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.

  • Made For You High Rise Palazzo Pants

    These palazzo pants are made for you on vacation or pretending while sipping on cocktails poolside! They feature a high-rise waist, pleat front detailing, and a wide-leg silhouette. Complete the look in the matching top.

    Shop Matching Top: Made For You Tie Front Bandeau Top

    Fit & Features

    • High-rise waist
    • Pleat front detailing
    • Wide-leg silhouette
    • Pull-on/off styling
    • Textured lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0631

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forever Chic Drawstring Halter Top

    Bring on the chic with a halter top that is perf for a time under the sun! The top features a halter neck, a drawstring neck ties, dual drawstrings at the sides, and cropped hem. The top is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with denim shorts.

    Fit & Features

    • Halter neck 
    • Drawstring neck ties
    • Dual drawstrings at sides
    • Cropped hem 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06001-4110

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Summer Days Cuffed Shorts

    These lightweight linen-blend shorts were made for those effortless summer days. They feature a mid-rise smocked waist, an adjustable tie-front drawstring, a cuffed hem, and a relaxed fit. Style these casual shorts with a fitted bodysuit and slides.

    Fit & Features

    • Mid-rise elasticized smocked waist
    • Adjustable tie-front drawstring
    • Front pockets, faux back pockets
    • Cuffed hem
    • Non-stretch woven linen fabric
    • Runs true to size

    Style Number/Barcode: 06303-0185

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunkissed Sultry Bikini Top

    Showcase a sunkissed sultry look in this alluring bikini top. It features a square neckline with a center square-shaped cutout at the bust, adjustable spaghetti straps for a customized fit, and a strappy tie-back design. Style with the matching bikini bottoms.

    Shop Matching Bottoms: Sunkissed Sultry Bikini Bottoms

    Fit & Features

    • Square neckline
    • Center square-shaped cutout
    • Adjustable spaghetti straps
    • Tie-back design
    • No padding
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0680

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho-Chic Celestial Charm Chain Belt

    Style up your festival 'fit with this boho-chic chain belt! It features a layered design with dangling moon, sun, and star charms for a trendy celestial vibe. Pair this belt over a curve-hugging mini dress with fab booties.

    Fit & Features

    • Layered design
    • Moon, sun, and star charms
    • Adjustable fit, lobster clasp closure

    Style Number/Barcode: 07301-0469

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wing It Butterfly Charm Anklet

    Wing your look in this stylish butterfly charm anklet featuring a dainty chain, rhinestone drops, and an adjustable lobster clasp closure. Complete the look in a cute bikini set and cover-up.

    Fit & Features

    • Butterfly charms
    • Rhinestone drops
    • Dainty chain
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07003-0341

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Cutie Straw Floppy Hat

    Show off your playful side in this straw floppy hat featuring an oversized design and a ribbon trim. Complete the look in a cute sundress for a day spent in the sun.

    Fit & Features

    • Oversized design
    • Floppy brim
    • Ribbon trim
    • Straw material

    Style Number/Barcode: 07302-0498

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Saddle Up Straw Cowboy Hat

    Back in the saddle again looking so country-chic! This straw cowboy hat is the perfect finishing touch to your music festival outfit. It features a classic curved brim and a unique beaded string with a knot-tie accent.

    Fit & Features

    • Curved brim
    • Beaded string, knot-tie accent
    • Adjustable interior string with bead
    • Straw material

    Style Number/Barcode: 07302-0587

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Babe Tie-Dye Mini Skirt

    You're a total bold babe when it comes to your style, so this mini skirt was made for you. It features a high-rise waist, side ruched detailing leading to an adjustable drawstring at the hem, a short, curve-hugging fit, and a trendy all-over tie-dye print. Style with the matching crop top and statement earrings.

    Shop Matching Top: Bold Babe Tie-Dye Crop Top

    Fit & Features

    • High-rise waist
    • Side ruching, adjustable drawstring at the hem
    • Mini-length, form-fitting silhouette
    • Tie-dye print
    • Soft brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0599

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vintage-Chic Oval Sunglasses

    Accessorize your summer looks with these vintage-chic shades! The sunglasses feature oval-shaped tinted lenses with a tortoise-shell plastic frame. Style with a trendy shoulder bag.

    Fit & Features

    • Oval-shaped tinted lenses
    • Tortoise-shell plastic frame

    Style Number/Barcode: 07008-0961

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Talks Strappy Bikini Top

    Sit pretty poolside in this sultry bikini top! It features a sleeveless tank-style bodice with a plunge v-neckline with a strappy design, removable padding, and a hook-back closure. Composed of a sleek-lined knit fabric. Style with matching bottoms and oversized sunnies

    Shop The Matching Bottoms: Sultry Talks Hipster Bikini Bottoms

    Fit & Features

    • Sleeveless tank style straps
    • Plunge v-neckline with a strappy design
    • Removable padding for support and shaping
    • Hook-back closure
    • Sleek knit lined fabric
    • Fits true to size

    Style Number/Barcode: 07104-0608

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All This Love Cowl Halter Crop Top

    A sweet crop top with a sultry open back and cowl halter neckline that dresses up your favorite jeans.

    Fit & Features

    • Smooth knit stretchy fabric
    • Cowl halter neckline, spaghetti strap tie
    • Open back
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000087

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Babe Tie-Dye Crop Top

    You're a total bold babe when it comes to your style, so this crop top was made for you. It features a sleeveless halter neckline with spaghetti straps and a center O-ring accent, an alluring center cutout at the bust, a cropped, form-hugging fit, and a trendy all-over tie-dye print. Style with the matching mini skirt and statement earrings.

    Shop Matching Bottoms: Bold Babe Tie-Dye Mini Skirt

    Fit & Features

    • Sleeveless halter neckline, front O-ring accent
    • Spaghetti straps, tie at the back of the neck
    • Center cutout at the bust
    • Cropped, form-hugging fit
    • Tie-dye print
    • Soft brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4010

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun In Fringe Mesh Swim Wrap

    Have fun in the sun looking stylish in this fringe mesh swim wrap! It features a side-tie knot closure, sheer design, and fringe trimming. Complete your vacay look in a fab bikini set.

    Fit & Features

    • Side-tie knot closure
    • Sheer mesh design
    • Fringe trimming
    • Moderate stretch

    Style Number/Barcode: 07305-0383

    Category Name: Vacation Looks

    Price: $1.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Do It Like Bey Layered Belly Chain

    Showcase your inner diva at the pool party in this layered belly chain featuring three snake chains and a lobster clasp closure. Complete the look in a sultry bikini set for a pool party.

    Fit & Features

    • Layered design
    • Three snake chains
    • Lobster clasp closure

    Style Number/Barcode: 07301-0444

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Shady Square Oversized Sunglasses

    Shade your eyes from the sun's rays in these oversized sunglasses featuring square plastic frames, tortoise patterns, and gradient lenses. Complete the look in a chic jumpsuit for wine tasting.

    Fit & Features

    • Square plastic frames
    • Oversized design
    • Tortoise pattern
    • Gradient lens

    Style Number/Barcode: 07008-0962

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring That Glow Swim Top

    Bring that glow to your poolside look with this bright swim top that will have all eyes on you! It features a convertible bandeau fit with spaghetti straps you can tie in a halter style, a cross-front design, as a one-shoulder neckline, or as a cute bralette. Style with the matching swim bottoms and some sleek shades.

    Shop Matching Bottoms: Bring That Glow Swim Bottoms

    Fit & Features

    • Convertible bandeau fit
    • Spaghetti straps
    • No padding
    • Moderate stretch
    • Runs true to size

      Style Number/Barcode: 07104-0682

      Category Name: Vacation Looks

      Price: $4.97 $19.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Sultry Silhouette One-Piece Swimsuit

      Showcase a sultry silhouette in this chic one-piece! The swimsuit features a plunging V-neck and back, tank shoulder straps, a padded bust, sheer mesh inserts at the seams, a high waist design, and a semi-cheeky fit. Style with a flowy kimono and strappy sandals.

      Fit & Features

      • Deep V-neck and back
      • Tank shoulder straps
      • Removable padding
      • Sheer mesh inserts, nude hue
      • High waist design, semi-cheeky fit
      • Moderate stretch
      • Runs true to size


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

      Style Number/Barcode: 07109-0297

      Category Name: Vacation Looks

      Price: $4.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Major Mermaid Vibes Bikini Top

      Bring gorgeous mermaid vibes to your poolside look with this alluring bikini top. It features a V-wired bust, adjustable spaghetti straps for a customized fit, and an all-over metallic fishnet design. Style with the matching bikini bottoms.

      Shop Matching Bottoms: Major Mermaid Vibes Bikini Bottoms

      Fit & Features

      • V-wired bust, no padding
      • Adjustable spaghetti straps
      • Back strap, slide-hook closure
      • Metallic fishnet design, full lining
      • Moderate stretch
      • Runs true to size

      Style Number/Barcode: 07104-0633

      Category Name: Vacation Looks

      Price: $4.97 $22.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Secret Garden Chiffon Flowy Shorts

      This floral chiffon top is perfect for a garden party! Featuring long peasant sleeves, a surplice v-neckline, back smocked panel, and a cropped hem. Complete the look in the matching top.

      Shop Matching Top: Secret Garden Chiffon Surplice Top

      Fit & Features

      • High-rise waist
      • Back zipper, hook and eye closure
      • Flowy silhouette
      • Floral pattern
      • Chiffon-lined fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 06403-0216

      Category Name: Vacation Looks

      Price: $6.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Simple Chic Vibe Swim Tank

      Simple yet so chic, this swim tank will elevate your poolside look. It features a scoop neckline, an alluring center cutout at the bust with dual tortoise-shell O-ring accents, thin tank shoulder straps, and a back bar strap design. Style with the matching swim bottoms.

      Shop Matching Bottoms: Simple Chic Vibe Swim Bottoms

      Fit & Features

      • Scoop neckline
      • Removable padding
      • Center cutout, dual tortoise-shell O-rings
      • Tank shoulder straps
      • Back bar strap detailing
      • Ribbed fabric, moderate stretch
      • Runs small, size up one size

        Style Number/Barcode: 07104-0609

        Category Name: Vacation Looks

        Price: $4.97 $18.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Wrapped In Sultry Style Cover-Up

        Wrap yourself in chic and sultry style with this alluring fishnet cover-up. The swim wrap features an asymmetrical curve-hugging silhouette you can tie at the waist. Layer this wrap over your fave bikini with strappy sandals.

        Fit & Features

        • Asymmetrical form-fitting silhouette
        • Tie-waist detail
        • Sheer fishnet material
        • Minimal stretch

        Style Number/Barcode: 07305-0385

        Category Name: Vacation Looks

        Price: $4.97 $12.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Spiraling Chic Metal Arm Cuff

        This chic spiral arm cuff will add the perfect touch to your night look! Perfect for styling with a sleek satin long dress for a dressy dinner party.

        Fit & Features

        • Spiral metal design
        • Stretches-to-fit

        Style Number/Barcode: 07003-0349

        Category Name: Vacation Looks

        Price: $4.97 $10.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Island Ready Printed Tie-Front Top

        Look like you're ready to jet set off on an island getaway in this printed top! It features short flutter sleeves, a V-neckline, a tie-front design, and a cropped fit. The all-over palm leaf print brings those vacay vibes. Style with the matching mini skirt!

        Shop Matching Bottoms: Island-Ready Printed Mini Skirt

        Fit & Features

        • Short flutter sleeves
        • V-neckline
        • Tie-front
        • Cropped, form-hugging fit
        • Palm leaf print
        • Brushed knit fabric, moderate stretch
        • Runs true to size

        Style Number/Barcode: 06202-0305

        Category Name: Vacation Looks

        Price: $9.97 $21.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free