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.

  • Floral Focus Off The Shoulder Top

    Your whole squad will focus in on your adorable floral top and want to know the deets! With its smocked detailing and loose sleeves, this piece is just too cute.

    Fit & Features

    • Off the shoulder neckline
    • Long loose sleeves | Smocked cuffs
    • Stretchy smocked bodice
    • Slight ruffle hem
    • Woven fabric | All over rose print

    Model is 5'7" with 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0467

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Zebra Front Slit Midi Dress

    Make a bold first impression in this statement dress! Pair with your fave leather jacket and some heels for a cute OOTN! 

    Fits & Features

    • Adjustable Spaghetti Straps
    • V Neckline I Back Zip With Hook & Eye Closure
    • Lined At The Bodice
    • Midi Length Silhouette I Front Slit 
    • Woven Fabric I Zebra Print Throughout 
    • Relax Fit I No Stretch 

    Style Number/Barcode: 05102-0368

    Category Name: Vacation Looks

    Price: $12.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lace Up Ditsy Floral Crop Top

    Lace up into this absolutely adorable ditsy floral printed crop! Pair with some denim for a casual cute vibe.

    Fit & Features

    • Long puffed sleeves with elastic banded cuffs
    • Sweetheart neckline
    • Lace up lattice front
    • Smocked back
    • Cropped
    • Woven fabric

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

    Style Number/Barcode: 06003-0437

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lydia Floral A-Line Dress

    Special Occasion

    Enchant them all as you walk right past them in our beautiful Lydia! Her flowy silhouette enhances the way you enter (and exit!) a room. 

    Fits & Features

    • Deep V Neckline I Pleating Accents At The Bust
    • Adjustable Spaghetti Straps Cross At The Back 
    • Back Zip With Hook & Eye Closure 
    • Flowy, Floor Length Skirt I A-Line Silhouette I Mini Length Lining
    • Chiffon Fabric I Floral Prints Throughout 
    • Relax Fit 

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

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0663

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bloom Babe Ditsy Surplice Top

    Blossom and bloom in this adorable top! 

    Fits & Features

    • Plunging V Neckline | Surplice Front Design 
    • Cuffed Long Sleeves
    • Smocked Waistband 
    • Cropped Hemline
    • Relaxed, Form-Fitting Silhouette
    • Ditsy Floral Print Throughout 

     

    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0436

    Category Name: Vacation Looks

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic With An Edge Satin Tie Front Top

    Chic with an edge, this satin tie front top can easily be layered on to make a trendy 'fit. It features a lapel collar, V neckline, tie front closure, and a cropped hem. The top is composed of a leopard print satin-like fabric with no stretch. Pair this top with mom jeans and strappy heels.

    Fit & Features

    • Lapel collar
    • V neckline
    • Tie front closure
    • Long sleeves with a button to cuff
    • Cropped hem
    • Leopard print
    • Satin-like fabric with no stretch

    Style Number/Barcode: 06204-0362

    Category Name: Vacation Looks

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Fierce Satin Leopard Print Crop Top

    Keep your 'fit forever fierce in this trendy satin leopard print crop top!

    Fit & Features

    • Deep V neckline
    • Long exaggerated sleeves | Elastic banded cuffs
    • Partial button down front
    • Cropped
    • Satin-like fabric | No stretch

    Style Number/Barcode: 06003-0558

    Category Name: Vacation Looks

    Price: $11.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Boho-Chic Tie-Front Top

    Get that boho-chic vibe going in this adorable tie-front top! It features long blouson sleeves, a deep V neckline, a tie detail that can be tied in the front or the back, and a cropped, form-hugging fit. Complete your outfit with printed flare pants and strappy sandals.

    Fit & Features

    • Long sleeves with elastic banded cuffs
    • Deep V neckline
    • Tie detail that can be tied in the front or the back
    • Cropped, form-fitting style
    • Sheer dot textured woven fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06204-0297

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Call Me Later Oversized Square Sunglasses

    For when you're not taking calls—just compliments. These oversized square sunglasses bring bold energy with glam rhinestone side detailing and an effortlessly luxe look.

    Fit & Features

    • Oversized square-shaped design
    • Plastic frame with glossy finish
    • Thick arms with rhinestone cutout accents
    • Built-in nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000060

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fresh Pick Flowers Mini Dress

    A sweet addition to any wardrobe! This fabulous floral dress features adjustable spaghetti straps falling into a v-neckline, self-ties and keyhole detail at back. The garment is composed of scuba fabric with a sleek knit lining. It offers a form-hugging fit with plenty of stretch. Zipper not included. 

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

    Style Number/Barcode: 05101-0012

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Kendra Two Piece Lace & Chiffon Dress

    Special Occasion

    Take everyone's breath away as you walk out in our beautiful Kendra! 

    Fits & Features

    • Glitter Lace Top With Full Knit Lining I Glitter May Transfer
    • Tank-Inspired Straps I Back Zip With Hook & Eye Closure
    • Scallop V Neckline & Crop Hem I Padded Bust
    • Lined Chiffon Skirt With All Over Floral Print
    • A-Line Silhouette I High Rise Waist 
    • Floor Length Hem I Back Zip With Hook & Eye Closure 
    • Form Hugging Fit I Slight Stretch 

    Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size 3.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05006-0084

    Category Name: Vacation Looks

    Price: $9.97 $129.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Katia Two Piece Lace & Chiffon Dress

    Special Occasion

    Have a mesmerizing moment in our beautiful Katia! Her glowing hue and floral prints will have everyone's eyes trailing your every move! 

    Fits & Features

    • Lace & Sequined, Scallop-Trim Crop Top I High Neckline
    • Dual Hook & Eye Closure At Nape Of Neck I Back Zip With Hook & Eye
    • Floral Printed, Lined Chiffon Skirt 
    • High Rise Waist, Floor Length Hem I A-Line Silhouette 
    • Back Zip With Hook & Eye Closure 
    • Moderate Stretch

    Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size 3. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05006-0103

    Category Name: Vacation Looks

    Price: $68.97 $129.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Polly Formal High Slit Dress
    Special Occasion

    Bring the glamour in the ever so lovely Polly dress! She features a vibrant yellow hue, a sleeveless bodice, a plunging V neckline, padded cups, princess seams and adjustable narrow straps. Her slim fit bodice leads to an elongating sweeping floor length A-Line skirt that is accented with a high side slit to show off your heel game! She offers a form hugging fit with minimal stretch.

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

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0089

    Category Name: Vacation Looks

    Price: $9.97 $89.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ahead Of The Curve Stud Earrings

    You're always ahead of the curve when it comes to accessorizing, boo! Rock these statement-making earrings. 

    • Textured Detailing
    • Curved Design
    • Post-Back Closure 

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

    Style Number/Barcode: 07001-0322

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Staying In Textured Slides

    Girl you are stayin in, you are chillin' in your slides, and u still look bomb!

    • Round toe
    • Low platform
    • Single band over the toe
    • Knit band with padded triangular detailing

    Style Number/Barcode: 07404-0096

    Category Name: Vacation Looks

    Price: $11.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Zip It O-Ring Swimsuit

    Zip up your look with this sexy one-piece swimsuit. You'll be bringin' the heat everywhere you go! 

    Fits & Features

    • Adjustable Narrow Spaghetti Straps
    • Square Neckline With O-Ring Zip Front
    • Back Bar Accent With Hook & Eye Closure With Low Open Back
    • Full Coverage Bottoms 
    • Removable padding

     

    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: 07109-0132

    Category Name: Vacation Looks

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Animal Instincts Skinny Belt 3 Pack

    Amp up your everyday look with this three pack of trendy belts that offer a little variety to your look! Use any of these belts to level up your simple denim + tee looks!

    • Set of three belts
    • Double O-ring buckle closure
    • One Snake print belt
    • One Leopard print belt
    • One simple sleek black belt w/ etched buckle
    • Faux leather

    Style Number/Barcode: 07301-0094

    Category Name: Vacation Looks

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Wild One Shoulder Swimsuit

    You're a wild one when it comes to your style and your swimwear is no different! Get a fierce look your whole squad will be wanting in this one shoulder printed one piece.

    Fit & Features

    • One shoulder with a tank strap
    • Removable padding
    • Removable spaghetti strap on other shoulder
    • Asymmetrical neckline
    • Major side cut outs with criss cross detailing
    • Cheeky bottom
    • Animal print

    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: 07109-0164

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Chiffon Off The Shoulder Blouse

    You are the goddess of flow! This oh so flattering floral top gives a romantic touch to your everyday look when you pair it with your favorite high waist jeans!

    Fit & Features

    • Off the shoulder neckline
    • Long sleeves with banded wrist
    • Lined bodice
    • Cropped hemline
    • Banded hemline with stretch
    • Chiffon with floral pattern

    Style Number/Barcode: 06003-0329

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring That Floral Flair Midi Dress

    Girl, bring that floral flair in this adorable printed midi dress!

    Fit & Features

    • Spaghetti straps
    • V neckline
    • Padded bust
    • High waist seam
    • Mid-length, curve hugging fit
    • Scuba knit fabric | Plenty of stretch

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

    Style Number/Barcode: 05101-0308

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rita Floral Chiffon Dress

    Special Occasion

    You'll be best dressed in this flowy dress! Give a twirl in our beautiful Rita! 

    Fits & Features

    • Surplice V Neckline
    • Unlined, Long Sleeves With Button Cuffs 
    • Elastic, Narrow Waistband I Waist Tie 
    • Floor Length Skirt I A-Line Silhouette I Mini Length Lining 
    • Chiffon Fabric With Floral Prints Throughout 
    • Form Hugging Fit I Moderate Stretch 
    • Back Zip With Hook & Eye Closure

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0630

    Category Name: Vacation Looks

    Price: $24.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bell Sleeve Beauty Floral Mini Dress

    You'll be a total beauty in this adorable bell sleeve floral mini dress!

    Fit & Features

    • Off the shoulder neckline
    • Long bell sleeves
    • Stretchy smocked bust
    • Flowy skirt
    • All over floral print
    • Knit fabric | Plenty of stretch

    Style Number/Barcode: 05102-0502

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Eyes On The Prize Aviator Sunglasses

    Giving chic energy with zero effort. These aviator sunglasses bring sharp lines and cool-girl vibes to every fit—perfect for your next content drop or post-brunch stroll.

    Fit & Features

    • Classic aviator silhouette
    • Dark lenses

    Style Number/Barcode: 07008-000044

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Waist Shape-wear Shorts

    Sometimes you need a little extra support, and these high waist shape-wear shorts do just that!

    Fit & Features

    • Extra high waist fit
    • Body-sculpting
    • Moderate stretch
    • Mid-thigh hemline
    • Thigh + waist control

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics and lingerie are considered final sale merchandise FINAL SALE and CLEARANCE merchandise may not be returned or exchanged. 

    Style Number/Barcode: 07102-0011

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free