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.

  • Dreaming of Florals Corset Top

    Dream of a floral outfit with this adorable top! The top features a floral print, a sweetheart neckline with padded cups, a corset-styled bodice, ruched cap sleeves, and a cropped hem. The top is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with a wrap skirt and mules. 

    Fit & Features

    • Sweetheart neckline, padded cups
    • Corset-styled bodice, smocked back
    • Ruched cap sleeves
    • Floral print
    • Cropped hem 
    • Lightweight woven fabric
    • Relaxed fit, minimal stretch, runs true to size 

    Style Number/Barcode: 06003-1839

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Siesta Keys Tropical Maxi Dress

    Take a vacation to Siesta Keys looking fab in this tropical maxi dress! It features a sleeveless, v-neck, spaghetti straps, and a tie-front bust atop a cutout bodice leading to the form-fitting silhouette with a sultry side slit. Complete your vacay look in a straw hat and your fave sunglasses.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Tie-front bust
    • Cutout bodice
    • Form-fitting silhouette
    • Side slit, maxi hem
    • Tropical print
    • Fits true to size

    Style Number/Barcode: 05102-4377

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pop Of Color Two-Pack Anklet Set

    Get the perfect pop of color with this anklet set featuring one multi-color stone and one dainty chainlink layer each with lobster clasp closures. Complete the look in a casual jumpsuit for a coffee meet-up.

    Fit & Features

    • Two-pack set
    • One multi-color stone
    • One dainty chainlink
    • Lobster clasp closures

    Style Number/Barcode: 07003-0346

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Braids For Days Block Heel Mules

    These stylish block heel mules will have you looking trendy for days! Featuring dual braided straps, almond toe, and a faux leather footbed. Complete the look in a flowy casual dress for a picnic date.

    Fit & Features

    • Almond toe
    • Block heels
    • Dual braided straps
    • Faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07401-3702

    Category Name: Vacation Looks

    Price: $4.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Life Made Easy Linen Halter Maxi Dress

    Look effortlessly put together in this breezy striped linen maxi dress for a Duffy boat cruise or beachside brunch! It features a sleeveless, halter v-neck with tie-closure, a partial open-back with tie, hidden side pockets, and a flowy, maxi-length silhouette with a sultry front slit. Complete the look in a straw floppy hat and sandals. 

    Fit & Features

    • Sleeveless, halter v-neck, tie-closure
    • Partial open-back with tie
    • Hidden side pockets
    • Flowy silhouette
    • Front high-cut slit
    • Maxi-length hem
    • Striped linen fabric, lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4468

    Category Name: Vacation Looks

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl On The Go Square Sunglasses

    Made for the girl on the go. These square-frame sunglasses bring effortless cool to every outfit, whether you're brunch-bound or dodging exes at the beach party.

    Fit & Features

    • Square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000047

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunday's Match Striped Wide Leg Pants

    Sunday has met its perfect match! Slip-on these trendy striped pants for brunches with friends. It features an elasticized waistband, wide-leg silhouette, on linen fabric with lining and no stretch. Complete the look in the matching top.

    Shop The Matching Top: Sunday's Match Striped Linen Top

    Fit & Features

    • Elasticized waistband
    • Wide-leg silhouette
    • Striped pattern
    • Linen fabric, lined, no stretch
    • Fits true to size

    Style Number/Barcode: 06302-0620

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pom Perfect Round Straw Crossbody

    You'll be ready for a summer picnic with this perfect straw crossbody featuring a round silhouette, top handle, attached shoulder strap, multi-colored pom poms on the front, and a zipper closure. Complete the look in a cute matching set.

    Fit & Features

    • Round silhouette
    • Top handle
    • Attached shoulder strap
    • Multi-colored pom poms
    • Top zipper closure
    • Spacious interior with pocket
    • Woven straw material

    Style Number/Barcode: 07203-0979

    Category Name: Vacation Looks

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Stud Rhinestone Bikini Top

    Hey, glam stud! Flaunt your shine in this bikini top featuring a strapless, bandeau style with front rhinestone bars and smooth-lined knit fabric. Complete the look in the matching bikini bottoms for a Vegas pool party.  

    Shop Matching Bottoms: Glam Stud Rhinestone Bikini Bottoms

    Fit & Features

    • Strapless bandeau-style
    • Front six rhinestone bars
    • Smooth-lined knit fabric
    • No padding
    • Runs small, size up one size

    Style Number/Barcode: 07104-0698

    Category Name: Vacation Looks

    Price: $10.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple Glam Rhinestone Bikini Top

    Simple and sultry, this trendy bikini top brings a subtle hint of glamour. It features a V-wired bust design and adjustable spaghetti straps with rhinestone detailing to add a stylish sparkle. Complete your poolside look with the matching bikini bottoms.

    Shop Matching Bottoms: Simple Glam Rhinestone Bikini Bottoms

    Fit & Features

    • V-wired bust design
    • Adjustable spaghetti straps, mini rhinestone embellishments
    • Back metal bar closure
    • No padding
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0699

    Category Name: Vacation Looks

    Price: $12.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Style On Lock PVC Espadrille Wedges

    Have your style on lock for the sunnier days ahead with these chic wedges featuring a square toe, dual PVC straps, and an espadrille sole. Complete the look in a flirty sundress. 

    Fit & Features

    • Square toe
    • PVC dual straps
    • Espadrille sole
    • Wedge style
    • Runs true to size

    Style Number/Barcode: 07406-0302

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slay The Trend High Rise Denim Shorts

    Slay the denim trend in these flattering high-rise shorts featuring distressed accents, a v-cut silhouette, and a raw frayed hem on premium vintage-inspired medium wash denim fabric with cool color fading. Complete the look in a sultry bustier for a summer night out.

    Fit & Features

    • High-rise waist
    • Distressed accents, v-cut silhouette
    • Raw frayed hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, color fading, no stretch
    • Fits true to size

    Style Number/Barcode: 06603-0254

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Who's That Girl Boho Maxi Skirt

    Everyone will be asking who's that girl in this boho maxi skirt! Create a trendy free spirit vibe in this high-rise skirt featuring an elasticized waistband, flowy silhouette, and a sultry front slit on the maxi-length hem. Complete the look in a crochet crop top.

    Fit & Features

    • High-rise elasticized waist
    • Flowy silhouette
    • Front slit
    • Maxi-length hem
    • Boho paisley print
    • Woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06301-0134

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Dainty Floral Tie-Front Top

    This chic dainty floral printed top will elevate your weekend looks. It features long bishop sleeves with puff shoulders, a V-neckline with a tie-front design, and a majorly cropped hem. Style with high-rise denim and sleek hoop earrings.

    Fit & Features

    • Long bishop sleeves, puff shoulders, cinched hems
    • V-neckline, tie-front
    • Cropped fit
    • Dainty floral print
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-1627

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunny Day Floral Corset Top

    A sunny day calls for this cute floral corset top! Featuring a sleeveless, sweetheart neck, wide straps, a built-in padded bust with underwire support, flexible boning inserts along the cropped bodice, and back hook-eye closures. Complete the look in jeans for a girl's day.

    Fit & Features

    • Sleeveless, sweetheart neck, wide straps
    • Built-in padded bust, underwire support
    • Flexible boning inserts
    • Cropped hem
    • Back hook-eye closures
    • Floral woven fabric, no stretch, fits true to size

    Style Number/Barcode: 06003-1829

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Island Palms Strappy Midi Dress

    Enter paradise island in this sultry midi dress perfect for a dinner with a view! It features a sleeveless, square neck, spaghetti straps, high waist seam, and a strappy open-back, bodycon silhouette, side ruched seam, and slit along the hem. Complete the look in statement fringe earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam, strappy open-back
    • Bodycon silhouette
    • Side ruched seam and slit
    • Midi-length hem
    • Palm print, knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4508

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Main Squeeze Striped Halter Wrap Top

    One go in this halter top and it surely will be your main squeeze! It features a collared plunge V-neck, sultry open-back design, and a wrap tie-front cropped hem. Complete the look in high-rise jeans for a summer date night.

    Fit & Features

    • Sleeveless, collared plunge V-neck
    • Halter bodice
    • Open-back design
    • Wrap tie-front 
    • Cropped hem
    • Striped pattern, sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1318

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Style Sleeveless Romper

    Get that effortless style that's perf for summer in this casual and cute sleeveless romper. It features tank shoulder straps, a deep V neck and back, a high waist with smocked detailing, trendy side cutouts, and flowy shorts. Pair this gauze romper with strappy sandals and hoop earrings.

    Fit & Features

    • Tank shoulder straps
    • Deep V neck and back
    • High waist, smocked detailing
    • Side cutouts
    • Flowy shorts
    • Gauze fabric
    • Runs true to size

    Style Number/Barcode: 06303-0140

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Sunset Halter Bodysuit

    Style up this trendy bodysuit for drinks at sunset with the girls! It features a sleeveless cross-front halter neckline, an alluring keyhole cutout at the bust, a thong bottom, and an all-over tropical palm leaf print. Pair this bodysuit with a high-rise mini skirt and mules.

    Fit & Features

    • Sleeveless cross front halter neckline, spaghetti straps
    • Keyhole cutout at the bust
    • Cross-back strap design
    • Thong bottom, dual snap button closure
    • Form-hugging fit
    • Tropical palm leaf print
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4286

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Breezy Crochet Bolero Sweater

    Layer on this crochet bolero sweater for an effortlessly breezy, cute look! 

    Fit & Features

    • Sheer crochet fabric
    • Long sleeves with flare cuffs
    • Open front design
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000051

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Ribbed Knit Cropped Tank

    Elevate your casual summer 'fits with this trendy cropped tank! It features a sleeveless scoop neckline with a notched front design, tank shoulder straps, a center cutout at the hem, and a cropped, form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch. Style this tank with distressed denim shorts.

    Fit & Features

    • Sleeveless scoop neckline
    • Notched front design
    • Tank shoulder straps
    • Center cutout at the hem
    • Cropped, form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1299

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All About Basic Slit Tank Top

    Start with the basics. This sleeveless tank top is essential for building the perfect wardrobe! Featuring a square neck, wide straps, a form-fitting design, and trendy side slit accents along the cropped hem. Complete the look in high-rise jeans and sandals.

    Fit & Features

    • Sleeveless, square neck, wide straps
    • Form-fitting design
    • Side slit accents
    • Cropped hem
    • Double-layered modal fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4367

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Back Beauty Linen Halter Skater Dress

    They'll love to watch you leave in this gorgeous skater dress featuring a sleeveless, halter neck with tie closure, and a smocked bodice that leads to a flowy, skater short silhouette with an open back and lattice bar accents. Complete the look in sleek hoop earrings for a day date. 

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Smocked bodice
    • Flowy skater silhouette
    • Short-length hem
    • Open-back, lattice bar accents
    • Linen fabric, lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4404

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Flower Lattice Tank Top

    Look prettier than the island flowers in this tropical floral tank top featuring a sleeveless V-neck, spaghetti straps, and a lattice front trim on a cropped hem. Complete the look in the matching skirt and sandals. 

    Shop Matching Skirt: Island Flower High Slit Midi Skirt

    Fit & Features

    • Sleeveless, V-neck, spaghetti straps
    • Lattice front trim
    • Cropped hem
    • Tropical floral print
    • Stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 06001-4015

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale