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.

  • Dearest Charm Bow Print Skater Dress

    Show off your charm in this bow print skater dress boasting flirty details like puff sleeves and a short-length hem perfect for styling with sandals.

    Fit & Features

    • Bow print, woven fabric, woven lining
    • Puff short sleeves
    • Square neckline, bust tie
    • Stretchy smocked bodice
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3981

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Into Action Floral Skater Dress

    Spring into your seasonal closet by adding this floral skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a ruched bust with tie-front detail, and a fit-and-flare silhouette with a short ruffled hem. The dress is composed of chiffon fabric with a stretchy knit lining. Complete the look in trendy wedge sandals and a bracelet.

    Fit & Features

    • Sleeveless V-neck, adjustable spaghetti straps
    • Ruched bust, tie-front detail
    • Back zipper and hook-eye closure
    • Fit and flare skater silhouette
    • Short ruffled hem
    • Floral print, chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4889

    Category Name: Vacation Looks

    Price: $5.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Instant Fave Faux Suede Platform Sneakers

    A pair of faux suede sneakers feature a round toe, rubber gum platform sole that elevates the look, a lace-up front, and a side striped design. Perfect for everyday styling.

    Fit & Features

    • Faux suede material
    • Round toe
    • Rubber gum platform sole
    • Lace-up front
    • Side striped design
    • Runs true to size

    Style Number/Barcode: 07407-0232

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Eye-Catching Halter Ruffle Chiffon Mini Dress

    You'll look positively eye-catching in this floral mini dress at weddings or garden parties! The halter crew neckline and open back ooze elegance, while the ruffled bodycon silhouette flatters your curves. With a mini-length hem, this dress is perfect for any occasion. Complete the look with earrings.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Halter crew neckline, spaghetti strap tie
    • Open back
    • Ruffled bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5627

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Confident Cutie Sleeveless V-Neck A-Line Mini Dress

    Get ready to feel confident and cute in this basic A-line mini dress perfect for styling up or down! The soft and stretchy rib knit fabric includes a full knit lining for added coverage. This dress is perfect for any occasion with a flattering V-neckline, delicate spaghetti straps, and a stylish A-line silhouette. Complete the look in a chunky choker and sneakers!

    Fit & Features

    • Soft and stretchy rib knit fabric, full knit lining
    • V-neckline
    • Spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5651

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set For Good High Rise Texture Mini Skirt

    You'll be set for good in this stylish mini skirt all season! Featuring a flattering high rise waist and bodycon silhouette, this mini-length skirt offers the perfect fit. Complete the look with the matching top.

    Shop Matching Top: Set For Good Cap Sleeve Slit Texture Crop Top

    Fit & Features

    • Texture sheer fabric, knit lining, minimal stretch
    • High rise waist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1034

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling The Vibe Rhinestone Star Charm Platform Sneakers

    You'll be feeling the vibe of these athleisure sneakers perfect for casual coffee shop runs and errands! These playful kicks feature a round toe, a lace-up placket with a rhinestone star charm, and a comfy footbed with a platform sole and gel insert. Complete the look in a comfy lounge set.

    Fit & Features

    • Round toe
    • Lace-up placket, rhinestone star charm decor
    • Chunky platform sole with gel insert
    • Comfortable footbed
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07407-0227

    Category Name: Vacation Looks

    Price: $30.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Babe In Disguise Square Sunglasses

    For when you feel low-key these square sunglasses are perfect for throwing on! They feature a square design, tinted lenses to help protect from the sun, and a comfortable fit. Complete the look with simple earrings.

    Fit & Features

    • Square design
    • Tinted lenses
    • Comfortable fit

    Style Number/Barcode: 07008-1083

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Chic Style Long Sleeve Ribbed Knit Midi Dress

    The perfect blend of casual and chic, this ribbed knit midi dress features a V-neckline, long fitted sleeves, and a form-hugging silhouette. Style with hoop earrings and sneakers for a cute everyday look.

    Fit & Features

    • Hacci ribbed knit fabric, plenty of stretch
    • V-neckline
    • Long fitted sleeves
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5920

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual And Stylish Cargo Pocket Vest

    When casual meets stylish like this sleeveless vest, you know it's going to be a closet staple! This vest features a collar neckline, a button-down front, and trendy cargo flap pockets for convenience, and a cropped hem for a modern touch. Complete the look in high-rise jean shorts for any occasion!

    Fit & Features

    • Windbreaker-type woven fabric, no stretch
    • Collar neckline
    • Button down front
    • Cargo flap pockets
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1787

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: OLIVE

    Available Size: L, XL

    Product Badge:
    • Sale
  • Picturesque Cutie Lace-Up Floral Bustier

    Look and feel cute in this lace-up floral bustier that brings the adorable factor to any outfit!

    Fit & Features

    • Floral print, eyelet woven-lined fabric
    • Sweetheart neckline
    • Underwire bust
    • Adjustable spaghetti straps
    • Lace-up back. flexible boning
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2776

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pair To Perfection Metallic Lace-Up Sneakers

    These metallic sneakers pair perfectly with your everyday outfits. They feature a round-toe, a lace-up front closure, and a rubber gum sole. 

    Fit & Features

    • Round toe
    • Metallic material
    • Lace-up front closure
    • Rubber gum sole
    • Runs true to size

    Style Number/Barcode: 07407-0231

    Category Name: Vacation Looks

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Has Sprung Floral Bubble Hem Skater Dress

    Let your beauty bloom in this adorable floral skater dress with the sweetest allure. The corset bodice will highlight your waist while the short skater skirt offers the cutest fit-and-flare silhouette.

    Fit & Features

    • Floral-printed woven fabric with knit lining, minimal stretch
    • Sleeveless sweetheart neckline, padded bust with underwire
    • Thin tank shoulder straps
    • Corset bodice, tie-front detail, high waist seam
    • Smocked back design, zipper with hook and eye closure
    • Short skater skirt with bubble hem, fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3826

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • One Sided Sleeveless Cutout Bodysuit

    Show off your good side in this sleeveless bodysuit for any casual plans! Featuring a cutout one-shoulder neckline, this form-hugging bodysuit is designed to accentuate your curves. The thong bottom with snap button closures adds a secure fit. Complete the look in denim shorts for a day out.

    Fit & Features

    • Double-lined brushed knit stretchy fabric
    • Cutout one-shoulder neckline
    • Form-hugging fit
    • Thong bottom, snap-button closures
    • Runs true to size

    Style Number/Barcode: 06001-5239

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Social Season Braided Strap Mules

    Step into any social event on your calendar in these braided strap platform mules to elevate your look!

    Fit & Features

    • Block heel
    • Square toe
    • Braided straps
    • Platform sole
    • Runs true to size

    Style Number/Barcode: 07401-000075

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strut And Snap Ribbed Knit Midi Dress

    Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Square neckline
    • Tank shoulder straps
    • Metal button accents
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1167

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Breeze High-Rise Crochet Palazzo Pants

    Feel the breeze on the weekend in these crochet palazzo pants at festivals, concerts, or out at the fair! Featuring a high-rise elasticized waistband and a wide-leg silhouette, these pants offer a flattering fit on crochet fabric lined with stretch knit. Complete the look in a crop top.

    Fit & Features

    • Crochet fabric lined with stretch knit
    • High-rise elasticized waistband
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0822

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sporty Luxe Corduroy Baseball Cap

    Fit & Features

    • Corduroy material 
    • Wide brim
    • Baseball cap design
    • Adjustable back strap

    Style Number/Barcode: 07302-1736

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Icing On The Cake V-Neck Lace Skater Dress

    The perfect lace skater dress that'll take your day somewhere magical! Perfect for rehearsal dinners, birthdays, or graduation. This dress features a flattering V-neckline, spaghetti straps, and a playful cross-back design. Its skater silhouette and surplice ruffled short-length hem will keep you twirling all day! Complete the look in strappy block heels.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • V-neckline, spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3667

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

  • Style in Check Straw Tote Bag

    Always keep your style in check with this checkered straw tote bag, perfect for carrying all of your essentials.

    Fit & Features

    • Top handles
    • Checkered pattern
    • Spacious interior
    • Straw material

    Style Number/Barcode: 07203-000020

    Category Name: Vacation Looks

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Artsy Babe Paisley Bodycon Slit Midi Dress

    Strut like an artsy babe in this paisley mesh midi dress showcasing a flattering bodycon silhouette with a flirty front slit. Complete the look with a handbag.

    Fit & Features

    • Paisley print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5932

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Carefree Energy Halter Bodycon Mini Dress

    Be a cute sight in this halter mini dress boasting a flattering bodycon fit that perfectly flaunts your curves on vacay or a chic staycation!

    Fit & Features

    • Texture knit stretchy fabric
    • Halter neckline, spaghetti strap ties
    • Knotted bust accent
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2302

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hint Of Romance Lace Trim Mini Skort

    They know you've got it. Add a romantic vibe in this lace trim mini skort perfect for any plans.

    Fit & Features

    • Ponte knit fabric
    • High-rise waist
    • Bodycon fit
    • Lace trim mini-length hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000003

    Category Name: Vacation Looks

    Price: $26.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Match High-Rise Lace Mini Skirt

    You in this lace mini skirt plus your weekend plans equals the perfect match! Pair the skirt with the matching top.

    Fit & Features

    • Lace fabric lined with sewn-in knit
    • High-rise waist
    • Adjustable side ties
    • Bodycon fit
    • Ruffled mini-length hem
    • Runs true to size 

    Shop The Matching Top: Perfect Match Long Sleeve Lace Crop Top

    Style Number/Barcode: 06501-1128

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

    Product Badge:
    • Sale