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.

  • Sultry Cutouts Fitted Bodysuit

    Stun in this sultry fitted bodysuit that was made for a night out! It features a trendy mock neckline, a single long fitted sleeve, a top asymmetrical cutout, a side cutout, and a thong bottom. Style this bodysuit with faux leather pants and clear mules.

    Fit & Features

    • Mock neckline
    • Single long fitted sleeve
    • Top asymmetrical cutout
    • Side cutout at the waist
    • Thong bottom, dual snap button closure
    • Form-hugging fit, brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-3959

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Energy Strapless Floral Mesh Maxi Dress

    Bring major energy in this strapless floral mesh maxi dress design to flaunt your figure in a bodycon fit and show some skin with a high-side slit. Pair with mules.

    Fit & Features

    • Floral print, mesh fabric, soft and stretchy knit lining
    • Strapless neckline
    • High-side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-4074

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cozy Season Long Sherpa Coat

    'Tis the season to bundle up and stay cozy! This long faux sherpa coat features a collared neckline, long sleeves, a button-down front, and a relaxed and comfortable fit. Layer this adorable coat over your fave sweater dress and complete the look with knee-high boots.

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Complete button-down front, tortoise-shell colored buttons
    • Dual front pockets
    • Relaxed fit
    • Faux sherpa fabric, smooth lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0280

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chill Vibes Denim And Corduroy Jacket

    Layer on the chill vibes with this cute and casual jacket! It features a collared neckline, long sleeves, a button-down front, a frayed hem, and a relaxed fit. The jacket is composed of denim and corduroy fabrics for a trendy look. Style it with a basic tee, jeans, and classic sneakers.

    Fit & Features

    • Collared neckline
    • Long sleeves, single-button details
    • Complete button-down front
    • Dual buttoned chest pockets
    • Frayed hem
    • Denim and corduroy fabrics, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1081

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Glam Cabby Hat

    Bring elevated glam vibes to your look with this chic cabby hat! It features a traditional cabby hat design with a short brim and a sleek chain-link detail. The tweed material has a stylish metallic thread woven throughout. Pair this hat with hoop earrings.

    Fit & Features

    • Traditional cabby hat design
    • Short brim
    • Chain and stud details
    • Tweed material, metallic thread detailing
    • Smooth woven lining

    Style Number/Barcode: 07302-0451

    Category Name: Vacation Looks

    Price: $6.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Fab Leopard Gloves

    Keep it trendy and fab with gloves that are perf for those chilly days. The gloves feature a leopard print and fleece lining. The index finger and thumb feature exterior nylon lining that makes it easy to use phones, tablets, and more without having to remove gloves. Complete the look with a trench and boots.

    Fit & Features

    • Leopard print
    • Fleece lining
    • Exterior nylon lining at index and thumb
    • Knit fabric 

    Style Number/Barcode: 07304-0014

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lady In Faux Fur Cuff Gloves

    Look and feel fab in these faux fur cuff gloves featuring a 5-finger design with 'magic touch tips' for using your touch screen device comfortably. Complete the look in a chic coat.

    Fit & Features

    • Faux fur cuffs
    • 5-finger design
    • Magic touch tips for using a touch screen
    • Comfortable and warm
    • Fits true to size

    Style Number/Barcode: 07304-0013

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Chic High Slit Slip Dress

    Keep it effortlessly chic in a slip dress that stuns with ease. The dress features a sleeveless V-neck, spaghetti straps, a flirty high side slit on the slip-styled silhouette, and a midi length. The dress is composed of a lightweight woven nylon fabric that offers a relaxed fit with minimal stretch. Complete look with mules and a dainty chain necklace. 

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Bra-friendly
    • Slip-styled silhouette
    • Midi length, high side slit
    • Lightweight woven fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1310

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Steal The Spotlight Leopard Slit Midi Dress

    Steal the spotlight looking so fierce in this leopard midi dress! It features a sleeveless V-neckline, spaghetti straps, a flowy midi-length hem, and a front slit perfect for showing off some skin. Style with a pair of strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length hem, flowy silhouette
    • Front slit
    • Leopard print
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4306

    Category Name: Vacation Looks

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flannel Weather Plaid Shacket

    It's officially flannel weather and this plaid shacket is just the ticket! It features cozy long sleeves with button cuffs, a collared neckline, button-flap pockets, and a button-down front. The shacket is composed of a soft-woven fabric with no stretch. Complete the look in skinny jeans.

    Fit & Features

    • Button cuffed long sleeves
    • Collared neckline
    • Button-flap pockets
    • Button-down front
    • Plaid pattern, soft-woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1272

    Category Name: Vacation Looks

    Price: $15.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Trendsetter Snake Envelope Crossbody

    Create a major trendsetting moment with a crossbody that elevates your style. The crossbody features a snake print, an envelope-shaped body, a fold-over closure, and a chain shoulder strap. Complete look with a trench dress and boots. 

    Fit & Features

    • Snake print
    • Rectangular-shape
    • Envelope fold-over closure
    • Hidden front pocket
    • Chain shoulder strap
    • Faux leather material 

    Style Number/Barcode: 07203-0840

    Category Name: Vacation Looks

    Price: $8.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Snow Sparkle Rhinestone Pom Beanie

    Sparkle a snowy day in this rhinestone beanie featuring a faux fur pom, cable knit design, and a sherpa lining for extra warmth. Complete your look with a cozy sweater.

    Fit & Features

    • Faux fur pom
    • Rhinestone detailing
    • Cable knit design
    • Sherpa lining

    Style Number/Barcode: 07302-0458

    Category Name: Vacation Looks

    Price: $2.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Butterfly Chain Detail Panama Hat

    Add a touch of trendy glamour to your fall look with this adorable Panama hat. It features a wide flat brim adorned with a dainty butterfly charm chain. Style this hat with sleek hoop earrings.

    Fit & Features

    • Wide flat brim
    • Rhinestone butterfly charm chain
    • Faux wool material

    Style Number/Barcode: 07302-0457

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Velvet Burnout Tie-Front Top

    Show up in style in this chic detailed tie-front top. It features long bishop sleeves, an open front with a tie closure creating a flattering V-neckline, and a cropped, form-hugging fit. The sheer mesh fabric features an all-over velvet burnout floral pattern. Complete the look with faux leather pants and mules.

    Fit & Features

    • Long bishop sleeves, elastic cinched hems
    • Open front, tie closure
    • V-neckline
    • Cropped, form-hugging fit
    • Sheer mesh fabric, velvet burnout floral pattern
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0253

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie Spotted Leopard Pom Beanie

    Look and feel cute in this leopard beanie featuring a pom on the top and a ribbed, foldable cuff. Complete the look with a cozy sweater and leggings.

    Fit & Features

    • Leopard pattern
    • Pom on the top
    • Ribbed, foldable cuff
    • Knit fabric

    Style Number/Barcode: 07302-0439

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetest Day Scoop Neck Ruffle Eyelet Skater Dress

    The sweetest days are spent in this eyelet skater dress soaking up the sun with pretty details like sheer trim designs and a ruffled mini-length hem.

    Fit & Features

    • Eyelet lace fabric, stretchy knit lining
    • Scoop neckline, ruffle trim
    • Adjustable spaghetti straps
    • Sheer trim designs on the bodice
    • Ruffled tier mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3936

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Ryder Rhinestone Panama Hat

    Add a touch of glam to your western fit in this panama hat featuring a rhinestone band, wide brim, on faux wool material. Complete the look with a denim jacket.

    Fit & Features

    • Rhinestone band
    • Wide brim
    • Faux wool material

    Style Number/Barcode: 07302-0454

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Glamour Rhinestone Panama Hat

    Showcase trendy glamour with this sparkly detailed Panama hat. It features a traditional Panama hat design, a wide brim, and a rhinestone embellished band. The hat is composed of a faux wool material. Style it with a chic blazer and hoop earrings.

    Fit & Features

    • Traditional Panama hat design
    • Wide brim
    • Wide rhinestone embellished band
    • Faux wool material

    Style Number/Barcode: 07302-0453

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Stylish Faux Wool Boater Hat

    This basic faux wool boater hat has a simple yet chic style, making it a perf addition to your fall look. It features a short flat brim, a flat top, and a ribbon band accent. Pair this hat with a faux leather jacket.

    Fit & Features

    • Short flat brim
    • Flat top
    • Ribbon band
    • Faux wool material

    Style Number/Barcode: 07302-0428

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cuddle Up Knit Blanket Scarf

    Cuddle up in a scarf that warms up your look! The scarf features an oversized style and a short fringe. The scarf is composed of a soft-to-the-touch knit fabric that offers a relaxed fit with a moderate stretch. Complete look with ankle booties

    Fit & Features

    • Oversized style
    • Short fringe
    • Cashmere-like knit fabric

    Style Number/Barcode: 07305-0360

    Category Name: Vacation Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual-Cozy Long Line Plaid Shacket

    Layer on this casual-cozy shacket for an effortlessly stylish look! It features a collared neckline, long sleeves, a complete button-down front, hidden side pockets, and a long line silhouette with a relaxed fit. Wear this shacket with ankle booties.

    Fit & Features

    • Collared neckline
    • Long sleeves, double button details
    • Button-down front
    • Hidden side pockets
    • Long line silhouette, relaxed fit
    • Woven fabric, no stretch, plaid print
    • Runs true to size

    Style Number/Barcode: 06204-1257

    Category Name: Vacation Looks

    Price: $19.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cozy Plush Plaid Scarf

    Cozy on up in this plush woven scarf that will go with your everyday winter looks. It features a cute plaid print with neutral tones, fringe detailing at the hems, and an oversized blanket fit. Style this soft woven scarf with a sweater dress and booties.

    Fit & Features

    • Plaid print
    • Neutral tones
    • Fringe detailing
    • Oversized blanket fit
    • Woven fabric, no stretch

    Style Number/Barcode: 07305-0365

    Category Name: Vacation Looks

    Price: $2.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chill Out Plaid Shacket

    Chill out in a cozy shacket to layer over your looks this season! The shacket features a collared neckline, a multi-button down front, two chest pockets, long sleeves, and a long line length. The shacket is composed of a brushed faux wool fabric that offers a relaxed fit with minimal stretch. Complete look with distressed jeans and ankle booties.

    Fit & Features

    • Collared neckline
    • Multi-button down front 
    • Two chest pockets
    • Long sleeves
    • Longline length, plaid print
    • Faux wool fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06204-1278

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rhinestone And Pearl Luxe Knit Beanie

    Bring the luxe with a beanie that adds that sparkling touch to your outfit. The beanie features a knit body, faux pearl accents, rhinestones, and a faux fur pom pom accent. Complete look with a sweater and high waist jeans. 

    Fit & Features

    • Knit material 
    • Faux pearl accents
    • Rhinestones
    • Faux fur pom pom accent 

    Style Number/Barcode: 07302-0391

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free