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.

  • So Fab Ruffled And Smocked Mini Dress

    Keep it so fab in a smocked dress that keeps your look effortlessly cute! The dress features an off-the-shoulder neckline, a sweetheart bust with a tie-front, and short sleeves with a ruffled hem. The back features a stretchy smocked fabric to provide a relaxed fit. The dress is composed of a lined lightweight woven fabric that offers a form-hugging fit. Complete look with wedges.

    Fit & Features

    • Off-the-shoulder neckline
    • Short sleeves with a ruffled hem
    • Sweetheart bust with a tie-front
    • Smocked back 
    • Lightweight woven fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1106

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Strappy One-Piece Swimsuit

    Showcase a stylish vibe as you lounge poolside in this chic strappy one-piece swimsuit. It features three spaghetti straps on each side that lead to a trendy cross-back design, a deep V neckline with a sultry lattice front, a high cut silhouette with strappy details at the hips, and a semi-cheeky fit. Layer on a flowy mesh duster and complete your look with some cute sunnies.

    Fit & Features

    • Three spaghetti straps on each side
    • Cross-back design
    • V neckline with a lattice front
    • High cut silhouette
    • Strappy details at the hips
    • Semi-cheeky fit


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

    Style Number/Barcode: 07109-0260

    Category Name: Vacation Looks

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Stylish Tie-Front Top

    Showcase your effortless style in this tie-front top that is perf for the warmer weather. It features flowy kimono-style sleeves, a tie-front closure creating a V neckline, and a cropped fit. The lightweight woven fabric showcases a chic all-over striped pattern. Pair this top with your fave distressed denim shorts.

    Fit & Features

    • Kimono-style sleeves
    • Tie-front closure
    • V neckline
    • Cropped
    • Striped woven fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06204-0547

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Stunner Puff Sleeve Mini Dress

    You'll be a total stylish stunner in this adorable floral mini dress! It features short puff sleeves, a square neckline with a front keyhole cut out and tie at the bust, and a short, curve-hugging silhouette. The all-over floral print makes the dress a perfect option for brunch dates and shopping trips with your girls. Complete the look with a pair of cute wedges.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • Elastic square neckline
    • Front keyhole cut out and tie at the bust
    • Back zipper, hook and eye closure
    • Mini-length, form-hugging fit, moderate stretch 
    • Floral print
    • Smooth knit fabric, fully lined
    • Runs true to size

    Style Number/Barcode: 05102-4339

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Trendsetter Block Heels

    You're always on top of the latest trends, and these chic block heels are no exception! They feature an open almond toe, a toe strap, a thin ankle strap, a closed-back with a zipper, and a sturdy block heel. Style these heels with light-wash mom jeans and a floral blouse for the perf outfit.

    Fit & Features

    • Open almond toe
    • Toe strap
    • Ankle strap
    • Closed-back with a zipper
    • Block heel
    • PU material
    • Runs true to size

    Style Number/Barcode: 07401-2673

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In My Feels High-Rise Midi Skirt

    Whether you're on vacay or sitting poolside, this high-rise midi skirt will have you feeling yourself! Pair with the matching top.

    Fit & Features

    • Stretchy knit fabric
    • High-rise waist
    • Column silhouette
    • Midi-length hem
    • Runs true to size

     

    Shop The Matching Top: In My Feels Scoop Neck Bra Top

    Style Number/Barcode: 06501-1138

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meli Mid-Rise Cutoff Denim Shorts by Windsor Denim

    The Meli cutoff denim shorts by Windsor Denim are a closet staple that needs to be in your wardrobe! They feature a flattering mid-rise waist, a traditional five-pocket and belt loop design, a trendy button-down front closure, distressed details, and a frayed cutoff hem. The medium-wash denim fabric offers plenty of stretch for comfortable wear. Style these shorts with a basic tee and sneakers for a laidback, cute look.

    Fit & Features

    • Mid-rise waist
    • Distressed details and a cutoff hem
    • Traditional five-pocket and belt loop design
    • Button-down front
    • Medium-wash denim fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06603-0148

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Casual-Chic Moment Maxi Dress

    Have a major casual-chic moment in this must-have maxi dress! It features short sleeves, a V neckline, and a flowy silhouette with a rounded hem and side slits. Tie the front hem in a knot to add a trendy detail. Pair this maxi dress with adorable new sandals for a laidback look.

    Fit & Features

    • Short sleeves
    • V neckline
    • Flowy silhouette
    • Rounded hem and side slits
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1072

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheer Appeal Chiffon High Low Duster

    Keep it stylish in a sheer duster that is perfect to layer over your favorite mini dresses or as a coverup for your swimsuit. The duster features a V-neckline, short ruffled sleeves, a multi-button front, and a high-low hem. The duster is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch.

    Fit & Features

    • V-neckline
    • Short ruffled sleeves
    • Multi-button down front
    • High-low hem
    • Sheer chiffon fabric
    • Relaxed fit, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06204-0633

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty And Fluttery Chiffon High Low Duster

    Keep it flirty in a sheer duster that is perfect to layer over your favorite mini dresses or as a coverup for your swimsuit. The duster features a V-neckline, short ruffled sleeves, a multi-button front, and a high-low hem. The duster is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch. 

    Fit & Features 

    • V-neckline 
    • Short ruffled sleeves
    • Multi-button down front
    • High-low hem 
    • Sheer chiffon fabric 
    • Relaxed fit, minimal stretch 
    • Fits true to size 

    Style Number/Barcode: 06204-0634

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Dreams Tie Waist Kimono

    Transport to the tropics with a kimono to channel those island vibes. The kimono features a gorgeous tropical floral print, kimono sleeves, a tie waist belt with an elastic back, and a mid-thigh length. The kimono is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a cami top and skinny jeans. 

    Fit & Features

    • Tropical floral print
    • Kimono sleeves
    • Tie-waist belt with elastic back 
    • Mid-thigh length 
    • Sheer chiffon fabric
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06204-0522

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheer Sophistication Chiffon Coverup

    Keep it sophisticated with a sheer coverup that brings the style to your look. The coverup features a draped open front, quarter length kimono-style sleeves, tie waist belt, an elastic back detail, and a mid-thigh length. The coverup is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a lace bra and panty set. 

    Fit & Features

    • Draped open front
    • 3/4 kimono-styled sleeves
    • Tie-waist belt 
    • Mid-thigh length 
    • Sheer chiffon fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06204-0516

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Boho Vibes Tie Front Top

    Bring those bold bohemian vibes to your everyday look with this printed top. The top features a plunging sweetheart neckline with a tie front accent, sleek spaghetti straps, and a cropped hem. The knit fabric showcases an all-over medallion print to achieve that perf boho-chic look. Pair these pants with the matching flared pants and cute sandals.

    Shop Matching Flared Pants: Bold Boho Vibes Flared Pants

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie front accent
    • Spaghetti straps
    • Bohemian medallion print
    • Cropped hem
    • Brushed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06001-3122

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Beauty Mesh Long Sleeve Duster

    Showcase your beauty in this lightweight mesh floral printed duster! It features long fitted sleeves, a long flowy fit, and an all-over gorgeous floral pattern. Layer this duster over your favorite bodysuit and style it with high waist jeans for the perf everyday outfit.

    Fit & Features

    • Long fitted sleeves
    • Flowy fit
    • Lightweight mesh fabric
    • Floral print

    Style Number/Barcode: 06202-0107

    Category Name: Vacation Looks

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Trendsetter Oversized Sunglasses

    Showcase your major trendsetter status in these fab oversized sunglasses. They feature an oval design with tinted lenses and a matte black plastic frame. Pair these sunnies with your fave casual dress and clear heels.

    Fit & Features

    • Oval oversized design
    • Tinted lenses
    • Matte black plastic frame
    • 100% UV protection

    Style Number/Barcode: 07008-0820

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Butterfly Gemstone T-Strap Sandals

    Elevate your spring style with these trendy T-strap sandals! They feature a round toe, a T-strap design with a gorgeous gemstone butterfly accent, an open back, and a flat sole. Pair these jelly sandals with a casual dress and a denim jacket.

    Fit & Features

    • Round toe
    • T-strap design
    • Gemstone butterfly accent
    • Open back
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-0675

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Perfect Look Paper Bag Shorts

    These adorable woven shorts will give you the perfect look for your picnic date with bae! They feature a classic high-rise paper bag waist with a tie-front detail, front pockets, and a fitted silhouette. Complete your romantic outfit with a flirty lace bodysuit and your fave pair of sandals.

    Fit & Features

    • High-rise elasticized paper bag waist
    • Tie-front belt
    • Front pockets, single faux back pocket
    • Fitted silhouette
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0143

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendsetting Babe Block Heel Booties

    Level up your look like the trendsetting babe you are in these adorable booties! They feature an almond toe, a stacked block heel, an inner zipper closure, and an above the ankle design. The booties are composed of a faux pony hair-like material with an all-over cow print for that must-have western vibe. Pair these booties with a denim skirt.

    Fit & Features

    • Almond toe
    • Stacked block heel
    • Inner zipper closure
    • Above the ankle design
    • Faux pony hair-like material
    • Cow print
    • Runs true to size

    Style Number/Barcode: 07403-1234

    Category Name: Vacation Looks

    Price: $23.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Western Vibes Block Heel Booties

    Add these block heel booties to your outfit to get those trendy western vibes you've seen all over social media. They feature an ankle-high design with dual cutouts, a pointed toe, a stacked block heel, and an all-over cow print. Pair these booties with light-wash mom jeans and a basic tee.

    Fit & Features

    • Ankle-high design
    • Dual cutouts
    • Pointed toe
    • Stacked block heel
    • Cow print
    • Runs true to size

    Style Number/Barcode: 07403-1238

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sun Soaked Cutie Satin Scarf Top

    Let the sun kiss your shoulders in this cute satin paisley scarf top perfect for festivals or weekend getaways! Featuring a strapless neckline and a tie-back design, style with denim shorts for an effortless look.

    Fit & Features

    • Silky non-stretch satin fabric
    • Paisley print
    • Strapless straight neckline
    • Smocked back, tie-back design
    • Angled hem
    • Runs true to size

    Style Number/Barcode: 06003-2732

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Rise Vintage Cutoff Shorts

    Create a throwback moment with shorts that give that vintage feel. The shorts feature a high rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, moderate distressing, and a cutoff hem. Complete look with a button down crop top and chunky sneakers. 

    Fit & Features

    • High rise waist
    • Single-button with zipper closure 
    • Traditional five-pocket with belt loop design 
    • Moderate distressing 
    • Faded finish 
    • Cutoff hem
    • Form hugging fit, runs true to size

    Style Number/Barcode: 06603-0146

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take A Gaze Gauze Tie Front Top

    Gaze on this adorable top that brings the charm! It features a plunging tie front, quarter-length kimono-styled sleeves, and a cropped hem. The top is composed of a lightweight gauze knit fabric that offers a form hugging fit with minimal stretch. Complete look with high waist jeans. 

    Fit & Features

    • Plunging V-neckline
    • Tie-front bodice
    • Quarter-length kimono sleeves
    • Cropped hem 
    • Gauze fabric
    • Form hugging fit
    • Minimal stretch 

    Style Number/Barcode: 06204-0794

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sandy Shores Tropical Floral Crop Top

    This vibrant tropical floral crop top will transport you to the sandy shores of a tropical paradise. With its stunning print and strapless neckline, this crop top is perfect for any summer occasion. Pair with the matching skirt.

    Fit & Features

    • Tropical floral print, stretchy knit fabric
    • Strapless neckline
    • Fitted crop hem
    • Runs true to size

     

    Shop the Matching Skirt: Sandy Shores Tropical Floral Maxi Skirt

    Style Number/Barcode: 06001-000141

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Chic Denim Block Heels

    Keep it chic in block heels that bring those casual vibes to your look. The heels feature an open back, a lace-up back, four denim straps, an open almond toe, and a block heel. Complete look with a white mini dress. 

    Fit & Features

    • Lace-up back 
    • Four denim straps
    • Open almond toe
    • Block heel 
    • Denim material 

    Style Number/Barcode: 07401-2694

    Category Name: Vacation Looks

    Price: $15.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale