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.

  • Fabulously Retro Ruched Tie Dye Dress

    Keep it fab and retro with a mini dress that is perf for your next night out! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, dual ruched drawstrings, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and butterfly earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross straps
    • Dual ruched drawstrings 
    • Mini-length silhouette 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1079

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drawn To Tie Dye Ruched Mini Dress

    Get drawn to this cute dress that gives off those totally retro feels. The dress features a sleeveless crew neckline with a racer front, a tie-dye print, and ruched drawstrings that allow you to customize the length of the dress. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with sleek hoops and mules

    Fit & Features

    • Sleeveless crew neckline
    • Racer bust
    • Tie-dye print
    • Ruched drawstrings 
    • Mini/midi length silhouette 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1080

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Out In Style Sandals

    Level up your look this season and step out in these stylish sandals. They feature an open square toe, a braided strap, an open back, and a flat sole. Pair these faux leather sandals with light-wash denim and a floral crop top.

    Fit & Features

    • Open square toe
    • Braided strap
    • Open back
    • Flat sole
    • PU material
    • Runs true to size

    Style Number/Barcode: 07404-0677

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getaway Bound Floral Bikini Top

    Get ready for your weekend getaway with this adorable bikini top! It features adjustable spaghetti straps, molded cups, a back hook closure, and an all-over tropical floral print. Complete the look with the matching bikini bottoms and a pair of sunglasses.

    Shop Matching Bottoms: Getaway Bound Floral Bikini Bottoms

    Fit & Features

    • Adjustable spaghetti straps
    • Molded cups
    • Back hook closure
    • Tropical floral print
    • Runs true to size


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

    Style Number/Barcode: 07104-0523

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Diva Vibes Cat-Eye Sunglasses

    Bring the diva vibes to your look with these stylish sunglasses! They feature an oversized square cat-eye design with a tortoise-shell print. Pair these shades with a chic crossbody purse.

    Fit & Features

    • Oversized square cat-eye design
    • Tortoise-shell print
    • Plastic frame

    Style Number/Barcode: 07008-0833

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Babe Sleeveless Midi Dress

    Hey babe, show off your adorable style in this floral midi dress that is perf for spring. It features a sleeveless square neckline, thin ruffle shoulder straps, a fitted bodice, and a flowy mid-length silhouette with a thigh-high slit. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Thin ruffle shoulder straps
    • Fitted bodice
    • Flowy mid-length silhouette
    • High front slit
    • Ditsy floral print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0741

    Category Name: Vacation Looks

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Sweetheart Lace Mini Dress

    Keep it sweet and stylish with a mini dress that features gorge details! The dress features a sweetheart neckline, short sleeves, a floral lace body, and a mini-length silhouette. The dress offers a form-hugging fit. Complete look with wedges and charm necklaces. 

    Fit & Features

    • Sweetheart neckline
    • Padded cups, underwire
    • Short sleeves
    • Floral lace body
    • Mini length silhouette
    • Form hugging fit 
    • Runs true to size

    Style Number/Barcode: 05101-0963

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take It Easy Straw Fanny Pack Belt

    Take it easy with a cute fanny pack belt to carry all your essentials with you! The belt features a faux leather band and an attached small straw fanny pack with fold-over closure. Complete look with neutral-hued pants for that seamless look. 

    Fit & Features

    • Faux leather band 
    • Attached fanny pack with fold-over closure 
    • Straw 

    Style Number/Barcode: 07203-0568

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Trendsetter Four-Pack Necklace Set

    Bring the bling to your look with this trendy necklace set. It features four necklaces, the shortest layer a dainty chain with a center script charm that reads "Babygirl," and the second layer a thick twisted chain. The third necklace has a center rhinestone adorned cross charm, and the fourth necklace has a center rectangular-shaped charm. Pair all of these necklaces together with a basic tee and denim for a cool look.

    Fit & Features

    • Four-pack necklace set
    • Layered design
    • Script charm that reads "Babygirl"
    • Twisted chain
    • Rhinestone cross charm
    • Rectangular-shaped charm
    • Adjustable lobster clasp closures

    Style Number/Barcode: 07002-0708

    Category Name: Vacation Looks

    Price: $0.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dainty Lace Ruched Mesh Mini Dress

    Make hearts flutter in this gorgeous dainty lace and mesh mini dress. It features a sleeveless bodice, adjustable spaghetti straps, a V neckline with a sheer lace ruffle trim, all-over ruched detailing, and a short, curve-hugging silhouette with a front drawstring and a sheer lace ruffle hem. The dress is composed of a sheer mesh fabric with floral lace details and a full knit lining. Complete your look with duster earrings and cute wedges.

    Fit & Features

    • Adjustable spaghetti straps
    • V neckline with a sheer lace ruffle trim
    • Ruched detailing
    • Mini-length, form-fitting style
    • Front drawstring and sheer lace ruffle hem
    • Sheer mesh fabric with floral lace details and a full knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-0955

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Stunning Crochet Waist Maxi Dress

    You'll look effortlessly stunning in this flowy maxi dress that is perfect for the warmer months. It features spaghetti straps that lead to a cross-back design, a lace top with a V neckline, a sheer crochet high waist, and a flowy floor-length gauze skirt with a side slit. Complete the look with on-trend wedges.

    Fit & Features

    • Spaghetti straps
    • Cross back design
    • Lace top, V neckline
    • Sheer crochet high waist
    • Floor-length gauze skirt, side slit
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-0754

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty And Floral High Low Chiffon Kimono

    Play up your sweet side with a kimono that is perfect to layer over your looks. The kimono features a draped open front, long sleeves, a floral print, and a flowy high-low silhouette. The kimono is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a mini dress and wedges

    Fit & Features

    • Draped open front
    • Long sleeves
    • Floral print
    • High-low silhouette
    • Sheer chiffon fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06204-0806

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready To Vacay Bikini Top

    Start those vacay vibes with a bikini top that will have you ready to bask in the sun! The top features a halter neck with neck ties, a sexy square cut out at the bodice, and back ties. Complete look with the matching bikini bottoms and sunnies for that weekend getaway!

    Shop Matching Bikini Bottoms: Ready To Vacay Bikini Bottoms

    Fit & Features

    • Halter neck 
    • Bandeau-styled bodice
    • Square-shaped cutout 
    • Back ties
    • Form-hugging fit 
    • Runs true to size

    Style Number/Barcode: 07104-0653

    Category Name: Vacation Looks

    Price: $4.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Babe High-Rise Slit Maxi Skirt

    From farmer's market to the beach, this flowy maxi skirt is ready to create stylish looks for any adventure! With a flattering high-rise waist, a flirty front slit, and a tiered silhouette, this skirt is essential for spring to summer.

    Fit & Features

    • Chambray woven fabric
    • High-rise waist
    • Front slit
    • Tiered flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06301-0208

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High-Rise Button-Up Cutoff Denim Shorts

    Refresh your wardrobe with these cutoff denim shorts that are perf for warm weather! They feature a high-rise waist, a traditional five-pocket and belt loop design, a button-up front, and a frayed, cutoff hem. Pair these shorts with a floral crop top and strappy sandals.

    Fit & Features

    • High-rise waist
    • Traditional five-pocket and belt loop design
    • Button-up front
    • Frayed, cutoff hem
    • Distressed details
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 06603-0154

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Quilted Glamour Double Buckle Sandals

    Bring the glam with sandals that make a chic statement! The sandals feature an adjustable ankle strap, a diamond quilted body, a double row of buckled straps, an open almond toe, and a textured sole. Complete look with a blouse and cutoff shorts to finish off your look! 

    Fit & Features

    • Adjustable ankle strap
    • Diamond quilted body
    • Double row of buckled straps
    • Open almond toe
    • Textured sole

    Style Number/Barcode: 07404-0673

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet And Flirty Floral Tie-Front Top

    Bring the sweet and flirty vibes to your springtime look with this adorable floral top! It features long dramatic bell sleeves with crochet trim details, a V neckline, a tie-front, and a cropped fit. Complete the outfit with high-rise denim shorts and strappy sandals.

    Fit & Features

    • Long flowy bell sleeves with crochet trim details
    • V neckline
    • Tie-front
    • Cropped
    • Floral chiffon fabric
    • Runs true to size

    Style Number/Barcode: 06204-0815

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Sweetheart Floral Mini Dress

    Showcase your sweet style in this adorable floral printed mini dress! It features short sleeves, a V neckline, ruching at the bust with a front drawstring, a small cutout under the bust, and a short, form-hugging silhouette. The unlined knit fabric offers plenty of stretch. Complete your look with dainty earrings and a cute crossbody purse.

    Fit & Features

    • Short sleeves
    • V neckline
    • Ruching at the bust with a front drawstring
    • Small cutout under the bust
    • Ruching down the sides
    • Mini-length, form-hugging fit
    • Unlined knit fabric with plenty of stretch
    • Floral print
    • Runs true to size

    Style Number/Barcode: 05102-0679

    Category Name: Vacation Looks

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Flirty Floral Tie-Front Top

    Get a sweet and flirty look in this adorable tie-front top. It features long blouson sleeves, a V neckline, a tie-front, and a cropped fit. The semi-sheer chiffon fabric has an all-over floral print, making the top a perf option for a daytime date. Complete your outfit with a denim mini skirt and sandals.

    Fit & Features

    • Long blouson sleeves with cinched hems
    • V neckline
    • Tie-front
    • Cropped
    • Semi-sheer chiffon fabric
    • Floral print
    • Runs true to size

    Style Number/Barcode: 06204-0832

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Honey Charm Layered Chain Link Necklace

    Layer on the style with a stylish necklace that keeps your look on-point! The necklace features a seven-row layer of a mix of dainty and chunky chain links, a honey script charm, and a lobster clasp closure. Complete look with a crop top and skinny jeans. 

    Fit & Features

    • Seven-row layer
    • Dainty chain link
    • Chunky chain link
    • Honey script
    • Lobster clasp closure 

    Style Number/Barcode: 07002-0718

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Chic Ruffled Eyelet Mini Dress

    You'll be looking too chic with a mini dress that brings all those cute deets! The dress features an elastic square neckline, short puff sleeves, a lace-up front, an eyelet design, and a mini-length silhouette with a ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

    Fit & Features

    • Elastic square neckline, puff short sleeves
    • Front lace-up 
    • Form-fitting, mini-length, ruffle hem
    • Eyelet lace fabric, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1163

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What A Catch Fishnet Bikini Top

    You'll be looking like a cute catch with this bikini top! The top features triangle cups, a halter neck tie, back ties, and a fishnet overlay. Complete the look with the matching bikini bottoms and sunnies. 

    Shop Matching Bikini Bottoms: What A Catch Fishnet Bikini Bottoms

    Fit & Features

    • Triangle-shaped cups, removable padding 
    • Halter neck ties
    • Back ties
    • Fishnet overlay 
    • Form hugging fit
    • Runs true to size

     

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

    Style Number/Barcode: 07104-0542

    Category Name: Vacation Looks

    Price: $5.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Flutter Sleeve Chiffon High-Low Duster

    Layer on this floral chiffon duster for a cute picnic date or sunset stroll. It features short flutter sleeves, a V neckline, a high waist with a stretchy smocked back, front button details, and a flowy, high-low fit. The sheer and airy chiffon fabric showcases an all-over floral print for a pretty vibe. Complete your outfit with a casual dress and strappy sandals.

    Fit & Features

    • Short flutter sleeves
    • V neckline
    • High waist with a stretchy smocked back
    • Front buttons
    • Flowy, high-low silhouette
    • Sheer floral chiffon fabric
    • No stretch

    Style Number/Barcode: 06204-0797

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Babe Sleeveless Denim Jumpsuit

    Channel a retro vibe with a jumpsuit that brings the flare to your look! The jumpsuit features a sleeveless scoop neckline, a zippered front, tank straps, a tie waist belt with belt loops, side pockets, and a straight leg with flared hem. Complete look with wedges

    Fit & Features

    • Sleeveless scoop neckline
    • Zippered front
    • Tank shoulder straps
    • Tie waist belt with belt loops
    • Side pockets
    • Straight leg with a flared hem 
    • Form hugging fit runs true to size

    Style Number/Barcode: 06602-0219

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free