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.

  • Cheetah Daze One Shoulder Bikini Top

    Add some spice to your swimwear with this cheetah bikini top featuring a one-shoulder neckline, asymmetrical strap with cutout detail, removable padding on lined fabric. Complete the look in the matching bikini bottoms. 

    Shop The Matching Bikini Bottoms: Cheetah Daze Cutout Bikini Bottoms

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Asymmetrical strap, cutout detail
    • Removable padding
    • Cheetah print
    • Lined fabric
    • Runs true to size

    Style Number/Barcode: 07104-0636

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pool Party High Waist Swim Bottoms

    Get the cutest look for all your summer pool parties with these trendy high waist swim bottoms! They feature cutout details on the sides and a semi-cheeky fit. Style with the matching swim top and cool shades.

    Shop Matching Top: Pool Party One-Shoulder Swim Top

    Fit & Features

    • High-rise waist
    • Side cutouts
    • Semi-cheeky fit
    • Moderate stretch
    • Runs true to size

     

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

    Style Number/Barcode: 07105-0784

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pool Party One-Shoulder Swim Top

    Get the cutest look for all your summer pool parties with this trendy one-shoulder swim top! It features an asymmetrical dual strap design with a front cutout detail and removable padding. Style with the matching swim bottoms and cool shades.

    Shop Matching Bottoms: Pool Party High Waist Swim Bottoms

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Asymmetrical dual strap design, spaghetti strap, tank strap
    • Front cutout detail
    • Removable padding
    • Moderate stretch
    • Runs true to size

      Style Number/Barcode: 07104-0637

      Category Name: Vacation Looks

      Price: $9.97 $18.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Metallic Moment Bikini Top

      Have your moment under the sun! Stun in this sultry bikini top featuring a deep V-neckline, shoulder straps, and a wide bust band. Complete the look in the matching bikini bottoms.

      Shop Matching Bikini Bottoms: Metallic Moment Bikini Bottoms

      Fit & Features

      • Deep V-neckline, shoulder straps
      • Wide bust band
      • Metallic fabric
      • Slip-on/off styling
      • Moderate stretch
      • Runs true to size

      Style Number/Barcode: 07104-0630

      Category Name: Vacation Looks

      Price: $4.97 $22.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Boho Charm Coin Drop Earrings

      These charming boho earrings feature a filigree design, drop accent, and coin charm detailing. Complete the look in a sleek bustier for a night out.

      Fit & Features

      • Filigree design
      • Drop accent
      • Coin charm detailing
      • Push closure

       

      Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

      Style Number/Barcode: 07001-1265

      Category Name: Vacation Looks

      Price: $3.97 $9.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Top Down Square Sunglasses

      Cruise with the top down in these fab square sunglasses featuring a rose gold trim, oversized tortoise plastic frames, and gradient lens. Complete the look in a sultry casual dress for a day out.

      Fit & Features

      • Oversized tortoise plastic frames
      • Rose gold trim at the top
      • Gradient lens
      • 100% UV protection

      Style Number/Barcode: 07008-0956

      Category Name: Vacation Looks

      Price: $4.97 $10.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Get Together Pleat Wide-Leg Pants

      Get together with the girls in these cute high-rise pants for an ocean brunch! They feature pleat front detailing, a wide-leg silhouette, and hidden side pockets to keep your hands warm. Complete the look in the matching top.

      Shop Matching Top: Get Together Smocked Crop Top

      Fit & Features

      • High-rise waist, side zipper closure
      • Hidden side pockets
      • Pleat front detailing
      • Wide-leg silhouette 
      • Linen woven-lined fabric, no stretch
      • Runs true to size

      Style Number/Barcode: 06302-0649

      Category Name: Vacation Looks

      Price: $6.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Soak Up The Sun Square Sunglasses

      Enjoy a sunny day out in these square sunglasses that offer UV protection and a stylish look with your fit!

      Fit & Features

      • Square frames
      • Tinted lenses
      • 100% UV protection

      Style Number/Barcode: 07008-000016

      Category Name: Vacation Looks

      Price: $2.97 $9.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Get Together Smocked Crop Top

      Get together with the girls in this cute crop top for an ocean brunch! It features a sleeveless, one-shoulder neckline with a shoulder strap and an all-over smocked bodice. Complete the look in the matching pants.

      Shop Matching Pants: Get Together Pleat Wide-Leg Pants

      Fit & Features

      • Sleeveless, one-shoulder neckline
      • Shoulder strap
      • All-over smocked bodice
      • Cropped hem
      • Runs true to size

      Style Number/Barcode: 06003-1787

      Category Name: Vacation Looks

      Price: $6.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Social Butterfly Duster Earrings

      Have plans? Of course, you do! Keep your outfit on point in these butterfly duster earrings featuring rhinestone embellishments, a dainty linear chain-link, and a post-back closure. Complete the look in an oversized denim jacket.

      Fit & Features

      • Rhinestone butterfly charms
      • Dainty linear chain-link 
      • Post-back closure

       

      Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

      Style Number/Barcode: 07001-1226

      Category Name: Vacation Looks

      Price: $4.97 $10.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Gone On Vacay Espadrille Cork Wedges

      Take a vacay from your heels and slip on these trendy espadrille wedges! They feature an almond toe, platform cork sole, criss-cross toe strap, and a buckle ankle strap. Complete the look in a flowy maxi dress and Panama hat.

      Fit & Features

      • Almond toe
      • Platform cork sole
      • Criss-cross toe strap, buckle ankle strap
      • Espadrille trim
      • Faux leather footbed
      • Runs true to size

      Style Number/Barcode: 07406-0301

      Category Name: Vacation Looks

      Price: $12.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Statement Rhinestone Chain Bra

      Make a glam statement with this rhinestone chain bra to elevate your babe status! It features a plunge v-neck, triangle-shaped cups, and an adjustable lobster clasp closure. Complete the look in a panama hat for a trendy festival vibe.

      Fit & Features

      • Plunge v-neck
      • Triangle-shaped cups
      • Lobster clasp closure
      • Rhinestone chain design

      Style Number/Barcode: 07107-0750

      Category Name: Vacation Looks

      Price: $6.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Rise And Stun Cutout Bikini Top

      Rise and stun in this bikini top perf for a day spent under the sun. It features a square neck, adjustable spaghetti straps, and a cutout caged design. Complete the look in the matching bikini bottoms.

      Shop The Matching Bikini Bottoms: Rise And Stun String Bikini Bottoms

      Fit & Features

      • Square neck
      • Adjustable spaghetti straps
      • Cutout caged design
      • Lined fabric
      • Moderate stretch
      • Runs true to size

      Style Number/Barcode: 07104-0705

      Category Name: Vacation Looks

      Price: $4.97 $15.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Layers Of Rhine Necklace

      This layered rhinestone necklace is perfect for dressing up an outfit! It features a five-row design with a mix of snake chains and rhinestones with a lobster clasp closure. Complete the look in a sultry cocktail dress.

      Fit & Features

      • Five-row layered design
      • Snake chains 
      • Rhinestones
      • Lobster clasp closure

      Style Number/Barcode: 07002-1173

      Category Name: Vacation Looks

      Price: $6.97 $14.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Throw It Back Rhine Wedge Sandals

      Throw it back to the early 2000s in these stunning sandals! They feature a rounded almond toe, wedge sole, and rhinestone thong straps on a comfort foam footbed. Complete the look in a crop top and flared pants.

      Fit & Features

      • Rounded almond toe
      • Wedge sole
      • Rhinestone thong straps
      • Comfort foam footbed
      • Runs true to size

      Style Number/Barcode: 07406-0314

      Category Name: Vacation Looks

      Price: $8.97 $16.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Remy High-Rise Distressed Shorts

      The Remy distressed denim shorts are a classic staple for casual everyday looks. They feature a high-rise waist, subtle destructed detailing, and a raw-cut hem. The shorts offer a semi-cheeky fit with a moderate stretch. Style with a crop top and sandals.

      Fit & Features

      • High-rise waist
      • Five-pocket and belt loop design
      • Front button, hidden zipper closure
      • Subtle distressing, raw-cut hem
      • Semi-cheeky fit
      • Denim fabric, moderate stretch
      • Runs true to size

      Style Number/Barcode: 06603-0301

      Category Name: Vacation Looks

      Price: $6.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Desert Queen Boho Flare Pants

      You're the queen of the desert in these boho flare pants featuring an elasticized high-rise waist and a form-fitting silhouette. Complete the look in the matching top for the perf music festival outfit! 

      Shop The Matching Top: Desert Queen Boho Halter Top

      Fit & Features

      • High-rise elasticized waist
      • Form-fitting silhouette
      • Flare hem
      • Boho-inspired print
      • Pull-on/off styling
      • Fits true to size

      Style Number/Barcode: 06502-0717

      Category Name: Vacation Looks

      Price: $6.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Desert Queen Boho Halter Top

      You're the queen of the desert in this boho top featuring a sleeveless, halter neck, cropped hem, and a partial open with cross strap detail. Complete the look in the matching bottoms for the perf music festival outfit! 

      Shop The Matching Bottoms: Desert Queen Boho Flare Pants

      Fit & Features

      • Sleeveless, halter neck, spaghetti straps
      • Cropped hem
      • Partial open back with cross straps
      • Boho-inspired print
      • Fits true to size

      Style Number/Barcode: 06001-3757

      Category Name: Vacation Looks

      Price: $6.97 $21.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Vacay Bound Bandeau Halter Top

      Pack this adorable bandeau top in your carry-on before you jet set off on your vacay! It features a sleeveless halter neckline with a cross-front strap design, a center cutout at the bust, and a majorly cropped, form-hugging fit. The lightweight woven fabric offers minimal stretch. Complete the look with the matching mini skirt.

      Shop Matching Bottoms: Vacay Bound Ruched Mini Skirt

      Fit & Features

      • Sleeveless halter neckline
      • Spaghetti straps, cross-front design, tie closure at back of the neck
      • Center cutout at the bust
      • Ruched detailing
      • Cropped, form-hugging fit
      • Woven fabric, minimal stretch
      • Runs true to size

      Style Number/Barcode: 06003-1757

      Category Name: Vacation Looks

      Price: $6.97 $21.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Vacay Bound Ruched Mini Skirt

      Slip into this mini skirt to nail those vacay shots on the perfect getaway! The skirt features a high-rise waist, a ruched body, a center drawstring, and a mini-length hem. The skirt is composed of a lined lightweight knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching bandeau halter top.

      Shop Matching Top: Vacay Bound Bandeau Halter Top

      Fit & Features

      • High-rise waist
      • Ruched body
      • Center drawstring
      • Mini length hem
      • Lined knit fabric
      • Hidden back zipper closure with hook and eye
      • Form-hugging fit, moderate stretch
      • Runs true to size

      Style Number/Barcode: 06301-0117

      Category Name: Vacation Looks

      Price: $9.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Flirty Flair Crepe Faux Wrap Dress

      Short, sweet, and extra flirty this mini dress is just what you need for every occasion! It features a sleeveless, square neck, spaghetti straps, princess seams on the bodice, and a faux wrap asymmetrical skirt with side pleating. Complete the look in platform heels.

      Fit & Features

      • Sleeveless, square neck
      • Spaghetti straps
      • Princess seams on bodice
      • Faux wrap asymmetrical skirt
      • Side pleating
      • Crepe fabric, moderate stretch
      • Fits true to size

      Style Number/Barcode: 05103-4241

      Category Name: Vacation Looks

      Price: $19.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Cut It Out Babe Midi Dress

      Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.

      Fit & Features

      • Stretchy rib knit fabric, contrast trim
      • Square neck, tank shoulder straps
      • Cutout bodice
      • Side slit
      • Bodycon silhouette
      • Midi-length hem
      • Runs true to size

      Style Number/Barcode: 06005-000045

      Category Name: Vacation Looks

      Price: $18.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Clear View PVC Espadrille Wedges

      You might want to get a clear view of these chic wedges! They feature a square toe, espadrille sole, dual PVC clear straps, and a faux leather footbed. Complete the look in a trendy skater dress for brunch with the girls.

      Fit & Features

      • Square toe
      • Espadrille sole
      • Dual PVC clear straps
      • Faux leather footbed
      • Runs true to size

      Style Number/Barcode: 07406-0312

      Category Name: Vacation Looks

      Price: $15.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Open Season Caged Comfort Sandals

      It's open-toe season and these sandals are here for it! They feature a round toe, comfort foam sole, and a caged strap design with adjustable buckle closure. Complete the look in a casual sundress for a picnic lunch.

      Fit & Features

      • Round toe
      • Comfort foam sole
      • Caged strap design
      • Adjustable buckle closure
      • Runs true to size

      Style Number/Barcode: 07404-1024

      Category Name: Vacation Looks

      Price: $12.97 $23.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale