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.

  • Fiercely Chic Leopard Midi Skirt

    Your outfit will look fierce and chic with this leopard midi skirt featuring an elasticized high-rise waist, form-hugging silhouette, and a sultry front slit on brushed knit fabric. Complete the look in a silky tie-front top for a sunset dinner.

    Fit & Features

    • Elasticized high-rise waist
    • Form-hugging silhouette
    • Front slit
    • Midi-length hem
    • Leopard print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0818

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rocker-Chic Rhinestone Fringe Denim Jacket

    Layer on this distressed and embellished denim jacket for a glam rocker-chic look! It features a collared neckline, long sleeves, a complete button-down front, pockets, distressed detailing, eye-catching rhinestone fringe on the back, and a cropped, relaxed fit. The cotton fabric has no stretch. Complete your cool-girl 'fit with a corset top and faux leather shorts.

    Fit & Features

    • Collared neckline
    • Long sleeves, button details
    • Button-down front, dual chest pockets
    • Distressing
    • Back rhinestone fringe design
    • Cropped, relaxed fit
    • Cotton fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06203-0482

    Category Name: Vacation Looks

    Price: $29.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Glam Rhinestone Denim Jacket

    Layer on this trendy rhinestone denim jacket for a casual glam vibe! It features a collared neckline, long sleeves, a button-down front, flap chest pockets, all-over sparkly rhinestone embellishments, and a trucker jacket fit. Style with faux leather pants and clear heels.

    Fit & Features

    • Collared neckline
    • Long sleeves, single buttons details
    • Button-down front
    • Flap chest pockets with button detailing, side pockets
    • All-over rhinestone embellishments
    • Trucker fit
    • Cotton denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06203-0484

    Category Name: Vacation Looks

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Denim Babe Belted Long Jean Jacket

    Look and feel like a babe in this forever classic denim jacket! It features long sleeves with buttoned cuffs, a collar neckline, a button-down front, distressed accents throughout, four-pocket styling, a belted waist, and a longline hem. Complete the look in a basic bodysuit for a coffee run!

    Fit & Features

    • Long sleeves, buttoned cuffs
    • Collar neckline
    • Button-down front
    • Four-pocket styling
    • Belted waist, longline hem
    • Distressed denim fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06203-0194

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lots To Love Block Heel Booties

    There is a lot to love about these nubuck booties and all the ways you can style them! They feature an almond toe, block heel, and side zipper closure, and fit above the ankle. Complete the look in a chic duster trench coat for a day in the city!

    Fit & Features

    • Almond toe
    • Block heel
    • Side zipper closure
    • Above the ankle length
    • Nubuck material
    • Runs true to size

    Style Number/Barcode: 07403-1570

    Category Name: Vacation Looks

    Price: $12.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Example Tie-Front Lace Trim Crop Top

    You'll be giving off plenty of sweet and sexy vibes in this crop top! Featuring delicate cap sleeves, a flattering lace trim scoop neckline, and dual tie-front closures, this crop top effortlessly adds a touch of romance to any outfit. Complete the look in denim jeans for any casual plans!

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Cap sleeves
    • Lace trim scoop neckline
    • Dual tie-front closures
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06202-0476

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Motorcycle Babe Graphic Crop Tee

    Ride like a babe wearing this graphic crop tee! It features short sleeves, a crew neck with a slit and safety pins, and a front script that reads "Classic American Motorcycles" on stretchy jersey knit fabric. Complete your edgy look in distressed denim jeans.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Slit with safety pins
    • Front graphic script reads "Classic American Motorcycles"
    • Cropped hem
    • Stretchy jersey knit
    • Runs true to size

    Style Number/Barcode: 06002-1442

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Teach Me Tonight Crepe Maxi Skirt

    Teach everyone the art of sultry in this crepe maxi skirt features a high-rise waist, cutout side with lattice bar insets, a form-hugging silhouette, and long length. Complete the look in the matching top and stilettos for drinks and dancing!

    Shop The Matching Top: Teach Me Tonight Crepe Crop Top

    Fit & Features

    • High-rise waist
    • Cutout side with lattice bars
    • Form-hugging silhouette
    • Maxi-length hem
    • Lined crepe fabric
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06501-0736

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Teach Me Tonight Crepe Crop Top

    Teach everyone the art of sultry in this crepe crop top featuring a strapless neckline with a front cutout and lattice bar inset and flexible boning. Complete the look in the matching skirt and stilettos for drinks and dancing!

    Shop The Matching Skirt: Teach Me Tonight Crepe Maxi Skirt

    Fit & Features

    • Strapless neckline
    • Front cutout with lattice bars
    • Flexible boning
    • Cropped hem
    • Lined crepe fabric
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06001-4525

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Growl Play Leopard Knit Cardigan

    Play up your basics for this growl-iscious cardigan featuring cozy long sleeves, ribbed cuffs, button-down front closures, cropped hem, and leopard pattern on a cozy and soft purl knit fabric. Complete the look booties.

    Fit & Features

    • Cozy long sleeves
    • Ribbed cuffs
    • Front button-down closures
    • Cropped hem
    • Leopard pattern
    • Soft and cozy purl knit
    • Fits true to size

    Style Number/Barcode: 06005-1511

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Mood Printed Midi Skirt

    This fab high-rise midi skirt will put you in a bold style mood! It features an elastic band at the waist, ruched detailing down the side seams with adjustable drawstrings at the hem, a midi-length, curve-hugging fit, and an all-over multi-colored abstract print that will catch everyone's eye. The lined mesh fabric offers a moderate stretch. Pair with the matching tube top and strappy heels for a night out with the girls.

    Shop Matching Top: Bold Mood Printed Bustier Tube Top

    Fit & Features

    • High-rise waist, elastic band
    • Ruching down the side seams
    • Adjustable drawstrings at the hem
    • Midi-length hem, form-hugging silhouette
    • Multi-colored abstract print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0732

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Teddy Bear Faux Sherpa Crop Jacket

    The look and feel of your favorite teddy in the comfort of this faux sherpa crop jacket! Stay cozy and cute this season in this jacket featuring drop shoulder long sleeves with buttoned cuffs, a collar neckline, front button-down closures, and flap pockets. Complete the look in trendy lug boots. 

    Fit & Features

    • Drop shoulder long sleeves
    • Buttoned cuffs
    • Collar neckline
    • Front button-down closures
    • Flap pockets, cropped hem
    • Faux sherpa, lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06201-0345

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Your Favorite Puffer Crop Jacket

    Head into the colder season in your new favorite puffer crop jacket! It features long sleeves, a standing collar, side pockets, a front zipper, and a back draw cord for a customizable fit. The jacket this composed of an insulated nylon woven fabric designed to help keep you cozy and protected from the elements! Complete the look in trendy skinny jeans and booties. 

    Fit & Features

    • Long sleeves
    • Standing collar neckline
    • Side pockets, front zipper closure
    • Back adjustable drawcord
    • Cropped length
    • Insulated nylon-woven lined fabric
    • Fits true to size

    Style Number/Barcode: 06201-0344

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect Puffer Crop Jacket

    Achieve an effortlessly cool streetwear vibe by styling this puffer crop jacket for a day in the city! It features long sleeves with elasticized cuffs, a collar neckline, a front zipper, and hidden side pockets. The jacket is composed of an insulated nylon-woven fabric designed to help keep you warm and protected from the elements! Complete the look in skinny jeans. 

    Fit & Features

    • Long sleeves with elasticized cuffs
    • Collar neckline
    • Front zipper, hidden side pockets
    • Cropped length
    • Insulated nylon-woven fabric
    • Fits true to size

    Style Number/Barcode: 06201-0340

    Category Name: Vacation Looks

    Price: $11.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Enticing Beauty Cutout Jumpsuit

    Show off your enticing beauty in this elevated jumpsuit! It features a sleeveless asymmetric one-shoulder neckline with a wide shoulder strap, a twist-front design at the bust, a bold keyhole cutout at the waist, a high waist silhouette, wide pant legs, and a form-hugging fit. The knit fabric offers a moderate stretch. Style with platform heels for a girl's night out.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Wide shoulder strap
    • Twist-front design at the bust
    • Front keyhole cutout at the waist
    • High waist silhouette, wide pant legs
    • Form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2210

    Category Name: Vacation Looks

    Price: $23.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Harper Mid-Rise Frayed Skinny Jeans by Windsor Denim

    Forever flattering and so stylish, what more could you ask for? This pair of Harper mid-rise skinny jeans by Windsor Denim feature a skinny-leg silhouette, a clean design with no distressing, and a trendy frayed hem. The medium-wash denim fabric has a vintage-inspired color fade effect and offers a form-hugging fit with a moderate stretch. Style with your favorite bodysuit and clear heels.

    Fit & Features

    • Mid-rise waist
    • Skinny-leg silhouette
    • Clean design, no distressing
    • Frayed hem
    • Five-pocket design, belt loops, front button, hidden zipper closure
    • Medium-wash denim fabric, color fade effect
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0356

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chromatic Babe Crop Puffer Jacket

    Your future is looking chromatic! Create a total babe vibe with this iridescent puffer crop jacket featuring long sleeves, a standing collar, front zipper, and side pockets, and a back drawcord to customize the fit. The jacket is composed of an insulated nylon-woven fabric designed to help keep you warm and protected from the elements! Complete the look in sleek booties.

    Fit & Features

    • Long sleeves, standing collar 
    • Front zipper, side pockets
    • Adjustable back drawcord
    • Cropped length
    • Insulated nylon-woven fabric
    • Chrome iridescent design
    • Fits true to size

    Style Number/Barcode: 06201-0339

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fashion Strut Faux Leather Platform Booties

    The world is your runway fashionista in these strut-worthy faux leather booties featuring an almond toe, block heel, side zipper closure, and platform sole. Complete the look in skinny denim jeans.

    Fit & Features

    • Almond toe
    • Block heel
    • Side zipper closure
    • Platform sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1562

    Category Name: Vacation Looks

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Status Croc-Embossed Handbag

    Showcase your trendy status with this chic croc-embossed handbag! Featuring an angled shape, a top handle design, and an included adjustable shoulder strap, this bag is perf for everyday wear. Style with statement earrings.

    Fit & Features

    • Angled shape
    • Top handle design
    • Magnetic button closure
    • Removable adjustable shoulder strap
    • Croc-embossed pattern
    • Faux leather fabric
    • Woven interior, single zippered pocket

    Style Number/Barcode: 07204-0674

    Category Name: Vacation Looks

    Price: $4.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Babe Halter Plunge Neck Romper

    Perfect for a day or night out, this romper will make you stand out from the crowd with its flowy and flattering design. The halter plunge neck adds a touch of daring while the open back enhances your silhouette. 

    Fit & Features

    • Knit fabric, stretchy knit shorts lining
    • Plunge halter neckline, tie straps
    • Open back
    • Flowy mini skirt overlay
    • Runs true to size

    Style Number/Barcode: 06503-000064

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall Back On Block Heel Booties

    This season, you'll be reaching for these sleek faux leather booties featuring a trendy square toe, block heel, side zipper closure, and fit above the ankle. Complete the look in a plaid coat for a PSL run!

    Fit & Features

    • Square toe
    • Block heel
    • Side zipper closure
    • Above the ankle fit
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1558

    Category Name: Vacation Looks

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Sleek Round Sunglasses

    These simple sleek round sunglasses are perfect for an everyday chic look. They feature a metal frame with hexagon-shaped tinted lenses and thin metal arms. Style these shades with hoop earrings.

    Fit & Features

    • Metal frame
    • Hexagon-shaped tinted lenses
    • Rubber nose pads
    • Thin metal arms

    Style Number/Barcode: 07008-0957

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take A Look Sweater Midi Dress

    Let everyone take a look at you in this sweet sweater midi dress perfect for the autumn season! This dress features a sleeveless halter neck with tie closure, a bodycon silhouette, and a cutout waist with a front slit along the hem. Complete the look in pointy-toe booties.

    Fit & Features

    • Sleeveless halter neck with tie closure
    • Bodycon silhouette
    • Cutout waist, front slit
    • Midi-length hem
    • Rib-knit sweater fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1416

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edgy Stunner Graphic T-Shirt Dress

    Show off an edgy style with this on-trend graphic t-shirt dress! It features a crew neckline with a notched design with safety pin detailing, short sleeves, a mini-length, fitted silhouette, and a motorcycle and eagle graphic with the script "American Motorcycles Road Lifestyle 1974." Complete your 'fit with combat boots.

    Fit & Features

    • Crew neckline, notched design, safety pin detailing
    • Short sleeves
    • Mini-length hem, form-hugging fit
    • Motorcycle and eagle graphic
    • Script that reads, "American Motorcycles Road Lifestyle 1974"
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1445

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free