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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.

  • Tropics Babe High Slit Midi Dress

    Hit the tropics in this gorge midi dress! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, a ruched side seam, and a midi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a floppy hat and sandals. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross at the back 
    • Tropical print 
    • Ruched side seam 
    • Midi length silhouette, high side slit
    • Smooth knit fabric 
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-1799

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Passion Ruffled Midi Dress

    Show off your passion for florals with a midi dress that brings the romance! The dress features a sleeveless square neckline, spaghetti straps, a gorgeous blooming floral print, and a midi-length silhouette accented with a flirty ruffled high slit. The dress is composed of a lined crepe fabric that offers a curve-hugging silhouette with a moderate stretch. Style the look with platform wedges and a butterfly necklace.

    Shop Ivory Floral Version: Ruffled For Florals Midi Dress

    Shop Solid Color Version: Add Some Flair Ruffle Detail Midi Dress

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Strapless or adhesive bra recommended
    • Cross-back strap design, front slit, ruffled hem
    • Midi-length silhouette
    • All-over floral print
    • Lined crepe fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1066

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crochet Cutie Mini Skirt

    Live out your boho dreams in this cute crochet mini skirt! The skirt features a high-rise waist, drawstring, a crochet knit pattern throughout, and a mini-length silhouette. Complete look with the matching crop top.

    Shop Matching Crop Top: Crochet Cutie Triangle Crop Top

    Fit & Features

    • High rise waist
    • Drawstring
    • Crochet knit
    • Mini length silhouette
    • Form hugging fit, runs true to size
    • Skirt is unlined
    • Bikini bottoms pictured not included

    Style Number/Barcode: 06501-0355

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Vibes Lace-Up Crop Top

    Chanel those tropical vibes with a crop top that will have you ready to bask in the sun! The top features a square neckline, lace-up front, long sleeves, tropical print, and a cropped hem. The top is composed of a chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with denim shorts. 

    Fit & Features

    • Square neckline
    • Lace-up front
    • Long sleeves
    • Tropical print 
    • Cropped hem
    • Chiffon fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06003-1291

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tie Dye Frenzy Satin Scarf Top

    Wrap yourself in a satin scarf top to keep it stylish this season! The top features a sleeveless square neckline with a handkerchief bodice, a tie-dye pattern, tie-back ties, and a smocked back. The top is composed of a satin fabric that offers a relaxed fit with minimal stretch. Complete look with high waist jeans. 

    Fit & Features

    • Sleeveless square neckline
    • Handkerchief bodice
    • Tie-dye pattern 
    • Tie-back ties
    • Smocked back, cropped hem
    • Satin fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06003-1279

    Category Name: Vacation Looks

    Price: $4.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keep It Groovy Tie-Dye Maxi Dress

    Keep your summer look groovy and on-trend with this tie-dye maxi dress! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a high waist seam, and a floor-length silhouette with a thigh-high side slit. Style this dress with strappy sandals for a laid-back vibe.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • Floor-length silhouette, high side slit
    • Relaxed fit
    • Brushed knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-0745

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Style Cutout Maxi Dress

    Showcase a stunning style this season in this trendy maxi dress. It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to the back, and a floor-length, curve-hugging silhouette. Pair this sultry dress with hoop earrings and sleek heels.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual waist cutouts that lead to the back
    • Floor-length, form-hugging fit
    • Ribbed cotton fabric
    • Runs true to size

    Style Number/Barcode: 05102-4079

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Flirty Floral Mini Dress

    This flirty floral mini dress is a must-have for summer parties! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a back zipper closure, ruched detailing, and a short, form-hugging fit. Style this dress with a chic charm necklace and wedges.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Back zipper closure
    • Ruching
    • Mini-length, curve-hugging silhouette
    • Mesh fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-1497

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Chic Strappy Sandals

    These basic strappy sandals will give you that casual chic look that's so popular this season! They feature an open round toe, a wide strappy design, and a flat sole. Style these sandals with a tee and denim shorts for the perf summer 'fit.

    Fit & Features

    • Open round toe
    • Wide strappy design
    • Flat sole
    • Runs true to size

     

    Style Number/Barcode: 07404-0905

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy In Tie-Dye Mini Dress

    You'll be the trendy member of your squad in this casual tie-dye knit mini dress. It features a sleeveless crew neckline, tank shoulder straps, an exposed seam that runs down the center, and a short, curve-hugging fit. Style this dress with booties for an edgy vibe.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Center exposed seam
    • Mini-length, form-hugging fit
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4175

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring The Heat Maxi Dress

    Bring the heat to your next vacay in this tropical printed maxi dress! It features an off-the-shoulder neckline, a flowy overlay with short sleeves, a high waist, a floor-length silhouette with a relaxed fit, and a thigh-high side slit. The all-over tropical palm leaf print is perf for your summer getaway! Style this dress with strappy sandals.

    Fit & Features

    • Off-the-shoulder neckline
    • Flowy overlay with short sleeves
    • High waist
    • Floor-length silhouette, relaxed fit, high side slit
    • Knit fabric, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-0778

    Category Name: Vacation Looks

    Price: $22.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Vacay Vibes Tie-Front Top

    Bring on those dreamy vacay vibes with this tropical printed top! It features long blouson sleeves with cinched ruffled hems, a deep V-neckline, a cute tie-front detail, and a cropped fit. The lightweight gauze fabric has a pretty tropical leaf print. Complete the look with high waist shorts and strappy sandals.

    Fit & Features

    • Long blouson sleeves, cinched ruffled hems
    • Deep V-neckline
    • Tie-front
    • Cropped fit
    • Gauze fabric, tropical leaf print
    • Runs true to size

    Style Number/Barcode: 06003-1293

    Category Name: Vacation Looks

    Price: $4.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Days Espadrille Platform Heels

    Channel those summer vibes with espadrille heels that are pef for your next BBQ! The heels feature an adjustable ankle strap, a triple row strap design, and an espadrille platform heel. Complete look with a romper and butterfly earrings. 

    Fit & Features

    • Adjustable ankle strap
    • Triple row strap design 
    • Espadrille platform heel

    Style Number/Barcode: 07404-0797

    Category Name: Vacation Looks

    Price: $12.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Bombshell One-Shoulder Bikini Top

    Beachy bombshell will be your vibe in this one-shoulder bikini top designed with lurex knit fabric for a trendy metallic sheen. Pair with the matching bikini bottoms and sarong for a sun-kissed look!

    Shop Matching Set: Beachy Bombshell Bikini Top, Beachy Bombshell V-Cut Bikini Bottoms, Beachy Bombshell Short Sarong

    Fit & Features

    • Lurex knit fabric, metallic sheen
    • One-shoulder asymmetric strap
    • Sweetheart padded bust with ruching, removable padded bra cups
    • Back hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-0725

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Getaway Linen Skater Dress

    Planning a weekend getaway? Don't forget to pack this adorable linen dress for an effortlessly chic look. The dress features a sleeveless V-neckline, halter spaghetti straps, a tie-back detail, a high waist, and a flirty and flowy skater silhouette. Style this dress with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps
    • Tie-back detail
    • High waist
    • Flowy skater skirt
    • Linen fabric
    • Runs true to size

    Style Number/Barcode: 05102-1085

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Flirty Ditsy Floral Skater Dress

    Cute and flirty, this ditsy floral skater dress is a summer staple! It features a strapless square neckline and a drop waist skater skirt silhouette. Style this dress with wedges for weekend brunch with the girls.

    Fit & Features

    • Strapless square neckline
    • Drop waist skater skirt silhouette
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-4177

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Absolute Bombshell Cutout Mini Dress

    This sultry mini dress will have you looking like an absolute bombshell! It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to a back cutout, and a mini-length, curve-hugging silhouette. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual waist cutouts that lead to a back cutout
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4166

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreaming of Vacay Tie-Front Romper

    This adorable romper will have you dreaming of your next vacay! It features flutter cap sleeves, a V-neckline, a tie-front detail, a sultry front waist cutout, relaxed-fitting shorts, and a tropical palm leaf print. Complete the look with chic sandals.

    Fit & Features

    • Flutter cap sleeves
    • V-neckline
    • Tie-front
    • Front waist cutout
    • High waist, relaxed-fitting shorts
    • Knit fabric, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 06503-0241

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic And Chic High Rise Denim Shorts

    Keep it basic and chic in denim shorts that are perf for the season! The shorts feature a high rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, and a frayed cutoff hem. Complete look with a bodysuit. 

    Fit & Features

    • High rise waist
    • Single-button with hidden zipper closure
    • Traditional five-pocket with belt loop design 
    • Frayed cutoff hem
    • Form hugging fit
    • Runs true to size 

    Style Number/Barcode: 06603-0164

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Trendy Sleeveless Jumpsuit

    Keep it so sleek with a jumpsuit that is per to take you from work to happy hour! The jumpsuit features a sleeveless square neckline, adjustable spaghetti straps, and a wide leg. Complete look with clear mules and statement earrings. 

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Wide leg
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 06502-0544

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss Jetsetter Tropical Mesh Duster

    Set off on a tropical vacay in this fab duster! The duster features a tropical palm leaf print, kimono sleeves, and a long flowy length. The duster is composed of a sheer mesh fabric that offers a relaxed fit with a moderate stretch. Complete look with a tie front top and high waist shorts. 

    Fit & Features

    • Tropical palm leaf print
    • Kimono sleeves
    • Long flowy length 
    • Sheer mesh fabric 
    • Relaxed fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 06202-0178

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Wanderer Floral Flared Pants

    You'll look like a total wanderlust beauty in these boho floral printed pants! They feature a high-rise waist, a trendy lace-up front, a form-hugging silhouette, and flared pant legs. Style these pants with a crop top and strappy sandals.

    Fit & Features

    • High-rise waist
    • Lace-up front
    • Form-hugging fit
    • Flared pant legs
    • Knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 06502-0589

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Goddess Strapless Jumpsuit

    You'll look like a gorgeous goddess on your next vacay in this strapless jumpsuit! It features a square neckline, a high waist, flowy wide pant legs, and a stunning all-over tropical palm leaf print. Style this jumpsuit with hoop earrings and wedges.

    Fit & Features

    • Strapless square neckline
    • High waist
    • Wide pant legs
    • Knit fabric, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 06502-0389

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Diva Halter Jumpsuit

    Showcase your fashion diva side in this fab denim jumpsuit! It features a sleeveless V-neckline with a wrap-front design, halter spaghetti straps, a high waist with a tie-front belt, a form-hugging silhouette, and pant legs with a flared hem. Style this jumpsuit with clear heels.

    Fit & Features

    • Sleeveless V-neckline, wrap-front design
    • Halter spaghetti straps
    • Back zipper and hook and eye closure
    • High waist, tie-front belt
    • Front and back pockets
    • Form-hugging fit, flared hem
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0235

    Category Name: Vacation Looks

    Price: $22.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale