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.

  • Paper Bag Tie Waist Denim Shorts

    Change up your denim game with these adorable paper bag tie waist denim shorts! Pair with a basic tee and some cute wedges to get the perf spring time look.

    Fit & Features

    • High rise elastic banded paper bag waist
    • Tie front belt
    • Button down closure
    • Two front and back pockets
    • Denim fabric | Moderate stretch

    Style Number/Barcode: 06603-0041

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Waist Rolled Hem Jeans Shorts

    Black denim shorts are an essential part of a spring and summer wardrobe! This pair's rolled frayed hem detail is sooo cute. Pair with a basic tee and you're good to go!

    Fit & Features

    • High rise waist
    • Traditional five pocket and belt loop design
    • Front button closure
    • Frayed rolled hem
    • Denim fabric | No stretch

    Style Number/Barcode: 06603-0077

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Get It Together Cinch Jumpsuit

    Girl, look put-together look without the effort! The Get It Together jumpsuit is an effortlessly easy way to look chic. Pair it with some heels to add on some height and a little confidence boost 

    Fits & Features

    • Spaghetti Straps 
    • V Neckline I Square Back
    • Cinch Detail At Center Front Bodice I Elastic Inner Waistband 
    • Wide Leg Openings 
    • Textured Knit Fabric
    • Form Hugging Fit I Plenty Of Stretch 

     

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

    Style Number/Barcode: 06502-0283

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glowed Up Goddess Swim Tank

    Hot fire alert! This swim tank is fit for a bronzed up goddess like u baby! Don't forget to pick up the matching bottoms of course!

    Fit & Features

    • Deep v neckline
    • Tank straps
    • Cut out detailing center bust
    • Lined
    • Ribbed material | Moderate stretch
    • Removable padding | Bar hook closure at back
    • Matching bottoms: 07105-0500

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

    Style Number/Barcode: 07104-0349

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie Style Striped Knit Bodycon Mini Dress

    Show off your cutie style in this adorable mini dress made with striped ribbed knit fabric with high stretch. The strapless sweetheart neckline features a knot detail at the bust and a small keyhole cutout for a trendy detail.

    Fit & Features

    • Striped ribbed knit fabric, knit bust lining, high stretch
    • Strapless sweetheart neckline, no-slip strip
    • Knot detail at the bust, small keyhole cutout
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000016

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heaven Sent Double Cross Pendant Necklace 2 Pack

    Babe you are heaven sent, amen! Style with a single necklace, or wear both for a layered look!

    • Set of two necklaces
    • Cross pendant
    • Adjustable lobster clasp closure
    • Dainty chain

    Style Number/Barcode: 07002-0348

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Anything But Simple Swim Tank

    Make your look a little more than just simple when you choose a unique color for your swim suit! Don't forget the bright swim bottoms to complete ur flattering look!

    Shop Matching Bottoms: Anything But Simple Swim Bottoms

    Fit & Features

    • Scoop neckline
    • Tank straps
    • Fully lined
    • Removable padding
    • Moderate stretch
    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: 07104-0320

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glowed Up Goddess Swim Bottoms

    Hot fire alert! This swim tank is fit for a bronzed up goddess like u baby! Don't forget to pick up the matching swim top of course!

    Fit & Features

    • High waist fit
    • Strappy hip cut out detailing
    • Ribbed material | Moderate stretch
    • Lined
    • Cheeky bottom 
    • Matching swim top: 07104-0349

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

    Style Number/Barcode: 07105-0500

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Anything But Simple Swim Bottoms

    Make your look a little more than just simple when you choose a unique color for your swim suit! Don't forget the bright swim top to complete ur flattering look!

    Shop Matching Top: Anything But Simple Swim Tank

    Fit & Features

    • High waist fit
    • High hip
    • Fully lined
    • Moderate stretch
    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: 07105-0476

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Front And Center Jaguar Cheeky Swim Bottoms

    Keep all eyes front and center when you step out in this elegant and sexy swimsuit! Don't forget to pick up the matching top to complete your look!

    Shop Matching Top: Front And Center Jaguar Triangle Swim Top

    Fit & Features

    • High hip design
    • Mid-rise fit
    • Lined
    • Nylon | Moderate stretch
    • Jaguar pattern

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

    Style Number/Barcode: 07105-0463

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Front And Center Jaguar Triangle Swim Top

    Keep all eyes front and center when you step out in this elegant and sexy swimsuit! Don't forget to pick up the matching bottoms to complete your look!

    Shop Matching Bottoms: Front And Center Jaguar Cheeky Swim Bottoms

    Fit & Features

    • Dainty triangle design
    • No-padding
    • Adjustable spaghetti straps
    • Square back with hook closure
    • Nylon | Moderate stretch
    • Jaguar pattern
    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0306

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Fling Floral Chiffon Ruffle Dress

    Embrace the florals and ruffles in this romantic mini dress! It features peasant long sleeves, a plunge v-neckline, and a babydoll style silhouette with flirty ruffle trim on floral chiffon-lined fabric. Complete the look in a boho ring set.

    Fits & Features

    • Plunging V Neckline
    • Sheer Roomy Long Sleeves I Elastic Cuffs
    • Back Zipper With Hook & Eye Closure 
    • Dual Buton Detail At Nape Of Neck I Cut Out At Back 
    • Mini Length Hemline 
    • Lined Chiffon Fabric With Floral Print I Ruffle-Trim Detail
    • Minimal Stretch 

    Style Number/Barcode: 05102-0470

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Babe Tie Front Top

    Hey there major boho babe! Layer on this tie frop top and have perf effortless beauty look!

    Fit & Features

    • Long sleeves | Elastic banded cuffs | Detailed crochet trim
    • V neckline | Tie front
    • Cropped
    • Sheer woven fabric
    • No stretch

    Style Number/Barcode: 06204-0426

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Babe Flared Pants

    Keep it boho chic with these totally fab pants bby! 

    Fit & Features 

    • High Rise Waist
    • Multi-Colored Bohemian Print 
    • Brushed Knit Fabric 
    • Form Hugging Fit
    • Moderate Stretch 

    Style Number/Barcode: 06502-0264

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Chiffon Long Sleeve Skater Dress

    We're falling for this floral look! It's the perf dress for that special outing you got lined up 

    Fits & Features

    • Surplice V Neckline
    • Cuffed & Unlined, Sheer Long Sleeves 
    • Zipper At Back 
    • Mini Length | Flowy Skater Skirt 
    • Lined, Chiffon Fabric 
    • Minimal 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: 05101-0192

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rich Lifestyle Over-sized Square Sunglasses

    Live that rich lifestyle when you step out in these over-sized shadez! Perfect with a summer dress and a floppy hat!

    • Over-sized design
    • Skinny arms
    • Double stud detailing
    • Dark lenses

    Style Number/Barcode: 07008-0686

    Category Name: Vacation Looks

    Price: $4.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You've Got It Mini Faux Leather Croc Backpack

    You've got it going on girl! Take on the essentials to your next adventure with this ever so cute leather backpack!

    • Mini design
    • Front zipper pouch
    • Faux leather
    • Croc embossed pattern
    • Adjustable straps
    • Two inner pockets

    Style Number/Barcode: 07203-0276

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Can't Miss Her Neon Push-Up Swim Top

    Be the center of attention, in this eye catching swim suit! Don't forget to pick up the matching bottoms to complete the look!

    Shop Swim Bottoms: Can't Miss Her Neon Hipster Swim Bottoms

    Fit & Features

    • Push up design
    • Twist front detailing
    • Double spaghetti straps
    • Double key ring detail at the back
    • Tie back 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: 07104-0294

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Breeze Strapless Slit Maxi Dress

    Enjoy a sunset dinner by the beach in this chic strapless maxi dress showcasing a high slit for effortless movement and a flattering bodycon silhouette.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, twist accent
    • Bodycon silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000052

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Can't Miss Her Neon Hipster Swim Bottoms

    Be the center of attention, in this eye catching swim suit! Don't forget to pick up the matching top to complete the look!

    Shop Matching Top: Can't Miss Her Neon Push-Up Swim Top

    Fit & Features

    • Mid-rise fit
    • High hips
    • Cheeky bottom
    • Tie detailing at the hip
    • Fully lined
    • Neon | Moderate stretch

    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: 07105-0450

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling Star Chain Belt

    Sport this belt, and let them know ur the star here. Style with your high waist bottoms, or create the perfect accent when you style atop your bikini!

    • Chain link design
    • Drop star detailing
    • Lobster clasp closure

    Style Number/Barcode: 07301-0132

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made For Sunny Dayz One Piece Bathing Suit

    Babe you were made for sunny days, and your tan lewks so bomb when you wear white!!

    Fit & Features

    • One piece white swimsuit
    • Adjustable spaghetti straps
    • V neckline | Mesh inserts
    • Cheeky bottom
    • Mesh hip detailing
    • Moderate stretch
    • Padded

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

    Style Number/Barcode: 07109-0133

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pic-Worthy Panama Hat

    Do it for the gram babe, this pic worthy panama gives us that blogger on vacay vibe that we all know and love!

    • Wide brim
    • Belted detailing
    • Faux wool

    Style Number/Barcode: 07302-0119

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eyelet Detail Floral Romper

    This romper is so sweet & adorable - just like you! Get major girl next door vibes pairing this with some cute wedges!

    Fit & Features

    • Three quarter length puff sleeves | Ruffle hems
    • Sweetheart neckline | Tie front detail
    • Front key hole cut out
    • Hidden back zipper | Hook and eye closure
    • High waist seam
    • Fitted shorts
    • Floral printed eyelet cut out woven fabric | Woven lining

    Style Number/Barcode: 06303-0053

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance