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.

  • Sweet Day Turtleneck Knit Crop Top

    It's always a sweet day when you can slip on this turtleneck crop top featuring long sleeves, and adjustable side ruched ties, and is composed of stretchy rib-knit fabric. Style with a midi skirt to complete your cute look!

    Fit & Features

    • Long sleeves
    • Turtleneck
    • Adjustable side ruched ties
    • Cropped hem
    • RIb-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4643

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple Sleek Faux Leather Crossbody Purse

    This simple and sleek faux leather crossbody purse is perfect for taking from day to night. It features a fold-over design with a thin metal trim, a magnetic snap button closure, and a chain-link shoulder strap. Style with your fave pair of hoop earrings.

    Fit & Features

    • Rectangular shape
    • Fold-over design, thin metal trim
    • Magnetic snap button closure
    • Chain-link shoulder strap
    • Single zippered pocket on the interior
    • Faux leather fabric

    Style Number/Barcode: 07203-1034

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet In Tweed V-Neck Sweater

    Show your sweet side! This tweed plaid sweater features long dolman sleeves, a V-neck, and a relaxed fit hem. Complete the look in faux leather pants for a dinner party!

    Fit & Features

    • Long dolman sleeves
    • V-neck
    • Relaxed fit hem
    • Plaid tweed fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1600

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Autumn Feels Turtle Neck Sweater

    The perfect turtle neck sweater to give you the autumn feels! It features cozy long sleeves with ribbed cuffs, a relaxed fit, and a ribbed hem on pointelle knit fabric. Complete the look in leggings and booties.

    Fit & Features

    • Long sleeves with ribbed cuffs
    • Turtle neck
    • Relaxed fit
    • Ribbed hem
    • Pointelle knit design
    • Soft and comfortable
    • Fits true to size

    Style Number/Barcode: 06005-1476

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Love This Shine V-Neck Knit Sweater

    Bring the shine this holiday season in this cropped sweater featuring cozy, long balloon sleeves, a v-neck, relaxed silhouette, crafted on sparkly lurex ribbed-knit fabric that's soft and comfortable. Complete the look in faux suede booties and jeans.

    Fit & Features

    • Long balloon sleeves
    • V-neck
    • Relaxed silhouette
    • Cropped hem 
    • Soft and comfortable
    • Sparkly lurex ribbed-knit, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06005-1471

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Season Chill Popcorn Knit Sweater

    This season, embrace the chill in this cozy popcorn knit sweater featuring a trendy, off-the-shoulder neckline, balloon long sleeves, and a relaxed fit. Complete the look in high-rise jeans and boots.

    Fit & Features

    • Off-the-shoulder neckline
    • Balloon long sleeves
    • Relaxed fit
    • Soft and cozy
    • Popcorn knit design
    • Fits true to size

    Style Number/Barcode: 06005-1478

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple Chic Double Buckle Belt

    Upgrade your everyday 'fit with this simple chic faux leather belt. It features a bold double buckle front design and a stretchy back for comfortable wear. Style with your favorite bodysuit and high-rise dress pants.

    Fit & Features

    • Double buckle front design
    • Stretchy back
    • Faux leather material
    • Adjustable buckle closures

    Style Number/Barcode: 07301-0558

    Category Name: Vacation Looks

    Price: $2.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lovely Chic Rhine Layered Necklace

    The perfect layered necklace to dress up your favorite blouse! It features three rhinestone layers, a teardrop charm, and a lobster clasp closure. 

    Fit & Features

    • Three rhinestone layers
    • Teardrop charm
    • Lobster clasp closure

    Style Number/Barcode: 07002-1286

    Category Name: Vacation Looks

    Price: $2.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Got It Covered Surplice Sweater

    You'll be ready for any outing with this sweater in your lineup! It features long sleeves, a turtleneck with a fold-over design, a relaxed crop silhouette, and an open surplice back design on soft knit fabric. Style with chic booties to complete the look.

    Fit & Features

    • Long sleeves
    • Turtleneck, fold-over design
    • Relaxed crop silhouette
    • Open surplice back design
    • Sweater knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1477

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Button Me Up Faux Leather Shorts

    Get yourself into these fab and sultry faux leather shorts on a Friday night out! They feature a high-rise waist, six-button front accents, and a back zipper closure. Complete the look in a basic bodysuit and boots.

    Fit & Features

    • High-rise waist
    • Six-button front accents
    • Back zipper closure
    • Faux leather fabric
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06403-0282

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Small Town Girl Puffer Crop Vest

    Whether you're a small-town girl or a city-slicker, this puffer crop vest is essential for adding that extra layer on chilly days! It features a sleeveless standing collar neckline, front zipper closure, side pockets, and a hem drawcord for a customizable fit. The vest is composed of an insulated woven fabric designed to help keep you cozy and protected from the elements! Complete the look in a chenille sweater and jeans!

    Fit & Features

    • Sleeveless standing collar neckline
    • Front zipper closure
    • Side pockets
    • Cropped length
    • Adjustable drawcord hem
    • Insulated woven lined fabric
    • Fits true to size

    Style Number/Barcode: 06201-0323

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be Happy Face Faux Sherpa Slippers

    These faux sherpa slippers will bring a smile to your face! They feature a closed, round toe, a front happy face, an open ankle, a soft lined footbed, and a rubber traction bottom. Complete the look in a cropped hoodie for lounging!

    Fit & Features

    • Closed round toe
    • Front happy face
    • Soft lined footbed
    • Rubber traction bottom
    • Faux sherpa material
    • Runs true to size

    Style Number/Barcode: 07408-0109

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Sleek Square Strappy Flat Sandals

    Chic and sleek! These flat sandals offer endless styling options with sleek dual straps and a statement square accent, they're perfect for day or night fun.

    Fit & Features

    • Square toe 
    • Dual straps, square accent
    • Flat sole with trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000011

    Category Name: Vacation Looks

    Price: $18.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Action High Rise Cargo Pants

    Take action by adding these cargo pants to your fashion closet! They feature a high-rise drawstring waist with tie-front closure, side pockets, a wide-leg silhouette, and a single flap pocket. The pants are composed of sleek, non-stretch nylon fabric. Style with a faux leather corset for an edgy look!

    Fit & Features

    • High-rise drawstring waist, tie-front closure
    • Side pockets
    • Wide-leg silhouette
    • Single flap pocket
    • Sleek non-stretch nylon fabric
    • Fits true to size

    Style Number/Barcode: 06302-0711

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Call Me Cutie Cable Knit Tube Top

    They'll call you a cutie in this cable knit tube top! It features a strapless and sleeveless neckline and an ultra-cropped hem. Complete the look in the matching cardigan perfect for a brisk day in the city!

    Shop Matching Cardigan: Call Me Cutie Cable Knit Cardigan

    Fit & Features

    • Strapless and sleeveless neckline
    • Ultra-cropped hem
    • Soft and comfortable
    • Cable knit design
    • Runs true to size

    Style Number/Barcode: 06005-1683

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Call Me Cutie Cable Knit Cardigan

    They'll call you a cutie in this cable knit cardigan! It features balloon long sleeves, an open-front design, and an ultra-cropped hem. Complete the look in the matching top perfect for a brisk day in the city!

    Shop Matching Top: Call Me Cutie Cable Knit Tube Top

    Fit & Features

    • Balloon long sleeves
    • Open-front design
    • Ultra-cropped hem
    • Soft and comfortable
    • Cable knit design
    • Runs true to size

    Style Number/Barcode: 06005-1682

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fall Chill Striped Crop Sweater

    Enter chill mode this fall wearing this cozy striped sweater featuring long sleeves with ribbed cuffs, a crew neck, and a cropped hem on soft brushed knit fabric. Complete the look in trendy skinny jeans and boots.

    Fit & Features

    • Long sleeves, ribbed cuffs
    • Crew neck
    • Cropped hem
    • Striped pattern
    • Soft brushed knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1590

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping Knit Chic Mock Neck Sweater

    Keep your winter wardrobe chic with this trendy knit sweater! Featuring a mock neckline with a V-neck front cutout, long dolman-style sleeves, and a relaxed fit, this sweater can be effortlessly dressed up or down. The knit fabric offers minimal stretch. Pair with denim and sneakers for the day and sleek faux leather leggings and ankle booties for the night.

    Fit & Features

    • Mock neckline
    • V-neck front cutout
    • Long dolman sleeves
    • Mid-length hem, relaxed fit
    • Knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1601

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • You're The One Tie-Front Midi Dress

    This rib knit midi dress will be the one you'll adore for casual outings and more! The dress features long sleeves, a surplice v-neckline, a faux wrap bust atop a flirty cutout bodice with a tie-front closure, and a bodycon silhouette. Style with faux suede booties for the perf autumn look!

    Fit & Features

    • Long sleeves
    • Surplice v-neckline
    • Faux wrap bust
    • Cutout bodice, tie-front closure
    • Bodycon, midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4843

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Shine Leopard Crop Wrap Top

    Shimmer and shine, unveil your wild side in this glitter striped leopard crop top for a night on the prowl. It features dramatic long bell sleeves, a plunge v-neckline, and a wrap-around design so you can customize the style. Complete the look in PVC mules.

    Fit & Features

    • Long bell sleeves
    • Plunge v-neckline
    • Customizable wrap-around design
    • Cropped hem
    • Glitter striped leopard print
    • No stretch
    • Fits true to size

    Style Number/Barcode: 06003-1818

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Houndstooth Fringe Blanket Scarf

    Keep it chic with a scarf that adds a stylish touch to your layered outfits. The scarf features a trendy houndstooth pattern, a short fringe trim, and an oversized blanket style. The scarf is composed of a soft knit fabric. Complete look with a sweater and high waist jeans.

    Fit & Features

    • Houndstooth pattern
    • Short fringe trim
    • Oversized blanket style
    • Soft knit fabric 

    Style Number/Barcode: 07305-0339

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step It Up Collared Mini Sweater Dress

    Step up your everyday fall 'fits with this trendy mini sweater dress. It features a johnny collar, a V-neckline with a partial button-down front, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Style with sleek hoop earrings and knee-high boots.

    Fit & Features

    • Johnny collar
    • V-neckline, partial button-down front
    • Long fitted sleeves
    • Mini-length hem
    • Fitted bodycon silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1534

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sagittarius Graphic Crop Tee

    It's your season Sagittarius babes! This graphic crop tee is perfect for your birthday party outfit! The top features short sleeves, a crew neck, and a front script that reads, "Sagittarius/It's The Fire In Me". Complete the look in sleek faux leather shorts and boots!

    Fit & Features

    • Short sleeves
    • Crew neck
    • Front script reads, "Sagittarius/It's The Fire In Me"
    • Cropped hem
    • Jersey knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1499

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off Duty Chunky Platform Sneakers

    Elevate your off-duty streetwear vibe in these chunky platform sneakers boasting high fashion inspiration! They feature an almond toe, front lace-up closure, faux leather and mesh knit detailing, and a rubber grip sole. Complete the look in a cool puffer jacket for a day out with friends!

    Fit & Features

    • Almond toe
    • Front lace-up closure
    • Faux leather and mesh knit detailing
    • Chunky platform design
    • Rubber grip sole
    • Runs true to size

    Style Number/Barcode: 07407-0213

    Category Name: Vacation Looks

    Price: $12.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free