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.

  • Fab And Frayed Cutoff Denim Shorts

    These frayed cutoff denim shorts will be a summer staple in your closet! They feature a high-rise waist, cutoff hems with destructed frayed detailing, and a form-hugging fit. Style these light wash denim shorts with a graphic tee and sandals.

    Fit & Features

    • High-rise waist
    • Cutoff, frayed hem
    • Form-hugging fit
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Light wash denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0271

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect Summer Style Straw Wedges

    Show off perfect summer style in these adorable straw wedges! They feature an open almond-shaped toe, wide toe straps in a criss-cross design, an open back, and a wedge heel. Pair these wedges with your fave sundress and hoop earrings!

    Fit & Features

    • Open almond-shaped toe
    • Wide toe straps, criss-cross design
    • Open back
    • Straw wedge heel, straw straps
    • Faux leather sole
    • Runs true to size

    Style Number/Barcode: 07406-0294

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shimmering Beauty Rhinestone Belly Chain

    Shimmer and glimmer in this dazzling rhinestone belly chain! It features a gorg layered design with mini rhinestone embellishments and a center O-ring accent. The belly chain includes a lobster clasp closure. Style with a sultry bikini and chic shades.

    Fit & Features

    • Three-row layered design
    • Mini rhinestone embellishments
    • Center O-ring accent
    • Lobster clasp closure

    Style Number/Barcode: 07301-0465

    Category Name: Vacation Looks

    Price: $5.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Glam Rhinestone Belly Chain

    Sassy yet glam, show off your true chic self in this rhinestone belly chain! Complete your vibe in a sultry bikini set for a pool party.

    Fit & Features

    • Rhinestone chain
    • Lobster clasp closure

    Style Number/Barcode: 07301-0467

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Love The Look Lace-Up Crop Top

    You'll love the look of this trendy soft brushed knit crop top. It features a sleeveless mock neckline, tank shoulder straps, lace-up detailing at the side seams with cutout accents, and a cropped, form-hugging fit. Style with a mini skirt and mules.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Lace-up details at the side seams, small cutouts
    • Ruching
    • Cropped, form-hugging fit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4295

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just Like Magic Chrome Sandals

    Add sparkle and glow to everyday or dressy look in these chrome sandals featuring a square toe, rhinestone embellished strap, and a slide-on/off styling. Perfect for styling with a classic little black dress.

    Fit & Features

    • Square toe
    • Rhinestone embellished band
    • Slide-on/off styling
    • Chrome footbed
    • Runs true to size

    Style Number/Barcode: 07404-1008

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Staple Oversized Sunglasses

    Block the rays with these trendy staple sunglasses featuring an oversized, metal square frame, gradient colored lens, rubber nose supports, and a sleek design. Complete your outfit with a cute crossbody bag.

    Fit & Features

    • Oversized metal square frame
    • Gradient colored lens
    • Rubber nose supports
    • Sleek design
    • 100% UV protection

    Style Number/Barcode: 07008-0945

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mix It Up Twist Cutout Bodysuit

    Mix up your closet in vibrant color! This sleeveless bodysuit features spaghetti straps, a color block design, and a V-neck with a twisted bust atop a sultry cutout bodice. Complete the look in denim shorts and strappy mules.

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Twisted bust, cutout bodice
    • Thong bottom, dual snap button closure
    • Color block design
    • Form-fitting
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4305

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunkissed Florals Twist Crop Top

    Let the sunshine on this flirty floral crop top perf for a brunch with the girls! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, twist accent bodice, and a back smocked panel with zipper closure. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Sunkissed Florals A-Line Skirt

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Twist accent bodice
    • Cropped hem
    • Back smocked panel, zipper closure
    • Floral print, lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1824

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Flow Halter Jumpsuit

    You love an effortless, carefree look, so this lightweight jumpsuit is perfect for your weekend plans. It features a sleeveless halter neckline, a center keyhole cutout, a backless design, a high waist seam, a form-hugging fit, and flared pant legs. Style with a layered charm necklace.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
    • Center keyhole cutout
    • Open back
    • High waist seam
    • Form-hugging fit, flared pant legs
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-1023

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On Edge High Rise Fray Denim Shorts

    Keep your style on edge in these high-rise denim shorts! They feature a flattering high-rise waist, distressed accents, and a frayed cutoff hem on vintage-inspired dark wash denim with a color fade effect. Complete the look in a graphic top and sandals.

    Fit & Features

    • High-rise waist
    • Distressed accents
    • Frayed cutoff hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Dark wash denim, color fade effect, no stretch
    • Fits true to size

    Style Number/Barcode: 06603-0236

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Destination Vacay Tropical Floral Mini Dress

    Jet set to your destination vacay in this tropical floral print mini dress, perfect for sunset happy hour. Designed with a square neck, adjustable spaghetti straps, and a short fitted silhouette, style with gold hoops and slide-on sandals.

    Fit & Features

    • Scuba knit fabric, stretchy knit lining
    • Tropical floral print
    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Mini-length fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05102-6077

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Illusion Mesh Straw Hat

    Bring the drama with a hat that is anything but basic! The hat features an illusion mesh body and a wide brim. Complete your look with a midi dress and sunnies that will have you brunch ready! 

    Fit & Features

    • Illusion mesh body
    • Wide brim

    Style Number/Barcode: 07302-0583

    Category Name: Vacation Looks

    Price: $7.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Fab Oversized Sunglasses

    Style up your summer looks with these trendy fab oversized shades! The sunglasses feature a plastic square-shaped frame with thin arms and tinted lenses. Complete your outfits with a mini shoulder bag.

    Fit & Features

    • Oversized plastic square-shaped frame
    • Thin arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-0930

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Zoey Sleeveless Chiffon Party Dress

    Special Occasion

    You'll look oh-so-darling in the Zoey chiffon party dress! She features a sleeveless square neckline, adjustable spaghetti straps, an open back with a lace-up strappy design, a fitted high waistband, and a short party skirt with a flared-out silhouette. The lined chiffon fabric features an all-over floral burnout pattern for a pretty look. Perfect for a semi-formal wedding, complete your guest outfit with chic heels.

    Fit & Features

    • Sleeveless square neckline
    • Adhesive bra recommended
    • Adjustable spaghetti straps
    • Open back, lace-up strappy design, tie closure
    • High waistband, short party skirt, fit and flare silhouette
    • Lined chiffon fabric, floral burnout pattern
    • Runs true to size

    Style Number/Barcode: 05001-1002

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Retreat Mesh Mini Dress

    Look like you're ready to jet-set off to an island retreat in this mesh mini dress! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, curve-hugging fit. The lined mesh fabric features an all-over tropical palm leaf print. Complete your look with espadrille wedges.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting silhouette
    • Tropical palm leaf print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4534

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Summer Style Floral Romper

    Showcase a sweet summer style in this flirtatious floral romper. It features a strapless square neckline, a stretchy smocked bodice, a high waist with a tie-front belt, flowy shorts, and an all-over dainty floral print pattern. Complete the look with espadrille sandals.

    Fit & Features

    • Strapless square neckline
    • Stretchy smocked bodice
    • High waist, tie-front belt
    • Flowy mid-thigh length shorts
    • Floral print
    • Lightweight woven fabric
    • Runs true to size

    Style Number/Barcode: 06403-0179

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Butterflies Huggies Set

    Swoon for this whimsical huggie earrings set! It features a variety of six sets each with dainty rhinestone designs with a post-back closure. Complete the look in a charming linen sundress for an outdoor party.

    Fit & Features

    • Six-pack variety set
    • Dainty rhinestone designs
    • Post-back closure

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-1280

    Category Name: Vacation Looks

    Price: $4.00 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunkissed Florals A-Line Skirt

    Let the sunshine on this flirty floral skirt perf for brunch with the girls! It features an elasticized high-rise waist, a tiered flowy a-line silhouette, and a short-length hem. Complete the look in the matching top.

    Shop Matching Top: Sunkissed Florals Twist Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Tiered flowy a-line silhouette
    • Short-length hem
    • Floral print, lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0124

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready Set Vacay Gauze Maxi Dress

    Pack this flowy lightweight maxi dress in your carry-on as you jet set off on vacay! It features a sleeveless V-neckline, halter spaghetti straps, a smocked high waist with chic cutouts leading to an open strappy back, and a floor-length maxi silhouette with a side slit and a relaxed fit. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Smocked high waist, cutouts leading to open back
    • Strappy back design
    • Maxi-length silhouette, side slit
    • Woven gauze fabric, mini skirt knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4497

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Palisades Paisley High Rise Pants

    Look pretty in these paisley pants for a retro vibe! It features a high-rise elasticized waistband, pleat detailing, and wide-leg silhouette crepe woven fabric. Complete the look in the matching top.

    Shop Matching Top: Palisades Paisley Tie-Front Top

    Fit & Features

    • High-rise elasticized waistband
    • Pleat detailing
    • Wide-leg silhouette
    • Paisley print
    • Crepe woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-0461

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blushing Tropics Button-Up Top

    Make all the cheeks blush when you step out in this tropic chiffon top! Featuring long sleeves with button cuffs, a collared neckline, a button-down front, and a flowy silhouette. Complete the look in the matching top. 

    Shop Matching Top: Blushing Tropics Bandeau Top

    Fit & Features

    • Long sleeves, button cuffs
    • Collared neckline
    • Button-down front
    • Flowy silhouette
    • Floral tropic print
    • Chiffon fabric
    • Runs true to size

    Style Number/Barcode: 06003-1659

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Beauty Printed Midi Skirt

    Bring that trendy bohemian style to your summer look with this lightweight woven midi skirt. It features a high-rise fitted waist, a side knot detail leading to a wrap-front design, a midi-length, flowy fit, and an all-over boho-inspired multi-print pattern. Complete the outfit with a neutral bodysuit.

    Fit & Features

    • High-rise waist, back zipper closure
    • Side knot detail
    • Wrap-front design, front slit
    • Midi-length, flowy silhouette
    • Multi-print pattern
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0131

    Category Name: Vacation Looks

    Price: $14.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunflower State Chiffon Corset Top

    It's full bloom ahead! Create a sweet look in this chiffon floral corset top featuring adorable puff sleeves, a ruched sweetheart neck, hook-eye front closures, and a cropped hem. Complete the look in denim shorts.

    Fit & Features

    • Puff sleeves
    • Ruched sweetheart neck
    • Front hook-eye closures
    • Cropped hem, back smocked panel
    • Sunflower print
    • Partially sheer texture chiffon fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1641

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance