Vacation Dresses & Outfits

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STYLE SPOTLIGHT

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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.

  • Rodeo Aesthetic Western Concho Belt

    Cinch together your western look with this concho belt featuring square shapes with colored stones on a chain with a secure lobster clasp closure. Perfect for styling with cowboy boots.

    Fit & Features

    • Square shapes with colored stones
    • Chain
    • Lobster clasp closure

    Style Number/Barcode: 07301-0674

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style On Point Cat-Eye Sunglasses

    These cat-eye sunglasses are here to make sure your style is always on point! They feature tinted lenses and a comfortable fit. Complete the look with a denim jacket and sandals!

    Fit & Features

    • Cat-eye silhouette
    • Tinted lenses
    • Comfortable fit

    Style Number/Barcode: 07008-1086

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Living Aviator Sunglasses

    A pair of cool aviator sunglasses featuring a sleek metal frame, smokey tinted lenses with 100% UV protection, and rubber nose supports. Perfect for everyday styling.

    Fit & Features

    • Sleek metal frame
    • Smokey tinted lenses
    • 100% UV protection
    • Rubber nose supports

    Style Number/Barcode: 07008-1103

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

  • Western Life Colored Stone Concho Chain Belt

    A statement concho chain belt features textured squares with colored stones and an adjustable lobster clasp closure. Style with a denim short dress and boots.

    Fit & Features

    • Textured squares with colored stones
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07301-1192

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Drinks Platform Block Heels

    These fab platform block heels were made to be worn while sipping on some drinks at sunset! They feature an open almond-shaped toe with an adorable knotted toe strap design, a thin adjustable ankle strap with a buckle closure, a closed back, a tall platform sole, and a chunky block heel. Style with your fave summer dress for happy hour!

    Fit & Features

    • 5" Block heel
    • Open almond toe, knotted toe strap design
    • Adjustable ankle strap with buckle closure, closed back
    • Platform sole, padded faux leather insole
    • Natural heels are woven material with a metallic threaded design
    • Denim heels are denim material
    • Runs true to size

    Style Number/Barcode: 07401-4857

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charmed Strapless Ruffled Woven Skater Romper

    They'll be oh-so-charmed by you in this flirty ruffled woven skater romper! Designed with a breezy woven fabric, it features a strapless straight-across neckline, flexible boning at the bodice for added structure, a tie-back design for a stylishly cinched waist, an adorable short ruffled overlay over flowy shorts, and a fit-and-flare silhouette. Complete your look with hoop earrings and sneakers for a cute and casual vibe.

    Fit & Features

    • Woven fabric, stretchy knit lining
    • Strapless straight neckline, flexible boning
    • Tie-back design
    • Back zipper with hook-eye closure
    • Ruffled overlay, flowy shorts
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 06403-0400

    Category Name: Vacation Dresses & Outfits

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Mood Collared Linen Crop Top

    This breezy linen crop top is a sunny day staple! Designed with a lightweight linen-blend fabric, this top is perfect for your summer weekend plans. It features a collared V-neckline with a partial button-down front, a single chest pocket, cap sleeves, a twist-front cropped hem, and a relaxed fit. Style with wide-leg pants and sandals.

    Fit & Features

    • Linen-blend fabric
    • Collared V-neckline
    • Chest pocket, button-down front
    • Cap sleeves
    • Side zipper closure
    • Twist-front cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06003-2431

    Category Name: Vacation Dresses & Outfits

    Price: $30.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: M, L

  • Gleam Always Snake Chain Necklace

    Always gleam in this essential snake chain necklace to give every outfit the perfect accessory! Complete the look in a bodycon dress for any occasion. 

    Fit & Features

    • Snake chain
    • Back adjustable chain with clasp closure

    Style Number/Barcode: 07002-1817

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Vibes High Slit Woven Midi Skirt

    This airy woven midi skirt will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric with a mini-length lining, it features a high waist with the cutest tie detail, a high-cut side slit to showcase some leg, and a flowy slim-fit silhouette. Style with the matching crop top for a fabulous 'fit!

    Shop Matching Orange Top: Sunny Vibes Bow Back Woven Crop Top

    Fit & Features

    • Woven fabric with mini-length knit lining, minimal stretch
    • High-rise elasticized waist
    • Tie detail
    • High side slit
    • Flowy slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 06401-0651

    Category Name: Vacation Dresses & Outfits

    Price: $29.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: S, L

  • Sunny State Mid-Rise Distressed Denim Shorts

    Grab your besties and make plans to rock these mid-rise denim shorts for fun under the sun! The mid-rise waist and form-hugging fit flatter your curves, while the distressed accents and cut-off hem add a touch of edge. Complete the look in a cute bodysuit and platform sneakers!

    Fit & Features

    • Denim fabric, minimal stretch
    • Mid-rise waist
    • Distressed accents, cut-off hem
    • Form-hugging
    • Front button and hidden zipper closure, five-pockets
    • Runs true to size

    Style Number/Barcode: 06603-0388

    Category Name: Vacation Dresses & Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L, XL

  • Trendy Adventure Strapless Paisley Satin Crop Top

    Endless summer adventures call for this trendy paisley satin crop top! Featuring a flattering strapless neckline, a stretchy smocked bandeau lining, and a tie-back closure for the perfect fit. Complete the look in denim shorts and sunglasses!

    Fit & Features

    • Paisley print, non-stretch satin fabric
    • Strapless neckline
    • Tie back design
    • Stretchy smocked bandeau lining
    • Pointed crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2544

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Catch Tie Front Knit Bandeau

    Catch this stylish bandeau top for the ultimate vacation look! Featuring a strapless sweetheart neckline and a tie-front bust for a flirty allure while the ultra-cropped hem adds a trendy touch. Complete the look with the matching skirt.

    Shop Matching Bottoms: Stylish Catch High Rise Slit Midi Skirt

    Fit & Features

    • Knit fabric, sewn-in knit lining, minimal stretch
    • Strapless sweetheart neckline
    • Tie-front bust
    • Ultra-cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2418

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

  • Social Butterfly Flower Hoop Earrings Set

    The perfect three-pack earring set to adorn all of your outfits for everything on the calendar! This set has one pair of rhinestone embellished butterflies, one pair of flowers, and one pair of rhinestone trim hoop earrings each with post-back closures. Complete the look with dressy heels.

    Fit & Features

    • Thre-pack earrings set
    • One pair of rhinestone butterflies
    • One paid of flowers
    • One pair of rhinestone trim hoop earrings
    • Post-back closures

     

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

    Style Number/Barcode: 07001-2032

    Category Name: Vacation Dresses & Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

  • Loving Heart Shell Necklace

    Fall for this heart shell necklace to adorn your vacation or weekend outfit! Complete the look in cute sandals.

    Fit & Features

    • Heart shell charm
    • Cord strand
    • Lobster clasp closure

    Style Number/Barcode: 07002-1838

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

  • Keep It Chic Doorknocker Hoop Earrings

    Keep your everyday 'fits chic and on-trend with these sleek doorknocker hoop earrings! They feature a large teardrop-shaped post with a hanging hoop design. Include a post-back closure. Complete the look with a ring set.

    Fit & Features

    • Large teardrop post
    • Hanging hoop design
    • Post-back closure

     

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

    Style Number/Barcode: 07001-1986

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: Out of Stock

  • Season Staple Denim Print Faux Leather Shoulder Bag

    Trendy with a chic structure, this denim print faux leather shoulder bag is a staple for the season. Designed with a medium-wash denim print on smooth faux leather material, this bag is a fabulous must-have! It features a small half-moon shape with curved seam accents, a snap button closure with a buckle strap accent, a top zipper closure to secure your essentials in the spacious woven interior, and an adjustable shoulder strap. Pair with the matching heels for a seamlessly stylish 'fit!

    Shop Matching Heels: Season Staple Denim Print Faux Leather Stiletto Heels

    Fit & Features

    • Faux leather material with medium-wash denim print
    • Small half-moon design
    • Snap button closure with buckle strap accent
    • Top zipper closure
    • Woven interior with pouch and zippered pocket
    • Adjustable shoulder strap
    • Black is solid faux leather material

    Style Number/Barcode: 07203-2018

    Category Name: Vacation Dresses & Outfits

    Price: $28.90

    Availability: Out of Stock

  • Whimsical Chic Organza Butterfly Statement Earrings

    Create an enchanting spring or summer party look with these whimsical butterfly statement earrings! They feature a gorgeous long cascading design with a dainty chain, large and small sheer organza butterfly accents, and a sparkling round rhinestone detail at the end. Include a fish hook closure. Style with a ring set.

    Fit & Features

    • Long linear design
    • Dainty chain
    • Sheer organza butterfly accents
    • Round rhinestone detail
    • Fish hook closure, rubber stopper


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

    Style Number/Barcode: 07001-1991

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Flair Oversized Square Sunglasses

    Add that chic flair to your everyday looks with these sleek square sunglasses! They feature an oversized square-shaped design, a trendy tortoiseshell plastic frame and arms, built-in nose pads for support, and tinted lenses. Style these shades with a faux leather handbag.

    Fit & Features

    • Oversized square-shaped design
    • Tortoiseshell plastic frame and arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1072

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: Out of Stock

  • Fab Trendsetter Rectangle Sunglasses

    Top off your fab summer 'fits with these trendy shades! The sunglasses feature a rectangular-shaped design, a plastic frame with a glam metallic sheen, built-in nose pads, and tinted lenses. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Rectangular-shaped design
    • Plastic frame, metallic sheen
    • Built-in nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-1090

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Perfect Day Puff Espadrille Wedge Sandals

    From beach vacations to sunset cocktails, these wedge sandals are perfect for summer fun! Featuring a square toe and a unique woven puff strap, you'll stand out in style. The espadrille platform wedge sole and padded faux leather footbed add comfort and elevated trendiness. Complete the look with a chic purse.

    Fit & Features

    • 2" Wedge heel
    • Square toe
    • Woven puff strap
    • Espadrille platform sole
    • Padded faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07406-0358

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Best Times Doorknocker Earrings

    The best times start with the best accessories like these earrings! They feature a statement doorknocker design and a post-back closure. Complete the look in a bodycon dress for date night.

    Fit & Features

    • Dooknocker design
    • Post back closure

     

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

    Style Number/Barcode: 07001-2031

    Category Name: Vacation Dresses & Outfits

    Price: $7.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Structure Cuff Bracelet

    You'll obsess over the sleek structure of this trendy cuff bracelet! It features a teardrop-shaped overlapping design with a snap closure. Style with hoop earrings.

    Fit & Features

    • Teardrop-shaped overlapping design
    • Snap closure

    Style Number/Barcode: 07003-0557

    Category Name: Vacation Dresses & Outfits

    Price: $12.90

    Availability: Out of Stock

  • Feeling The Vibe Rhinestone Star Charm Platform Sneakers

    You'll be feeling the vibe of these athleisure sneakers perfect for casual coffee shop runs and errands! These playful kicks feature a round toe, a lace-up placket with a rhinestone star charm, and a comfy footbed with a platform sole and gel insert. Complete the look in a comfy lounge set.

    Fit & Features

    • Round toe
    • Lace-up placket, rhinestone star charm decor
    • Chunky platform sole with gel insert
    • Comfortable footbed
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07407-0226

    Category Name: Vacation Dresses & Outfits

    Price: $30.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 9, 10

  • Casual And Stylish Cargo Pocket Vest

    When casual meets stylish like this sleeveless vest, you know it's going to be a closet staple! This vest features a collar neckline, a button-down front, and trendy cargo flap pockets for convenience, and a cropped hem for a modern touch. Complete the look in high-rise jean shorts for any occasion!

    Fit & Features

    • Windbreaker-type woven fabric, no stretch
    • Collar neckline
    • Button down front
    • Cargo flap pockets
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1787

    Category Name: Vacation Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L, XL