
      • Ribbed knit fabric, plenty of stretch
      • Runs true to size

      Style Number/Barcode: 05102-0524

      Category Name: Vacation Looks

      Price: $9.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Casual Cutie Denim Romper

      Keep it casually cute in this adorable denim romper! Pair with some booties and you'll be stylin' 

      Fit & Features

      • Short puff sleeves
      • Sweetheart neckline | No slip strip
      • Bust seam detailing
      • Back zipper | Hook and eye closure
      • High waist
      • Fitted shorts
      • Denim fabric | Moderate stretch

      Style Number/Barcode: 06603-0059

      Category Name: Vacation Looks

      Price: $9.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Feelin' Fine Chain Sunglasses

      Feel like a dime when you style sunglasses with all of ur summer looks! They have a high end finish and a sleek black vibe that we are obsessed with!

      • Skinny frame
      • Chain detail
      • 100% UV 
      • Geometrical shape

      Style Number/Barcode: 07008-0717

      Category Name: Vacation Looks

      Price: $4.97 $9.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • State The Facts Cat Eye Sunglasses

      It's a fact that you look amazin' in cat eye sunglasses! Style with a sweet summer dress and an over-sized straw purse for a complete vibe!

      • Over-sized
      • Cat eye design
      • Golden line accent atop
      • 100% UV protection

      Style Number/Barcode: 07008-0714

      Category Name: Vacation Looks

      Price: $4.97 $9.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Truly Posh Over-sized Square Sunglasses

      Keep it posh and sleek with a pair of over-sized sunnies! Style with a vintage inspired kimono, or even a jumpsuit!

      • Over-sized square frame
      • Ombre effect
      • Skinny arms
      • 100% UV protection

      Style Number/Barcode: 07008-0711

      Category Name: Vacation Looks

      Price: $4.97 $9.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Too Cool For 'Em Oval Sunglasses

      Hunny you are too kewl in those stunner shades! Style with an all black 'fit and make a statement with them!

      • Oval design
      • Thick white frame
      • 100% UV protection
      • Dark lenses

      Style Number/Barcode: 07008-0716

      Category Name: Vacation Looks

      Price: $4.97 $8.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • So Sleek Block Heel Booties

      Take these perfectly polished babes from work to weekend without a hitch! Booties feature a, faux leather outer, a gently pointed toe, a low shaft with back zip, and a stabilizing, medium-height block heel. Complete look with a shacket and skinny jeans.

      Fit & Features

      • Around the ankle fit
      • Back zipper closure
      • Pointed toe
      • Block heel
      • Faux leather material
      • Runs small to size


      Please be advised that these boots run a 1/2 size too small.

      Style Number/Barcode: 07403-0228

      Category Name: Vacation Looks

      Price: $4.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Serving Curves Keyhole Maxi Dress

      Serving curves and confidence—this dress eats every time. The keyhole cutout and body-hugging silhouette? A certified head-turner for nights that don’t end early.

      Fit & Features

      • Stretchy textured knit fabric
      • Scoop neckline with spaghetti straps
      • Front keyhole cutout at bust
      • Form-hugging silhouette
      • Maxi-length hem
      • Runs true to size

      Style Number/Barcode: 05102-000166

      Category Name: Vacation Looks

      Price: $9.97 $35.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Keeping Knit Cropped Top

      Keep it cropped and fab in this top! Pair this knit top with distressed denim with lots of fringe!

      Fit & Features

      • Crew Neckline
      • Short Sleeves
      • Unlined Textured Knit Fabric
      • Cropped Hem 
      • Relaxed Fit 
      • Plenty of Stretch 
      • Undergarments and Liners Sold Separately 


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

      Style Number/Barcode: 06001-2576

      Category Name: Vacation Looks

      Price: $6.97 $16.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • As Good As Knit Gets Mini Dress

      This chic white knit mini dress is as good as it gets! Paired with some glam earrings and strappy heels, you'll be lookin' fine bb!

      Fit & Features

      • Spaghetti straps
      • Wrap front V neckline
      • Ruched side detailing
      • Short envelope hem
      • Ribbed knit fabric
      • Plenty of stretch

      Style Number/Barcode: 05102-0620

      Category Name: Vacation Looks

      Price: $12.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Wide Leg Leopard Mesh Pants

      Bring the flare with these fierce pants! The leopard print purrrfectly pairs with your favorite bold pieces! Pair with platforms for a boho vibe!

      Fit & Features

      • High Rise Elastic Waist 
      • Leopard Print
      • Sheer 
      • Unlined Mesh Fabric 
      • Form Hugging Fit 
      • Moderate Strech 
      • Flared Hem 

       

      Style Number/Barcode: 06502-0307

      Category Name: Vacation Looks

      Price: $11.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free