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.

  • Staple Strap Sandals

    Make these sandals a staple to your closet! The simple design features a single strap as well as an adjustable ankle strap with a buckle closure. They also feature a chain detailing around the edge of the foot. They are composed of a faux leather material that makes them work with any outfit!

    Style Number/Barcode: 07404-0027

    Category Name: Vacation Looks

    Price: $12.97

    Availability: Out of Stock

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  • Staple Strap Sandals

    Make these sandals a staple to your closet! The simple design features a single strap as well as an adjustable ankle strap with a gold hued buckle closure. They also feature a chain detailing around the edge of the foot. They are composed of a faux leather material that makes them work with any outfit!

    Style Number/Barcode: 07404-0025

    Category Name: Vacation Looks

    Price: $12.97

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playa Wedge Espadrille

    Hit the beach and beyond with this elevated take on the classic espadrille. Sandals have a slim ankle strap, crisscross toe, and a small, woven wedge heel. Sandals are made from a faux suede material and have a faux leather lining.

    Style Number/Barcode: 07404-0039

    Category Name: Vacation Looks

    Price: $12.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Showstoppin' Staple Long Sleeve Maxi Dress

    Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!

    Fit & Features

    • Hacci rib knit fabric, plenty of stretch
    • Fitted long sleeves
    • Crew neckline
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5331

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feelin' Fine In Rhine Slides

    Change up the game in these fierce slides for the diva in you! They feature an easy slip on design, a wide strap that is embellished with clear rhinestones and a black textured foot bed. 

    Style Number/Barcode: 07404-0449

    Category Name: Vacation Looks

    Price: $12.00 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One, Two Strap Sandals
    Let me see you one, two strap! These cute sandals keep it poppin' with a basic two strap design composed of a faux suede. The open toe sandals have an open back for an easy slip on slide.

    Featured in our 2018 Dive into paradise Resort Lookbook

    Style Number/Barcode: 07404-0417

    Category Name: Vacation Looks

    Price: $17.90

    Availability: Out of Stock

    Product Badge:
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  • X Strap Slip On Sandals

    Slip on this minimal style that packs a lot of comfort! Sandals have a wide X strap design for easy slip-on wear, and an insole with a slight cushion. Sandals are composed of a faux leather material.

    Style Number/Barcode: 07404-0446

    Category Name: Vacation Looks

    Price: $12.00 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cut The Block Heel Sandals

    Cut out the unnecessary and instead indulge in cute sandals! This pair features a caged, faux leather upper, a peep toe, a laser cut-out design with an ankle strap and buckle, and a cute block heel.

    Style Number/Barcode: 07404-0441

    Category Name: Vacation Looks

    Price: $12.00 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bands Make Her Dance Mules

    Get excited over these cute double, band mules! They have a wide, two strap design paired with an open toe and a cute block heel. The shoes are composed of a smooth, nubuck material.

    Style Number/Barcode: 07404-0445

    Category Name: Vacation Looks

    Price: $18.00 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strap It Down Sandals

    Secure your pretty little feet in these cute sandals! They have a wide toe strap paired with a buckle ankle strap and a flat sole. Both straps are composed of a smooth faux leather material.

    Style Number/Barcode: 07404-0398

    Category Name: Vacation Looks

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strappy Sling Back Sandals

    Get in the swing of summer things in these strappy flat black sandals! They feature an open toe design with two straps, and an adjustable sling back strap. Sandals are composed of a faux leather material. 

    Style Number/Barcode: 07404-0022

    Category Name: Vacation Looks

    Price: $12.97

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheer-ly On Trend Mesh Duster
    You'll clearly be on trend with this stylishly sheer mesh duster! It features long fitted sleeves, a front tie waist, waist high side slits, and a relaxed fit. The black cover up is composed of a lightweight, airy fabric and offers plenty of stretch for comfortable wear!

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06202-1133

    Category Name: Vacation Looks

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic And Spotted Mini Dress

    Get a chic and spotted look in this adorable trendy little mini! The dress features an off the shoulder neckline with short cuffed sleeves with ruffle trim detailing, a front keyhole cut out with a tie closure, a stretchy smocked back, and a short, form hugging fit. The dress is composed of a lightweight woven fabric with a cute all over animal print.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0342

    Category Name: Vacation Looks

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle It Up Smocked Midi Dress

    Play up your look with this adorable ruffled and smocked midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back with a ruffle hem, ruffle tiers, and a stretchy smocked body with a mid-length form hugging fit. Dress is composed of a lightweight woven fabric.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0341

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lil' Thing Mini Skirt
    Show your curves in this super cute mini skirt. This piece features an elasticized waist, an all  over smocked back, and is made of a breathable cotton fabric. The fabric itself has no stretch.

    Style Number/Barcode: 06501-0084

    Category Name: Vacation Looks

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Issa Vibe Tie Front Crop Top
    You're giving off positive vibes in this sexy top. This piece features elasticized shoulders, an adjustable tie front, a back strap and elasticized sleeve openings. Fabric is a cotton synthetic blend and has no stretch.

    Style Number/Barcode: 06003-0352

    Category Name: Vacation Looks

    Price: $11.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Madame Bell Sleeve Blouse

    Pretty ladies deserve pretty blouses. This wrap top features a tie closure with an off the shoulder styling and adjustable shoulder straps. Topped with ruffle trim and elasticized sleeve openings, this garment is made of a cotton blend fabric with no stretch.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0354

    Category Name: Vacation Looks

    Price: $11.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Rhinestone Square Buckle Belt

    Glam up your look with this rhinestone square buckle belt! It features a black hued faux leather belt embellished with small silver rhinestones and has a rhinestone detailed square buckle. Complete the look in a rhinestone trim denim jacket for extra glitz!

    Fit & Features

    • Faux leather material
    • Small rhinestones
    • Detailed rhinestone square buckle
    • Adjustable fit

    Style Number/Barcode: 07301-1024

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ravishing Ruched Mini Dress

    This dress is a daytime delight. It features ruffled sleeves, a hidden back zipper closure, an adjustable drawstring skirt. It's made of a lightweight linen fabric with zero stretch and full lining.

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0243

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fab In Floral Lace Back Mini Dress

    Look your absolute best in this fab floral mini dress! It features a plunging V neckline, spaghetti straps that lead to a partially exposed lace back with a zipper closure, and a form hugging bodycon fit. Dress is composed of a scuba knit fabric with a moderate stretch. 

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small. 

    Style Number/Barcode: 05101-0156

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Necessary Basic Midi Dress

    Because we all need this necessary basic midi in our closet! The dress features a sleeveless bodice, spaghetti straps, a square neck and back, and a mid-length, curve hugging fit. The smooth knit fabric offers plenty of stretch for comfortable wear.

    Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0256

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rhine So Fine Bikini Top

    Look so fine in rhine with this glam embellished black bikini top! It features a lined triangle design with spaghetti straps that tie at the neck and back. Mini rhinestones adorn the front for a flashy and sparkly look. Don't forget the matching swim bottoms!

     

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0236

    Category Name: Vacation Looks

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In The Clear Wedge Heels
    Clearly, your look is on point. These heels feature an open toe, a clear PVC top, an open ankle, and a clear lucite wedge heel. Shoes include a faux leather lining.

    Style Number/Barcode: 07406-0046

    Category Name: Vacation Looks

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylishly Sheer Mesh Duster
    Make a stylishly sheer statement with this gorg flowy black mesh duster! It features a sleeveless bodice, tank-like shoulder straps, a drape front, high side slits, and a drawstring tie waist to cinch your look. The taupe duster is composed of a lightweight mesh fabric that offers plenty of stretch with a breathable feel.

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06202-1132

    Category Name: Vacation Looks

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance