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.

  • Come In Clutch Round Purse

    This chic round purse will for sure come in clutch!

    • Round design with flat bottom
    • Metal top handle
    • Detachable chain and faux leather shoulder strap
    • Faux leather material

    Style Number/Barcode: 07203-0189

    Category Name: Vacation Looks

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Electric Love Mesh Rhinestone Choker

    Bby ur style is euphoric, top it all of with the electric shine of rhinestones, and the edgy touch of mesh!

    • Thick mesh design
    • Rhinestone embellished
    • Adjustable lobster clasp closure
    • Black choker has charcoal rhinestones
    • Multi choker has iridescent rhinestones

    Style Number/Barcode: 07002-0367

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Eight Pack Glitter Acrylic Hair Clips

    Style up your pretty tresses with these glam glitter hair clips!

    • Eight pack
    • Oversized design
    • Glitter acrylic material
    • Snap closure

    Style Number/Barcode: 07006-0124

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Shade Is Real Over-sized Square Sunglasses

    Girl the shade is real with these sunnies! They give a little sass that cannot be missed! Pair with a flowy dress for maximum sassss!

    • Over-sized 
    • Square design
    • Dark lenses
    • Textured golden frame
    • Dainty arms

    Style Number/Barcode: 07008-0722

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 2 Pack Baguette Rhinestone Bobby Pins

    Sweep your hair back with a glimmering touch! We are loving baguette style stones, they give you a unique finish!

    • Set of two bobby pins
    • Slide on 
    • Baguette rhinestones

    Style Number/Barcode: 07006-0109

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Printed Essential Face Mask

    Stay safe but keep it cute with this printed mask!

    • Wash Before and After Use is Recommended
    • Not a Medical Grade Mask
    • Final Sale

    Style Number/Barcode: 07305-0106

    Category Name: Vacation Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Like Summer Crochet Bralette Top

    Sweet like summer, this crochet bralette top was made to flirt. With a plunging V-neck, scalloped trim, and open tie-back design, it's your new go-to for coastal vibes. Style with the matching maxi skirt.

    Shop Matching Bottoms: Sweet Like Summer Crochet Maxi Skirt

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Sleeveless plunge V-neckline
    • Tank shoulder straps
    • Scalloped trim
    • Open back, tie-back spaghetti straps
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000229

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Scrunchies For All Ur Moods 3-Pack

    Get a pack of scrunchies in your life that hits all ur moods! Sleek, funky, girly! Pair with a simple crew neck on a lazzy day and bring ur hair to life!

    • 3 Pack
    • Satin 
    • One black | One leopard print | One Lavender
    • Stretchy

    Style Number/Barcode: 07006-0143

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Do You Double Rim Sunglasses

    Just do you boo! Show off your style in these oversized shades.

    • Round Double Rim
    • Oversized Frame

    Style Number/Barcode: 07008-0743

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Classic Fit High-Rise Distressed Denim Shorts

    You'll love the classic fit of these high-rise distressed denim shorts, a summertime essential! Perfect for pairing with a crop top and sandals.

    Fit & Features

    • Cotton denim fabric, no stretch
    • High-rise waist
    • Five-pocket and belt loop design
    • Hidden front zipper and button closure
    • Distressed detailing, frayed hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06603-0454

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off Shoulder Puff Sleeve Mini Dress

    With puff sleeves and an off-shoulder neckline, you'll be making a trendy and stylish statement in this romantic little number! 

    Fits & Features 

    • Off Shoulder Neckline I No-Slip Interior Slip 
    • Puff Long Sleeves With Ruffle Accents At The Cuffs & Shoulders
    • Smocked Back I Zipper With Hook & Eye Closure
    • Mini Length Silhouette 
    • Woven Fabric I Smooth Knit Lining 
    • Ties At The Hem 
    • Relaxed Fit I Minimal Stretch 

    Style Number/Barcode: 05102-0596

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off the Shoulder Long Sleeve Crop Top

    Keep it simply basic in a crop top. This festival-ready top features an off the shoulder elastic neckline, long sleeves with elastic cuff and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with a slight stretch. Complete your outfit with high waist jeans and a pair of wedges. 

    Fit & Features

    • Elastic off the shoulder neckline
    • Long sleeves with elastic cuff 
    • Lightweight woven fabric
    • Relaxed fit 
    • Slight stretch 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0861

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Thin Rhinestone Square Buckle Belt

    Channel glam with a rhinestone belt. For those occasions when you're feeling a little extra, throw on a narrow belt that features a rhinestone embellishment and a small square buckle. The belt is composed of faux leather material. Pair this glitzy belt with high waist jeans.

    Fit & Features

    • Narrow faux leather band
    • Small square buckle
    • Rhinestones
    • Adjustable  

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. 

    Style Number/Barcode: 07301-0214

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleeveless Spaghetti Strap Cami Top

    Keep it casual in a trendy cami top. This top features a sleeveless bodice, a v-neckline, spaghetti straps and an open back with a twisted bar strap accent. The top is composed of a lightweight woven fabric that offers a relaxed fit with a slight stretch. Complete your look with a pair of high waist shorts and statement earrings. 

    Fit & Features

    • Sleeveless bodice 
    • V-neckline 
    • Open back 
    • Twist-back bar strap accent 
    • Lightweight woven fabric 
    • Relaxed fit, slight stretch 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-1012

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Woven Tie Front Bell Sleeve Crop Top

    Stun in a flowy bell sleeve crop top for a bohemian vibe. This essential top features a plunging tie front bodice, two-tiered flowy long sleeves, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete your look with cut off shorts and sleek slides for a laid-back look you can wear to brunch with your girls. 

    Fit & Features

    • Plunging tie-front bodice
    • Flowy long bell sleeves
    • Cropped hem 
    • Composed of a lightweight woven fabric
    • Relaxed fit 
    • Minimal stretch

     

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

    Style Number/Barcode: 06204-0534

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chiffon Cap Sleeve Tie Front Crop Top

    Keep it casual in tie front top. Step out in a casually cute top that features a plunging tie front bodice, unlined chiffon cap sleeves, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with slight stretch. Complete your look with high waist jeans and mini crossbody. 

    Fit & Features

    • Plunging tie-front bodice
    • Unlined cap sleeves 
    • Cropped hem 
    • Lightweight woven fabric 
    • Relaxed fit, slight stretch 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0535

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Shoulder Crochet Crop Top

    Keep it cute in a crochet crop top. The top features an off the shoulder neckline with a sweetheart bust, a crochet lace overlay with medallion accents at the hem and short sleeves. The top is composed of a partially lined crochet lace fabric that offers a relaxed fit. Complete your outfit with the matching skirt and heels. 

    Shop Matching Skirt: Crochet High Low Skirt

    Fit & Features

    • Off the shoulder neckline, sweetheart bust
    • Crochet lace overlay
    • Short sleeves
    • Cropped hem 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0583

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Slit Floral Knit Maxi Dress

    Upgrade your dress with a floral print. The floral maxi dress features a sleeveless bodice, a plunging V-neckline, and spaghetti straps that lead to a partially open back with a square neck. The relaxed fit waist leads to a curve-hugging maxi length silhouette that is accented with a high side slit to reveal a hint of leg. The dress is composed of a smooth knit fabric that offers a form hugging fit.  Complete your brunch-ready look with statement heels and extra-large hoops. 

    Fit & Features

    • Sleeveless v-neckline 
    • Spaghetti straps
    • Partially open back
    • Floral print 
    • Maxi length silhouette
    • High side slit 
    • Knit fabric 

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0645

    Category Name: Vacation Looks

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ribbed Knit Ditsy Floral Mini Dress

    Keep it sweet in a ditsy floral dress. Perfect for brunch, this mini dress features a sleeveless bodice with a sweetheart neckline and supportive tank-like straps. The back features an open back with two ribbed bar back straps. The relaxed fit waist leads to a curve-hugging mini-length silhouette. Keep accessories minimal to let the ditsy floral print command attention. 

    Fit & Features

    • Sleeveless bodice
    • Sweetheart neckline
    • Open back with bar straps
    • Ditsy floral print
    • Mini length silhouette 

    Style Number/Barcode: 05102-0439

    Category Name: Vacation Looks

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cropped Tie Front Woven Floral Top

    Keep on trend in a floral top. Keep it fab this season in a floral top that features a plunging tie front bodice, long sleeves with elastic cuff and an all-over floral print. The crop top is composed of a lightweight woven fabric that offers a relaxed fit with a minimal stretch. Complete your look with cut off denim shorts and sandals for a laid back look. 

    Fit & Features 

    • Plunging tie-front bodice
    • Long sleeves with elastic cuff
    • Floral print 
    • Cropped hem 
    • Lightweight woven fabric
    • Relaxed fit, slight stretch  

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0428

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleeveless V Neck Ruffled Floral Mini Dress

    Get frilly in a ruffled floral dress. Celebrate with your squad in a floral mini dress that features a sleeveless bodice, a plunging V neckline, and spaghetti straps. The relaxed fit waist leads to a mini-length silhouette with a frilly ruffled hem. The all-over floral print features bright hues that contrast with the dark background. Complete your look with wedges and sunglasses.

    Fit & Features

    • Sleeveless V neckline
    • Spaghetti straps
    • Floral print 
    • Mini-length silhouette
    • Ruffled hem
    • Lightweight knit fabric with a moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0517

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleeveless Crossback Floral Ruffled Mini Dress

    Get crossed up in a floral mini dress. Make a statement this season in a mini dress that features a charming floral print, a scoop neckline, and spaghetti straps. The back features an open back design with cross-strap ties. The relaxed fit waist features a ruffled hem and leads to a mini length silhouette with matching ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with a slight stretch.  Complete your look with neutral-hued wedges and a floppy hat. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Floral print 
    • X-back 
    • Ruffles 
    • Mini length silhouette
    • Lightweight woven fabric, slight stretch 

    Style Number/Barcode: 05102-0581

    Category Name: Vacation Looks

    Price: $15.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Shoulder Chiffon and Smocked Ditsy Print Top

    Bring on the charm in a ditsy top. This season must-have features an off the shoulder neckline, a smocked bodice, an all-over floral ditsy print, long chiffon sleeves, and a cropped hem.  The top is composed of combination chiffon and smock knit fabric.  Complete your outfit with high waist shorts and fringe earrings for a casually cute look. 

    Fit & Features

    • Off the shoulder neckline
    • Smocked bodice
    • Chiffon long sleeves
    • Ditsy floral print
    • Chiffon long sleeves
    • Relaxed fit, moderate stretch 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0870

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mornings In Tulum Tropical Tie-Front Crop Top

    Waking up in paradise got sweeter with this tropical crop top in your luggage! It boasts flowy short sleeves and a tie-front design perfect for styling over a bikini. Pair with the matching pants.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Short sleeves
    • Tie-front design
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Pants: Mornings In Tulum Tropical Wide-Leg Pants

    Style Number/Barcode: 06202-000015

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free