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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 Distressed Cuffed Shorts

    A trendy edition to your closet, these paper bag cuffed shorts will go with all of your spring time looks!

    Fit & Features

    • High rise elastic banded paper bag waist
    • Front button | Hidden zipper closure
    • Two front and back pockets
    • Slight distressed detailing 
    • Cuffed hems
    • Denim fabric | No stretch

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

    Style Number/Barcode: 06603-0063

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Denim Dream Culotte Jumpsuit

    Look like a dream in denim in this trendy culotte jumpsuit! Tie your look together with some cute heels!

    Fit & Features

    • Ruffle tank-like shoulder straps
    • Slight sweetheart neckline
    • Stretchy smocked back
    • High waist | Tie front belt
    • Side zipper closure
    • Cropped culotte pant legs
    • Jean fabric | 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: 06602-0096

    Category Name: Vacation Looks

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Soak It Up Buckle Swim Tank

    Soak up the sun because life is cool by the pool babe, and you are the coolest with ur top of the line swimsuit style! Don't forget to pick up the matching swim bottoms for a full on lewk!

    • Tank style swim top
    • Cut out detail 
    • Buckle accent
    • Hook closure
    • Moderate stretch
    • Matching bottoms: 07105-0461

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

    Style Number/Barcode: 07104-0304

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle It Up Flowy Romper

    Ruffle your fab look up with this flowy romper, perf for a stroll with your bae!

    Fit & Features

    • Long sleeves | Elastic banded cuffs | Ruffle detailing
    • Wrap front V neckline | Snap button closure
    • Back button closure | Large keyhole cut out
    • Elastic banded high waist
    • Shorts with ruffle hem | Flowy overlay
    • Woven fabric | No stretch

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

    Style Number/Barcode: 06303-0051

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spring Time Chic Tie Front Bodysuit

    Get ready for a spring time chic vibe with this adorable tie front bodysuit! Paired with some light wash denim and cute wedges, you'll be ready for brunch with the girls!

    Fit & Features

    • Cap sleeves
    • Tie front | Keyhole cut out
    • High waist seam
    • Scoop back
    • Thong bottom | Dual snap button closures
    • Ribbed knit fabric | Plenty of stretch

    Style Number/Barcode: 06002-0445

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Vibes Tie Front Top

    Get all those effortless beachy vibes in this lightweight, flowy tie front top!

    Fit & Features

    • Flowy kimono sleeves
    • V neckline
    • Tie front detail
    • Striped print
    • Rayon woven fabric | No stretch

    Style Number/Barcode: 06204-0403

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Button Detail Ribbed Knit Bodysuit

    The perfect simple & stylish bodysuit you need in your closet! Pair with some high rise jean shorts and strappy sandals for that laid back, casual cute vibe!

    Fit & Features

    • Tank-like shoulder straps
    • Deep V notched neckline
    • Partial snap button front
    • Cheeky bottom | Dual snap button closures
    • Ribbed knit fabric | Plenty of stretch
    • Form hugging fit

    Style Number/Barcode: 06001-2574

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take A Stroll Denim Overall Shorts

    Take a stroll down memory line in these 90s-inspired overalls! Wear a lightweight long sleeve underneath or pair it with an oversized band tee for a laidback look! 

    Fits & Features

    • Racerback Straps With Snap Buckle Closure 
    • Front Bib Pocket With Small Coin Pocket
    • 4-Pocket Styling 
    • Buttons At The Side Seam
    • Rolled Hem 
    • Denim Fabric I Moderate Stretch 

    Style Number/Barcode: 06603-0064

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tied And True Knit Top

    You have an adorable sense of style, and this knit top will give you that casual cute look you love! Pair with some light wash jeans for the perfect everyday outfit!

    Fit & Features

    • Adjustable tie shoulder straps
    • Twist front accent
    • Mid-length, form hugging fit
    • Ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06001-2673

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Daze Tie Front Top

    Get into a boho daze with this casual & cute tie front top! Style with some high waist jeans or layer over a bikini for the perf beach day look!

    Fit & Features

    • Flowy three quarter length kimono sleeves
    • V neckline
    • Tie front detail
    • Rayon crinkle woven fabric | No stretch

    Style Number/Barcode: 06204-0986

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Coast Dream Paisley Bodycon Slit Maxi Dress

    Enjoy a vacay or day out by the sunshine coast in this paisley maxi dress with a flattering bodycon fit and side slit for effortless movement!

    Fit & Features

    • Paisley boho print, mesh fabric, sewn-in brushed knit lining
    • Square neckline
    • Spaghetti straps, criss cross back
    • Bodycon silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5928

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Yummy Embroidered Baseball Cap

    Bae you got that yummy yum, style with your all black jogger suit, and stay flexin'

    • Traditional design
    • Adjustable backing
    • "Yummy" embroidered script

    Style Number/Barcode: 07302-0171

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tired Of The B.S Baseball Cap

    Oh hunny, aren't we all tired of the b.s? ughh let em know when you throw on this baseball cap with an over sized hoodie and biker shorts!

    • Traditional design
    • Adjustable backing
    • Embroidered " Tired of the B.S" script

    Style Number/Barcode: 07302-0172

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • O-Ring Detail High Waist Swim Bottoms

    Bask in the sun on your next vacay lookin' fine in these simply chic high waist swim bottoms!

    Shop Matching Top: O-Ring Detail Bandeau Swim Top

    Fit & Features

    • High rise waist
    • Side wooden O-ring detail
    • Cheeky bottom

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

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

    Style Number/Barcode: 07105-0454

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • O-Ring Detail Bandeau Swim Top

    Bask in the sun on your next vacay lookin' fine in this simply chic bandeau swim top!

    Shop Matching Bottoms: O-Ring Detail High Waist Swim Bottoms

    Fit & Features

    • Strapless sweetheart neckline
    • Center wooden O-ring detail
    • Back clasp closure

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

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

    Style Number/Barcode: 07104-0298

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soak It Up High Waist Swim Bottoms

    Soak up the sun because life is cool by the pool babe, and you are the coolest with ur top of the line swimsuit style! Don't forget to pick up the matching swim top for a full on lewk!

    • High waist swim bottoms
    • Cheeky bottom
    • Moderate stretch
    • Matching top: 07104-0304

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

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

    Style Number/Barcode: 07105-0461

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea-foam Knotted Swim Bottoms

    Spend your days lying sea-side in a picture perfect swimsuit all summer long! Just don't forget to pick up your matching swim top!

    Shop The Matching Top: Sea-foam Tie Front Swim Top

    Fit & Features

    • Mid-rise fit
    • Self tie hip detailing
    • Cheeky bottom
    • Moderate stretch

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

    Style Number/Barcode: 07105-0464

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea-foam Tie Front Swim Top

    Spend your days lying sea-side in a picture perfect swimsuit all summer long! Just don't forget to pick up your matching swim bottoms!

    Shop The Matching Bottoms: Sea-foam Knotted Swim Bottoms

    Fit & Features:

    • Tie front detail
    • Removable padding
    • Cap sleeves
    • Lined
    • Bar hook closure
    • Moderate stretch

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

    Style Number/Barcode: 07104-0307

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Places To Be Square Toe Wedges

    Places to be, people to see, pedis to show off! Change out your old wedges for something a little different! Square toe is here to stay!

    • Open square toe
    • Single band over the toe
    • Adjustable pin buckle closure
    • Silver hardware
    • Wedge heel
    • Faux suede

    Style Number/Barcode: 07406-0079

    Category Name: Vacation Looks

    Price: $22.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Welcome To Paradise Ruffle Swim Top

    One ticket for paradise please! We are all packed and ready to go, but we are not heading out before picking up a paradise go-to palm leaf swimsuit! Don't forget to pick up the matching swim bottoms to complete the look!

    Fit & Features

    • Adjustable spaghetti straps
    • Push-up cups | Non- removable
    • Ruffled trim
    • Bar hook closure
    • Palm leaf pattern
    • Bow detailing center bust
    • Matching bottoms: 07105-0469

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

    Style Number/Barcode: 07104-0313

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Welcome To Paradise Ruffle Swim Bottoms

    One ticket for paradise please! We are all packed and ready to go, but we are not heading out before picking up a paradise go-to palm leaf swimsuit! Don't forget to pick up the matching swim top to complete the look!

    Fit & Features

    • Mid-rise fit
    • Ruffled trim
    • Self tie closures at the hip
    • Palm leaf pattern | Moderate stretch
    • Fully lined
    • Matching top: 07104-0313

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

    Style Number/Barcode: 07105-0469

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let's Get Cheeky High Hip Swim Bottoms

    Let's get a little cheeky this summer in a swimsuit that screams fun and flirty! Don't forget ur matching top to complete the look!

    Shop Matching Bottoms: Let's Get Cheeky Wired Swim Top

    Fit & Features

    • High hip design
    • Cheeky bottom
    • Fully lined
    • Nylon | 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: 07105-0477

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let's Get Cheeky Wired Swim Top

    Let's get a little cheeky this summer in a swimsuit that screams fun and flirty! Don't forget to pick up ur matching swim bottoms to complete the look!

    Shop Matching Bottoms: Let's Get Cheeky High Hip Swim Bottoms

    Fit & Features

    • Wired
    • Adjustable spaghetti straps
    • Bar hook closure center back
    • Fully lined
    • Nylon | 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: 07104-0323

    Category Name: Vacation Looks

    Price: $19.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Vibes Skater Dress

    Escape on vacay in this gorg tropical printed skater dress! Pair with some heels and accessorize with a cute woven bag and live it up!

    Fit & Features

    • Off the shoulder square neckline | Ruffle trim
    • Long sleeves | Elastic banded hems
    • High rise elastic banded waist
    • Tie front belt
    • Flowy skater skirt | Woven lining
    • All over colorful palm print

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

    Style Number/Barcode: 05102-0603

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free