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.

  • Cozy In Cable Knit Turtleneck Sweater

    Cozy and cute, what could be better for your autumn closet than this cable knit turtleneck sweater? It features long sleeves, a foldover neck, and a cropped distressed hem. Complete the look in faux leather pants.

    Fit & Features

    • Long sleeves
    • Foldover turtleneck
    • Crop, distressed hem
    • Cable knit design
    • Fits true to size

    Style Number/Barcode: 06005-1538

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Winter Must-Have Cropped Puffer Vest

    This adorable cropped puffer vest is a winter must-have! It features a sleeveless collared neckline, a complete zip front, and a cinched elastic cropped hem for a fab fit. The vest is composed of a lined nylon-woven fabric with insulation to help keep you warm and protected from the elements. Style over a long sleeve bodysuit with cargo pants.

    Fit & Features

    • Sleeveless collared neckline
    • Zip front
    • Cinched elastic cropped hem
    • Insulated and lined nylon-woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06201-0369

    Category Name: Vacation Looks

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Winter Chic Houndstooth Knit Beanie

    This chic knit beanie is perfect for elevating your winter wardrobe. It features an all-over houndstooth pattern, a ribbed hem, and a faux fur pom accent. Style with a sweater and faux leather leggings.

    Fit & Features

    • Houndstooth pattern
    • Ribbed hem
    • Faux fur pom
    • Knit fabric, minimal stretch

    Style Number/Barcode: 07302-0871

    Category Name: Vacation Looks

    Price: $4.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Essentially Cozy Chenille PJ Robe

    Cozy vibes all around! Snuggle up in this chenille PJ robe featuring long sleeves, and an open-front design, belted tie-front, belt loops, pockets, and a relaxed fit. Complete the look with the matching top and bottoms.  

    Shop The Matching Set: Essentially Cozy Chenille PJ Top, Essentially Cozy Chenille PJ Joggers

    Fit & Features

    • Long sleeves
    • Open front design
    • Pockets
    • Belted tie-front, belt loops
    • Soft and comfortable
    • Chenille fabric
    • Fits true to size

    Style Number/Barcode: 07106-0089

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Babe Over-The-Knee Boots

    Show off total retro vibes in these sleek faux leather boots! They feature an over-the-knee height with an inner zipper closure, a pointed toe, and a stacked block heel. Style with your fave mini dress.

    Fit & Features

    • Over-the-knee height
    • Inner zipper closure
    • Pointed toe
    • Stacked block heel
    • Faux leather material, elastic detail at the back
    • Runs true to size

    Style Number/Barcode: 07402-0815

    Category Name: Vacation Looks

    Price: $34.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Autumn Chic Mini Sweater Dress

    This form-hugging sweater dress will give you that autumn chic vibe! It features a crew neckline, long fitted sleeves, asymmetrical ruched detailing with an adjustable drawstring, and a short, fitted silhouette. The stretchy ribbed knit fabric has a trendy space-dye design for an eye-catching look. Style with knee-high boots.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Asymmetrical ruching, side drawstring
    • Mini-length hem, form-hugging fit
    • Stretchy ribbed sweater knit fabric
    • Space-dye design
    • Runs true to size

    Style Number/Barcode: 06005-1584

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Full Throttle Motocycle Graphic Tee

    Live life on the edge in this trendy cropped graphic tee! It features a crew neckline with a cut notched front design, short sleeves, a motorcycle and wings graphic with the scripts "Full Throttle" and "Live To Ride, Ride To Live," and a form-hugging fit. The cotton-blend fabric offers a moderate stretch. Style with distressed denim.

    Fit & Features

    • Crew neckline, notched front design
    • Short sleeves
    • Motorcycle, wings, and flames graphic
    • Script that reads "Full Throttle" and "Live To Ride, Ride To Live"
    • Cropped hem, form-hugging fit
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1457

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Girl Cargo Skinny Pants

    Show off your cool-girl style in these trendy cargo skinny pants. They feature a mid-rise waist, a button-front closure, faux cargo-style flap pockets, and a tapered, form-hugging fit. The woven cotton-blend fabric has no stretch. Style with a graphic tee and combat boots.

    Fit & Features

    • Mid-rise waist
    • Belt loops
    • Hidden zipper, button-front closure
    • Front pockets, faux cargo-style flap pockets
    • Skinny-leg silhouette, form-hugging fit
    • Woven cotton-blend fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0700

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pour The Whiskey Graphic Crop Tee

    Show off what kind of a girl you are! This graphic crop tee features cap sleeves, a crew neck, and front text that reads, "Whiskey Bent And Hell Bound" printed on soft and stretchy jersey knit fabric. Complete the look in trendy distressed jeans for happy hour!

    Fit & Features

    • Cap sleeves
    • Crew neck
    • Front text that reads, "Whiskey Bent And Hell Bound"
    • Cropped hem
    • Jersey knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1460

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Down To Business Ponte Leggings

    Get your style down to business this season! These ponte knit leggings are designed for work or play in a sleek elasticized high-rise waistband, faux front zipper pockets, a skinny leg design, and tapered hem. Complete the look in a plaid vest and booties.

    Fit & Features

    • High-rise elasticized waistband
    • Faux front zipper pockets
    • Skinny-leg design
    • Tapered hem
    • Sculpting design
    • Ponte knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06502-2226

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Scorpio Season Graphic Crop Tee

    It's time to celebrate the season of the Scorpio! This graphic crop tee features cap sleeves, a crew neck, and a front script that reads, "It's The Scorpio In Me" printed on soft and stretchy jersey knit fabric. Complete the look in a faux leather mini skirt for a party!

    Fit & Features

    • Cap sleeves
    • Crew neck
    • Front script reads, "It's The Scorpio In Me"
    • Cropped hem
    • Soft and stretchy
    • Jersey knit fabric
    • Fits true to size

    Style Number/Barcode: 06002-1475

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Romance Floral Lace-Up Maxi Dress

    Evoke chic romance on date night in this gorgeous floral maxi dress designed with an open lace-up strappy back and floor-length form-hugging silhouette. Style with a sleek handbag and stiletto heels.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • Sleeveless deep V-neckline
    • Spaghetti straps
    • Open cross-back lace-up strappy design
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000111

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, XL

    Product Badge:
    • Sale
  • Cute In Checkered Faux Sherpa Jacket

    Achieve a cute streetwear style layering on this checkered hoodie jacket featuring long sleeves, an open-front design, hidden side pockets, oversized silhouette, crafted on faux sherpa-lined fabric. Complete the look in edgy booties.

    Fit & Features

    • Long sleeves
    • Hoodie neckline
    • Open-front design
    • Hidden lined side pockets
    • Oversized silhouette
    • Checker pattern, faux sherpa fabric, lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0360

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cheer Spirit Ponte Pleated Skirt

    Catch the stylish spirit of this ponte pleated skirt everyone will be cheering for! It features a high-rise waist, skater silhouette, and a short-length hem. Complete the look in a basic bodysuit.

    Fit & Features

    • High-rise waist
    • Skater silhouette
    • Pleating
    • Short-length hem
    • Ponte knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06501-0708

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • French Girl Wool Beret

    Elevate your outfit to french girl status with this faux wool beret perfect for styling with a chic trench coat for a day out and about!

    Fit & Features

    • Beret style
    • Wool material

    Style Number/Barcode: 07302-1322

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rhinestone Star Beaded Beanie

    Shine bright this holiday season with a cozy beanie that keeps it glam! This ribbed knit beanie features a fold-over hem with rhinestone embellishments in star designs and sparkly beaded detailing. Style with a sweater dress and a faux leather jacket.

    Fit & Features

    • Ribbed knit fabric
    • Fold-over hem
    • Rhinestone embellishments, star designs
    • Beaded detailing

    Style Number/Barcode: 07302-1323

    Category Name: Vacation Looks

    Price: $8.00 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Like Me Over The Knee Boots

    Smooth and sultry, these over-the-knee boots are the ticket to an elevated style! They feature an almond toe, block heel, and side zipper closure, an adjustable drawcord at the top, and are composed of faux suede material. Complete the look in high-rise skinny jeans.

    Fit & Features

    • Almond toe
    • Side zipper closure
    • Block heel
    • Over-the-knee shaft length
    • Adjustable drawcord at the top
    • Faux suede material
    • Runs true to size

    Style Number/Barcode: 07402-0851

    Category Name: Vacation Looks

    Price: $12.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Peep This Chic Cutout Booties

    Check out these chic nubuck booties and imagine all the ways you'd style them! They feature an almond peep toe, platform sole, stacked thin block heel, cutout sides, and an adjustable buckle strap and back zipper closure. Complete the look in a wide-leg jumpsuit for cocktail hour.

    Fit & Features

    • Almond peep toe
    • Platform sole
    • Stacked thin block heel
    • Cutout sides
    • Adjustable buckle strap and back zipper closure
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-1567

    Category Name: Vacation Looks

    Price: $4.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Sparkle Layered Necklace

    Showcase a gorgeous sparkle with this embellished layered necklace. It features a three-row layered design. The shortest layer features a chain-link design with thin clear glass stones at the center, and the two longer layers feature mini rhinestone embellishments. Style this necklace with simple stud earrings.

    Fit & Features

    • Three-row layered design
    • Shortest layer features a chain-link design, thin clear glass stones at the center
    • Two longer layers feature mini rhinestone embellishments
    • Adjustable chain, lobster clasp closure

    Style Number/Barcode: 07002-1273

    Category Name: Vacation Looks

    Price: $5.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Mood Striped Knit Sweater

    You'll be in a totally cozy mood in this adorable striped knit sweater! It features a crew neckline, long dolman-style sleeves, distressed detailing at the hems, and a mid-length, relaxed fit. The thick knit fabric has minimal stretch. Style with dark wash denim and ankle boots.

    Fit & Features

    • Crew neckline
    • Long dolman-style sleeves
    • Distressing at the hems
    • Mid-length, relaxed fit
    • Striped pattern
    • Knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1597

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fresh And Chic Crossbody Purse

    This sleek faux leather crossbody purse will make your everyday 'fits fresh and chic. It features a rectangular shape with a curved design at the bottom, a fold-over with snap-button closure, and a chain-link and faux leather shoulder strap. Style with hoop earrings.

    Fit & Features

    • Rectangular shape, bottom curved design
    • Fold-over with snap-button closure
    • Chain-link and faux leather shoulder strap
    • Spacious and lined interior
    • Faux leather material

    Style Number/Barcode: 07203-1065

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Glam Rhinestone Ring Set

    This trendy rhinestone ring set is perfect for that everyday glam vibe! The pack features six rings including one statement ring and five thin dainty rings, all with rhinestone embellishments. Style this set with sleek hoop earrings.

    Fit & Features

    • Six-pack metal ring set
    • One statement ring
    • Five thin band rings
    • Rhinestone embellishments

    Style Number/Barcode: 07004-0303

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 90s Chick Boyfriend Denim Jacket

    Take it back to a 90s chick look with this boyfriend denim jacket featuring long sleeves with button cuffs and drop shoulder seams, a collar neckline, button-down closures, front flap pockets, and a cropped hem with a cinched elastic back band. Perfect for styling with high-rise jeans.

    Fit & Features

    • Long sleeves, button cuffs, drop shoulder seams
    • Collar neckline
    • Button-down closures
    • Front flap pockets
    • Cropped hem, cinched elastic back band
    • Medium-wash denim fabric
    • Runs true to size

    Style Number/Barcode: 06203-0449

    Category Name: Vacation Looks

    Price: $17.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Posh And Pleated Long Sleeve Crop Top

    Posh and pleated, this long sleeve crop top is a fall must-have. It features a deep V-neckline, long peasant sleeves, a cinched front design with a drawstring, and a cropped, form-hugging fit. The trendy pleated knit fabric offers a moderate stretch. Style with faux leather pants and heels.

    Fit & Features

    • V-neckline
    • Long peasant sleeves
    • Cinched front, drawstring
    • Cropped hem
    • Pleated detailed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4524

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale