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.

  • Paradise Floral Ruched Midi Dress

    Fly to paradise in this perfect floral midi dress featuring a sleeveless, square neck, spaghetti straps, bodycon fit, and a side ruche with a tie so you can customize the fit. Complete the look in stylish mules.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon fit
    • Midi-length hem
    • Side ruche with tie
    • Floral pattern
    • Stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05101-1362

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 90's Moment Rectangular Sunglasses

    Throw it back to the '90s in these trendy sunglasses featuring small plastic rectangular frames and arms with grommet insets. Complete the look in a faux leather blazer.

    Fit & Features

    • Small rectangular frames
    • Grommet insets on arms
    • Plastic material 

        Style Number/Barcode: 07008-0922

        Category Name: Vacation Looks

        Price: $3.97 $9.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Rays For Daze Square Oversized Sunglasses

        Shade your eyes from the rays in these edgy sunglasses! They feature oversized square frames and chain-link arms. Complete the look in a faux leather jacket for hanging with friends.

        Fit & Features

        • Oversized square frames
        • Chain-link arms
        • Nose pads

        Style Number/Barcode: 07008-0925

        Category Name: Vacation Looks

        Price: $5.97 $12.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Ready For My Vacay Mesh Kimono

        Be sure to pack this breezy mesh kimono for your island getaway! It features mid-length loose sleeves, a draped open front with a tie-front belt to stylishly cinch your waist, a flowy silhouette, and an all-over palm leaf print. Layer this lightweight kimono over your fave bikini for the perf beachside coverup.

        Fit & Features

        • Mid-length, loose kimono-style sleeves
        • Open front, tie-front belt
        • Flowy, relaxed fit
        • Palm leaf print
        • Sheer mesh fabric, moderate stretch
        • Runs true to size

        Style Number/Barcode: 06202-0263

        Category Name: Vacation Looks

        Price: $23.97 $36.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Sultry Snake Mesh Seam Detail Top

        Look sultry in this snake mesh crop top featuring fitted, long sleeves, a crew neck, and on-trend seam detail on a cropped silhouette. Complete the look in a bralette.

        Fit & Features

        • Fitted long sleeves
        • Crew neck
        • Seam detail throughout
        • Crop hem
        • Snake pattern
        • Sheer mesh fabric
        • Fits true to size, moderate stretch

        Style Number/Barcode: 06001-3888

        Category Name: Vacation Looks

        Price: $6.97 $24.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • First Look Lace-Up Crop Top

        This top is a must-have for making that stunning first impression! The top features an off-the-shoulder neckline, a sweetheart bust with a lace-up front, long sleeves, and a cropped hem. The top is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching maxi skirt.

        Shop Matching Maxi Skirt: First Look Ruched Maxi Skirt

        Fit & Features

        • Off-the-shoulder neckline
        • Sweetheart bust
        • Lace-up front 
        • Cropped hem 
        • Smooth knit fabric 
        • Form hugging fit, moderate stretch 
        • Runs true to size

        Style Number/Barcode: 06001-3925

        Category Name: Vacation Looks

        Price: $6.97 $26.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • First Look Ruched Maxi Skirt

        This skirt is a must-have for making that stunning first impression! The skirt features an elastic high rise waist, ruching throughout, a high side slit, and a maxi length hem. The skirt is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching crop top.

        Shop Matching Crop Top: First Look Lace-Up Crop Top

        Fit & Features

        • Elastic high-rise waist
        • Ruching 
        • High side slit
        • Maxi length hem 
        • Smooth knit fabric 
        • Form-hugging fit, moderate stretch
        • Runs true to size

        Style Number/Barcode: 06501-0576

        Category Name: Vacation Looks

        Price: $6.97 $29.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Stop and Stun Floral Slit Maxi Dress

        Serving petal power with every step. This floral print maxi stuns with a draped cowl neckline and a high front slit that brings the drama (and the legs).

        Fit & Features

        • Floral print, mesh-lined fabric
        • Cowl neckline
        • Spaghetti straps
        • Form-hugging fit
        • High front slit
        • Maxi-length hem
        • Runs true to size

        Style Number/Barcode: 05101-000348

        Category Name: Vacation Looks

        Price: $9.97 $52.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Simple Staple Ribbed Knit Top

        This ribbed knit top is a simple staple you need in your wardrobe! It features a scoop neckline, short sleeves, and a mid-length, form-hugging fit. Style this basic top with your fave pair of denim and a layered necklace.

        Fit & Features

        • Scoop neckline
        • Short sleeves
        • Mid-length, form-hugging fit
        • Ribbed knit fabric, moderate stretch
        • Runs true to size

        Style Number/Barcode: 06002-1144

        Category Name: Vacation Looks

        Price: $6.97 $19.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Breezy Floral Chiffon Short Kimono

        Easy, breezy, and effortless, this floral chiffon kimono is the perfect layer! It features 3/4 length sleeves, an open-front design, and a high-low hem. Complete the look in a sultry slip dress and heels.

        Fit & Features

        • 3/4 length sleeves
        • Open-front design
        • Floral pattern
        • High-low hem
        • Airy chiffon fabric, no stretch
        • Fits true to size

        Style Number/Barcode: 06204-1152

        Category Name: Vacation Looks

        Price: $18.97 $26.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Trendsetting Vibes Embroidered Denim Jacket

        Bring the trendsetting vibes to your outfits this season with this cool light wash denim jacket. It features a collared neckline, long sleeves with buttons to cuff, a complete button-down front, pockets, an all-over embroidered star pattern, and a frayed hem. Style this jean jacket with aviator sunglasses and a cute crossbody purse.

        Fit & Features

        • Collared neckline
        • Long sleeves, single buttons to cuff
        • Button-down front
        • Buttoned chest pockets, side pockets
        • Embroidered star pattern, frayed hem
        • Light wash denim fabric, no stretch
        • Runs true to size

        Style Number/Barcode: 06203-0460

        Category Name: Vacation Looks

        Price: $9.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Vintage Era Cat Eye Sunglasses

        Create a head-to-toe vintage-inspired look starting with these cat-eye sunglasses! They feature a plastic frame, sturdy arms, and a curved lens. Complete the look in a trendy denim jacket.

        Fit & Features

        • Cat-eye style
        • Plastic frames
        • Sturdy arms
        • Curved lens

        Style Number/Barcode: 07008-0921

        Category Name: Vacation Looks

        Price: $4.97 $10.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Blossom With Beauty Floral Chiffon Kimono

        Blossom with beauty in this breezy chiffon kimono! It features three-quarter length sleeves, an open front, a flowy silhouette, and an all-over floral print with pretty pastel hues. Style this kimono over a basic tank and denim shorts.

        Fit & Features

        • Three-quarter length sleeves
        • Open front
        • Flowy, relaxed fit
        • Floral print
        • Sheer chiffon fabric, no stretch
        • Runs true to size

        Style Number/Barcode: 06204-1155

        Category Name: Vacation Looks

        Price: $18.97 $29.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Sleek And Stunning Ruched Mini Skirt

        Keep it sleek and stunning with a mini skirt that makes a stylish statement. The mini skirt features an elastic high-rise waist, ruched side seams, and a mini-length silhouette. The skirt is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with the matching crop top and mules.

        Shop Matching Top: Sleek And Stunning Ruched Crop Top

        Fit & Features

        • Elastic high-rise waist
        • Ruched side seams
        • Mini-length silhouette
        • Smooth knit fabric
        • Form-hugging fit, moderate stretch
        • Runs true to size

          Style Number/Barcode: 06501-0649

          Category Name: Vacation Looks

          Price: $9.97 $22.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Ships Free
        • See You Again Crepe Wrap Mini Dress

          Flirty and cute, this crepe mini dress is perfect for running into your ex. It features a sleeveless square neckline, spaghetti straps, an open-back design with lace-up closure, and an asymmetrical wrap skirt with a side ruched seam. Complete the look in linear earrings and heels.

          Fit & Features

          • Sleeveless, square neck, spaghetti straps
          • Open-back design with lace-up closure
          • Asymmetrical wrap skirt
          • Side ruched seam
          • Bodycon silhouette, mini-length hem
          • Crepe knit fabric, moderate stretch
          • Runs true to size

          Style Number/Barcode: 05103-4288

          Category Name: Vacation Looks

          Price: $9.97 $38.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Stylish Tribe High-Rise Flare Pants

          Show up with your tribe looking so boho cute! This high-rise pant features an elasticized waist, a flared hem, and a tribal pattern on brushed knit fabric with a moderate stretch. Style with the matching bottoms.

          Shop The Matching Top:

          Fit & Features

          • High-rise elasticized waist
          • Flared hem
          • Tribal pattern
          • Pull-on/off styling
          • Brushed knit fabric, moderate stretch
          • Fits true to size

          Style Number/Barcode: 06502-0780

          Category Name: Vacation Looks

          Price: $9.97 $26.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Handle It Draped Trench Coat

          Handle your business in this high fashion trench coat. It features long sleeves, a draped collar neckline, and a belted tie waist. Composed of soft nylon-blend fabric with no stretch. Finish the look in sleek hoop earrings

          Fit & Features

          • Long sleeves
          • Draped collar neckline
          • Belted tie waist
          • Soft nylon-blend fabric
          • Fits true to size, no stretch

          Style Number/Barcode: 06204-1354

          Category Name: Vacation Looks

          Price: $9.97 $32.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Sheer And Chic Tie Front Top

          Keep it sheer and chic with a tie-front top to lay over your favorite bustier! The top features a plunging V-neckline, tie-front accent, long blousant sleeves, and a cropped hem. The top is composed of a sheer crinkle-textured woven fabric that offers a relaxed fit with minimal stretch.

          Fit & Features

          • Plunging V-neckline
          • Tie-front accent
          • Long blousant sleeves
          • Cropped hem 
          • Crinkle-texture fabric 
          • Relaxed fit, minimal stretch 
          • Runs true to size

          Style Number/Barcode: 06204-1051

          Category Name: Vacation Looks

          Price: $9.97 $24.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Venom Snake Surplice Crop Top

          Flaunt your sassy side in this snake print crop top featuring cap sleeves, a plunge v-neckline with a surplice accent, and side ruched detail that lets you adjust the fit. Complete the look in trendy jeans for a cute look.

          Fit & Features

          • Cap sleeves
          • Plunge v-neckline
          • Surplice accent, side ruched detail
          • Snake print
          • Cropped hem
          • Brushed knit fabric, moderate stretch
          • Fits true to size

          Style Number/Barcode: 06002-1118

          Category Name: Vacation Looks

          Price: $10.97 $24.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Road Trip Distressed Denim Jacket

          You can never go wrong in a classic denim jacket for your next road trip! It features long sleeves with button cuffs, a collared neckline, distressed accents, faux flap chest pockets, bottom slot pockets, and a button-down front. Complete the look in comfy joggers.

          Fit & Features

          • Long sleeves, button cuffs, collared neckline
          • Faux flap chest pockets, bottom slot pockets
          • Button-down front
          • Distressed accents
          • Denim fabric, no stretch
          • Fits true to size

          Style Number/Barcode: 06203-0197

          Category Name: Vacation Looks

          Price: $16.97 $37.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Ships Free
        • Tie The Knot Floral Crop Top

          Take the plunge and rock this floral frock! It features long peasant sleeves, a plunge v-neckline with a tie-front, and an ultra cropped hem. This top is composed of chiffon woven fabric with no stretch. Complete the look in jeans.

          Fit & Features

          • Long peasant sleeves
          • Plunge v-neck
          • Tie-front
          • Ultra cropped hem
          • Floral pattern
          • Woven chiffon fabric
          • Fits true to size, no stretch

          Style Number/Barcode: 06204-1223

          Category Name: Vacation Looks

          Price: $9.97 $32.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Chic Factor Oversized Sunglasses

          Amp up the chic factor of your everyday 'fits with these sleek oversized sunglasses. They feature an oversized slightly angled design with a thin gold metal frame and nose bridge, thin gold metal arms with long cutouts, tinted lenses, and built-in nose pads for support. Pair these stylish shades with hoop earrings.

          Fit & Features

          • Oversized angled design
          • Thin gold metal frame and nose bridge
          • Thin gold metal arms with long cutouts
          • Tinted lenses
          • Built-in nose pads

          Style Number/Barcode: 07008-1097

          Category Name: Vacation Looks

          Price: $2.97 $10.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Ships Free
        • Floral Forever Chiffon Mini Skirt

          Floral will be forever trending! This cute mini skirt features a high-rise waist, back zipper closure, and a front ruched accent with tie closure on chiffon-lined fabric with no stretch. Finish the look in a sweater top for a girl's day.

          Fit & Features

          • High-rise waist
          • Front ruched accent, tie closure
          • Ditsy floral pattern
          • Mini-length hem
          • Back zipper closure
          • Chiffon-lined fabric
          • Fits true to size, no stretch

          Style Number/Barcode: 06401-0430

          Category Name: Vacation Looks

          Price: $9.97 $29.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Chic Number Keyhole Halter Dress

          Keep it chic in this little number! Have a saucy night out in this halter mini dress featuring a twist halter neckline with a sultry keyhole and a bodycon silhouette. Complete the look in statement earrings.

          Fit & Features

          • Twist halter neckline
          • Keyhole on front
          • Bodycon silhouette
          • Short length hem
          • Slinky knit fabric, moderate stretch
          • Runs true to size

          Style Number/Barcode: 05103-4309

          Category Name: Vacation Looks

          Price: $9.97 $38.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale