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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.

  • Effortless Summer Days Crop Top

    This trendy crop top is perfect for those effortless summer days. It features a sleeveless cowl neckline, halter spaghetti straps, an open back with tie-back straps, and a cropped fit with a front angled hem. The brushed knit fabric has an all-over marble print pattern. Style with cut-off denim shorts and sneakers.

    Fit & Features

    • Sleeveless cowl neckline
    • Halter spaghetti straps, tie closure
    • Open back, tie-back straps
    • Cropped fit, front angled hem
    • Marble print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4144

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely Day Peasant Crop Top

    It's always a lovely day with this peasant crop top in your closet. It features short puff sleeves, a sweetheart neck, and two adjustable tie-front closures on lined woven fabric. Complete the look in high-rise jeans for shopping downtown.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck
    • Two adjustable tie-front closures
    • Cropped hem
    • Lined woven fabric
    • Fits true to size

    Style Number/Barcode: 06003-1795

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Iconic Getaway Tie-Waist Wrap Fringe Skirt

    Get ready for an iconic getaway with this tie-waist wrap fringe skirt perfect for days spent under the sun or sipping on drinks poolside!

    Fit & Features

    • Crochet knit design, sewn-in knit lining
    • Wrap-tie waist
    • Back zipper and hook-eye closure
    • Cascading fringe hem
    • Runs true to size

    Style Number/Barcode: 06501-000032

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Soaked Chain Straw Floppy Hat

    Soak up the sun wearing this floppy straw hat featuring a chic chain trim and a wide brim to shade your eyes. Complete the look in a darling sundress.

    Fit & Features

    • Floppy design
    • Chain trim
    • Wide brim
    • Straw material

    Style Number/Barcode: 07302-0506

    Category Name: Vacation Looks

    Price: $7.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Here For The Drama Sunglasses

    You're all about that chic dramatic style! These bold shades will be the perfect pair to complete your look. They feature a flat top design with square-shaped tinted lenses, a plastic frame, and gold accents on the arms. Style these sunglasses with sleek hoop earrings.

    Fit & Features

    • Flat-top design
    • Square-shaped tinted lenses
    • Plastic frame
    • Gold accents on the arms
    • 100% UV Protection 

    Style Number/Barcode: 07008-0913

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Beauty Halter O-Ring Dress

    You'll be a beautiful view on the beach in this halter midi dress featuring a sleeveless, sweetheart neck, a front O-ring atop the cutout bodice that leads to the form-fitting silhouette. Complete the look with a straw purse.

    Fit & Features

    • Sleeveless, sweetheart halter neck
    • Front O-ring
    • Cutout bodice
    • Form-fitting silhouette
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4443

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Swirls Slit Maxi Skirt

    Bring the 70s vibes to the party in this retro swirl print maxi skirt featuring a high-rise waist, a sultry front slit, and a flowy silhouette. Complete the look in the matching top and statement earrings. 

    Shop The Matching Top: Retro Swirls One Shoulder Top

    Fit & Features

    • High-rise waist
    • Front slit
    • Flowy silhouette
    • Maxi length hem
    • Swirl print
    • Lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06501-0660

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Retro Swirls One Shoulder Top

    Bring the 70s vibes to the party in this retro swirl print crop top featuring an on-trend, one-shoulder neckline, sleek bungee spaghetti strap, and a fitted hem. Complete the look in the matching skirt and statement earrings. 

    Shop The Matching Skirt: Retro Swirls Slit Maxi Skirt

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Bungee spaghetti strap
    • Crop fitted hem
    • Swirl print
    • Lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4265

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Plunge V-Neck Halter Bodysuit

    Show off a chic, sultry style in this lightweight knit bodysuit. It features a plunging V-neckline with a wrap-front design, a mock neckline with halter straps, an alluring open back, and a thong bottom. Complete your night-out look with vintage-inspired jeans and strappy mules.

    Fit & Features

    • Deep V-neckline, wrap-front design
    • Mock neckline, halter straps, tie at the back of the neck
    • Open back
    • High waist seam
    • Thong bottom, dual snap button closures
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4287

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunrise Cute Straw Dual Buckle Belt

    Create the perfect cute look for a sunrise breakfast with this straw belt featuring dual buckle closure and a wide silhouette. Complete the look in a woven maxi dress and sandals.

    Fit & Features

    • Dual buckle closures
    • Wide silhouette
    • Straw exterior, faux leather lining

    Style Number/Barcode: 07301-0497

    Category Name: Vacation Looks

    Price: $5.97 $17.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pleat Treat Square Toe Wedges

    These square toe wedges are such a treat! They feature a twisted pleat strap, wedge sole, and PU material. Complete the look in a flirty sundress for a daytime event. 

    Fit & Features

    • Square toe
    • Wedge sole
    • Pleat twisted strap
    • PU material
    • Runs true to size

    Style Number/Barcode: 07406-0316

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Jungle Cruise Geo Tie-Back Romper

    You'll look stylish for a cruise through the jungle in this geo print knit romper featuring a sleeveless, square neck, spaghetti straps, open back with tie closure, high waist, and flowy short-length hem. Complete the look in hoop earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, tie closure
    • High waist
    • Flowy short-length hem
    • Geo print, knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06503-0977

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Purrfect Cat Eye Sunglasses

    These cat-eye sunglasses are simply purrfect for wearing all season! They feature a sleek and retro frame, gradient tinted lenses, and chain-link arms. Complete the look in a denim jumpsuit for a summer carnival.

    Fit & Features

    • Sleek and retro frame
    • Cat-eye style
    • Gradient tinted lenses
    • Chain-link arms

    Style Number/Barcode: 07008-0944

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Ice Rhinestone Chain Link Collar

    Flaunt your ice and love for shine in this chain-link collar featuring rhinestone accents and a lobster clasp closure. Complete the look in a sultry satin dress.

    Fit & Features

    • Chain-link
    • Rhinestone accents
    • Lobster clasp closure

    Style Number/Barcode: 07002-1208

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Versatile Shine Snake Chain Necklace

    The perfect base layer to create an effortless shine! This four snake chain necklace features a delicate design and lobster clasp closures. Complete the look in a sleek black dress for a cute 90s fit.

    Fit & Features

    • Four snake chain layers
    • Delicate design
    • Lobster clasp closure

    Style Number/Barcode: 07002-1209

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Eyes On Me Rhinestone Earrings

    All eyes on you in these statement earrings featuring three eye designs on a post-back closure. Complete the look in a little black dress for a girl's night out.

    Fit & Features

    • Three eye designs
    • Rhinestones
    • Post-back closure

     

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

    Style Number/Barcode: 07001-1275

    Category Name: Vacation Looks

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Meet Me In Floral Mesh Maxi Dress

    Serving soft glam with a side of romantic drama. This mesh halter maxi dress hugs in all the right places and moves like a dream—perfect for weddings, rooftop hotel bars, or any event where looking unforgettable is the vibe.

    Fit & Features

    • Floral print, mesh-lined fabric
    • V-neckline
    • Curve-hugging silhouette
    • Center back slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000385

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: MAUVE

    Available Size: XS, S, M, L, XL

  • Sparkle And Shine Six-Pack Rings

    Sparkle and shine with this glam ring set featuring six stylish and minimalistic designs perfect for accessorizing with your dressy outfit.

    Fit & Features

    • Six-pack ring set
    • Stylish and minimalistic designs
    • Rhinestone accents
    • Sleek gold bands

    Style Number/Barcode: 07004-0247

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Quite A Beauty Rhine Bracelet Set

    Adorn your wrist with this chic three-pack set featuring one circle rhinestone bracelet, one single strand rhinestone bracelet, and one chain-link bracelet. Complete the look in sparkly sandals.

    Fit & Features

    • Three-pack set
    • One rhinestone circle bracelet
    • One single strand rhinestone bracelet
    • One chain-link bracelet

    Style Number/Barcode: 07003-0343

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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