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.

  • Boho Bliss Crochet Lace Crop Top

    The cute crochet lace detailing of this crop top makes it so boho-chic! The top features a sleeveless V-neckline, adjustable spaghetti straps, a floral crochet lace design, and a cropped fit with a scalloped trim. Style with printed flare pants and espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Floral crochet lace design
    • Partially smocked back
    • Cropped fit, scalloped trim
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1791

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Glam Ruched Short Dress

    Keep it glam on your tropical getaway with a mini dress that brings those island vibes! The dress features a tropical floral print, a sleeveless square neckline, spaghetti straps, ruching, and a short length with a rounded hem. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a straw hat

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching
    • Tropical floral print
    • Short length hem
    • Lined smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4683

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Standout In Glam Thong Wedge Sandals

    Stand out in these glam sandals while soaking up the sun! They feature a round toe, clear stone embellished thong strap, wedge sole, and a comfort foam footbed. Complete the look in a chic swimsuit and wrap.

    Fit & Features

    • Round toe
    • Clear stone embellished thong strap
    • Wedge sole
    • Comfort foam footbed
    • Slide-on/off styling
    • Runs true to size

    Style Number/Barcode: 07404-1012

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Silky Chic Kimono Tie-Front Top

    Silky and so chic! Luxe up your look in this satin crop top featuring three-quarter-length kimono sleeves, a plunge V-neckline, a tie-front closure, and a cropped hem. Complete the look in trouser shorts and sandals for vacation.

    Fit & Features

    • Three-quarter-length kimono sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Cropped hem
    • Silky satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1298

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Tide Halter Cutout Midi Dress

    Flaunt this midi dress on your island getaway! Designed to accentuate your fab figure on a sleeveless, halter neck with tie closure, and sultry side cutouts on the form-fitting silhouette. Complete the look in strappy mules for a sunset dinner.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Side cutouts
    • Partial open-back design
    • Form-fitting silhouette
    • Midi-length hem
    • Sweater-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1313

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Views Floral Midi Dress

    Soak in those stunning vacay views in this chic floral midi dress! It features a sleeveless bodice, a wrap-front V-neckline, spaghetti straps, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some skin. The smooth and stretchy knit fabric features an all-over tropical floral print. Complete the look with strappy heels.

    Fit & Features

    • Sleeveless bodice, wrap-front V-neckline
    • Spaghetti straps
    • Fitted midi-length silhouette, asymmetrical hem
    • Form-hugging fit
    • Tropical floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4441

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soul Swirls Mesh Cover Up

    Unveil your retro soul in this swirl print cover-up featuring long sleeves, a v-neckline, bodycon fit, and a center front drawstring so you can customize the fit. Complete the look in a string bikini set and sunglasses.

    Fit & Features

    • Long sleeves
    • V-neckline
    • Bodycon fit
    • Center front adjustable drawstring
    • Bodycon fit, mini-length hem
    • Sheer stretchy mesh swirl print fabric
    • Fits true to size

    Style Number/Barcode: 06001-4307

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect For Paradise Midi Dress

    This curve-hugging midi dress is perfect for your vacation in paradise, or to just look like you're on one! It features a sleeveless V-neckline, spaghetti straps, a midi-length asymmetrical hem to showcase some leg, and an all-over tropical floral print to match the vibe of a vacay. Style this dress with strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length asymmetrical hem
    • Form-fitting silhouette
    • Tropical floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4474

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Alluring One-Piece Swimsuit

    So alluring, this one-piece swimsuit will give you that sexy poolside look. It features a one-shoulder neckline with a thin tank strap, a padded bust, daring sheer mesh inserts in a wrap design to create a chic silhouette, and a semi-cheeky fit. Style this swimsuit with a flowy duster.

    Fit & Features

    • One-shoulder neckline, thin tank shoulder strap
    • Removable padding
    • Sheer mesh inserts in a wrap design
    • Semi-cheeky fit
    • Moderate stretch
    • Runs true to size


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

    Style Number/Barcode: 07109-0284

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Tassels Rhinestone Belt

    Glam and glitzy, create the perfect shine with this tassel belt featuring rhinestone drops, a layered design, and a lobster clasp closure. Complete the look in a glitter bikini set for a pool party.

    Fit & Features

    • Rhinestone drop tassels
    • Layered design
    • Lobster clasp closure

    Style Number/Barcode: 07301-0431

    Category Name: Vacation Looks

    Price: $6.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Glam Espadrille Sandals

    Bring the casual glam to your summer looks with these embellished sandals. They feature an open round toe, dual rhinestone adorned straps, an espadrille trim, and a flat sole with contrast stitching. Style with a flowy midi dress and a layered necklace.

    Fit & Features

    • Open round toe
    • Dual rhinestone embellished straps
    • Espadrille trim
    • Flat sole, contrast stitching
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1069

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Making Waves Linen Tie Front Top

    All eyes on you strolling the beach in this linen tube top on vacay! It features a strapless, sleeveless, square neck with a flirty tie-front and a smocked back panel on a cropped hem. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Making Waves Linen High Rise Shorts

    Fit & Features

    • Strapless, sleeveless, square neck
    • Tie-front detail
    • Smocked back panel
    • Cropped hem
    • Linen woven fabric, double-lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1558

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Gorgeous Floral Romper

    Showcase an effortlessly gorgeous look in this breezy floral printed romper! It features a sleeveless V-neckline, adjustable spaghetti straps, a sheer crochet waist design, and flowy shorts. The semi-sheer chiffon fabric includes a knit lining. Style this romper with chic mules.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Back zipper, hook and eye closure
    • Sheer crochet waist design
    • Flowy shorts
    • All-over floral print
    • Semi-sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0207

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slip Into Something Floral Mesh Maxi Dress

    The dress you “accidentally” wear to steal the spotlight. This floral mesh maxi drapes you in a soft cowl neckline with a low back and curve-hugging fit that’s ready for cocktails at sunset!

    Fit & Features

    • Floral print, mesh fabric, soft and stretchy knit lining
    • Cowl halter neckline with tie straps
    • Low cut back
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000341

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Glam Gauze Knit Mini Dress

    Keep it glam and carefree with a mini dress that gives off that effortless vibe! The dress features a sleeveless V-neckline with crochet trim, adjustable spaghetti straps that cross at the back, an unlined crochet lace waist, an open back with ties, and a mini length silhouette with tiered ruffles. The dress is composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules

    Fit & Features

    • Sleeveless V-neckline, crochet trim
    • Adjustable spaghetti straps, cross-back 
    • Unlined crochet lace waist
    • Open back with ties
    • Tiered ruffles, mini-length silhouette
    • Lined gauze knit fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1098

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Breeze Halter Bodysuit

    Breezy and blissful. awaken paradise in this halter bodysuit featuring a sleeveless bodice, tie closure, and an o-ring inset atop a form-fitting silhouette, dual snap-button closure, and a thong bottom. Complete your island vacay look in a midi skirt.

    Fit & Features

    • Sleeveless, halter, tie closure
    • O-ring inset
    • Form-fitting
    • Dual snap-button closure, thong bottom
    • Tropical print, knit-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4133

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Life's Sweet Puff Sleeve Tie Top

    Life is so much sweeter with this cute puff sleeve top! It features a sweetheart neckline with a cinched bust, cropped hem, and an open back with tie closure. Complete the look in a flirty mini skirt for a day out with the girls.

    Fit & Features

    • Short puff sleeves, elastic cinched hems
    • Sweetheart neckline
    • Cinched bust
    • Cropped hem
    • Open-back, tie closure
    • Lined woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1835

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Essential Basic Tube Top

    This essential basic tube top is the perfect base to create an insta-worthy outfit of the day! This top features a strapless, sleeveless, square neckline and a fitted crop hem on cotton-lined fabric. Complete the look in trendy best-selling bottoms and heels.

    Fit & Features

    • Strapless, sleeveless
    • Square neckline
    • Cropped hem 
    • Lined cotton fabric
    • Moderate stretch
    • Runs true to size 

    Style Number/Barcode: 06002-1264

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Vibes Bandeau Bikini Top

    This bikini top is a total vibe for summer! Enjoy the sunshine in this sleek swim top featuring a convertible strap design so you can style it multiple ways and removable padding for support and shaping. Complete the look in the matching bikini bottoms and sunglasses.

    Shop Matching Bikini Bottoms: Summer Vibes Cheeky Bikini Bottoms

    Fit & Features

    • Convertible tie design
    • Removable padding for support and shaping
    • Runs true to size

    Style Number/Barcode: 07104-0695

    Category Name: Vacation Looks

    Price: $4.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty Clear PVC Cork Wedges

    It's pretty clear these wedges belong in your closet! They feature an almond toe, a wide PVC strap, and a cork platform sole. Complete the look in a cute matching set for a vacation.

    Fit & Features

    • Almond toe
    • Wide PVC strap
    • Cork platform sole
    • Runs true to size

    Style Number/Barcode: 07406-0317

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Daze Halter Sweater Dress

    Bring the summer vibes with this bright and trendy halter sweater dress. It features a sleeveless scoop neckline, halter spaghetti straps, an open back with a tie-back design, and a midi-length, curve-hugging silhouette. The lightweight sweater knit fabric showcases an all-over multi-hued chevron pattern. Complete the look with espadrille sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Open back, tie-back strap design
    • Midi-length, form-fitting silhouette, scalloped hem
    • Multi-hued chevron pattern
    • Unlined sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1312

    Category Name: Vacation Looks

    Price: $12.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's Ready For Brunch Crop Top

    The answer is always yes to brunch! Have the cutest look of your squad in this adorable ditsy floral printed top. It features a sleeveless subtle sweetheart neckline, adjustable spaghetti straps, ruched detailing at the bust, and a cropped fit with a tie-back design. Complete the outfit with the matching mini skirt and your fave mules.

    Shop Matching Bottoms: She's Ready For Brunch Mini Skirt

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Ruching at the bust
    • Back zipper closure
    • Cropped, form-hugging fit, tie-back design
    • Ditsy floral print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1754

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Jetset Getaway Tropical Midi Dress

    Wanna get away? Jetset off to paradise with this tropical floral dress in your lineup! It features a sleeveless scoop neck, spaghetti straps, a cross-back strap design with a tie closure, a form-fitting silhouette, a side ruched seam, and an asymmetrical midi hem with a side slit. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Open-back, cross-back strap design, tie closure
    • Form-fitting silhouette
    • Side ruched seam
    • Asymmetrical midi-length hem, side slit
    • Tropical floral print, stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 05102-4373

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Cruise Floral Midi Dress

    You'll be ready for a sunset cruise on the water in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, side ruched detailing, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some leg. The dress features an all-over tropical floral print. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross-back strap design
    • Side ruching
    • Midi-length, form-fitting silhouette, asymmetrical hem
    • Tropical floral print
    • Stretchy knit fabric, partial lining at the bust
    • Runs true to size

    Style Number/Barcode: 05102-4375

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale