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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.

  • Spring Refresh Cropped Denim Jacket

    Refresh your spring wardrobe with this trendy denim jacket. Featuring a collared neckline, long sleeves, a button-down front, and a cropped fit with a frayed hem, this jacket will step up your everyday looks. Style with a cute hair claw clip!

    Fit & Features

    • Collared neckline
    • Long sleeves, buttons to cuff
    • Complete button-down front
    • Buttoned chest pockets, side pockets
    • Cropped fit, frayed hem
    • Denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06203-0440

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Barely Blushing Floral Mini Dress

    Soft girl, but make it sultry. This floral mini dress clings in all the right ways, with delicate straps and a dreamy texture that feels flirty but effortless!

    Fit & Features

    • Floral print, burnout texture, mesh fabric, stretchy knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000165

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lug Forever Nubuck Strap Sandals

    The lug trend will forever be in style! Show up to the pool party in these nubuck sandals featuring an almond toe, short heel, adjustable buckle ankle strap, and a chunky design. Complete the look in a trendy straw hat.

    Fit & Features

    • Almond toe, short heel
    • Lug sole
    • Adjustable buckle ankle strap
    • Chunky design
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07404-1001

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Call of The Wild Midi Slit Dress

    Answer the call in a fierce midi dress! Showcase your unique style in this geometric crepe midi dress featuring a sleeveless, V-neck, sleek spaghetti straps, and a slim-fit silhouette with a front slit accent. Complete the look in lattice booties.

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Slim-fit silhouette
    • Front slit accent
    • Midi-length hem
    • Geometric print
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4649

    Category Name: Vacation Looks

    Price: $4.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life's A Breeze Floral Cutout Midi Dress

    This floral cutout midi dress makes getting ready a breeze! It features short puff sleeves and a ruched sweetheart bodice with a flirty waist cutout that leads to a flowy, midi-length silhouette with a slit accent. Composed of a chiffon-lined fabric with no stretch. Style with a trendy mini tote.

    Fit & Features

    • Short puff sleeves
    • Ruched sweetheart bust
    • Waist cutout, smocked back
    • Midi-length silhouette with slit accent
    • Floral pattern
    • Chiffon fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1551

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Retreat Chiffon Peplum Tank Top

    Flirty and floral, this peplum tank top is ready for your next retreat! It features a classic sleeveless, v-neck, adjustable spaghetti straps, a built-in padded bust, and a cute ruffled crop hem with a smocked back. Complete the look in trendy skinny jeans and heels.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Built-in padded bust, smocked back
    • Ruffled crop hem
    • Floral pattern
    • Chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1603

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Everyday Staple Crop Top

    This basic ribbed knit crop top is a casual everyday staple! It features a crew neckline, long fitted sleeves, trendy ruched side detail for a customized fit, and a cropped, form-hugging fit. Style this top with your fave pair of jeans and sleek hoop earrings.

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Side ruching, drawstrings at hem
    • Cropped, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1082

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Sexy Graphic Crop Tee

    You're sexy and you know it! Let this graphic tee do the talking for when boys start lingering. It features short sleeves, a crew neck, and a front script that reads, 'Too Sexy For Your Boy'. Complete the look in a faux leather mini skirt.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Front script that reads, 'Too Sexy For Your Boy'
    • Cropped hem
    • Fits true to size

    Style Number/Barcode: 06002-1114

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shimmery Sunkissed Tank Swim Top

    Showcase a sunkissed glow this season in this shimmery tank swim top. It features a sleeveless square neckline with a notched front detail, tank shoulder straps, a padded bust, and a trendy small front cutout. The ribbed knit fabric features shimmery metallic thread woven throughout. Style with the matching swim bottoms.

    Shop Matching Bottoms: Shimmery Sunkissed Swim Bottoms

    Fit & Features

    • Sleeveless square neckline, notched front detail
    • Tank shoulder straps
    • Removable padding
    • Front cutout under the bust
    • Ribbed knit fabric, metallic thread woven throughout
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0634

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Cutie Wrap Mini Skirt

    Keep it casual with a mini skirt that is perf for pairing with a casual tee or dressy blouse. The skirt features an elastic high-rise waist, a wrap design, and a mini-length hem. The skirt is composed of a lined brushed knit fabric that offers a form-hugging fit with a moderate stretch. 

    Fit & Features

    • Elastic high-rise waist
    • Wrap design 
    • Mini-length hem
    • Brushed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0588

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Front Row Lace-Up Exposed Seam Top

    This long sleeve top deserves a front-row seat in your closet! Features long sleeves, a plunge v-neck, exposed seam detail, and a trendy lace-up front on the cropped hem. Complete the look in high-rise shorts and sandals.

    Fit & Features

    • Long sleeves
    • Plunge v-neck
    • Lace-up front
    • Exposed seam detail
    • Rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06001-3900

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • She's So Chic Tie-Waist Jumpsuit

    They'll all want the deets on your chic look with this tapered tie-waist jumpsuit! It features a lightweight woven top with a sleeveless V-neckline, adjustable spaghetti straps, and sleek woven pants with a paper bag waist with a tie-front belt. Style this jumpsuit with neutral block heels.

    Fit & Features

    • Textured woven top, sleeveless V-neckline
    • Adjustable spaghetti straps, hidden side zipper, hook and eye closure
    • Woven pants, high-rise paper bag waist
    • Tie-front belt, side pockets
    • Tapered pant legs
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06402-0426

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild At Heart Crochet Halter Top

    Channel your bohemian side with a crochet top that will have you ready for festival season! The top features a halter neck, neck ties to easily adjust, and a fringe hem. The top is composed of an unlined crochet knit fabric that offers a relaxed fit with minimal stretch. Complete look with cutoff shorts. 

    Fit & Features

    • Halter neck 
    • Adjustable ties at neck
    • Fringe hem 
    • Crochet knit fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1273

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Spree Chiffon Tie-Back Top

    Fall for florals this spring! Create a cute look in this chiffon crop top featuring long peasant sleeves, a square neckline, and a cross-over hem with tie-back closure. Complete the look in denim shorts and knee-high boots.

    Fit & Features

    • Long peasant sleeves
    • Square neckline
    • Criss-over crop hem
    • Tie-back closure
    • Floral pattern
    • Chiffon fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1916

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Island Views Tropical Cowl Mini Dress

    You may be in paradise but you'll be the main view in this tropical mini dress! Features a sleeveless, cowl neck, sleek spaghetti straps, bodycon silhouette, and an asymmetrical mini-length hem with a side ruched tie. Complete the look in hoop earrings and heels.

    Fit & Features

    • Sleeveless, cowl neck, spaghetti straps
    • Bodycon silhouette
    • Asymmetrical mini-length hem
    • Side ruched tie
    • Tropical pattern
    • Texture knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 05102-4366

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendsetting Frames Square Sunglasses

    These square sunglasses are perfect for creating trendy looks while driving or in any sunny place!

    Fit & Features

    • Colored square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000017

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Paradise Calls Tropical Midi Dress

    Vacation on the mind? You're going to need this tropical midi dress with paradise written all over it! Features a sleeveless, v-neck, adjustable spaghetti straps, a form-fitting silhouette, and a side ruched seam on an asymmetrical midi hem. Complete the look in lace-up sandals for a dinner with a view.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Form-fitting silhouette
    • Side ruched seams
    • Asymmetrical midi hem
    • Tropical pattern
    • Texture knit fabric, moderate stretch. fits true to size

    Style Number/Barcode: 05102-4367

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Preppy Vibes Crop Top

    Casual yet preppy, this crop top is a chic staple. It features a collared V-neckline, a wrap-front design, long sleeves with single buttons to cuff, and a cropped fit. Style this lightweight woven top with high-rise denim and mules.

    Fit & Features

    • Collared V-neckline
    • Wrap-front design
    • Long sleeves, single buttons to cuff
    • Hidden side zipper
    • Cropped, fitted silhouette
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1718

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Cropped Puff Sleeve Top

    Keep it chic in a crop top that is perf for that next brunch date! The top features a sweetheart neckline with a no-slip strip, a pleated bodice, short puff sleeves, and a cropped hem with back ties. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with a maxi skirt and sandals. 

    Fit & Features

    • Sweetheart neckline
    • No-slip strip 
    • Pleated bodice 
    • Short puff sleeves, ruffled hems
    • Cropped hem, back ties
    • Lightweight woven fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1917

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spot My Stripes Button-Down Top

    Everyone will spot these stripes on this adorable button-down top featuring 3/4 length cuffed sleeves, a collared neckline, a front pocket, and an elasticized cropped hem. Complete the look in a denim mini skirt.

    Fit & Features

    • Collared neckline
    • 3/4 length cuffed sleeves
    • Front pocket
    • Button-down closures
    • Elasticized crop hem
    • Striped pattern
    • Poplin woven fabric, no stretch, fits true to size

    Style Number/Barcode: 06003-1792

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Goals Flat Top Sunglasses

    Reach your goals to get glam with these flat-top sunglasses featuring rhinestone embellished trim, curved gradient lens, and plastic nose and arm support. Complete the look in a sultry bustier and jeans.

    Fit & Features

    • Flat-top design
    • Rhinestone embellished trim
    • Curved gradient lens
    • Plastic nose and arm support

    Style Number/Barcode: 07008-0923

    Category Name: Vacation Looks

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • New Look Round Metal Sunglasses

    Rock a new look in these round sunglasses featuring a metal frame, gradient lens, and rubber nose support. Complete the look in a cool moto jacket.

    Fit & Features

    • Round metal frame
    • Gradient lens
    • Rubber nose support

    Style Number/Barcode: 07008-0929

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Side Longline Bikini Top

    Sitting beachside and looking so fine in this longline bikini top! It features a square neck, detachable spaghetti straps, removable padding, and a bandeau-style silhouette. Complete the look in the matching bikini bottoms.

    Shop The Matching Bottoms: Beach Side Hipster Bikini Bottoms

    Fit & Features

    • Squareneck
    • Detachable spaghetti straps
    • Removable padding
    • Longline hem
    • Bandeau-style silhouette
    • Lined knit fabric
    • Fits true to size

     

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

    Style Number/Barcode: 07104-0673

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Calabasas Caged Bikini Top

    Spend time under the sun in this caged bikini top featuring a plunge v-neck with strap detail, removable padding, and a caged-back design. Complete the look in the matching bikini bottoms.

    Shop The Matching Bikini Bottoms: Calabasas Lattice Bikini Bottoms

    Fit & Features

    • Plunge v-neck, strap detail
    • Removable padding
    • Caged-back design
    • Lined knit fabric
    • Fits true to size

     

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

    Style Number/Barcode: 07104-0674

    Category Name: Vacation Looks

    Price: $4.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale