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.

  • Fiercely Wild Leopard Print Sarong Wrap

    Wrap yourself in a captivating sarong for your next vacation getaway. This leopard print sarong is composed of lightweight woven fabric. Complete your look with a basic bikini and sassy slides. 

    Fit & Features 

    • Leopard print 
    • Wrap-design 
    • Lightweight woven fabric

    Style Number/Barcode: 07305-0087

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Basic Denim Jacket

    Every Fashionista knows a denim jacket is a wardrobe staple! Pair this basic jacket with cute sundresses this summer.

    Fit & Features

    • Button Down Front
    • Collard Neckline
    • Medium Wash Denim Fabric

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06203-0064

    Category Name: Vacation Looks

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Your Go To Cropped Denim Jacket

    When in doubt throw on this denim jacket on to finish your look! Pair it with your fav matching set and wedges.

    Fit & Features

    • Button Down Front
    • Collard Neckline
    • Medium Wash Denim Fabric
    • Two Front Pockets
    • Cropped Hem

    Style Number/Barcode: 06203-0071

    Category Name: Vacation Looks

    Price: $13.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Taste Tie-Front Printed Satin Top

    Give your look a pretty style with this satin crop top designed with chic short sleeves and a tie-front that flaunts your figure!

    Fit & Features

    • Printed satin woven fabric
    • Short sleeves
    • Tie-front
    • Ultra cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1875

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PEACH

    Available Size: S, M, L, XL

    Product Badge:
    • Sale
  • Blossomed Babe Floral Halter Midi Dress

    You'll blossom looking like a babe in this floral chiffon midi dress at every dressy soiree! . The stunning halter neckline features an eye-catching stone insert that draws attention, while the flowy midi-length hem creates a graceful silhouette.

    Fit & Features

    • Floral print, chiffon lined fabric
    • Halter neckline, stone insert, spaghetti strap tie-back closure
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4040

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 10 Row Layered Chain Necklace

    Layer on the glam with this necklace. For the days when you're feeling a little extra, layer on this 10-row chain necklace that features a tiered design to make a stylish statement. Complete your look with a plunging midi dress and wedges. 

    Fit & Features 

    • 10-row layer
    • Tiered design 
    • Chain-link pattern 

    Style Number/Barcode: 07002-0439

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Four Row Tiered Dainty Chain Necklace

    Add a dainty chain necklace to all your favorite looks! This dainty piece is perfect for dressing up when working from home or completing a chic set. The four-row design features a chain-link necklace set in a tiered design to create a layered effect.  

    Fit & Features 

    • Four-row 
    • Tiered design 
    • Chain-link pattern 
    • Lobster clasp closure

    Style Number/Barcode: 07002-0435

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pop of Floral Off the Shoulder Romper

    Impress in a floral romper on your vacation girl! This season must-have features an off the shoulder neckline with a ruffled popover accent and an-all over floral print. The relaxed fit bodice leads to a pair of fitted shorts. The romper is composed of a knit fabric that offers a form hugging fit. Complete your look with statement hoop earrings and wedges. 

    Fit & Features

    • Off the shoulder neckline
    • Popover accent
    • Floral print
    • Smooth knit fabric
    • Form hugging, moderate stretch

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06503-0143

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Catch This Floral Romper

    Look as beautiful as a bouquet in this gorgeous romper! 

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Plunging V Neckline I Button Front Closure 
    • Lace & Zipper Detail At Back 
    • Fully Lined, Crepe Fabric 
    • Wide Leg Openings 
    • Form Hugging Fit I Moderate Stretch 

     

    Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06403-0049

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Parker High Waist Light Denim Cut Off Shorts

    Oasis by Eunina

    Make some memories in cut off shorts. These must-have shorts feature a high rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design and a frayed cut-off hem. The shorts are composed of a light-medium wash denim fabric that offers a relaxed fit with a moderate stretch. Complete your outfit with a chic crop top and sleek sandals. 

    Fit & Features 

    • High rise waist 
    • Single-button with zipper closure 
    • Traditional five-pocket with belt loop design 
    • Frayed hem 
    • Light destruction 
    • Light-medium wash denim fabric
    • Relaxed fit, moderate stretch  

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06603-0123

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fierce Leopard Print Cover Up

    Make a splash with a fierce cover-up. This poolside must-have features a trendy leopard print and an oversized length to easily tie at the waist. The cover-up is composed of lightweight woven fabric. Complete your look with a bikini and wedges. 

    Fit & Features

    • Leopard print
    • Lightweight woven fabric

    Style Number/Barcode: 07305-0076

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleeveless Ruffled Striped Jumpsuit

    Keep it chic in a striped jumpsuit. Start the season in a head-turning jumpsuit that features a square neckline, ruffled shoulder straps, and an all-over striped pattern. The relaxed fit bodice leads to a straight leg fit with a flared hem. Complete your look with statement earrings and trendy heels. 

    Fit & Features

    • Square neckline 
    • Ruffled shoulder straps 
    • Striped pattern
    • Relaxed fit bodice
    • Straight leg fit, wide-leg hem 

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06502-0388

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tie Waist Short Sleeve Floral Crop Top

    Keep it flirty in a floral crop top this season. This must-have floral print top features a plunging wrap V-neckline, short sleeves, and a cropped hem with tie-waist straps. The top is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete outfit with the matching shorts and statement earrings. 

    Fit & Features

    • Plunging wrap v-neckline
    • Short sleeves
    • Cropped hem 
    • Floral print
    • Tie waist straps at the hem 
    • Gauze-knit fabric
    • Relaxed fit, minimal stretch 

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0866

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Bodycon Denim Midi Dress

    Make a denim dress a work from home must. The bodycon dress features a sleeveless bodice with a square neckline, thick shoulder straps that offer plenty of support, and vertical seams that lead to a midi length silhouette. The dress is composed of denim fabric that offers a form hugging fit that enhances curves. Dress up this midi with colorful pumps and statement earrings.

    Fit & Features

    • Sleeveless square neckline
    • Thick shoulder straps
    • Front vertical seams that lead from bust to hem
    • Midi length silhouette
    • Denim fabric
    • Form hugging fit 

    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0192

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Shoulder Basic Smocked Romper

    Keep it simply smocked in a romper. Make this romper a summer staple to take you from brunch to date night. The romper features an off the shoulder neckline, a smocked bodice, and a small keyhole with a tie-front accent. The relaxed fit bodice leads to a pair of wide-leg shorts. The romper is composed of a smocked fabric that offers a relaxed fit with a moderate stretch. Complete your look with a dainty necklace and wedges. 

    Fit & Features

    • Off the shoulder neckline 
    • Smocked bodice
    • Small keyhole with a tie-front accent at the center of the bodice
    • Wide-leg shorts
    • Smocked knit fabric
    • Relaxed fit, moderate stretch 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06303-0052

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfectly Cropped Basic Surplice Gauze Top

    Keep it cute in this basic crop top. The top features a plunging surplice V-neckline, short sleeves with elastic cuff, and a cropped hem. The top is composed of a gauze-like linen fabric that offers a relaxed fit with slight stretch. Complete your look with a pair of high waist jeans and statement hoop earrings. 

    Fit & Features

    • Plunging surplice V-neckline
    • Short sleeves with elastic cuff
    • Cropped hem 
    • Gauze fabric 
    • Relaxed fit 
    • Slight stretch 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0686

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wrapped In Florals Tie Waist Crop Top

    Wrap yourself in a floral top this season while you have fun in the sun. This must-have floral print top features a plunging wrap V-neckline, short sleeves, and a cropped hem with tie-waist straps. The top is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete outfit with the matching shorts and colorful earrings. 

    Shop the Matching Shorts: Wrapped In Florals High Waist Shorts

    Fit & Features

    • Plunging wrap v-neckline
    • Short sleeves
    • Cropped hem 
    • Floral print
    • Tie waist straps at the hem 
    • Gauze-knit fabric
    • Relaxed fit, minimal stretch 

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0865

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • High Waist Wide-Leg Shorts

    Keep it flirty in high waist shorts this season. These must-have shorts feature a high rise waist, an all-over floral print, and subtle pleating. The shorts are composed of a lightweight gauze fabric that offers a relaxed fit with minimal stretch. Complete outfit with the matching top and wedges. 

    Shop the Matching Top: Tie Waist Short Sleeve Floral Crop Top

    Fit & Features

    • High rise waist
    • Floral print
    • Pleating 
    • Wide-leg hem 
    • Gauze knit fabric
    • Relaxed fit, minimal stretch 

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06303-0073

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Summer Cutie Chambray Floral Romper

    Effortlessly cute for summer, this chambray romper flaunts an adorable embroidered floral pattern and flowy shorts perfect for styling with sandals.

    Fit & Features

    • Cotton-blend chambray fabric, woven lining, no stretch
    • Floral embroidered pattern
    • Sleeveless square neckline, ruched bust, spaghetti strap ties
    • Smocked back, zipper with hook-eye closure
    • Fitted bodice, high-rise waist, flowy shorts bottom
    • Romper in size small is 28" shoulder to hem with a 14" front rise and a 1.5" inseam
    • Runs true to size

    Style Number/Barcode: 06303-000003

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plunging Surplice Tie Back Gauze Crop Top

    Put your look together in a surplice top. This season essential top features a plunging surplice V-neckline, flowy Kimono-like quarter-length sleeves, and a cropped hem. The back features a large keyhole with a single-button closure at the nape of the neck and tie-back straps. The top is composed of a lightweight gauze-knit fabric that offers a relaxed fit with minimal stretch. Complete your look with high waist shorts and sleek sandals. 

    Fit & Features

    • Surplice v-neckline
    • 3/4 sleeves 
    • Cropped hem 
    • Open back with tie-back straps
    • Gauze fabric
    • Relaxed fit 
    • Minimal stretch 

     

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0838

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On Cloud Nine Satin Mini Dress

    Feel and look your best in this tropical print mini dress! Style it with white heels and a mini bag for date night with bae.

    Fit & Features

    • Spaghetti Straps
    • Tropical Print
    • Mini Length
    • Hidden Back Zipper

    Style Number/Barcode: 05101-0840

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Romance Chiffon Floral Mini Dress

    It's a match babe! Add this dreamy dress to cart and you'll be sweeping them off their feet! 

    Fits & Features 

    • Sweetheart Neckline I Lace-Up Bodice 
    • Square Back With Zipper & Hook And Eye Closure 
    • Sheer Long Sleeves I Elastic Cuffs
    • Mini Length Silhouette With Self Ties At The Front
    • Ruffle-Trim  At Shoulders, Neckline, Hem 
    • Lined Chiffon Fabric With Romantic Floral Print
    • Form Flattering Fit I Minimal Stretch 

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0707

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Moment Sleeveless Asymmetrical Ruched Midi Dress

    Create a tropical moment in a midi dress that brings the color this season. This vacation-ready dress features a sleeveless bodice, a plunging V-neckline and adjustable spaghetti straps that lead to an X-back design. The relaxed fit waist leads to a midi length silhouette with a ruched side seam and an asymmetrical high slit to show off a hint of skin. The all-over tropical print features bright hues that perfectly contrast the dark background. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete your look with a pair of heels and golden hoop earrings. 

    Fit & Features

    • Plunging V-neckline
    • Adjustable spaghetti straps
    • X-back 
    • Midi length silhouette 
    • Tropical print
    • Asymmetrical high side slit
    • Form hugging fit

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0231

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Yeah I'm Sassy Cat Eye Sunglasses

    Yeah bb you're a lil sassy, and we are here for it! Throw a little shade with these vintage inspired sunnies pair perfect with that sass!

    • Cat eye design
    • Dark brown lenses
    • Dark mauve frame with a little shimmer
    • Thick arms

    Style Number/Barcode: 07008-0735

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale