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.

  • Tropical Ruffled Ruched Mini Skirt

    Getaway with a tropical mini skirt. The vacation approved mini skirt features a high rise waist, a ruched accent throughout, a ruffled hem, and a tropical palm leaf print. Complete your picture-ready look with the matching crop top, playful wedges, and a glam floppy hat. 

    Shop Matching Crop Top: Tropical Twist Front Short Sleeve Crop Top

    Fit & Features

    • High rise waist 
    • Ruched accent throughout 
    • Ruffled hem 
    • Tropical palm leaf print 

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

    Style Number/Barcode: 06301-0046

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Acid Wash Denim Spaghetti Strap Button Mini Dress

    Get drawn to denim dresses this season. Slip into this curve-hugging dress for your next night out with bae. Fitted with a sleeveless sweetheart neckline, adjustable spaghetti straps to avoid wardrobe malfunctions, and corset-like seams that accentuate curves. The real details can be found in the multi-button down accent at the bodice that leads to a mini length silhouette. The light-medium acid wash denim fabric offers a form hugging fit. Complete your look with fab pumps and dainty accessories.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Corset-like seams
    • Button-down accent 
    • Adjustable spaghetti straps 
    • Mini length silhouette
    • Acid wash denim fabric 
    • Form hugging fit

    Style Number/Barcode: 05102-0474

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ditsy Floral Ruched High Slit Maxi Skirt

    This season, impress in fab floral sets. The vacation-ready ditsy high slit skirt features a flattering high rise waist, a ruched center with drawstring ties that leads to a high center slit and a sweeping maxi length silhouette with ruffled hem. Complete this trendy look with the matching tube top, a pair of hoops, and wedges for an effortlessly chic touch.  

    Shop Matching Top: Ditsy Floral Ruched Tube Top

    Fit & Features

    • High rise waist
    • Ruched center with drawstring ties
    • High center slit
    • Ditsy floral print
    • Lower back zipper closure

    Style Number/Barcode: 06401-0145

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Charmed Intent Bow Sandals

    No one can ignore the cute vibes of these bow sandals perfect for parties or graduations!

    Fit & Features

    • Square toe
    • Wide strap with statement bow
    • Flat sole
    • Padded insole
    • Patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1271

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lace Up Sweetheart Neck Denim Mini Dress

    Lace-up in classic denim to impress. This denim dress is designed with a sweetheart neckline, a corset-like bodice complemented with lace-up straps for a customized fit, and adjustable spaghetti straps. The curve-hugging mini length dress is composed of breathable medium-wash denim fabric. Pair this head-turning dress with statement earrings and bold heels to dress up this look. 

    Fit & Features

    • Sweetheart neckline
    • Corset-like seams at bodice
    • Lace-up ties at center of the bodice
    • Adjustable spaghetti straps
    • Mini length silhouette 
    • Denim fabric 

    Style Number/Barcode: 05102-0565

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ditsy Floral Ruched Tube Top

    This season, impress in fab floral sets. The vacation-ready ditsy tube top features a strapless sweetheart neckline and a ruched center with drawstring ties. Complete this trendy look with the matching high slit skirt, a pair of hoops, and wedges for an effortlessly chic touch.

    Shop Matching Skirt: Ditsy Floral Ruffled Maxi Skirt

    Fit & Features

    • Strapless tube design
    • Sweetheart neckline
    • Ruched center with drawstring ties
    • Back zipper and hook and eye closure
    • Ditsy floral print
    • Woven fabric with a knit lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1176

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crochet Chic Mini Dress

    Keep it chic and fab in this pretty mini dress! It features a sleeveless, v-neck, bungee spaghetti straps, a cutout accent along the bodice, and a form-fitting silhouette. The dress is composed of a lined crochet fabric with a moderate stretch. Complete look in strappy heels.

    Fits & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Built-in padded bust
    • Cutout accent along the bodice
    • Form-fitting silhouette
    • Mini-length hem
    • Lined, floral crochet fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-0003

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All About The Lace Skater Dress

    It's all about the lace in this dress! Bring the fun in this skater dress for a chic bachelorette party or stun on your next date night. The dress features a sleeveless V-neckline, spaghetti straps, a stylish sheer lace back, and a flowy skater-length silhouette. The dress is composed of a comfortable crepe fabric that offers a moderate stretch. Complete your look with dazzling earrings and statement pump heels. 

    Fits & Features

    • Sleeveless, v-neck, spaghetti straps
    • Sheer lace back, cutout accent
    • High waistband, back zipper closure
    • Flowy skater silhouette
    • Short-length hem
    • Lined crepe fabric, moderate stretch 
    • Fits true to size

    Style Number/Barcode: 05101-8634

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cross My Heart Cork Wedges

    We cross our hearts, these wedges are a must for the season! From the criss-cross strap detail to the fun cork wedge, they will become your go-to that perfectly pair with your frilly and floral sundresses! 

    • Adjustable Ankle Strap with Small Buckle
    • Open Toe 
    • Criss-Cross Straps 
    • Corked Wedge Heel

    Style Number/Barcode: 07406-0138

    Category Name: Vacation Looks

    Price: $22.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flower Power Cubic Zirconia Belly Chain

    Bring the beauty of florals to your poolside looks with this gorge belly chain! 

    • Single Row
    • Cubic Zirconia 
    • Mini Flower Accent 

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. 


    Style Number/Barcode: 07002-0450

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cubic Zirconia Belly Chain

    Sparkle poolside with a hint of glam! This belly chain gives even the most minimal looks a touch of glam!

    • Single Row 
    • Cubic Zirconia 

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 07002-0448

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cross My Heart Cork Wedges

    We cross our hearts, these wedges are a must for the season! From the criss-cross strap detail to the fun cork wedge, they will become your go-to that perfectly pair with your frilly and floral sundresses! 

    • Adjustable Ankle Strap with Small Buckle
    • Open Toe 
    • Criss-Cross Straps 
    • Corked Wedge Heel

    Style Number/Barcode: 07406-0133

    Category Name: Vacation Looks

    Price: $22.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cross My Heart Cork Wedges

    We cross our hearts, these wedges are a must for the season! From the criss-cross strap detail to the fun cork wedge, they will become your go-to that perfectly pair with your frilly and floral sundresses! 

    • Adjustable Ankle Strap with Small Buckle
    • Open Toe 
    • Criss-Cross Straps 
    • Corked Wedge Heel

    Style Number/Barcode: 07406-0132

    Category Name: Vacation Looks

    Price: $13.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blind 'Em Square Toe Rhinestone Sandals

    Blind 'em with a little rhinestone action babe! Whether you are chillin' poolside, or styling these with your high waist denim shorts we can def appreciate the bling!

    • Open square toe
    • Thick band over the toe
    • Rhinestone detailing 
    • Composed of jelly material
    • Slide on fit

    Style Number/Barcode: 07404-0585

    Category Name: Vacation Looks

    Price: $14.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Vibes Acid Wash Shorts

    We're all about those summer vibes, let the good times flow with these too cute cut off shorts! Pair this season staple with a pretty crop for a laid back look! 

    Fit & Features

    • High Rise Waist 
    • Single Button and Zipper Closure 
    • Traditional Five Pocket and Belt Loop
    • Acid Wash Denim 
    • Moderate Destructed Detail
    • Raw Edge Hem 
    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.   

    Style Number/Barcode: 06603-0118

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Issa Mood High Waist Shorts

    We're in the mood for some chic vibes with no effort. Throw on these high waist shorts to pair with your fav crops for the trendsetter in you!

    Fit & Features 

    • High Rise Fit 
    • Single Button and Zipper Closure 
    • Traditional Five Pocket and Belt Loop
    • Light Wash Denim Fabric
    • Raw Edge Hem 
    • Heavy Destruction 

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06603-0119

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy Paper Bag Tie Waist Shorts

    Get a preppy chic look styling up these paper bag tie waist shorts!  Pair with a cute crop top and some heels for the perf spring time vibe.

    Fit & Features

    • High rise paper bag waist
    • Tie front belt
    • Two front pockets
    • Woven fabric

    Style Number/Barcode: 06303-0066

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Open Cable Knit Halter Top

    The weekend is calling, and this cable knit top is here to make you stand out from any crowd! It boasts a flattering high halter neckline and open back with dual ties for a head-turning allure.

    Fit & Features

    • Cable knit fabric
    • High halter neckline
    • Open back with dual tie backs
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06005-2293

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flowy Feels Chiffon Romper

    Get those effortless boho flowy feels in this lightweight chiffon romper! Pair with some gladiator sandals to complete your vibe.

    Fit & Features

    • Off the shoulder neckline
    • Long flowy sleeves with slit detailing
    • Front tie closure with keyhole cut out
    • Elastic banded high waist seam
    • Flowy shorts
    • Sheer chiffon fabric | Short lining

    Style Number/Barcode: 06403-0056

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Time to Step Up Cork Wedges

    Step out in these statement wedges to pair with all your favorite sundresses! The corked detail makes this pair the perfect go-to for all your chic outings. They feature a wide faux leather strap over the toe and a corked wedge. 

    Fit & Features 

    • Open back 
    • Wide faux leather strap 
    • Peep toe
    • Corked wedge  

    Style Number/Barcode: 07406-0063

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • For The Love of Florals Mini Dress

    Show off your love of florals in this frilly and flirty mini dress! Throw on your favorite wedges and dainty pieces for a brunch ready look!

    Fit & Features 

    • Sweetheart Neckline
    • Sheer Chiffon Long Sleeves
    • Smocked Bodice 
    • Ruched Drawstring 
    • Daisy Floral Print
    • Smocked and Chiffon Fabric 

     

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small.  

     


    Style Number/Barcode: 05101-0845

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Baecation Metallic Swim Top

    Show off for bae in this sexy swim top. Pair it with the matching bottoms and you’ll look like a total babe when you hit the beach.

    Shop the Matching Bottoms: Baecation Metallic Swim Bottoms

    Fit & Features

    • Cinch Front Detail
    • Double Cross Straps
    • Metallic Fabric
    • Bottoms Sold Separately

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

    Style Number/Barcode: 07104-0476

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Vacation High Waist Swim Bottoms

    That's the dream, an endless vacation! The good news is that you have a swimsuit in your collection that lives through the season! Don't forget to pick up ur matching top!

    Shop Matching Top: Endless Vacation Tie Front Swim Top

    Fit & Features

    • High waist fit
    • Triangle design
    • Thick waist band
    • Cheeky coverage
    • Moderate stretch

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

    Style Number/Barcode: 07105-0551

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Ready Crochet Romper

    Time to show off those cute spring fits! Pair this sweet floral romper with some wedges and a mini bag.

     Fits & Features

    • Adjustable Spaghetti Straps 
    • Plunging V Neckline
    • Zipper Detail At Back 
    • Wide Leg Openings 
    • Crochet Waist Detail

    Style Number/Barcode: 06403-0048

    Category Name: Vacation Looks

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance