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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.

  • Flirty Vibes Butterfly Printed Mini Dress

    Showcase those sweet and flirty vibes in this trendy knit mini dress. It features spaghetti straps, a square neckline, ruching down the sides, ties at the hem, and a short, form-hugging silhouette. The lightweight ribbed knit fabric has an adorable colorful butterfly print, making it a perf dress for the spring season. Complete your look with a denim jacket and strappy sandals.

    Fit & Features

    • Spaghetti straps
    • Square neckline
    • Ruched detailing and ties at the hem
    • Mini-length, curve-hugging fit
    • Unlined ribbed knit fabric
    • Plenty of stretch
    • Colorful butterfly print

    Style Number/Barcode: 05102-1705

    Category Name: Vacation Looks

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Flowy Woven Maxi Dress

    Create an effortless and pretty look with this flowy woven maxi dress! It features dual adjustable spaghetti straps that lead to a cross-back design, a sheer detailed lace bust with lined cups, a V neckline, and a floor-sweeping silhouette. Complete the outfit with hoop earrings and strappy sandals.

    Fit & Features

    • Dual adjustable spaghetti straps
    • Cross-back design
    • Sheer lace bust with lined cups
    • V neckline
    • Smocked back
    • Flowy floor-length silhouette
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 05101-0531

    Category Name: Vacation Looks

    Price: $21.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glamorous Diva Square Frame Sunglasses

    Showcase your status as a glamorous fashion diva with these must-have sunglasses. They feature an oversized square-shaped design with open sides with metal details, a tortoise-shell-hued frame, and tinted lenses. Pair these sunnies with a trendy shoulder bag and heeled mules.

    Fit & Features

    • Oversized square-shaped design
    • Open sides with metal details
    • Tortoise-shell-hued frame
    • Tinted lenses

    Style Number/Barcode: 07008-0856

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Posh Criss Cross Block Heels

    Keep it posh and stylish with platform heels that elevate your outfits. The heels feature an open back, adjustable ankle strap, an open almond toe, criss-cross straps over the toe, a wide platform, and a block heel. The heels are composed of a faux nubuck material. Complete look with a ruffled mini skirt and tie front top. 

    Fit & Features

    • Open back 
    • Adjustable ankle strap
    • Open almond toe 
    • Criss-cross straps over the toe
    • Wide platform 
    • Block heel 
    • Faux nubuck material

    Style Number/Barcode: 07401-2733

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Style Off-The-Shoulder Romper

    Showcase a chic effortless style this season with this adorable romper. It features an off-the-shoulder neckline, short tiered sleeves, a cinched high waist, and flowy shorts. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Short tiered sleeves
    • Cinched high waist
    • Flowy shorts
    • Gauze fabric
    • Runs true to size

    Style Number/Barcode: 06303-0110

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Fun Flutter Sleeve Tie-Front Top

    This adorable tie-front top was made for weekend fun, designed with short flutter sleeves and an ultra-cropped hem. Style with the matching mini skort for the cutest vibe.

    Shop Matching Bottoms: Weekend Fun Ruffled Mini Skort

    Fit & Features

    • Cotton woven fabric with swiss dot pattern, no stretch, partial knit lining
    • V-neckline, tie-front design
    • Short flutter sleeves
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000011

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Trendsetting Diva Flat Top Sunglasses

    Showcase your trendy style like the fashion diva you are with these fab sunglasses! They feature an oversized design with square-shaped lenses, a flat top, and a plastic frame. Complete your look with a chic crossbody purse.

    Fit & Features

    • Oversized design
    • Square-shaped lenses
    • Flat top
    • Plastic frame

    Style Number/Barcode: 07008-0859

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wanderlust Beauty Smocked Tube Top

    You're a total wanderlust beauty, and this boho-chic top is a must for you! The top features a bohemian-print, a sleeveless sweetheart neckline, a twist-front accent, and a cropped hem. The top is composed of a stretchy smocked knit fabric that offers a relaxed fit with a moderate stretch. Complete look with flared bohemian pants.

    Shop Matching Flared Pants: Wanderlust Beauty Flared Pants

    Fit & Features

    • Sleeveless sweetheart neckline
    • Twist-front accent
    • Cropped hem
    • Bohemian print
    • Smocked knit fabric
    • Relaxed fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-3194

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laidback Vibes Maxi Skirt

    Showcase a cool, laidback style in this breezy maxi skirt! It features a high-rise waist with a tie-front detail, a flowy floor-length silhouette, and a stylish front slit. Complete your look with a crochet bralette and strappy sandals.

    Fit & Features

    • High-rise waist, elastic banded back
    • Tie-front
    • Flowy silhouette
    • Front slit
    • Lightweight gauze fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0088

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Essential Chic Surplice Gauze Jumpsuit

    Stun in a chic jumpsuit that is perf for keeping it casually cute! The jumpsuit features a plunging sleeveless V-neckline, halter neck ties, and an elastic waistband. The relaxed fit bodice leads to a straight leg accented with slant pockets. The jumpsuit is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules. 

    Fit & Features

    • Sleeveless V-neckline
    • Halter neck ties
    • Elastic waistband
    • Slant pockets 
    • Straight leg
    • Gauze knit fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06302-0187

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Chiffon High-Low Duster

    Bring the charm with a chic duster that is the perf lightweight layer for spring! It features short flutter sleeves, a V neckline, a front button closure, and a flowy high-low hem. The sheer chiffon fabric has no stretch. Wear this airy duster over your swimsuit as a pretty cover-up.

    Fit & Features

    • Short flutter sleeves
    • V neckline
    • Front button closure
    • High-low hem
    • Flowy fit
    • Sheer chiffon fabric with no stretch
    • Runs true to size

    Style Number/Barcode: 06204-0662

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Tassel Straw Clutch

    Fun and flirty! This dome-shaped clutch has a straw exterior and multi-colored tassel details with a zipper closure. Complete look with a ribbed mini dress and sunnies.

    Fit & Features

    • Dome-shaped
    • Straw exterior
    • Multi-colored tassel detail
    • Zipper closure

    Style Number/Barcode: 07203-0555

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Vibes Straw Tote

    Go for those summer vibes with this adorable basic straw tote! It features an open-top design and round handles. Complete your look with cute wedges and a trendy Panama hat.

    Fit & Features

    • Open-top design
    • Round handles
    • Straw material

    Style Number/Barcode: 07203-0569

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun's Out Straw Tote

    Style up your outfits with this adorable straw tote for the warmer months! It features an open-top, round handles, multiple pom accents, and a straw exterior. Complete your look with chic sunglasses and strappy sandals.

    Fit & Features

    • Open-top
    • Round handles
    • Pom accents
    • Straw material

    Style Number/Barcode: 07203-0571

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless And Breezy Chiffon Kimono

    Layer on this breezy chiffon kimono for an effortlessly stylish look! It features short sleeves, an open front, a tassel trim, and a flowy, relaxed fit. Pair this kimono over your fave swimsuit to lounge poolside.

    Fit & Features

    • Short sleeves
    • Open front
    • Tassel trim
    • Flowy, relaxed silhouette
    • Sheer chiffon fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-0830

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Good Vibes Ribbed One Piece Swimsuit

    Bring those good vibes this season with a swimsuit that is perfect for working on that summer glow! The swimsuit features a plunging V-neckline, a zippered front with a mini O-Ring accent, adjustable shoulder straps, and a plunging open back. Complete look with sunnies and sandals. 

    Fit & Features

    • Plunging V-neckline 
    • Zippered front with O-Ring accent
    • Adjustable shoulder straps
    • Plunging open back 
    • Cheeky bottom 
    • Ribbed 
    • Form hugging fit runs true to size

     

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

    Style Number/Barcode: 07109-0236

    Category Name: Vacation Looks

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Star Of The Show Rhinestone Drop Earrings

    You'll be the star of the show in these dazzling drop earrings! They feature a round post and a drop design with a dainty chain-link and a rhinestone adorned star accent. Complete the look with a statement ring and a trendy anklet.

    Fit & Features

    • Round post
    • Drop design
    • Chain-link
    • Rhinestone adorned star detail


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

    Style Number/Barcode: 07001-0745

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Aubrielle Formal Floral Chiffon A-Line Dress

    Special Occasion 

    Create a head-turning moment with a formal dress that brings the luxe to your evening. Aubrielle features a plunging V-neckline with a pleated bodice, thin adjustable cross-straps, a floral print, and a sweeping A-line silhouette. The dress is composed of a semi-sheer chiffon fabric that offers a relaxed fit. Complete your look with heels and a sleek envelope clutch.

    Fit & Features

    • Sleeveless V-neckline
    • Pleated bodice 
    • Thin adjustable cross-straps
    • Back zipper and hook and eye closure
    • Floral print 
    • A-line silhouette, relaxed fit
    • Semi-sheer chiffon fabric, mini skirt length lining
    • Runs true to size

    Style Number/Barcode: 05002-0697

    Category Name: Vacation Looks

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Free Spirit Knit Skater Dress

    Live your best in this season ready skater dress! 

    Fit & Features

    • Plunging V-Neckline
    • Halter Neck Tie Straps 
    • Skater Silhouette 
    • Fully Lined Gauze-Like Fabric 
    • Relaxed Fit
    • Minimal Stretch 

    Style Number/Barcode: 05102-0485

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Frill Seeker Ruffled Denim Shorts

    These denim shorts? Total heartthrob. With a mid-rise waist and ruffled hem, it’s giving playful, pretty, and just the right amount of sass for any OOTD.

    Fit & Features

    • Cotton denim fabric, no stretch
    • Mid-rise waist
    • Side zipper and hook-eye closure
    • Ruffled trim hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 06303-000015

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: XL

    Product Badge:
    • Sale
  • Fabulously Retro Ruched Tie Dye Dress

    Keep it fab and retro with a mini dress that is perf for your next night out! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, dual ruched drawstrings, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and butterfly earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross straps
    • Dual ruched drawstrings 
    • Mini-length silhouette 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1079

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drawn To Tie Dye Ruched Mini Dress

    Get drawn to this cute dress that gives off those totally retro feels. The dress features a sleeveless crew neckline with a racer front, a tie-dye print, and ruched drawstrings that allow you to customize the length of the dress. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with sleek hoops and mules. 

    Fit & Features

    • Sleeveless crew neckline
    • Racer bust
    • Tie-dye print
    • Ruched drawstrings 
    • Mini/midi length silhouette 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1080

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Out In Style Sandals

    Level up your look this season and step out in these stylish sandals. They feature an open square toe, a braided strap, an open back, and a flat sole. Pair these faux leather sandals with light-wash denim and a floral crop top.

    Fit & Features

    • Open square toe
    • Braided strap
    • Open back
    • Flat sole
    • PU material
    • Runs true to size

    Style Number/Barcode: 07404-0677

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getaway Bound Floral Bikini Top

    Get ready for your weekend getaway with this adorable bikini top! It features adjustable spaghetti straps, molded cups, a back hook closure, and an all-over tropical floral print. Complete the look with the matching bikini bottoms and a pair of sunglasses.

    Shop Matching Bottoms: Getaway Bound Floral Bikini Bottoms

    Fit & Features

    • Adjustable spaghetti straps
    • Molded cups
    • Back hook closure
    • Tropical floral print
    • Runs true to size


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

    Style Number/Barcode: 07104-0523

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale