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.

  • Dreamy And Chic Tie-Front Top

    Style this boho-inspired tie-front top for a dreamy and chic look! It features three-quarter length kimono-style sleeves, a plunging V neckline, a tie-front, and a wide sheer lace trim. Pair this top with a denim mini skirt and strappy sandals.

    Fit & Features

    • Three-quarter length kimono-style sleeves
    • Deep V neckline
    • Tie-front
    • Wide sheer lace trim
    • Woven fabric, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-0911

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun Soaked Espadrille Strappy Wedges

    Step into sunny style with these espadrille wedges in a strappy design that elevates any look! 

    Fit & Features

    • Wedge heel
    • Square toe
    • Criss cross straps
    • Closed ankle, back zipper closure
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000011

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Medallion Marvel Strapless Jumpsuit

    Make them marvel with a jumpsuit that channels a retro feel! The jumpsuit features a strapless square neckline, a medallion print, hidden side pockets, and a fitted straight leg. Complete the look with hoops and platform wedges for a gorge outfit.

    Fit & Features

    • Strapless square neckline
    • Medallion print
    • Hidden side pockets
    • Fitted straight leg
    • Knit fabric, form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06502-0551

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island It Girl One-Shoulder Cutout Maxi Dress

    Giving tropical baddie with a side of luxury, this one-shoulder maxi brings the heat with a bold leaf print, cutout waist, and gold hardware that says, "I didn’t come to play." It's made for vacation slays, beach weddings, or poolside parties!

    Fit & Features

    • Tropical leaf print, smooth stretchy knit fabric, short lining
    • One-shoulder neckline with hardware trim
    • Side cutout bodice
    • High side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000082

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Getaway Mesh Duster

    Look like you're jetting off to a tropical getaway in this chic mesh duster! It features long fitted sleeves, an open front, and a long, flowy silhouette. The sheer mesh fabric showcases an all-over neutral palm leaf print. Style this duster as a lightweight layer over a bodysuit and denim, and pair the look with heels.

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Long, flowy silhouette
    • Sheer mesh fabric
    • Neutral palm leaf print
    • Runs true to size

    Style Number/Barcode: 06202-0159

    Category Name: Vacation Looks

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Charmer Ditsy Floral Mini Dress

    Charm them all with a mini dress that makes a sweet impression! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print 
    • Mini-length silhouette
    • Ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1895

    Category Name: Vacation Looks

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Passion Gauze Knit Kimono

    Unleash your passion for florals with a kimono that radiates beauty and style. The kimono features a drape open front, short kimono sleeves, a floral print, and a flowy long length. The kimono is composed of a gauze knit fabric that offers a relaxed fit with a minimal stretch. Complete look with a crop top and cutoff shorts. 

    Fit & Features

    • Draped open front
    • Floral print
    • Kimono sleeves
    • Flowy long length 
    • Gauze knit fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06204-0886

    Category Name: Vacation Looks

    Price: $16.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropics Queen Swim Coverup

    Head off to the tropics with a swim coverup that instantly transports you to paradise! The cover-up features a tropical palm leaf print and composed of a sheer mesh fabric. Complete outfit with a swimsuit and sunnies

    Fit & Features

    • Tropical palm leaf print
    • Mesh fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 07305-0291

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Embraced In Beauty Chiffon Floral Duster

    Embrace yourself with florals in a pretty duster to layer over outfits. The duster features a draped open front, a floral print, long sleeves, and a flowy long length. The duster is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a crop top and button-up shorts. 

    Fit & Features

    • Draped open front
    • Long sleeves
    • Floral print
    • Flowy long length 
    • Sheer chiffon fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

     

    Style Number/Barcode: 06204-0898

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Spirit Flared Pants

    Channel your bohemian spirit with flared pants that showcase your indie side! The pants feature a high-rise waist, a bohemian-inspired print, and a flared wide-leg. The pants are composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with a crochet top

    Fit & Features

    • High rise waist
    • Bohemian-inspired print
    • Flared wide-leg hem
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06502-0573

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Florals On My Mind Tie Front Top

    Keep florals on your mind with a pretty top that keeps it frilly and flirty. The top features a plunging tie-front bodice, ruffled quarter-length sleeves, a ditsy floral print, and a cropped hem. Complete look with high waist shorts and earrings. 

    Fit & Features

    • Plunging V-neckline
    • Ditsy floral print
    • Ruffled 3/4 sleeves
    • Cropped hem 
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06204-0817

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Stunner Tie-Front Romper

    You'll be such a stylish stunner in this pretty printed romper! It features flowy kimono-style sleeves, a wrap-front V neckline, a tie-back accent at the neck, a high waist with a tie-front belt, and flowy shorts. The woven fabric has a chic all-over bohemian-inspired print. Complete the look with gold hoop earrings and strappy sandals for the perfect summer outfit.

    Fit & Features

    • Kimono-style sleeves
    • Wrap-front V neckline
    • Tie-back detail at the neck
    • High waist, tie-front belt
    • Flowy shorts
    • Woven fabric, bohemian-inspired print
    • Runs true to size

    Style Number/Barcode: 06303-0113

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Romance Ditsy Floral Mini Dress

    Fall in love with this adorable ditsy floral mini dress that is perfect for summer date nights. It features short puff sleeves, a sweetheart neckline with a center criss-cross bust detail, and a mini-length, curve-hugging silhouette. Complete the outfit with a charm necklace and clear heels.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Center criss-cross bust detail
    • Short, form-hugging fit
    • Knit fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-2103

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Love Double-Layer Skater Dress

    Fall head over heels for this pretty floral skater dress! It features a sleeveless square neckline, adjustable spaghetti straps, a back bow accent and lower back cutout, a fitted bodice with a high waist, and a flirty double-layered skater skirt with a flared-out silhouette. Style this dress with sleek hoop earrings and cute wedges for a summer date night.

    Fit & Features

    • Square neckline
    • Adjustable spaghetti straps
    • Back bow accent, lower back cutout
    • Fitted bodice, high waist
    • Double-layered skater skirt
    • Crepe fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05101-0653

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Beauty Crochet Crop Top

    You'll look like a total boho beauty in this cute crochet crop top! It features a crew neckline, short cap sleeves, a trendy lattice back design, and a cropped, form-hugging fit. Pair this sheer crochet top with denim shorts and strappy sandals for an effortlessly stylish outfit.

    Fit & Features

    • Crew neckline
    • Cap sleeves
    • Lattice back design
    • Cropped, form-hugging fit
    • Crochet fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-0951

    Category Name: Vacation Looks

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Darling Ditsy Floral Mini Skirt

    Achieve that sweet darling look that's trendy for summertime with this adorable mini skirt! It features a high-rise waist, a mini-length, curve-hugging silhouette, a ruffle hem, and an all-over ditsy floral print. Pair this skirt with the matching crop top and strappy sandals.

    Shop Matching Top: Sweet Darling Ditsy Floral Crop Top

    Fit & Features

    • High-rise waist
    • Short, form-hugging fit
    • Ruffle hem
    • Ditsy floral print
    • Smocked woven fabric
    • Runs true to size

    Style Number/Barcode: 06401-0310

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ladies' Night Abstract Floral Crop Top

    This stunning abstract floral crop top will turn heads with every wear on your next ladies' night!

    Fit & Features

    • Abstract floral print, mesh fabric, sewn-in knit lining
    • Adjustable drawstring shoulder straps
    • Plunge neckline
    • Side ruched seams
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000137

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Darling Ditsy Floral Crop Top

    Achieve that sweet darling look that's trendy for summertime with this adorable crop top! It features a strapless neckline with a tie-front accent, a cropped, form-hugging fit, and an all-over ditsy floral print. Pair this top with the matching mini skirt and strappy sandals.

    Shop Matching Bottoms: Sweet Darling Ditsy Floral Mini Skirt

    Fit & Features

    • Strapless neckline
    • Tie-front
    • Cropped, form-hugging fit
    • Ditsy floral print
    • Smocked woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-1296

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sealed With Glam Tie Front One Piece Swimsuit

    Seal your look with a glam swimsuit that brings the style! The swimsuit features a sleeveless sweetheart neckline, a cute tie front accent, adjustable spaghetti straps, a sexy cutout at the midriff, and a cheeky fit bottom. Complete look with slides and sunnies

    Fit & Features

    • Sleeveless sweetheart neckline, padded cups 
    • Adjustable spaghetti straps 
    • Tie-front accent
    • Cutout
    • Cheeky fit bottom

    Style Number/Barcode: 07109-0267

    Category Name: Vacation Looks

    Price: $15.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Leather Double Band Slides

    Slip on these stylish sandals to keep it basic and cute! The sandals feature an easy slip-on design, an open almond toe with a double band design, and a flat footbed. Complete look with a basic tee shirt and cutoff shorts

    Fit & Features

    • Slip-on design 
    • Open almond toe 
    • Double-band design 
    • Flat footbed
    • Faux leather material 

    Style Number/Barcode: 07404-0690

    Category Name: Vacation Looks

    Price: $12.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Vibes Cutoff Denim Shorts

    Get those lowkey effortless vibes with these high-rise denim shorts. They feature a traditional five-pocket and belt loop design, a front button closure, destructed detailing, and a frayed cutoff hem. Complete the look with a cute bodysuit and strappy sandals.

    Fit & Features

    • High-rise waist
    • Traditional five-pocket and belt loop design
    • Front button closure
    • Destructed detailing
    • Frayed cutoff hem
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 06603-0216

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Distressed To Impress Cutoff Denim Shorts

    These majorly distressed denim shorts will have your whole squad impressed with your style. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button closure, destructed detailing, and a cutoff hem. Complete the look with a graphic tee and sneakers.

    Fit & Features

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

    Style Number/Barcode: 06603-0210

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fab And Frayed Cutoff Denim Shorts

    Get a fab everyday look in these on-trend casual denim shorts. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button closure, destructed detailing, and a cutoff frayed hem. Style these shorts with your fave swimsuit and sandals for a summer beach trip with your squad.

    Fit & Features

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

    Style Number/Barcode: 06603-0209

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Must-Have Denim Shorts

    These high-rise denim shorts are a must-have for achieving that casual and laidback summertime look. They feature a traditional five-pocket and belt loop design, a front button and hidden zipper closure, slight distressed detailing, and a frayed hem. Complete the outfit with a cute crop top and sneakers.

    Fit & Features

    • High-rise waist
    • Traditional five-pocket and belt loop design
    • Front button and hidden zipper closure
    • Subtle distressed detailing
    • Frayed hem
    • Denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0189

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free