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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.

  • 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: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • She's Darling Ditsy Floral Crop Top

    Oh-so-darling, this ditsy floral crop top is perfect for weekend outings this spring! It features short kimono-style sleeves, a V-neckline, a tie-front design, and a cropped fit. The soft brushed knit fabric has plenty of stretch for comfortable wear. Style with the matching mini skirt.

    Shop Matching Bottoms: She's Darling Ditsy Floral Skirt

    Fit & Features

    • Short kimono-style sleeves
    • V-neckline
    • Tie-front
    • Cropped
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06202-0315

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual High Waist Linen Shorts

    Keep it casual with shorts that are perf for every day! The shorts feature a high-rise waist, a single button with zipper closure, a removable belt with an O-ring buckle, slant pockets, and a wide-leg hem. The shorts are composed of a lined linen fabric that offers a relaxed fit with minimal stretch. Complete look with a crop top.

    Fit & Features

    • High-rise waist
    • Single-button, zipper closure
    • Removable belt, O-ring buckle
    • Slant pockets
    • Wide-leg hem 
    • Lined linen fabric, relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06303-0195

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beauty Bloom Floral Tie Waist Top

    Wrap yourself with a floral top that brings the charm! This top features a surplice wrap V-neckline, long sleeves, and a tie waist along the cropped hem on brushed knit fabric. Complete the look with high-waist jeans. 

    Fit & Features

    • Surplice v-neckline
    • Long sleeves 
    • Tie waist 
    • Cropped hem
    • Floral print
    • Brushed knit fabric, moderate stretch
    • Runs true to size 

    Style Number/Barcode: 06001-3887

    Category Name: Vacation Looks

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dreamy Floral Mesh Duster

    Dreaming of florals? Make it come true with this mesh duster featuring long sleeves, an open-front design, and a longline hem on sheer knit fabric with plenty of stretch. Complete the look in a chic corset and jeans for a farmer's market.

    Fit & Features

    • Long sleeves
    • Open-front design
    • Longline hem
    • Floral pattern
    • Sheer knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06202-0317

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's Darling Ditsy Floral Skirt

    Oh-so-darling, this ditsy floral mini skirt is perfect for weekend outings this spring! It features a high-rise waist, side ruched detailing leading to a short slit, and a mini-length, form-fitting silhouette. The soft brushed knit fabric has plenty of stretch for comfortable wear. Style with the matching crop top.

    Shop Matching Top: She's Darling Ditsy Floral Crop Top

    Fit & Features

    • High-rise waist
    • Side ruching, adjustable drawstring, short slit
    • Mini-length, form-fitting silhouette
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0641

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale