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.

  • Retro Fab Floral Halter Crop Top

    Bring on the '70s vibes with this retro fab halter crop top! It features a sleeveless V-neckline, tie-back halter straps, an open back with tie-back straps, a cropped, form-hugging fit, and an all-over trendy floral print pattern. Style this top with light wash denim and cute mules.

    Fit & Features

    • Sleeveless V-neckline
    • Tie-back halter straps
    • Open back, tie-back straps
    • Cropped, form-hugging fit
    • Retro floral print pattern
    • Lightweight knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4283

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Chic Frayed Denim Shorts

    Bring major chic vibes in edgy denim shorts that are festival-ready! The shorts feature a high-rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, color block denim, and a frayed hem. Complete look with a crochet top

    Fit & Features

    • High rise waist
    • Colorblock denim
    • Cutoff hem with fringe trim
    • Single-button with zipper closure
    • Traditional five-pocket with belt loop
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06603-0288

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High-Rise Distressed Mom Shorts

    These vintage-inspired mom shorts are a stylish must-have. Featuring a high-rise waist, distressed detailing, a frayed hem, and a relaxed fit, these shorts will give your everyday outfits effortlessly trendy vibes. Pair with a crop top and sandals.

    Fit & Features

    • High-rise waist
    • Five-pocket and belt loop design
    • Front button closure
    • Distressed detailing, frayed hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06603-0287

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Edgy Oversized Denim Jacket

    Bring the edge to your look with a denim jacket that brings the drama! The jacket features a collared neckline, a multi-button down front, two small chest pockets, long sleeves with a single-button cuff, hidden side pockets, and a long line hem. The jacket is composed of denim fabric that offers a relaxed fit with minimal stretch. Complete look with a midi dress

    Fit & Features

    • Collared neckline
    • Multi-button down front
    • Two small chest pockets
    • Long sleeves 
    • Heavy destruction 
    • Hidden side pockets
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06203-0478

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blossom Beauty Floral Romper

    Blossom with beauty in this adorable strapless romper! It features a straight across elasticized neckline, a high waist seam, flowy shorts, and a pretty all-over floral print. The soft brushed knit fabric offers plenty of stretch for comfortable wear. Complete your spring-ready look with espadrille sandals.

    Fit & Features

    • Strapless straight across elasticized neckline
    • Elasticized high waist seam
    • Flowy shorts
    • Floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06503-0976

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Sassy Snake Print Wide-Leg Pants

    Give off major sassy vibes in these snake print pants! They feature a high-rise elasticized waist, a form-hugging fit throughout the leg, and a wide-leg hem. The lightweight snake-printed knit fabric features all-over lurex thread detailing for a cool metallic look. Style these pants with chic sunglasses.

    Shop Matching Top: So Sassy Snake Print Cropped Tank

    Fit & Features

    • High-rise elasticized waist
    • Form-hugging fit throughout the leg
    • Wide-leg hem
    • Snake print
    • Lurex knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0798

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Sassy Snake Print Cropped Tank

    Give off major sassy vibes in this trendy snake print cropped tank! It features a sleeveless V-neckline with a halter strap, a sultry lace-up front, and a cropped, form-hugging fit. The lightweight snake-printed knit fabric features all-over lurex thread detailing for a cool metallic look. Style this tank with chic sunglasses.

    Shop Matching Bottoms: So Sassy Snake Print Wide-Leg Pants

    Fit & Features

    • Sleeveless V-neckline
    • Halter strap
    • Lace-up front, tie closure
    • Cropped, form-hugging fit
    • Snake print
    • Lurex knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4016

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glow And Shimmer Bikini Top

    Glow and shimmer in this sultry bikini top! It features a sleeveless cross-front strap design, thin adjustable shoulder straps, a V-wired bust with padded cups, and a shimmery lurex fabric. Style with the matching bikini bottoms for a sunkissed look.

    Shop Matching Bottoms: Glow And Shimmer Bikini Bottoms

    Fit & Features

    • Sleeveless cross-front strap design
    • Thin adjustable shoulder straps
    • V-wired bust, padded cups
    • Back strap, bar closure
    • Lurex fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0622

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Glow Tank Swim Top

    Showcase a major glow on your vacay in this neon swim top! It features a sleeveless scoop neckline, an adjustable spaghetti strap and a thin tank strap, a sultry side slit, and a thin elasticized banded hem. Style with the matching swim bottoms.

    Shop Matching Bottoms: Major Glow High Waist Swim Bottoms

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti strap, thin tank strap
    • Side slit at hem
    • Elasticized banded hem
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0627

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Escape Tie-Front Crop Top

    Planning a weekend trip? You'll definitely want to bring this flirty tie-front crop top with you! Features long peasant sleeves, a plunge v-neckline made of crinkle woven fabric with no stretch. Complete the look in high-waisted shorts.

    Fit & Features

    • Long peasant sleeves
    • Plunge v-neckline
    • Tie-front 
    • Cropped hem
    • Crinkle woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1307

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Knits Pointelle Crop Top

    Keep your knits on point in this pointelle crop top featuring long sleeves, a collared neckline, and a button-down front. Complete the look in high-rise jeans and booties for a day out with friends.

    Fit & Features

    • Long sleeves
    • Collared neckline
    • Button-down front
    • Cropped hem
    • Pointelle knit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4102

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Ready Strapless Knit Tube Top

    A summer-ready staple, this knit tube top boasts a flirty cutout accent and a cropped hem perfect for styling with high-rise bottoms!

    Fit & Features

    • Sweater knit fabric
    • Strapless neckline
    • Cutout design
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-2301

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Instinct Satin Midi Dress

    Showcase your chic instinct in this satin snake midi dress featuring a classy, sleeveless, cowl neck, dual adjustable strappy design, and a flared hem. Complete the look in sleek stiletto heels for a dinner date.

    Fit & Features

    • Sleeveless, cowl neck
    • Dual adjustable strappy design
    • Flared midi hem
    • Snake pattern
    • Satin fabric, no stretch, fits true to size

    Style Number/Barcode: 05102-4655

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bohemian Oasis Scoop Neck Midi Dress

    Take the cutest pics in the desert in this boho-chic midi dress! Featuring a sleeveless, ruched scoop neck with front tie, spaghetti straps, and slim-fit silhouette. Complete the look in a trendy panama hat.

    Fit & Features

    • Sleeveless, ruched scoop neck, spaghetti straps
    • Front tie accent
    • Slim-fit silhouette
    • Midi-length hem
    • Geometric print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4652

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lots Of Heart Rhinestone Earrings

    These rhinestone earrings have a lot of heart to be yours! They feature heart-shaped designs on a linear chain with a post-back closure. Complete the look in a classy long dress for a formal affair.

    Fit & Features

    • Rhinestone heart-shaped designs
    • Linear chain
    • Post-back closure

     

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

    Style Number/Barcode: 07001-1152

    Category Name: Vacation Looks

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Idyllwild Floral Bust Tie Mini Dress

    Put your curves on display in this cute floral mini dress designed in a sleeveless, sweetheart neck with a ruched bust tie, spaghetti straps, and side ruched seams. Composed of a brushed knit fabric with a moderate stretch. Finish the look in hoop earrings.

    Fit & Features

    • Sleeveless, sweetheart neck, ruched bust tie
    • Spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Mini-length hem
    • Floral pattern, brushed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05102-4369

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Stunning Lovely Florals Mesh Mini Dress

    Bring the charm with a short dress that is perfect for a brunch date with bae! The dress features a pretty dainty floral print, an off-the-shoulder neckline, a sweetheart bust with a ruffled trim, supportive padded cups, and short sleeves. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges.  

    Fit & Features

    • Dainty floral print
    • Off the shoulder neckline
    • Sweetheart bust, ruffled trim
    • Padded cups, short sleeves
    • Short length hem 
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-1452

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hit The Jackpot Mid Rise Skinny Jeans

    You've really hit the jackpot with these ultra-flattering skinny jeans! They feature a classic mid-rise waist, trendy distressed accents, and a color fade effect on dark wash denim for the perfect vintage look. Complete the look in a cute tank top and booties.

    Fit & Features

    • Mid-rise waist
    • Distressed accents, color fade effect
    • Skinny-leg design
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06602-0370

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beach Night Denim Distressed Jacket

    Chilly nights at the beach call for this trendy denim jacket perfect to keep cozy and stylish. It features long sleeves with button cuffs, a collared neckline, a button-down front, a four-pocket design, and a distressed hem. Complete the look in a basic long sleeve top and leggings.

    Fit & Features

    • Long sleeves, button cuffs
    • Collared neckline
    • Button-down front
    • Flap pocket and side slot pockets
    • Distressed hem
    • Denim fabric, no stretch, fits true to size

    Style Number/Barcode: 06203-0439

    Category Name: Vacation Looks

    Price: $24.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Easy Denim Days Romper

    Easy days call for easy pieces. This denim romper is all you need to look stylish! The romper features a sleeveless square neckline, a cinching tie waist belt with belt loops, slant pockets, and a mid-thigh length. The romper is composed of a lined denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline 
    • Tie-waist belt with belt loops
    • Slant pockets
    • Mid-thigh length 
    • Denim fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06603-0226

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Adventuring Distressed Denim Shortalls

    Adventure awaits! Keep cute exploring a new city in these denim shortalls featuring trendy distressed accents, a frayed hem, and classic overall styling on medium wash denim with a vintage-inspired color fade effect. Complete the look in a graphic tee and sneakers.

    Fit & Features 

    • Distressed accents, frayed short hem
    • Adjustable shoulder straps with button closure
    • Front bib pocket and side pockets
    • Side button closures and belt loop accents
    • Medium wash denim, color fade effect, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06603-0282

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Snake Trend Mesh Crop Top

    This snake mesh crop top will always be a fierce contender! It features long sleeves, a mock neck, and exposed seam detail on sheer fabric with a moderate stretch. Finish the look in leather leggings and a basic tank.

    Fit & Features

    • Long sleeves
    • Mock neck
    • Exposed seam detail
    • Snake pattern
    • Cropped hem
    • Sheer mesh fabric, moderate stretch, fits true to size

    Style Number/Barcode: 06001-4098

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Needed Halter Crop Top

    A halter crop top like this is always needed for day or night fun! It features a sleeveless, halter neck with dual tie-back closures, a cropped hem, and an open-back design. Composed of stretchy rib-knit fabric. Style with faux leather leggings.

    Fit & Features

    • Sleeveless, halter neck
    • Dual tie-back closures
    • Cropped hem
    • Open-back design
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4238

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All That Bomber Jacket

    Girl, step out in a bomber that really is all that! The jacket features a zippered front closure with a mini o-ring accent, a drawstring hoodie, long sleeves with elastic cuff, and an elastic-smocked hem. The jacket is composed of a lightweight nylon knit blend that offers a relaxed fit with minimal stretch. Complete look with a crop top and skinny jeans. 

    Fit & Features

    • Zippered front closure 
    • Mini O-ring accent
    • Drawstring hoodie
    • Long sleeve, elastic cuff
    • Elastic-smocked hem 
    • Nylon knit fabric 
    • Relaxed fit, minimal stretch, runs true to size 

    Style Number/Barcode: 06204-1206

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free