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.

  • Stand Out In Stripes Tie Front Crop Top

    Stand out in stylish stripes with a top that elevates your casual outfits. The top features a striped pattern, plunging V-neckline with tie-front, quarter length sleeves with elastic hem, and a cropped hem. Complete look with high waist jeans

    Fit & Features

    • Plunging V-neckline 
    • 3/4 sleeves
    • Striped pattern 
    • Tie Front
    • Cropped hem 
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size  

    Style Number/Barcode: 06204-0888

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seeing Stars Necklace Multi Pack

    Channel a starry-eyed look with this cute necklace pack! The pack includes three necklaces with galactic-inspired designs. One necklace features a snake chain, one features a crescent moon charm, and one necklace features a starburst-designed charm with a rhinestone center accent. Complete look with a crop top and shorts.

    Fit & Features

    • Pack includes three necklaces
    • Snake chain 
    • Crescent moon
    • Starburst design with rhinestone center
    • Lobster clasp closure 

    Style Number/Barcode: 07002-0725

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sippin' On Henny Cap

    Let this cap say it all! The cap features a traditional baseball cap design and a script that reads "Henny" with olive branch accents. Complete look with a crop top and cutoff shorts for a laid-back look.

    Fit & Features

    • Baseball cap design 
    • "Henny" script 
    • Olive branch accent
    • Adjustable strap

    Style Number/Barcode: 07302-0314

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Allure Ruched Mini Skirt

    Let those tropic vibes allure you in with this cute mini skirt! The skirt features a high-rise waist, a tropical palm leaf print, ruched side seams, and a mini-length silhouette. Complete look with the matching crop top and wedges that will have you vacay ready! 

    Shop Matching Crop Top: Tropical Allure Mesh Crop Top

    Fit & Features

    • High rise waist 
    • Tropical palm leaf print
    • Mini length silhouette
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06501-0400

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Allure Mesh Crop Top

    Let those tropical vibes allure you in with this cute crop top! The crop features a sleeveless square neckline, bungee spaghetti straps, a tropical palm leaf print, and a cropped hem. Complete look with the matching mini skirt and wedges that will have you vacay ready. 

    Shop Matching Mini Skirt: Tropical Allure Ruched Mini Skirt

    Fit & Features

    • Sleeveless square neckline 
    • Bungee spaghetti straps 
    • Tropical palm leaf print 
    • Cropped hem 
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-3251

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Trendsetter Floppy Boater Hat

    Top off your summer look with this boater hat for a trendy glam vibe! It features a floppy brim, a thin rhinestone band with a tie-back detail, and is made of a straw-like material. Style this hat with a boho-chic crop top and denim shorts for festival season.

    Fit & Features

    • Floppy brim
    • Rhinestone trim band, tie-back detail
    • Straw-like material

    Style Number/Barcode: 07302-0319

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shimmering Beauty Mesh Fringe Wrap

    Layer on this shimmering mesh fringe wrap for a stunning summertime look! It features a sheer mesh fabric with a trendy fringe hem and embroidered sequins in a pretty floral design. Style this wrap as a chic cover-up over your fave bikinis.

    Fit & Features

    • Sheer mesh fabric, fringe hem
    • Embroidered sequins in a floral design

    Style Number/Barcode: 07305-0272

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawlessly Fab Crochet Crop Top

    Keep it flawless with a crochet top that brings the glam to your look! The crop top features a boat neckline, long sleeves, a crochet knit bodice, and a cropped hem. The crop top can be styled with an adhesive bra or as a swim coverup.

    Fit & Features

    • Boat neckline
    • Long sleeves
    • Crochet knit bodice
    • Cropped hem
    • Relaxed fit, slight stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0672

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fashionably Frayed Cutoff Denim Shorts

    These fashionably frayed denim shorts will be your go-to pair of denim this summer! They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button closure, and a cutoff frayed hem. Pair these shorts with your fave crop top and sandals.

    Fit & Features

    • High-rise waist
    • Traditional five-pocket and belt loop design
    • Front button closure
    • Cutoff frayed hem
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 06603-0169

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Beauty Tropical Maxi Dress

    Showcase your stunning beauty in this tropical maxi dress on your next weekend getaway! It features a sleeveless V neckline, spaghetti straps that lead to an open back with a strappy design, a high waist, and a floor-length hem with a relaxed fit. The knit fabric has an all-over palm leaf print to bring the vacay vibes. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless V neckline
    • Spaghetti straps
    • Open back, strappy design
    • High waist
    • Floor-length hem, relaxed fit
    • Knit fabric, palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-0525

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie Vibe Gingham Print Thong Strap Sandals

    You'll love the cute vibe these thong strap sandals bring to your weekend 'fits! The adorable gingham print is a spring and summer staple.

    Fit & Features

    • Faux leather material
    • Gingham print
    • Almond-shaped toe
    • Thong strap design
    • Open back, on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1249

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Bound Tropical Mini Dress

    Don't forget to pack this gorgeous mini dress for your summer vacay! It features a sleeveless square neckline, adjustable spaghetti straps, a back zipper closure, all-over ruching, and a mini-length, curve-hugging silhouette. The knit fabric has an all-over tropical floral print that will pair perfectly with a flowy sheer duster. Complete the look with mules.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Ruching
    • Short, form-hugging fit
    • Knit fabric, tropical floral print
    • Runs true to size

    Style Number/Barcode: 05103-3839

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic And Chic Bikini Bottoms

    Keep it basic and chic with bikini bottoms that will have you vacay-ready to bask in the sun! The bikini bottoms feature a high-rise waist, side ties, and a thong bottom. Complete look with the matching bikini top and a floppy hat. 

    Shop Matching Bikini Top: Basic And Chic Bikini Top

    Fit & Features

    • High rise waist
    • Side ties
    • Thong bottom
    • Form hugging fit
    • Runs true to size

     

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

    Style Number/Barcode: 07105-0514

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic And Chic Bikini Top

    Keep it basic and chic with a bikini top that will have you vacay-ready to bask in the sun! The bikini features triangle cups, halter neck ties, and back ties. Complete look with the matching bikini bottoms and a floppy hat. 

    Shop Matching Bikini Bottoms: Basic And Chic Bikini Bottoms

    Fit & Features

    • Triangle cups
    • Halter neck ties
    • Back ties
    • Form hugging fit
    • Runs true to size

     

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

    Style Number/Barcode: 07104-0364

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovestruck Butterfly Print Smocked Mini Dress

    Get lovestruck with this pretty butterfly print mini dress that brings the charm! The mini dress features a sleeveless sweetheart neckline with a cute tie-front accent, a cutout at the midriff, adjustable spaghetti straps, a smocked back, and a mini-length silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules

    Fit & Features

    • Sleeveless sweetheart neckline 
    • Tie-front accent
    • Adjustable spaghetti straps 
    • Cutout at the midriff 
    • Smocked back
    • Gauze knit fabric, mini length silhouette
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1230

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pop Of Floral Mesh Maxi Dress

    Add a pop of floral to your summer look with this gorgeous maxi dress. It features a sleeveless wrap-front V neckline, spaghetti straps, a cross-back design with a tie closure, a fitted high waist, and a floor-length skirt with dual front slits and a flowy silhouette. This dress is perfect for attending a summer wedding styled with basic heels and stud earrings.

    Fit & Features

    • Wrap-front V neckline
    • Spaghetti straps
    • Cross-back design, tie closure
    • Fitted high waist
    • Floor-length skirt, dual front slits, flowy silhouette
    • Floral printed sheer mesh fabric, short lining
    • Runs true to size

    Style Number/Barcode: 05101-0544

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Basic Band Sandals

    Keep it so sleek with basic sandals that perf for beach days and brunch! The sandals feature a slip-on design and open almond toe with a wide strap over the toe and a faux leather insole. Complete look with a bikini top and cutoff shorts.

    Fit & Features

    • Slip-on design 
    • Open almond toe 
    • Wide strap over the toe
    • Faux leather insole 

    Style Number/Barcode: 07404-0687

    Category Name: Vacation Looks

    Price: $12.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Two Strap Buckle Sandals

    Step out in style in these trendy sandals that are perf for casual brunch dates! They feature a round open toe, a dual strap design with double buckle detailing, and a slide-on fit. Pair these sandals with your favorite casual dress and a classic denim jacket.

    Fit & Features

    • Round open toe
    • Dual strap design
    • Double buckle detailing
    • Slide-on fit
    • Cork sole

    Style Number/Barcode: 07404-0685

    Category Name: Vacation Looks

    Price: $12.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wanderlust Beauty Tie Front Top

    You're a total wanderlust beauty, and this tie-front top is a must-have style for you. The top features a plunging V-neckline, a tie-front, short sleeves, and a bohemian-inspired paisley print. Complete your look with the matching pants and sandals for the perf warm-weather outfit.

    Shop Matching Pants: Wanderlust Beauty Flared Pants

    Fit & Features

    • V-neckline
    • Tie-front accent
    • Short sleeves
    • Bohemian-inspired paisley print
    • Cropped hem 
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06202-0184

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brunch-Ready Floral Midi Dress

    Style this adorable floral midi dress for weekend brunch with the girls! It features a sleeveless square neckline, spaghetti straps, a high waist, ruching, and a mid-length, curve-hugging silhouette. The knit fabric includes a knit lining and offers plenty of stretch. Complete the look with cute sunglasses and chic mules.

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • High waist
    • Ruching
    • Mid-length, form-hugging fit
    • Lined knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05101-1045

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shot Queen Tequila Script Cap

    Let this cap say it all, tequila queen! The cap features a traditional baseball brim and a script that reads: "Tequila, Salt & Lime". Complete the look with a white tee and cutoff shorts. 

    Fit & Features

    • Traditional baseball brim
    • Script reads" "Tequila, Salt & Lime" 

    Style Number/Barcode: 07302-0336

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Chic Clear Sandals

    Get a stylish and chic vibe when you add these clear sandals to your look! They feature a round open toe, a clear PVC wide strap, and a slide-on design. Pair these sandals with a floral mini dress for a casual day-time date.

    Fit & Features

    • Round open toe
    • Clear PVC wide strap
    • Slide-on design
    • Patent PU flat sole

    Style Number/Barcode: 07404-0686

    Category Name: Vacation Looks

    Price: $12.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Chic Criss-Cross Faux Suede Sandals

    Keep it so chic with sandals that elevate your look. The sandals feature a slip-on design, an open almond toe, criss-cross straps, and composed of a faux suede material. Complete look with a matching crop top and shorts set

    Fit & Features

    • Slip-on design 
    • Open almond toe 
    • Criss-cross straps
    • Faux suede material 

    Style Number/Barcode: 07404-0722

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leopard Pyramid Stud Jelly Thong Sandals

    Keep it fierce and chic with jelly sandals that let your inner diva show! The sandals feature a jelly body, a leopard print, pyramid-shaped studs, a bow accent, and an open almond toe with a thong strap. Complete look with cutoff shorts and a crop top. 

    Fit & Features

    • Jelly body
    • Leopard print
    • Pyramid-shaped studs
    • Bow accent
    • Open almond toe
    • Thong strap 

    Style Number/Barcode: 07404-0726

    Category Name: Vacation Looks

    Price: $12.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free