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.

  • Head-Turning Chic Marble Print Midi Dress

    Make heads turn in this eye-catching chic bodycon midi dress! It features a sleeveless square neckline, spaghetti straps, bold front and back waist cutouts, ruched detailing down the side seams, and a midi-length, curve-hugging silhouette. The stretchy knit fabric features an all-over abstract marble print pattern for a trendy vibe. Complete the look with clear heels.

     Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Abstract marble print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4837

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Fabulous Faux Fur Knit Duster

    Layer on this chic ribbed knit duster for a forever fabulous look! Featuring a removable faux fur collar accent, long fitted sleeves, a tie-front design, and a long-length flowy silhouette, this duster can be dressed up or down depending on your mood! The ribbed knit fabric offers a moderate stretch. Complete your look with ankle booties.

    Fit & Features

    • Removable faux fur collar, button attachments
    • Long fitted sleeves
    • Tie-front
    • Long-length flowy silhouette
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1431

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lowkey Luxe Rectangle Frame Sunglasses

    These sunglasses do not come to play. Sleek, structured, and effortlessly cool, they’re your go-to for effortless throw-on-and-go styling!

    Fit & Features

    • Sleek rectangular frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000066

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy In The City Faux Sherpa Coat

    Feel cozy and look cute for a day in the city slaying it in this faux sherpa coat featuring long sleeves, a collared neckline, single button closure, and a cropped hem. Layer over a basic bodysuit and jeans!

    Fit & Features

    • Long sleeves
    • Collared neckline
    • Single button closure
    • Cropped hem
    • Faux sherpa, smooth woven lining
    • No stretch
    • Fits true to size

    Style Number/Barcode: 06201-0349

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Resort Ready Eyelet Linen Platform Block Heels

    Elevate your spring-to-summer looks in these eyelet linen platform block heels, perfect for a resort vacation or weekend event.

    Fit & Features

    • Block heel
    • Square toe, criss cross toe strap
    • Platform sole
    • Luxe fit cushioned insole
    • Adjustable ankle strap, buckle closure
    • Eyelet linen material
    • Runs true to size

    Style Number/Barcode: 07401-5274

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Styled To Perfection Belted Trench Coat

    This chic faux wool trench coat will have you styled to perfection! It features a lapel collar, long sleeves, an open front with a tie-front belt to cinch the waist, and a short-length hem with a relaxed silhouette. Layer over a mock neck sweater with your fave pair of denim.

    Fit & Features

    • Lapel collar
    • Long sleeves, faux side pockets
    • Open front
    • Tie-front belt
    • Short-length hem, relaxed fit
    • Faux wool fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0311

    Category Name: Vacation Looks

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Chain Effect Midi Dress With Belt

    You'll make a chain reaction by stepping out in this rib knit tank midi dress featuring a sleeveless square neck, tank shoulder straps, a detachable chain belt with lobster clasp closure, and a form-hugging silhouette. Complete the look in a chic blazer for happy hour!

    Fit & Features

    • Sleeveless square neck
    • Tank shoulder straps
    • Detachable chain belt with lobster clasp closure
    • Form-hugging silhouette
    • Midi-length hem
    • Double-lined rib knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4882

    Category Name: Vacation Looks

    Price: $19.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • SoHo Girl Double-Breasted Trench Coat

    This faux sherpa trench coat is giving major city vibes! The coat features long sleeves, a lapel collar neckline, double-breasted button closures, side pockets, and a longline hem. Complete the look with a trendy bucket hat for a day spent downtown! 

    Fit & Features

    • Long sleeves
    • Lapel collar neckline
    • Double-breasted button closures
    • Side pockets
    • Longline hem
    • Faux sherpa, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0353

    Category Name: Vacation Looks

    Price: $16.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Layer On The Luxe Vibes Faux Fur Jacket

    Layer on the luxe vibes with this chic faux fur jacket! It features a collared neckline, long sleeves, a zip-front, plush faux fur fabric that is ultra-soft to the touch, seam detailing to give the illusion of a puffer design, lined side pockets, and a fitted silhouette with a cropped hem. The jacket includes a full lining. Style over a basic bodysuit with faux leather pants for an elevated look.

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Complete zip-front, lined side pockets
    • Plush faux fur fabric, smooth lining, no stretch
    • Seam detailing to give the illusion of a puffer design
    • Fitted silhouette, cropped hem
    • Runs true to size

    Style Number/Barcode: 06201-0301

    Category Name: Vacation Looks

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Trendy Florals Flocked Velvet Corset Top

    Create a head-turning look with this trendy floral corset top! It features a square neckline, long fitted sleeves with slit accents at the hems for a subtle flared-out design, a corset-style bodice with flexible boning, and a cropped, form-hugging fit. The knit fabric features an all-over flocked velvet floral pattern for a chic vibe. Style with faux leather pants and mules.

    Fit & Features

    • Square neckline
    • Long fitted sleeves, slit accents at the hems
    • Corset-style bodice, flexible boning
    • Back hook and eye closures
    • Cropped hem, form-hugging fit
    • Flocked velvet floral pattern
    • Sheer knit fabric, front knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4447

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lavish Life Satin Slit Midi Skirt

    You'll be living lavishly in your new must-have satin midi skirt perfect for dinner parties, celebrations, and holiday events! The skirt features a sleek high-rise waist, side zipper and hook-eye closure, a curve-hugging silhouette, and a high-cut side slit. Complete the look in a crop sweater and heels!

    Fit & Features

    • High-rise waist
    • Side zipper and hook-eye closure
    • Curve-hugging silhouette
    • High-cut side slit
    • Midi-length hem
    • Silky satin fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06401-0575

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Total Grudge Lug Sole Loafers

    These faux leather loafers are giving major grudge 90s babe vibes! They feature a round toe, chunky lug platform sole, and heel, and are composed of faux leather material. Complete the look in a trendy plaid matching set.

    Fit & Features

    • Round toe
    • Chunky lug platform sole and heel
    • Classic loafer style
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07405-0036

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Cool-Girl Vibes Knit Sneakers

    Style up these on-trend knit sneakers for a casual cool-girl vibe! They feature a lace-up front with adjustable drawcords, a textured sole, a lightweight knit design, and faux leather accents. Pair with a ribbed knit mini dress and your fave denim jacket.

    Fit & Features

    • Lace-up front, adjustable drawcords
    • Textured sole
    • Pull tabs
    • Knit design
    • Faux leather accents
    • Runs true to size

    Style Number/Barcode: 07407-0214

    Category Name: Vacation Looks

    Price: $4.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Icon Cow Faux Fur Long Coat

    Unveil an iconic diva status layering on this cow pattern coat and watch every head turn! The faux fur coat features long sleeves, a lapel collar neckline, an open-front design, hidden side pockets, and a relaxed long-length hem. Complete the look in thigh-high boots.

    Fit & Features

    • Long sleeves
    • Lapel collar neckline
    • Open-front design
    • Relaxed, long-length hem
    • Cow pattern 
    • Faux fur, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0352

    Category Name: Vacation Looks

    Price: $32.97 $72.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Slay The Chill Quilt Puffer Jacket

    Slay the chill and your fit' by layering on this quilted puffer jacket featuring long sleeves with elasticized cuffs, a standing collar neckline, front zipper closure, side pockets, and an adjustable drawcord crop hem. The jacket is composed of nylon-woven fabric with insulation to help keep you warm and protected from the elements. Complete the look in trendy lug boots.

    Fit & Features

    • Long sleeves, elasticized cuffs
    • Standing collar neckline
    • Front zipper closure, side pockets
    • Adjustable drawcord crop hem
    • Nylon-woven quilted fabric
    • Insulated and lined
    • Fits true to size

    Style Number/Barcode: 06201-0329

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Up Cable Knit Oversized Cardgian

    Cozy up in this adorable oversized cable knit cardigan for the cutest look! It features an open front, long dolman-style sleeves, dual front pockets, and a relaxed fit. Layer over a basic bodysuit with faux leather pants and ankle booties.

    Fit & Features

    • Open front
    • Long dolman-style sleeves
    • Dual front pockets
    • Oversized, relaxed fit
    • Cable knit fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1509

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Real Sweet Colorblock Chenille Sweater

    Real sweet and so soft! This color-block chenille sweater will be a cozy staple piece in your closet. It features long dolman sleeves, a crew neck, and a relaxed fit silhouette. The soft chenille knit fabric offers a moderate stretch. Complete the look in basic leggings and boots.

    Fit & Features

    • Long dolman sleeves
    • Crew neck
    • Relaxed silhouette
    • Color block pattern
    • Chenille knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1571

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Versatile Basic Rib Knit Crop Top

    Your new favorite basic to create all sorts of showstopping outfits! This rib knit crop top features long sleeves, a scoop neck, and a fitted hem. Complete the look in a plaid skirt, jacket, and booties for the perf autumn vibe!

    Fit & Features

    • Long fitted sleeves
    • Scoop neckline
    • Fitted cropped hem
    • Soft and stretchy
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1438

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Warm Embrace Cable Knit Sweater

    Cozy up on chilly autumn days in this cable knit sweater featuring the perfect oversized fit, long sleeves with ribbed cuffs, a mock neckline with a trendy cutout, and a relaxed hem. Complete the look in leggings and cute suede boots.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Long sleeves, ribbed cuffs
    • Mock neckline with cutout
    • Oversized silhouette
    • Relaxed fit hem
    • Cable knit design
    • Fits true to size

    Style Number/Barcode: 06005-1452

    Category Name: Vacation Looks

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Chic Over-The-Knee Slouch Boots

    Your look will always be chic in these bold over-the-knee boots! They feature a slouched design, a pointed toe, a sleek stiletto heel, and an inner zipper closure. Pair with a corset top and a faux leather skirt and strut in style!

    Fit & Features

    • Over-the-knee fit
    • Slouched design
    • Pointed toe
    • Stiletto heel
    • Zipper closure
    • Faux leather material, smooth lining
    • Runs true to size

    Style Number/Barcode: 07402-0830

    Category Name: Vacation Looks

    Price: $30.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fabulous Diva Leopard Print Faux Fur Coat

    Layer on this ultra-soft faux fur coat to showcase fabulous diva energy! The coat features a lapel collar, long sleeves, lined side pockets, a relaxed silhouette, and an all-over trendy leopard print pattern. The faux fur fabric includes a knit lining. Style with knee-high boots.

    Fit & Features

    • Lapel collar
    • Long sleeves
    • Lined side pockets
    • Relaxed fit
    • Leopard print
    • Faux fur fabric, knit lining with minimal stretch
    • Runs true to size

    Style Number/Barcode: 06201-0322

    Category Name: Vacation Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stacked On Style Lace-Up Boots

    Stack on the style with boots that dare to go bold! The faux suede boots feature an over-the-knee shaft length, a sexy bungee strap lace-up back, an inner zipper closure, a pointed toe, and a sleek stiletto heel. Complete the look with a sweater and mini skirt for a dinner date!

    Fit & Features

    • Over-the-knee shaft length
    • Lace-up bungee strap back 
    • Inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux suede material 
    • Runs true to size

    Style Number/Barcode: 07402-0825

    Category Name: Vacation Looks

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chill Tale Corduroy Faux Sherpa Shacket

    This tale is as chill as time! The corduroy shacket offers a cozy and cute look to bundle up in this season. It features long sleeves, button cuffs, a hooded neckline, four-pocket styling, a button-down front, and a longline hem with faux sherpa lining. Complete the look in knee-high boots.

    Fit & Features

    • Long sleeves, button cuffs
    • Hooded neckline
    • Four-pocket styling
    • Button-down front
    • Longline hem
    • Corduroy fabric, faux sherpa lining, no stretch
    • Fits true to size

    Style Number/Barcode: 06201-0307

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free