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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.

  • She's A Wildflower Strappy Back Maxi Dress

    Florals, fits, and full-on main character vibes. This floral mesh maxi dress hugs you in all the right places with a flirty strappy back and a vacay allure! 

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • V-neckline
    • Bungee strappy open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000097

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Minimalistic Chic PU Woven Sandals

    Achieve minimalistic style in these PU woven sandals perfect for open-toe weather! They feature an almond toe and a single band with a crocodile accent strap. Complete the look in linen joggers and a sleeveless top.

    Fit & Features

    • Almond toe
    • Single PU band
    • Crocodile accent strap
    • Comfort fit
    • Slide-on/off styling
    • Runs true to size

    Style Number/Barcode: 07404-1061

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fiercely Bold Cutout Swimsuit

    Make a splash in this fierce snake print swimsuit for a pool party or beach day. It features a one-shoulder strap design, cutout bodice, and a cheeky fit. Complete the look in oversized sunglasses.

    Fit & Features

    • One-shoulder strap design
    • Cutout bodice
    • Cheeky fit 
    • Snake print
    • Lined fabric
    • Runs true to size

    Style Number/Barcode: 07109-0295

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rhine Vibes PU Fanny Pack

    Bring the bling to your festival outfit with this rhinestone fanny pack perfect for carrying your must-have essentials. It features an adjustable strap, front zipper closure, and a spacious interior. Complete the look in a trendy graphic tee and distressed shorts. 

    Fit & Features

    • Adjustable buckle strap
    • Front zipper closure
    • Spacious interior
    • Rhinestone embellishments
    • PU material

    Style Number/Barcode: 07203-0986

    Category Name: Vacation Looks

    Price: $18.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Style Espadrille Wedges

    Step up your summer style with these cute espadrille wedges! They feature an open almond-shaped toe with a toe strap, an adjustable ankle strap, and an espadrille wedge heel. Pair these wedges with chic cat-eye sunglasses.

    Fit & Features

    • Open almond-shaped toe
    • Toe strap
    • Adjustable ankle strap, buckle detail
    • Espadrille wedge heel
    • Faux nubuck material
    • Runs true to size

    Style Number/Barcode: 07406-0291

    Category Name: Vacation Looks

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Almost Famous Sleek Square Sunglasses

    These sleek square sunglasses are on the rise to fame! They feature a metal frame and arms, gradient lens, and rubber nose supports. Complete the look in a casual bodycon dress and heels.

    Fit & Features

    • Sleek square metal frame
    • Gradient lens
    • Rubber nose supports
    • Metal arms
    • 100% UV protection

    Style Number/Barcode: 07008-0949

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Say High Nubuck Espadrille Wedges

    Say high to your new favorite espadrille wedges this spring! Perfect for strolling the boardwalk or going for brunch, they feature a stylish and comfortable design on an almond toe, platform sole, and nubuck straps with buckle closure. Complete the look in a flirty sundress.

    Fit & Features

    • Almond toe
    • Platform espadrille sole
    • Nubuck straps
    • Ankle buckle closure
    • Runs true to size

    Style Number/Barcode: 07406-0292

    Category Name: Vacation Looks

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Greek Islands Tie-Front Top

    The perfect tie-front top to take your trip to Greece! It features trendy peasant long sleeves, a plunge v-neckline, and a cropped hem on gauze woven fabric with a multi-print. Complete the look in oversized sunglasses.

    Fit & Features

    • Peasant long sleeves
    • Plunge v-neckline
    • Tie-front detail
    • Cropped hem
    • Multi-printed gauze woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1232

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Puff Love Square Neck Skater Dress

    There's a lot to love about this puff sleeve skater dress! Features a square neck, smocked bodice, a trendy waist cutout, and a tiered short skirt. Composed of linen woven fabric with an inner lining. Finish the look in floral earrings for a cute spring fit.

    Fit & Features

    • Short puff sleeves, square neckline
    • Smocked bodice, waist cutout
    • Tiered short skirt
    • Skater silhouette
    • Linen woven fabric, inner lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4343

    Category Name: Vacation Looks

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Palm Paradise Tie-Back Crop Top

    Enter paradise in this breezy palm print crop top featuring a mock neck atop a sultry front keyhole cutout, long peasant sleeves, and an open back with tie closure. Complete the look in a sleek faux leather skirt. 

    Fit & Features

    • Mock neck, button closures, long peasant sleeves
    • Front keyhole cutout
    • Cropped hem
    • Open-back with tie closure
    • Palm print
    • Stretchy knit-lined fabric
    • Fits true to size

    Style Number/Barcode: 06001-3877

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Back To Basics Ribbed Racer Bodysuit

    Bring your look back to basics with a bodysuit that is perfect for nailing that lowkey look this season. This sleeveless bodysuit features a square neckline, tank shoulder straps, and a trendy racerback with a lower back cutout on lined rib-knit fabric. Complete look with cutoff shorts and sandals. 

    Fit & Features

    • Square neckline
    • Tank shoulder straps
    • Racerback design
    • Lower back cutout 
    • Thong bottom, dual snap closure
    • Lined rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1195

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shift In Season Linen Belted Trench

    Cooler temps call for effortless style! Layer on this linen trench coat for an elevated look. It features long sleeves with button closures, a draped, collar neckline, and an open-front design with belted waist and slit accents along the long hem. Complete the look in a bodysuit and jeans.

    Fit & Features

    • Long sleeves, button closures
    • Draped collar neckline
    • Open-front design
    • Belted waist, slit accents, long hem
    • Linen woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1292

    Category Name: Vacation Looks

    Price: $6.97 $58.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In Business Crepe Tie-Waist Duster

    This crepe duster will surely be in business with your closet! It features long sleeves, draped collared neckline, an open front design, and a tie-waist belt on a longline hem. Complete the look in a sleek bodysuit and trousers.

    Fit & Features

    • Long sleeves
    • Draped collared neckline
    • Open-front design
    • Tie-waist belt
    • Longline hem
    • Crepe knit fabric, moderate stretch, fits true to size

    Style Number/Barcode: 06202-0323

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Denim Glam Flared Sleeveless Jumpsuit

    Bring the glam with a jumpsuit that channels that retro vibe! The jumpsuit features a sleeveless square neckline, a button-down front bodice, tank shoulder straps, and straight-leg pants with a flared hem. The jumpsuit is composed of a denim fabric that offers a form hugging fit. Complete look with mules. 

    Fit & Features

    • Sleeveless square neckline
    • Button-down bodice
    • Tank shoulder straps 
    • Back zipper closure
    • Straight leg fit, flared hem 
    • Form hugging fit, runs true to size 

    Style Number/Barcode: 06602-0319

    Category Name: Vacation Looks

    Price: $8.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Retro Mood Tortoiseshell Oval Sunglasses

    Lowkey iconic, highkey essential. These tortoiseshell oval sunglasses give your everyday 'fits that effortless vintage vibe—perfect for rooftop brunches, market strolls, or literally anytime you want to look cool.

    Fit & Features

    • Small oval-shaped design
    • Tortoiseshell plastic frame
    • Built-in nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000048

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Short Romance Knit Crop Top

    It may be short but your love for this knit crop top is sure to last! It features a sleek, sleeveless, cowl neck, and bungee spaghetti straps that cross on the open-back. Complete the look in a flirty mini skirt for a fab look.

    Fit & Features

    • Sleeveless, cowl neck
    • Bungee spaghetti straps
    • Cropped hem
    • Cross straps, open back
    • Brushed knit fabric
    • Fits true to size

    Style Number/Barcode: 06001-4092

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Basic Crew Racer Top

    Keep it minimal with a racer top that is perf for nailing those lowkey vibes! The top features a sleeveless crew neckline, a racerback, and a cropped hem. The top is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mom jeans and a dainty charm necklace.

    Fit & Features

    • Sleeveless crew neckline
    • Racerback 
    • Cropped hem
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06001-4170

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Groovy Babe Paisley Mesh Tunic Top

    You're one groovy babe! Embrace the retro vibes of this paisley mesh tunic top featuring trendy long bell sleeves, a mock neckline, an exposed seam detail on a form-fitting silhouette. Complete the look in a bralette and denim shorts.

    Fit & Features

    • Long bell sleeves
    • Mock neckline
    • Exposed seam detail
    • Form-fitting silhouette
    • Paisley pattern
    • Sheer mesh fabric, moderate stretch, fits true to size

    Style Number/Barcode: 06001-4127

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Living In Technicolor Bikini Top

    Sunshine calls for fab bright colors! Live it up with this bikini top that features The bikini top features a stylish kaleidoscope print, a halter neck with neck ties, a bandeau-styled bodice with a built-in no-slip gel strip, and a double row of back ties for a secure fit. Complete look with the matching bikini bottoms. 

    Shop Matching Bikini Bottoms: Living In Technicolor Bikini Bottoms

    Fit & Features

    • Kaleidoscope print
    • Halter neck 
    • Neck ties
    • Bandeau-styled bodice, no-slip strip
    • Double-row of back ties
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 07104-0694

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Clear Criss Cross Sandals

    Step out in sandals that are clearly on trend! The sandals feature an open back, an open almond toe, wide clear crisis cross straps, and are composed of a faux leather material. Complete look with a cute bikini set and sunnies! 

    Fit & Features

    • Open back 
    • Almond toe
    • Wide clear crisis straps
    • Comfort fit
    • Faux leather material 
    • Runs true to size

    Style Number/Barcode: 07404-1030

    Category Name: Vacation Looks

    Price: $9.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Breeze Linen Halter Skater Dress

    Feel the breeze this spring! This linen skater dress is perfect for your next daytime soiree featuring a sleeveless halter V-neckline, open-back design, dual tie-back closure, and a flowy, A-line skater silhouette. Composed of linen fabric with an inner knit lining with minimal stretch. Style with strappy heels.

    Fit & Features

    • Sleeveless, halter V-neck
    • Open-back design, dual tie-back closure, lower back elasticized waistband
    • Flowy, A-line skater silhouette
    • Above-the-knee length hem
    • Linen fabric, inner knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4414

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leopard Spots Strappy Crop Top

    You'll surely be spotted in this fab leopard crop top featuring long sleeves and an open plunge neckline with criss-cross straps. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Leopard Spots High Rise Flare Pants

    Fit & Features

    • Long sleeves
    • Open plunge neckline
    • Criss-cross straps
    • Cropped hem
    • Leopard print
    • Stretchy soft knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4134

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In Check High Rise Denim Mom Shorts

    Keep your look in check wearing these eye-catching denim mom shorts! They feature a classic high-rise waist, and a checkered pattern on a medium wash denim fabric with a frayed hem. Complete the look in a tie-front top and sneakers.

    Fit & Features

    • High-rise waist
    • Mom style
    • Checkered pattern
    • Frayed hem
    • Front button and hidden zipper closure
    • Five-pocket design, belt loop accents
    • Medium wash denim, no stretch, fits true to size

    Style Number/Barcode: 06603-0274

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Flutter Sleeve Chiffon Duster

    Layer on this flirty sheer chiffon duster over all of your cute summer 'fits! The duster features short flutter sleeves, a V-neckline, a button-front closure, and a high-low flowy silhouette. Style with a chic boater hat and oversized sunnies.

    Fit & Features

    • Short flutter sleeves
    • V-neckline
    • Button-front closure
    • Smocked back detail at the waist
    • High-low flowy silhouette
    • Sheer chiffon fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06204-1154

    Category Name: Vacation Looks

    Price: $14.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free