Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Artsy Energy Lace-Up Halter Crop Top

    You'll be bursting with artsy-cute energy in this halter crop top for festivals or weekend getaways! It features a sleeveless halter neckline with spaghetti straps that form the strappy back design and lace-up front, an underwire bust, and a ruched bodice, and is composed of abstract print chiffon fabric with lining. Style with denim shorts and sandals for a cute look!

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps
    • Strappy back, lace-up front
    • Underwire bust, ruched bodice
    • Cropped hem, back zipper closure
    • Abstract print
    • Lined chiffon fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06003-2090

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Beachy Tropical Print Cropped Bustier

    Create a casual beachy look with this on-trend tropical print bustier. It features a sleeveless sweetheart neckline, a tie-front design at the bust, adjustable spaghetti straps, and a fitted, cropped hem. The smooth knit fabric showcases a tropical palm leaf print. Style with denim shorts.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie-front bust design
    • Adjustable spaghetti straps
    • Fitted, cropped hem
    • Tropical palm leaf print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4829

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Let's Get Together Tiered Maxi Skirt

    You and this maxi skirt must get together soon! Start prepping for brunch under the sun in this maxi skirt featuring a high-rise elasticized waist, a tiered design, and a flowy silhouette. Complete the look with the matching top.

    Shop Matching Tops: Let's Get Together Twist Crop Top, Let's Get Together Tie-Front Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Tiered design
    • Flowy silhouette
    • Pull-on and off styling
    • Gauze woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0123

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Resort-Approved Linen Wrap Mini Skirt

    This linen-blend mini skirt is totally resort-approved and ready for you to pack in your carry-on! It features a high-rise elasticized waist, a wrap-front design with a side tie accent, subtle ruching, and a mini-length hem with a fitted silhouette. Style with a halter top and strappy sandals.

    Fit & Features

    • High-rise elasticized waist
    • Back zipper and hook-eye closure
    • Wrap-front design, side tie detail, ruching
    • Mini-length hem
    • Fitted silhouette
    • Linen-blend fabric
    • Runs true to size

    Style Number/Barcode: 06301-0158

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Festival Muse Printed Flare Pants

    You'll be a total festival muse in these printed flare pants that will draw everyone's attention. They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, a flared-out hem, and a trendy brush stroke print design. Style with a crop top and booties.

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Brush stroke print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2289

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Layered In Trendy Glamour Necklace Set

    You'll be layered in trendy glamour with this dainty necklace set. It features five necklaces with varying designs, including a dainty chain with sleek bar accents, a beaded chain with a circle charm with mini rhinestone stars, a flat chain, a paperclip chain, and a dainty chain with a star charm with a rhinestone center detail. Style the set all together with a basic tee to dress it up!

    Fit & Features

    • Five necklaces, varying designs
    • Dainty chain, bar accents
    • Beaded chain, circle charm, mini rhinestone stars
    • Flat chain
    • Paperclip chain
    • Dainty chain, star charm, rhinestone center
    • Adjustable back chains, lobster clasp closures

    Style Number/Barcode: 07002-1493

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fun And Free Boho High-Rise Flare Pants

    Envoke a fun and free-spirited style in these boho pants at concerts or summer festivals! They feature a flattering high-rise waist, a hip-hugging fit, and a flared hem on stretchy knit fabric. Complete the look in a crochet top and platform sandals!

    Fit & Features

    • High-rise waist, elastic band
    • Hip-hugging fit
    • Flared hem
    • Boho print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2343

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Boho Vibes Paisley Flare Pants

    Give off casual boho vibes in these paisley print flare pants. They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the leg, and a cute flared hem. The soft brushed knit fabric features an all-over multi-print paisley pattern. Style with a tie-front top and booties for your weekend plans!

    Fit & Features

    • High-rise waist, elastic band
    • Hip-hugging fit
    • Form-hugging fit throughout the leg
    • Flared hem
    • Multi-print paisley pattern
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2342

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Silhouette Plunge Halter Bodysuit

    Add this elevated basic bodysuit to your everyday lineup! It features a sleeveless plunge halter V-neckline, a partially open back, a thong bottom, and a form-hugging fit. The double-lined stretchy knit fabric offers a seamless design and has an ultra-soft buttery feel. Complete the look in a flirty woven skort and heels.

    Fit & Features

    • Sleeveless plunge halter V-neckline
    • Partially open back
    • Form-hugging fit
    • Thong bottom, dual snap-button closures
    • Double-lined stretchy knit fabric
    • Seamless design, buttery knit feel
    • Runs true to size

    Style Number/Barcode: 06002-1616

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Dream Ditsy Floral Mini Dress

    Create a dreamy summer vibe in this adorable floral mini dress perf for sunny weekends! It features a sleeveless V-neckline with ruching at the center of the bust, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The ditsy floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline, ruching at the bust
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Ditsy floral print
    • Brushed knit fabric, full lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5122

    Category Name: Vacation Looks

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spot Me In Leopard Slit Midi Dress

    You can be spotted all season in this leopard print midi dress perfect for a casual lunch or a wine night with friends! It features a sleeveless V-neckline, tank shoulder straps, and a form-hugging, slim silhouette with a flowy slit hem. Complete the look in sleek statement hoop earrings and sandals.

    Fit & Features

    • Sleeveless V-neckline, tank shoulder straps
    • Form-hugging, slim silhouette
    • Front slit
    • Midi-length flowy hem
    • Leopard print
    • Woven non-stretch fabric
    • Runs true to size

    Style Number/Barcode: 05102-4469

    Category Name: Vacation Looks

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trip To Paradise Tropical Print Maxi Dress

    This bold and alluring tropical print maxi dress calls for a trip to paradise! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a floor-length hem with a thigh-high front slit, and a flowy silhouette. The smooth knit fabric showcases a tropical palm leaf print. Style with strappy sandals for sunset drinks.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • Floor-length hem, high front slit, flowy silhouette
    • Tropical palm leaf print
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5025

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Beach Babe Tie-Front Top

    Style up this breezy tie-front top for a total beach babe look! The lightweight gauze top features long peasant sleeves with cinched hems, a V-neckline with a tie-front design, a fitted, cropped hem, and a subtle palm leaf print. Wear it alone with denim shorts or as a cover-up over your swimsuit!

    Fit & Features

    • Long peasant sleeves, cinched hems
    • V-neckline
    • Tie-front design
    • Fitted, cropped hem
    • Palm leaf print
    • Gauze fabric
    • Runs true to size

    Style Number/Barcode: 06204-1236

    Category Name: Vacation Looks

    Price: $17.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild And Chic Zebra Print Mini Sweater Dress

    Add a wild flair to your everyday look with this chic zebra print sweater dress. It features a sleeveless V-neckline, halter straps with a tie-back design, an open back, a mini-length hem, and a curve-hugging fit. The sweater knit fabric offers a moderate stretch. Style with a mini handbag and clear mules for a fashion-forward look.

    Fit & Features

    • Sleeveless V-neckline
    • Halter straps, tie-back design
    • Open back
    • Mini-length hem
    • Curve-hugging silhouette
    • Zebra print, sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1699

    Category Name: Vacation Looks

    Price: $3.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Island Breeze Tropical Print Midi Skirt

    Feel the island breeze as you stroll past the waves in this tropical print midi skirt. It features a high-rise waist, a hip-hugging fit, a midi-length hem with an alluring high side slit, and a flowy A-line silhouette. The smooth and stretchy knit fabric features a bold tropical palm leaf print. Style with a crop top and sandals.

    Fit & Features

    • High-rise elasticized waist
    • Hip-hugging fit
    • Midi-length hem, high side slit
    • Flowy A-line silhouette
    • Tropical palm leaf print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0843

    Category Name: Vacation Looks

    Price: $11.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Bit Of Sparkle Rhinestone Aviator Sunglasses

    Accessorize your 'fit with a bit of sparkle with these aviator sunglasses! They feature a rhinestone trim, a sleek metal frame, rubber nose supports,  and tinted lenses with UV protection. Complete the look with a trendy rhinestone denim jacket for a summer festival or concert!

    Fit & Features

    • Rhinestone trim
    • Sleek metal frame
    • Rubber nose supports
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-0994

    Category Name: Vacation Looks

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pleasure's All Mine Wooden Platform Mules

    Your feet will be pleased to meet these platform mules perfect for everyday styling! They feature a faux leather footbed, almond toe, wide foot strap, and a wood-inspired sole. Style with a chic crossbody bag for brunch or wine tasting!

    Fit & Features

    • Almond toe
    • Wide foot strap
    • Wood-inspired platform sole
    • Faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07401-4217

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Is Here Oversized Round Sunglasses

    Summer is here, and these chic oversized sunglasses will style perfectly with all your casual looks. They feature a round shape with a thin metal frame, a chain-link design on the arms, and tinted lenses. Pair with a layered charm necklace.

    Fit & Features

    • Oversized round shape
    • Thin metal frame
    • Chain-link design on the arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1013

    Category Name: Vacation Looks

    Price: $3.96 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual-Chic Affair Cat-Eye Sunglasses

    Make every day a casual-chic affair with these sleek sunglasses! They feature a geometric cat-eye shape with a plastic frame, gold bar accents on the sides, and tinted lenses. Style with a mini handbag.

    Fit & Features

    • Geometric cat-eye shape
    • Plastic frame, side gold bar accents
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1015

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • La Quinta Ditsy Floral Rib Knit Mini Dress

    Let your love for floral bloom in this rib knit mini dress perfect for a visit to the flower fields!  It features a ruffle trim sweetheart neckline and puff short sleeves, a flirty bust lace-up, a bodycon silhouette, and a mini-length hem. Complete the look in cute flat sandals and earrings.

    Fit & Features

    • Ruffle trim sweetheart neckline
    • Ruffle trim puff short sleeves
    • Bust lace-up
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral print, stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5171

    Category Name: Vacation Looks

    Price: $5.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Instantly Fab Oversized Square Sunglasses

    You'll look instantly fab when you accessorize your everyday looks with these oversized sunglasses. They feature a square-shaped design with a plastic frame, textured gold detailing on the sides, and tinted lenses. Style with a chic handbag.

    Fit & Features

    • Oversized square-shaped design
    • Plastic frame
    • Textured gold detailing
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1021

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drive Down The Coast Oversized Square Sunglasses

    These trendy oversized sunglasses are perfect for a breezy drive down the coast! They feature a square-shaped design with a tortoiseshell plastic frame, a sleek gold bar accent at the top, and tinted lenses. Style with a flowy sundress.

    Fit & Features

    • Oversized square-shaped design
    • Tortoiseshell plastic frame
    • Gold bar accent
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1022

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blissful Beauty Chiffon Ruffle Trim V-Neck Maxi Dress

    Enter every soiree looking blissfully beautiful in this chiffon maxi dress! Featuring a sleeveless V-neck with ruffle trim, adjustable spaghetti straps with a tie-back design, and a flattering babydoll-style silhouette, front slit, and maxi-length hem. Complete the look in lace-up stiletto heels and dainty earrings.

    Fit & Features

    • Sleeveless V-neckline with ruffle trim
    • Adjustable spaghetti straps, tie-back design
    • Babydoll-style silhouette
    • Front slit accent
    • Maxi-length hem
    • Airy chiffon fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2353

    Category Name: Vacation Looks

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Follow The Sun Sweetheart Mini Dress

    Dare to bare some skin on a sunny day in this flirty casual mini dress for hanging by the beach or downtown! It features a sleeveless sweetheart neckline, spaghetti straps, a bust tie with a keyhole accent, and flattering side ruched seams that accentuate your curves along the bodycon fit. Complete the look with cute sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Bust tie, keyhole accent
    • Side ruched seams, bodycon fit
    • Mini-length hem
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 05102-5127

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale