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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.

  • Worth It Linen Wide Leg Pants

    These linen-blend pants are worth taking on your next weekend adventure! They feature a high-rise waist, back zipper closure, side pockets, and a wide-leg silhouette. Complete the look in the matching top.

    Shop Matching Top: Worth It Linen Tube Top

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Side pockets
    • Wide-leg silhouette
    • Linen-blend fabric, lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0623

    Category Name: Vacation Looks

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hampton Vacay Crochet Trim Duster

    Head out to the Hamptons in this effortlessly stylish duster featuring flowy short sleeves, open-front design, crochet trim, tie-front closure, and a long-length hem on gauze woven fabric. Complete the look in a chic hat and sunnies.

    Fit & Features

    • Flow short sleeves
    • Open-front design
    • Crochet trim
    • Tie-front closure
    • Long-length hem
    • Gauze woven fabric
    • Fits true to size

    Style Number/Barcode: 06204-1175

    Category Name: Vacation Looks

    Price: $15.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blushing Tropics Bandeau Top

    Make all the cheeks blush when you step out in this tropic chiffon bandeau! Featuring a sleeveless, strapless, neckline with a front ruched tie and back smocked panel. Complete the look in the matching top. 

    Shop Matching Top: Blushing Tropics Button-Up Top

    Fit & Features

    • Strapless, sleeveless
    • Bandeau style
    • Front ruched tie
    • Back smocked panel
    • Floral tropic print
    • Chiffon fabric
    • Runs true to size

    Style Number/Barcode: 06003-1660

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vibes One Shoulder Top

    Getaway this weekend with a top that is too perf! The top features a one-shoulder neckline, an asymmetrical cutout, and a mid-length hem. The top is composed of a cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with cutoff shorts. 

    Fit & Features

    • One-shoulder neckline
    • Asymmetrical cutout 
    • Mid-length hem
    • Cotton knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06001-4289

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Abstract Art Satin Convertible Top

    Abstract art you can wear! Slay an art gallery opening in this fierce satin crop top featuring a convertible design so you can style it multiple ways and a smocked back. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Abstract Art Satin Wide Leg Pants

    Fit & Features

    • Sleeveless, strapless neckline, non-slip grip lining 
    • Lightly padded bust
    • Convertible multi-way wear
    • Smocked back
    • Cropped hem
    • Abstract print, satin fabric
    • Runs true to size

    Style Number/Barcode: 06003-1582

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sheer Secrets Chiffon Short Kimono

    The secret to elevating any outfit is this sheer short kimono featuring flowy 3/4 length bell sleeves, an open-front design with a tie belt closure, and a short-length hem. Complete the look in a lace bralette and shorts for a summer festival.

    Fit & Features

    • 3/4 length bell sleeves
    • Open-front design
    • Tie belt closure
    • Short-length hem
    • Sheer chiffon fabric
    • Fits true to size

    Style Number/Barcode: 06204-1184

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
    • Fits true to size

    Style Number/Barcode: 06303-0141

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Set The Mood Poplin Tie Front Top

    Set the mood for the squad in this chic crop top featuring a sleeveless, scoop neck, tie-front pleated bust, flexible boning, and a back zipper closure. Complete the look in a lace-up skirt for a girl's weekend.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Tie-front pleated bust
    • Flexible boning
    • Cropped hem
    • Back zipper closure
    • Poplin woven-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1453

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The One Ribbed Knit Crop Tank

    Make this crop top the one piece you can't live without! The cropped tank features a sleeveless scoop neckline, bungee cord spaghetti straps, a multi-strap back design, and a cropped hem. The tank is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with cutoff shorts. 

    Fit & Features

    • Sleeveless scoop neckline 
    • Bungee cord spaghetti straps
    • Multi-strap back design 
    • Cropped hem
    • Ribbed knit fabric 
    • Form hugging, moderate stretch, runs true to size

    Style Number/Barcode: 06002-1165

    Category Name: Vacation Looks

    Price: $6.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Comfort Level Strappy Sandals

    You'll be reaching for these strappy sandals on the daily! They feature a round toe, comfort fit sole, and ankle buckle closure. Complete your casual look in a sundress.

    Fit & Features

    • Round toe
    • Comfort fit sole
    • Strappy design
    • Ankle buckle closure
    • Runs true to size

    Style Number/Barcode: 07404-1031

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eye-Catching Cutout Strappy Slide Sandals

    Slip into these cutout strappy slide sandals for an eye-catching look this season!

    Fit & Features

    • Round toe
    • Strappy cutout design
    • Adjustable strap
    • Slide on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1277

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Paradise Graphic Knot Tee

    Enter vacay mode with this graphic tee in your lineup! It features short sleeves, a crew neck, and a front sunset and palm graphic and knot accent hem. Complete the look in a casual skirt and sneakers.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Sunset and palm graphic detail
    • Knot accent hem
    • Modal cotton fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1331

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Day To Day High Rise Denim Shorts By Windsor Denim

    These high-rise denim shorts by Windsor Denim will fit nicely into your day-to-day rotation. They feature a high-rise waist, distressed accents, a frayed hem, and slight color fading for the perfect vintage fit and feel. Complete the look in a trendy bodysuit.

    Fit & Features

    • High rise waist
    • Distressed accents
    • Frayed hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Slight color fading, denim fabric
    • Fits true to size

    Style Number/Barcode: 06603-0257

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Bloom Chiffon Crop Top

    This gorgeous floral chiffon crop top will brighten up your summer wardrobe! It features long bishop sleeves with cinched ruffled hems, a V-neckline with a cute tie design, a majorly cropped hem, and an all-over blooming floral print. Style this top with high-rise jeans and sleek gold hoops.

    Fit & Features

    • Long bishop sleeves, elastic ruffled hems
    • V-neckline
    • Tie design
    • Smocked back
    • Cropped
    • Floral print, sheer chiffon fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1647

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ticket To Paradise Slit Maxi Skirt

    Got your ticket to a paradise island? Make sure to pack this tropical maxi skirt perfect for relaxing poolside! It features a high-rise elastic waistband, form-fitting silhouette, and a sultry high-cut side slit on stretchy knit fabric. Complete the look in the matching top.

    Shop Matching Top: Ticket To Paradise Halter Crop Top

    Fit & Features

    • High-rise elastic waist
    • Form-fitting silhouette
    • Side high-cut slit
    • Maxi-length hem
    • Tropical print
    • Stretchy knit fabric
    • Runs true to size

      Style Number/Barcode: 06501-0605

      Category Name: Vacation Looks

      Price: $6.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ticket To Paradise Halter Crop Top

      Got your ticket to a paradise island? Make sure to pack this tropical crop top perfect for relaxing poolside! It features a sleeveless, halter neck, open-back with lace-up closure on stretchy knit fabric. Complete the look in the matching skirt.

      Shop Matching Bottoms: Ticket To Paradise Slit Maxi Skirt

      Fit & Features

      • Sleeveless, halter neck
      • Cropped hem
      • Lace-up, open-back
      • Tropical print
      • Stretchy knit fabric
      • Runs true to size

      Style Number/Barcode: 06001-4023

      Category Name: Vacation Looks

      Price: $6.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Island Flower High Slit Midi Skirt

      Look prettier than the island flowers in this tropical floral midi skirt featuring a high-rise waist and a front high-cut slit. Complete the look in the matching top and sandals.

      Shop Matching Top: Island Flower Lattice Tank Top

      Fit & Features

      • High-rise waist
      • Front high-cut slit
      • Maxi-length hem
      • Tropical floral print
      • Stretchy knit-lined fabric
      • Runs true to size

        Style Number/Barcode: 06501-0601

        Category Name: Vacation Looks

        Price: $6.97 $29.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Reese High Rise Mom Denim Shorts By Windsor Denim

        The perfect mom shorts that hug your curves in all the right places! Introducing the Reese high-rise mom denim shorts by Windsor Denim. They feature a flattering, ultra-high rise waist and a trendy cut-off hem on premium vintage-inspired light wash denim with a color fade effect. Complete the look in a cute graphic tee and sandals for the perf summer vibe.

        Fit & Features

        • Ultra high-rise waist
        • Mom-style silhouette
        • Cut-off hem
        • Front five-button fly, belt loop accents
        • Five-pocket styling 
        • Premium light wash denim, color fade effect, no stretch
        • Fits true to size

        Style Number/Barcode: 06603-0275

        Category Name: Vacation Looks

        Price: $9.97 $34.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Night Out Mood Crop Top

        You'll be ready for a chic night out in this sultry halter crop top! It features cross-front halter straps, a cross-back strap design, a trendy waist tie that can be styled in the front or back, and a majorly cropped, form-hugging fit. Complete the look with high-rise jeans and heeled mules.

        Fit & Features

        • Sleeveless bodice
        • Cross-front halter straps, cross-back strap design
        • Back zipper closure
        • Waist tie that can be styled in the front or back
        • Cropped, form-hugging fit
        • Woven fabric
        • Runs true to size

        Style Number/Barcode: 06003-1327

        Category Name: Vacation Looks

        Price: $6.97 $26.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Dreaming of Florals Corset Top

        Dream of a floral outfit with this adorable top! The top features a floral print, a sweetheart neckline with padded cups, a corset-styled bodice, ruched cap sleeves, and a cropped hem. The top is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with a wrap skirt and mules. 

        Fit & Features

        • Sweetheart neckline, padded cups
        • Corset-styled bodice, smocked back
        • Ruched cap sleeves
        • Floral print
        • Cropped hem 
        • Lightweight woven fabric
        • Relaxed fit, minimal stretch, runs true to size 

        Style Number/Barcode: 06003-1839

        Category Name: Vacation Looks

        Price: $6.97 $38.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Siesta Keys Tropical Maxi Dress

        Take a vacation to Siesta Keys looking fab in this tropical maxi dress! It features a sleeveless, v-neck, spaghetti straps, and a tie-front bust atop a cutout bodice leading to the form-fitting silhouette with a sultry side slit. Complete your vacay look in a straw hat and your fave sunglasses.

        Fit & Features

        • Sleeveless, v-neck, spaghetti straps
        • Tie-front bust
        • Cutout bodice
        • Form-fitting silhouette
        • Side slit, maxi hem
        • Tropical print
        • Fits true to size

        Style Number/Barcode: 05102-4377

        Category Name: Vacation Looks

        Price: $9.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Pop Of Color Two-Pack Anklet Set

        Get the perfect pop of color with this anklet set featuring one multi-color stone and one dainty chainlink layer each with lobster clasp closures. Complete the look in a casual jumpsuit for a coffee meet-up.

        Fit & Features

        • Two-pack set
        • One multi-color stone
        • One dainty chainlink
        • Lobster clasp closures

        Style Number/Barcode: 07003-0346

        Category Name: Vacation Looks

        Price: $3.97 $9.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Braids For Days Block Heel Mules

        These stylish block heel mules will have you looking trendy for days! Featuring dual braided straps, almond toe, and a faux leather footbed. Complete the look in a flowy casual dress for a picnic date.

        Fit & Features

        • Almond toe
        • Block heels
        • Dual braided straps
        • Faux leather footbed
        • Runs true to size

        Style Number/Barcode: 07401-3702

        Category Name: Vacation Looks

        Price: $4.97 $30.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Life Made Easy Linen Halter Maxi Dress

        Look effortlessly put together in this breezy striped linen maxi dress for a Duffy boat cruise or beachside brunch! It features a sleeveless, halter v-neck with tie-closure, a partial open-back with tie, hidden side pockets, and a flowy, maxi-length silhouette with a sultry front slit. Complete the look in a straw floppy hat and sandals. 

        Fit & Features

        • Sleeveless, halter v-neck, tie-closure
        • Partial open-back with tie
        • Hidden side pockets
        • Flowy silhouette
        • Front high-cut slit
        • Maxi-length hem
        • Striped linen fabric, lining, no stretch
        • Fits true to size

        Style Number/Barcode: 05102-4468

        Category Name: Vacation Looks

        Price: $6.97 $59.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale