Vacation Looks

HomeVacation Looks
Loading...

Now Trending

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.

  • Cause A Stir Long Sleeve Cutout Slit Maxi Dress

    Scheduled to cause a stir! This long sleeve maxi dress attracts all the attention with a sexy cutout bodice and high slit perfect for sultry dinner dates or vacation looks.

    Fit & Features

    • Smooth knit lined stretchy fabric
    • Fitted long sleeves
    • Sweetheart neckline
    • Cutout bodice
    • High side slit
    • Bodycon fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000034

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Signs Of Sunshine Halter Knit Crop Top

    Bare your shoulder on a sunny day in this cute halter knit crop top for festivals, concerts, or days at the beach!

    Fit & Features

    • Texture knit design
    • High halter neckline, spaghetti strap tie
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06005-2263

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Park Picnic V-Neck Eyelet Skater Dress

    Show up to the picnic at the park looking so cute in this eyelet skater dress boasting the prettiest details like a bust tie and ruffled mini-length hem! 

    Fit & Features

    • Eyelet lace fabric, sewn-in knit lining
    • V-neckline, bust tie
    • Adjustable spaghetti straps
    • Stretch smocked bodice
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3938

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dream Of Me Corset Lace-Up Floral Midi Dress

    Dreamy days call for this floral midi dress that makes your cottagecore romance a reality! With a gorgeous corset bodice, lace-up back, and voluminous A-silhouette, this dress is stunning for bridal showers or garden parties.

    Fit & Features

    • Delicate floral print, woven fabric, tulle and woven linings
    • V-neckline, adjustable spaghetti straps
    • Hidden side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace-up back
    • Voluminous A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3795

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Layered Cutie Oversized Crochet Cardigan

    From beach strolls to sitting by the fire pit, this crochet cardigan is the perfect layer for a cute look. It features an oversized silhouette with slouchy short sleeves, an open front design, and a mid-length hem. Complete the look in a cute denim romper and sandals!

    Fit & Features

    • Sheer crochet fabric, no stretch
    • Slouchy short sleeves
    • Open front design
    • Oversized silhouette
    • Runs true to size

    Style Number/Barcode: 06005-1999

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Fave Strapless Knit Crop Top

    This knit crop top will be a total fave to pair with cute denim shorts or jeans for an effortlessly cute look!

    Fit & Features

    • Knit fabric, moderate stretch
    • Strapless neckline
    • Fitted hanky-style crop hem
    • Runs true to size

    Style Number/Barcode: 06005-2273

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Charm Square Sunglasses

    Unlock retro charm in these square sunglasses perfect for styling with any outfit while protecting your eyes!

    Fit & Features

    • Sleek square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1126

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oops I Slayed Again Denim Micro Skort

    Low rise, high key hot. This denim micro skort gives Y2K it-girl vibes with built-in shorts that keep up when you’re dancing at concerts or backyard parties!

    Fit & Features

    • Acid wash denim fabric, stretchy knit shorts lining
    • Low-rise waist
    • Bodycon fit
    • Micro mini-length hem
    • Front button and hidden zipper closure
    • Belt loop accents
    • Runs true to size

    Style Number/Barcode: 06603-000082

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Pair Cutout Block Heel Mules

    The perfect pair of block heel mules with a trendy floral cutout design that puts the spring into every step!

    Fit & Features

    • 2.5" Block heel
    • Woven material
    • Open square toe
    • Floral cutout strap design
    • Open back, on-and-off styling
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-5309

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Cool Flat Top Square Sunglasses

    Pair these flat top sunglasses for a cool look while driving or out with friends on a sunny day! 

    Fit & Features

    • Flat top design
    • Square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1127

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful Cutie Halter Button Floral Skater Dress

    The prettiest dainty floral print decorates this blissful halter skater dress adorned with delicate faux buttons for a charming accent! 

    Fit & Features

    • Dainty floral print, linen-blend lined fabric
    • Halter V-neckline, back zipper and hook-eye closure
    • Faux button accents
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3934

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Chic Beaded Straw Cowboy Hat

    Add a western vibe to your vacay looks with this beachy chic straw cowboy hat featuring a beaded chinstrap.

    Fit & Features

    • Straw material
    • Structured top
    • Curved brim
    • Braided chinstrap with beaded accents
    • Interior adjustable strings

    Style Number/Barcode: 07302-1767

    Category Name: Vacation Looks

    Price: $3.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shores Of Love Crochet Mesh Sarong

    Give your beach or pool related activities this perfect crochet mesh sarong accessory! Tie your swimsuit look together with this effortless wrap with a tie-waist and sultry sheer design.

    Fit & Features

    • Crochet embroidered pattern
    • Sheer mesh fabric
    • Tie-waist
    • Form-hugging fit

    Style Number/Barcode: 07105-000002

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always On Point Square Frame Sunglasses

    Keep your style in check with these square frame sunglasses to block out the rays on sun-soaked days!

    Fit & Features

    • Square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1125

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Vibes Crochet Knit Crop Top

    This crochet knit crop top will bring those boho vibes to your trendy festival 'fit! Designed with a sleeveless V-neckline, style with the matching maxi skirt for an alluring look.

    Shop Matching Bottoms: Bohemian Vibes Crochet Knit Maxi Skirt

    Fit & Features

    • Sheer crochet knit fabric, knit bust lining
    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2255

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetly Romantic Floral Lace Crop Top

    Send a sweet and romantic vibe in this floral lace crop top to dress up a skirt or jeans for a casual date or party!

    Fit & Features

    • Floral lace fabric, sewn-in knit lining
    • Sheer fitted long sleeves
    • Cutout square neckline
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-5729

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful And Pretty Corset Lace-Up Midi Dress

    Playful and pretty, this corset midi dress has a timeless silhouette. It has a unique lace-up back, a flattering A-line fit, and convenient side pockets that warm your hands.

    Fit & Features

    • Woven poplin lined fabric lined with stretchy knit
    • Sweetheart neckline with bust tie
    • Adjustable shoulder straps
    • Lace-up back, side zipper and hook-eye closure
    • A-line silhouette, front slit, side pockets
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3968

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Mood Strapless Midi Dress

    This tropical midi dress will have you looking like a warm weather cutie on vacation or a weekend escape!

    Fit & Features

    • Tropical print, knit fabric with stretchy knit lining
    • Strapless neckline
    • Form-hugging bodice
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000014

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Alluring Silhouette Off-The-Shoulder Maxi Dress

    Show off your alluring curves in this off-the-shoulder maxi dress crafted from a rib knit fabric that fits like a glove! 

    Fit & Features

    • Rib knit stretchy fabric
    • Off-the-shoulder neckline
    • Twisted strap details
    • Bodycon silhouette
    • Flared maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6020

    Category Name: Vacation Looks

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Breezy Paisley Satin Scarf

    A chic paisley satin scarf you'll love styling with every look! Wrap this scarf around your head, tie it around your favorite bag or waist for a trendy and breezy vibe.

    Fit & Features

    • Paisley print
    • Smooth silky satin material
    • Versatile styling options

    Style Number/Barcode: 07305-0539

    Category Name: Vacation Looks

    Price: $3.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Transparency Espadrille Wedges

    Step into these stylish espadrille wedges with PVC clear straps that create seamless look!

    Fit & Features

    • Wedge heel
    • Square toe
    • PVC clear straps
    • Platform sole
    • Espadrille material
    • Runs true to size

     

    Style Number/Barcode: 07406-000005

    Category Name: Vacation Looks

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool In Camo Mid-Rise Denim Skirt

    Cool in camo, this mid-rise mini skirt is designed with a bodycon fit that flatters your figure while the frayed mini length hem adds an edgy touch!

    Fit & Features

    • Camouflage print, denim fabric, slight stretch
    • Mid-rise waist
    • Bodycon fit
    • Frayed mini-length hem
    • Front button and hidden zipper closure, belt loops
    • Two front pockets, two back flap pockets with button closures
    • Runs true to size

    Style Number/Barcode: 06601-0242

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetest Outing Tie Back Ruffled Skater Mini Dress

    Have the sweetest look in this tie back ruffled skater dress at bridal showers or graduations!

    Fit & Features

    • Woven fabric lined with stretch knit
    • Sweetheart neckline with bust tie
    • Adjustable spaghetti straps
    • Tie-back cutout design, zipper and hook-eye closure
    • Skater ruffled silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6101

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charmed Sass Floral Bodycon Slit Maxi Dress

    Show up to any event or party in this floral maxi dress for a charming allure with a hint of sass! Designed from a mesh fabric that hugs your curves in a bodycon fit, this dress is sure to turn heads.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Square neckline
    • Spaghetti straps
    • Side slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000072

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free