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.

  • Remy High-Rise Destructed Shorts By Windsor Denim

    Edge it up this season in the Remy jean shorts by Windsor denim! They feature a flattering high-rise waist, front distressed accents, and a destructed cut-off hem on medium-wash denim with color fading. Complete the look with a trendy crop top for a festival weekend or party!

    Fit & Features

    • High-rise waist
    • Front distressed accents
    • Destructed cut-off hem
    • Front button and hidden zipper closure, belt loop accents
    • Five-pocket styling
    • Medium wash denim, color fading, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0251

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Celestial Charm Necklace Set

    Layer on a boho-chic style with this celestial charm necklace set! It includes a single row snake chain necklace and a four-row layered dainty chain necklace featuring star and moon charms and rhinestone embellishments. Style with stud earrings.

    Fit & Features

    • Set of two necklaces
    • Single row snake chain necklace
    • Four-row layered dainty chain necklace
    • Star and moon charms, rhinestone embellishments
    • Adjustable chains, lobster clasp closures

    Style Number/Barcode: 07002-1481

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Bae Crew Neck Slit Maxi Dress

    A cute basic maxi dress for looking trendy on your off-duty days! It features short sleeves, a crew neck, a bodycon silhouette, and a high side slit to show off some leg! The dress is composed of a brushed knit stretchy fabric. Complete the look in flat sandals and a handbag.

    Fit & Features

    • Short sleeves
    • Crew neck
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-4786

    Category Name: Vacation Looks

    Price: $18.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trish Cargo Wide-Leg Jeans by Windsor Denim

    Create a trendy and fab everyday look with the Trish cargo wide-leg jeans by Windsor Denim. They feature a mid-rise waist, cargo-style side pockets, and a relaxed wide-leg fit. Style with a corset top and clear mules for casual weekend plans.

    Fit & Features

    • Mid-rise waist
    • Front button closure, belt loops
    • Dual front and back pockets
    • Cargo-style side pockets
    • Relaxed wide-leg silhouette
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0449

    Category Name: Vacation Looks

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Marvel In Marble Mini Skirt

    You'll be such a marvel in this marble mini skirt perfect for a girl's night out! It features a high-rise waist, all-over ruching, a mini-length hem, a curve-hugging fit, and a trendy marble print pattern on a lined mesh fabric. Complete the look with the matching bustier and heels.

    Shop Matching Top: Such A Marvel In Marble Bustier

    Fit & Features

    • High-rise waist
    • Side and back ruching
    • Mini-length hem
    • Curve-hugging silhouette
    • Marble print
    • Lined mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0807

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Brunch Eyelet Skater Dress

    This adorable skater dress is a perfect pick for weekend brunch! It features a sweetheart neckline, short puff sleeves with tie accents, a high waist seam, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight knit fabric features a dainty eyelet pattern for the prettiest look. Style with espadrille wedges.

    Fit & Features

    • Sweetheart neckline, shirring at the bust
    • Short puff sleeves, cinched hems, tie accents
    • High waist seam
    • Short skater skirt, ruffled hem
    • Fit and flare silhouette
    • Eyelet knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4915

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everlasting Pretty Floral Chiffon Skater Dress

    Freshen up your closet in this pretty floral chiffon dress for a blissful day date to jaunt through a garden party! It features sheer peasant long sleeves, a smocked and stretchy V-neck bodice, a fit and flare silhouette, and a flowy short-length hem. The dress is designed with a gorgeous floral pattern on airy chiffon with a stretchy knit lining. Complete the look with strappy platform heels.

    Fit & Features

    • Sheer peasant long sleeves
    • Smocked and stretchy V-neck bodice
    • Back zipper closure
    • Skater silhouette
    • Flowy short-length hem
    • Floral pattern, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4977

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Days Ahead Espadrille Platform Sandals

    These adorable espadrille platform sandals were made for sunny spring vibes! They feature an open almond-shaped toe, a wide toe strap, an adjustable ankle and heel strap, a platform sole, and a block heel. The sandals are composed of a braided jute material with a faux leather insole. Style with a flowy floral dress!

    Fit & Features

    • Open almond-shaped toe
    • Wide toe strap
    • Adjustable ankle and heel strap, buckle detail
    • Platform sole
    • Block heel
    • Braided jute material, faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-1103

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Found Love In Floral Lace Romper

    Love the way you look in this breezy floral romper for spring dates and events! It features a sleeveless V-neck, adjustable spaghetti straps that cross in the back, and a lace bodice with a sheer crochet waist leading to the flowy short hem. Complete the look in strappy platform heels.

    Fit & Features

    • Sleeveless V-neck
    • Adjustable spaghetti straps, cross-back design
    • Lace bodice with sewn-in knit lining, sheer crochet waist
    • Flowy short hem
    • Floral print, non-stretch chiffon fabric
    • Runs true to size

    Style Number/Barcode: 06303-0161

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Shine Rhinestone Dainty Ring Set

    Show off a trendy shine with this dainty ring set for everyday glamour! The pack features six metal rings including one thin ring with a center gemstone, one thin ring with a rhinestone embellished star design, one textured midi ring with rhinestones, one midi ring with a smiley face design, one stacked ring with sleek and twisted designs, and one statement ring with an all-around twisted design. Style with stud earrings.

    Fit & Features

    • Six-pack metal ring set
    • One thin ring, center gemstone
    • One thin ring, rhinestone star design
    • One textured midi ring, rhinestones
    • One midi ring, smiley face design
    • One stacked ring, sleek and twisted designs
    • One statement ring, all-around twisted design

    Style Number/Barcode: 07004-0331

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On That Western Trend Necklace And Earrings Set

    Get on that western trend with this adorable necklace and earrings set! It features a a dainty chain necklace with a single cowboy boot charm and matching cowboy boot stud earrings. Style with a distressed denim jacket for festival season!

    Fit & Features

    • Necklace and earrings set
    • Dainty chain necklace, cowboy boot charm 
    • Lobster clasp closure
    • Cowboy boot stud earrings
    • Post-back closures

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07002-1392

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Resort Worthy Espadrille Flat Sandals

    Give your feet a vacation from heels in these trendy sandals that give off resort vibes! They feature an almond toe, nubuck toe and wrap-around ankle strap with buckle closure, and an espadrille trim along the flat sole. Complete the look with a stylish crossbody bag.

    Fit & Features

    • Almond toe
    • Nubuck toe and wrap-around ankle strap
    • Buckle closure
    • Espadrille trim along flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1079

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blinged-Out Rhinestone Straight-Leg Jeans

    Love a blinged-out look? Style up these rhinestone embellished straight-leg jeans for a fab 'fit. Perfect for festival season, they feature a high-rise waist, a straight-leg silhouette, and mini rhinestone embellishments in curved designs for a cool illusion. The light wash rigid denim fabric has a trendy vintage-inspired look with no stretch. Pair with a crop top and mules.

    Fit & Features

    • High-rise waist
    • Straight-leg silhouette
    • Mini rhinestones, curved embellished designs
    • Belt loops, dual front and back pockets
    • Front button, hidden zipper closure
    • Light wash denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06602-0431

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Retro Diva Denim Catsuit

    This curve-hugging denim catsuit will make you a fab retro diva! It features an asymmetric one-shoulder neckline, a single adjustable spaghetti strap, a partially open back, a fitted high waist seam, and form-fitting pant legs. Style with sleek hoops and clear heels.

    Fit & Features

    • Asymmetric one-shoulder neckline
    • Single and adjustable spaghetti strap
    • Partially open back, zipper and hook-eye closure
    • Fitted high waist seam
    • Form-fitting pant legs
    • Denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0421

    Category Name: Vacation Looks

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Remy High-Rise Distressed Shorts By Windsor Denim

    Super flattering and fab! The Remy shorts by Windsor denim are perfect for refreshing your closet. They feature a high-rise waist, distressed accents, and a cut-off hem. The shorts are composed of premium denim fabric with minimal stretch. Complete the look with caged flat sandals for a weekend festival!

    Fit & Features

    • High-rise waist
    • Distressed accents
    • Cut-off hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0311

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Can't Stop This Shine Metallic Bow Sandals

    Shimmer and shine with each step in these sandals featuring a square toe, metallic bow strap, faux leather sole, and slide-on-and-off styling. Complete the look in a trendy crop jacket for a date night.

    Fit & Features

    • Square toe
    • Metallic bow strap
    • Faux leather sole
    • Slide-on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1120

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Mood Sheer Mesh Crop Top

    Get in a trendy mood with this alluring and edgy sheer mesh crop top! It features a crew neckline, loose short sleeves, a cropped hem, a relaxed fit, and a completely sheer mesh fabric. Create the perfect festival 'fit with the matching shorts and a pair of fab cowboy boots!

    Shop Matching Bottoms: Trendy Mood Sheer Mesh Shorts

    Fit & Features

    • Crew neckline
    • Loose short sleeves
    • Cropped hem
    • Relaxed fit
    • Sheer mesh fabric
    • Runs true to size
    • Bra not included

    Style Number/Barcode: 07103-0868

    Category Name: Vacation Looks

    Price: $8.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Mood Sheer Mesh Shorts

    Get in a trendy mood with these alluring and edgy sheer mesh shorts! They feature a high-rise waist with a faux front drawstring, a fitted silhouette, and a completely sheer mesh fabric. Create the perfect festival 'fit with the matching crop top and a pair of fab cowboy boots!

    Shop Matching Top: Trendy Mood Sheer Mesh Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Faux front drawstring
    • Fitted silhouette
    • Sheer mesh fabric, plenty of stretch
    • Runs true to size
    • Undergarment not included

    Style Number/Barcode: 07103-0870

    Category Name: Vacation Looks

    Price: $9.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twirl All Day Linen Skater Dress

    You'll be twirling all day in this linen skater dress perfect for a day date or Sunday brunch! It features a sleeveless, square neck, adjustable spaghetti straps, fitted bust, open-back with an elasticized band, and a flowy short hem. Complete the look in PVC strap heels.

    Fit & Features

    • Sleeveless, square neck, adjustable spaghetti straps
    • Fitted bust
    • Open-back, elasticized band
    • Flowy skater silhouette
    • Short length hem
    • Linen woven fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1667

    Category Name: Vacation Looks

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring The Heat Printed Wide-Leg Pants

    Bring the heat to your spring break look with these trendy pants that will get everyone's attention! They feature a high-rise waist, pleating, an exaggerated wide-leg silhouette with a relaxed fit, and a sassy abstract printed design. Style with the matching crop top to be vacay-ready!

    Shop Matching Top: Bring The Heat Printed Crop Top

    Fit & Features

    • High-rise waist, back elastic band
    • Pleating
    • Wide-leg silhouette, relaxed fit
    • Abstract printed design
    • Satin woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-0536

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendsetting Vibe Lace-Up Denim Shorts

    Show off a trendsetting vibe in these mid-rise denim shorts for festival season! The lace-up side design adds the perfect edge to your casual 'fits.

    Fit & Features

    • Denim fabric, moderate stretch
    • Mid-rise waist, belt loops
    • Front button and hidden zipper closure
    • Lace-up side design
    • Fitted
    • Runs true to size

    Style Number/Barcode: 06603-0472

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bring The Heat Printed Crop Top

    Bring the heat to your spring break look with this trendy crop top that will get everyone's attention! It features a sleeveless sweetheart neckline with a padded bust, thin halter straps with multiple ways to style, a stretchy smocked back, an ultra-cropped hem, and a sassy abstract printed design. Style with the matching wide-leg pants to be vacay-ready!

    Shop Matching Bottoms: Bring The Heat Printed Wide-Leg Pants

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust
    • Thin halter straps, multiple ways to style
    • Smocked back design
    • Ultra-cropped hem
    • Abstract printed design
    • Satin woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-2061

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Deets Crepe Lace-Up Midi Dress

    This crepe midi dress has the pretty deets you're looking for! The dress features a sleeveless square neck, spaghetti straps, an open lace-up back with tie closure, a ruched bust, and a bodycon silhouette. Complete the look in chic flat sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Open lace-up back, tie closure
    • Ruched bust
    • Bodycon silhouette
    • Midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4891

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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

    Bring the diva energy with these fabulous oversized sunglasses. They feature a square-shaped frame with a chic gold trim and tinted lenses. Style with hoop earrings.

    Fit & Features

    • Oversized design
    • Square-shaped plastic frame
    • Top gold trim
    • Tinted lenses

    Style Number/Barcode: 07008-0981

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free