Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Trendy Diva Rhinestone Denim Block Heels

    You'll be a total trendy diva with these sparkly rhinestone denim heels! They feature an open square-shaped toe, a wide toe strap, a thin adjustable ankle strap, a closed back, a block heel, and all-over rhinestones on the denim material. Style with a mini handbag.

    Fit & Features

    • Open square-shaped toe
    • Wide toe strap
    • Thin adjustable ankle strap, buckle detail, closed back
    • Block heel
    • Rhinestone embellishments
    • Denim material
    • Runs true to size

    Style Number/Barcode: 07401-4163

    Category Name: Vacation Looks

    Price: $14.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Festivities Chunky Platform Heels

    These bold platform heels were made for fun weekend festivities! They feature an open almond-shaped toe, dual braided straps, a chunky platform sole, and an ultra-tall block heel that will level up your look. Style with a sleek clutch for drinks with the girls!

    Fit & Features

    • Open almond-shaped toe
    • Dual braided straps
    • Open back
    • Chunky platform sole
    • Ultra-tall block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4286

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Rhinestone Buckle-Strap Sandals

    Casual with a glam touch, these buckle-strap sandals are a trendy style for the summer season. They feature a round toe, a two-strap design with adjustable buckles, sparkling rhinestone embellishments, an open back for easy on-and-off styling, and a flat sole. Pair with hoop earrings.

    Fit & Features

    • Round toe
    • Two-strap design, adjustable buckles
    • Mini rhinestones
    • Open back
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1137

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cross Paths Strappy Slide Sandals

    Let these faux leather sandals cross your path! Perfect for casual days out or somewhere by the water, these sandals feature an on-trend square toe, asymmetrical thin strappy design, a flat sole, and a slide-on-and-off styling. Complete the look with chic jewelry.

    Fit & Features

    • Square toe
    • Asymmetrical thin strappy design
    • Flat sole
    • Slide-on-and-off styling
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1090

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • You Better Work Lace-Up Crop Top

    Work it out girl with a crop top that slays! The crop top features a sleeveless square neckline, tank shoulder straps, a lace-up back, and a cropped hem. The top is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with high waist shorts and mules.

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Lace-up back 
    • Cropped hem
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1684

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Robyn High-Rise Crop Flare Jeans By Windsor Denim

    Kick up your style in the must-have Robyn jeans by Windsor denim perfect for adding to your spring-to-summer lineup! They feature a flattering high-rise waist, hip-hugging fit, distressed knee accent, and a flare crop raw hem on premium white denim with a moderate stretch. Complete the look in a trendy crop top and wedges for a pool party! 

    Fit & Features

    • High-rise waist, hip-hugging fit
    • Distressed knee accent
    • Flare cropped raw hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Premium white denim, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0413

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Language Of Romance Lace Babydoll Dress

    This lace babydoll dress speaks your language for romance! Let this short dress sweep you off your feet for wedding showers, graduations, or birthday brunches! It features three-quarter-length puff sleeves, a square neck, a stretchy smocked back, and an empire waist seam that flares out into the flowy hem. Complete the look in new sandals and a clutch!

    Fit & Features

    • Three-quarter-length puff sleeves
    • Square neck
    • Stretchy smocked back
    • Empire waist, fit and flare silhouette
    • Flowy short-length hem
    • Lace overlay, chiffon lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4973

    Category Name: Vacation Looks

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Loveliest Of Them All Chiffon Skater Dress

    You'll be the loveliest of them all in this chiffon skater dress - a stunning option for bridal showers, graduations, or dressy parties! The short dress features a sleeveless plunge V-neckline along the front and back, a ruched high waist, and a flowy fit and flare silhouette. Complete the look with rhinestone block heels for some shine!

    Fit & Features

    • Sleeveless plunge front and back V-neckline
    • Back zipper and hook-eye closure
    • Ruched high waist
    • Skater, fit and flare silhouette
    • Flowy short-length hem
    • Airy chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2160

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely In Floral Lace Trim Midi Dress

    You'll be a sight for sore eyes in this lovely floral midi dress - a flirty option for garden weddings, dressy birthdays, and day dates! The sleeveless dress features a sweetheart neckline with a romantic eyelash lace trim, adjustable spaghetti straps, a curve-hugging bodice, and a slit accent along the flowy hem. Complete the look with earrings and heels.

    Fit & Features

    • Sleeveless sweetheart neckline, padded wired bust, eyelash lace trim
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Curve-hugging bodice
    • Slit accent, midi-length hem, A-line silhouette
    • Delicate floral print
    • Sheer woven fabric, full lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2228

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet As Me Eyelet Lace Skater Dress

    This eyelet lace dress is sure to be the sweetest style in your closet! It features puff short sleeves, a sweetheart neck with a bust tie, ruched bust, and a fit and flare skater silhouette. Complete the look with a ring set and heels.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, bust tie
    • Ruched bust
    • Fit and flare skater silhouette
    • Short-length hem
    • Eyelet lace, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4924

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Palms Tropical One-Shoulder Dress

    This tropical mini dress will put you in vacay mode! Flaunt some skin in this sleeveless one-shoulder dress featuring a sleek bungee spaghetti strap, side ruched seams to accentuate your curves, and a bodycon fit. The dress is designed with a palm leaf print on stretchy knit-lined fabric. Complete your getaway look in platform wedges.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Bungee spaghetti strap
    • Side ruched seams
    • Bodycon fit, mini-length hem
    • Palm leaf print
    • Lined stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4956

    Category Name: Vacation Looks

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Zebra Side Tie Mini Skirt

    Why blend in when you can stand out! Stay ahead of the trend in this zebra print mini skirt featuring a high-rise waist, form-fitting silhouette, and dual side ties along the mini hem. Complete the look in the matching top.

    Shop The Matching Top: Wild Zebra Crop Tank Top

    Fit & Features

    • High rise waist
    • Form-fitting silhouette
    • Dual side ties
    • Zebra print
    • Knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06501-0642

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Zebra Crop Tank Top

    Why blend in when you can stand out! Stay ahead of the trend in this zebra print tank crop top featuring a v-neck, spaghetti straps, ruched seams along the bust, and a cropped hem. Complete the look in the matching skirt.

    Shop The Matching Skirt: Wild Zebra Side Tie Mini Skirt

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Ruched seam along the bust
    • Cropped hem
    • Zebra print
    • Knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4122

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made You Look Open Back Denim Jumpsuit

    Make every look back at you in this stunning denim jumpsuit perfect for a weekend trip or hitting up the country bar! It features a sleeveless square neck, tank-style straps, exposed front zipper closure, a backless design with a tie closure, a hip-hugging fit, and a flared raw hem. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless square neck, tank-style straps
    • Exposed front zipper closure
    • Backless design with tie closure
    • Hip-hugging fit, pockets
    • Flared raw hem
    • Medium wash denim, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0407

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Standout In Style Swirl Print Maxi Skirt

    Standout in this stylish swirl print maxi skirt on vacation or sitting poolside at a party! The skirt features a flattering high-rise waist, a curve-hugging silhouette, and a front ruched drawstring atop a flirty high slit along the maxi hem. Complete the look in a basic tank top and sandals!

    Fit & Features

    • High-rise waist
    • Curve-hugging silhouette
    • Front ruched drawstring
    • High front slit, maxi-length hem
    • Swirl print design
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06501-0830

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Eye-Catching Allure Printed Flare Pants

    Give off an eye-catching allure in these artsy and bold printed flare pants. They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, a flared hem, and a trendy brush stroke print design. Style with a crop top and sandals.

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Brush stroke print
    • Stretchy brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2263

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cali High-Rise Cross Waist Shorts By Windsor Denim

    Create the illusion of a sleek and chic hourglass figure in the Cali shorts by Windsor denim! They feature a flattering high-rise asymmetrical cross waist and an on-trend raw cut-off hem on premium medium-wash denim with color fading. Complete the look in a breezy crop blouse for a beach date!

    Fit & Features

    • High-rise asymmetrical cross waist
    • Raw cut-off hem
    • Front five button-fly closures
    • Five-pocket styling, belt loop accents
    • Premium medium wash denim, color fading
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0310

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daytime Chic Floral Ruffled Romper

    Create a daytime chic look for weekend brunch or a garden party with this adorable romper! It features a sleeveless sweetheart neckline with a ruched and padded bust and a tie-front accent, adjustable spaghetti straps, a high waist seam, fitted shorts with a cute ruffled hem, and a dainty garden floral print pattern on the lightweight woven fabric. Style with strappy mules.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Ruched and padded bust, tie-front detail
    • Adjustable spaghetti straps, back zipper and hook-eye closure
    • High waist seam, fitted shorts, ruffled hem
    • Garden floral print
    • Lined smooth woven fabric
    • Runs true to size

    Style Number/Barcode: 06403-0301

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Paisley Passion Side Cutout Romper

    Have a passion for paisley? Travel to your next destination in this boho sleeveless romper featuring a V-neck, wide shoulder straps, dual elasticized lattice cutouts on the side, a partial open-back, and a form-fitting silhouette. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless, V-neck, wide shoulder straps
    • Dual elasticized lattice cutouts on the side
    • Partial open-back
    • Form-fitting silhouette
    • Short-length hem
    • Paisley print, woven fabric
    • Runs true to size

    Style Number/Barcode: 06303-0216

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Heat Crochet Striped Crop Top

    Everyone will feel the heat of your style in this crochet striped crop top perfect for those desert festivals and pool parties! It features a sleeveless halter V-neckline, dual tie-back straps, an open back, and an ultra-cropped hem. Complete the look in trendy bottoms.

    Fit & Features

    • Sleeveless halter V-neckline
    • Dual tie-back strap closures
    • Open back
    • Ultra cropped hem
    • Striped crochet design
    • Runs true to size

    Style Number/Barcode: 06005-1635

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Up In Style Linen Wide Leg Trouser Pants

    Show up in these stylish linen trouser pants to create an effortlessly chic look! They feature a high-rise belted waist, belt loop accents, hidden side pockets, and front pleating going down the wide-leg silhouette. The lightweight linen fabric includes a woven lining. Complete the outfit in strappy-heeled sandals for a daytime casual soiree or a lunch date!

    Fit & Features

    • High-rise belted waist, metal buckle, belt loop accents
    • Hidden front zipper, hook and bar closure
    • Hidden side pockets
    • Front pleating
    • Wide-leg silhouette
    • Linen fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0748

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dreamy Summer Vibes Mesh Tie-Front Top

    Show off those dreamy summer vibes in this sheer mesh multi-colored top! Featuring long fitted sleeves, a tie-front design creating a V-neckline, a fitted, cropped hem, and a bold multi-color printed design, this top is the perfect lightweight layer for the season. Style over a basic bodysuit with denim shorts.

    Fit & Features

    • Long fitted sleeves
    • Tie-front design, V-neckline
    • Fitted, cropped hem
    • Multi-color printed design
    • Sheer mesh fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06202-0376

    Category Name: Vacation Looks

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Sensation Floral Chiffon Lace Romper

    You'll be a trendy sensation in this floral chiffon romper to create a breezy and cute look for family parties or celebrations! Featuring a sleeveless V-neck with button front accents, adjustable spaghetti straps, an eye-catching lace back design, and a flowy short hem. Complete the look in a chic layered necklace.

    Fit & Features

    • Sleeveless V-neck, button front accents
    • Lace-back design, zipper and hook-eye closure
    • Adjustable spaghetti straps
    • Flowy short hem
    • Watercolor floral print
    • Chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 06403-0249

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oh My Darling Floral Halter Mini Dress

    Let your crush know you've entered the room in this retro-cute mini dress perfect for getting their attention at parties! It features a sleeveless sweetheart neckline with a flirty ruffle trim, halter straps with tie-back closure, an underwire bust, a bodycon silhouette, and a curved ruffle trim hem. The dress is designed with an adorable ditsy floral print on mesh-lined fabric. Complete the look in strappy mules.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim
    • Halter straps, tie-back closure
    • Underwire bust
    • Bodycon silhouette
    • Ruffle trim, curved mini-length hem
    • Ditsy floral print, mesh-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4892

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale