Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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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.
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She's A Trendsetter Zebra Faux Fur Coat
Layer on this fab zebra-printed faux fur coat for a total trendsetter vibe. It features an open front with a lapel collar, long sleeves, front pockets, and a relaxed fit. The zebra-printed faux fur fabric is ultra-soft to the touch for cozy wear. Style over a sweater dress with ankle booties.
Fit & Features
- Open front, lapel collar
- Long sleeves
- Lined front pockets
- Relaxed fit
- Zebra print
- Faux fur fabric, smooth lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0335
Category Name: Vacation Looks
Price: $14.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cable Knit Vibes Crop Sweater
Embrace the autumn chill in this cable knit crop sweater featuring cozy long sleeves and a crew neckline on soft acrylic-knit fabric. Complete the look in jeans and knee-high boots.
Fit & Features
- Cozy long sleeves
- Crew neckline
- Cable knit design
- Cropped hem
- Soft acrylic-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1523
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Make Hearts Flutter Butterfly Hair Clip
Make his heart flutter in this whimsical butterfly hair claw clip! Perfect for sweeping your hair up into a chic updo. Complete the look in a casual dress for a day date.
Fit & Features
- Butterfly hair claw clip
- Sleek metal frame
Style Number/Barcode: 07006-0351
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutie At Heart Cutout Mini Skirt
Sweeten your every vibe in this bodycon mini skirt with a heart insert and a cutout that adds a cute look!
Fit & Features
- Smooth knit stretchy fabric
- High-rise waist
- Heart insert and cutout
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06501-000006
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Peek-A-Boo Faux Suede Booties
Peek-a-boo do you see these chic shoes? Strut the catwalk in these faux suede booties featuring a peep toe almond toe, block heel, and a front lace-up placket and side zipper closure. Complete the look in a wide-leg jumpsuit.
Fit & Features
- Peep almond toe
- Block heel
- Front lace-up placket
- Side zipper closure
- Faux suede material
- Runs true to size
Style Number/Barcode: 07403-1483
Category Name: Vacation Looks
Price: $38.90
Availability: Out of Stock
Product Badge:- Sale
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Close Up Square Toe Block Heels
You'll be ready for your close-up in these faux leather block heels featuring a trendy square toe, platform sole, and an adjustable buckle ankle strap. Complete your gorgeous look in a chic ring set.
Fit & Features
- Square toe
- Platform sole
- Block heel
- Adjustable buckle ankle strap
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3973
Category Name: Vacation Looks
Price: $4.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy In Cable Knit Turtleneck Sweater
Cozy and cute, what could be better for your autumn closet than this cable knit turtleneck sweater? It features long sleeves, a foldover neck, and a cropped distressed hem. Complete the look in faux leather pants.
Fit & Features
- Long sleeves
- Foldover turtleneck
- Crop, distressed hem
- Cable knit design
- Fits true to size
Style Number/Barcode: 06005-1538
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Winter Must-Have Cropped Puffer Vest
This adorable cropped puffer vest is a winter must-have! It features a sleeveless collared neckline, a complete zip front, and a cinched elastic cropped hem for a fab fit. The vest is composed of a lined nylon-woven fabric with insulation to help keep you warm and protected from the elements. Style over a long sleeve bodysuit with cargo pants.
Fit & Features
- Sleeveless collared neckline
- Zip front
- Cinched elastic cropped hem
- Insulated and lined nylon-woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0369
Category Name: Vacation Looks
Price: $17.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Winter Chic Houndstooth Knit Beanie
This chic knit beanie is perfect for elevating your winter wardrobe. It features an all-over houndstooth pattern, a ribbed hem, and a faux fur pom accent. Style with a sweater and faux leather leggings.
Fit & Features
- Houndstooth pattern
- Ribbed hem
- Faux fur pom
- Knit fabric, minimal stretch
Style Number/Barcode: 07302-0871
Category Name: Vacation Looks
Price: $4.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Essentially Cozy Chenille PJ Robe
Cozy vibes all around! Snuggle up in this chenille PJ robe featuring long sleeves, and an open-front design, belted tie-front, belt loops, pockets, and a relaxed fit. Complete the look with the matching top and bottoms.
Shop The Matching Set: Essentially Cozy Chenille PJ Top, Essentially Cozy Chenille PJ Joggers
Fit & Features
- Long sleeves
- Open front design
- Pockets
- Belted tie-front, belt loops
- Soft and comfortable
- Chenille fabric
- Fits true to size
Style Number/Barcode: 07106-0089
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Babe Over-The-Knee Boots
Show off total retro vibes in these sleek faux leather boots! They feature an over-the-knee height with an inner zipper closure, a pointed toe, and a stacked block heel. Style with your fave mini dress.
Fit & Features
- Over-the-knee height
- Inner zipper closure
- Pointed toe
- Stacked block heel
- Faux leather material, elastic detail at the back
- Runs true to size
Style Number/Barcode: 07402-0815
Category Name: Vacation Looks
Price: $34.97 $43.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Autumn Chic Mini Sweater Dress
This form-hugging sweater dress will give you that autumn chic vibe! It features a crew neckline, long fitted sleeves, asymmetrical ruched detailing with an adjustable drawstring, and a short, fitted silhouette. The stretchy ribbed knit fabric has a trendy space-dye design for an eye-catching look. Style with knee-high boots.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Asymmetrical ruching, side drawstring
- Mini-length hem, form-hugging fit
- Stretchy ribbed sweater knit fabric
- Space-dye design
- Runs true to size
Style Number/Barcode: 06005-1584
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Full Throttle Motocycle Graphic Tee
Live life on the edge in this trendy cropped graphic tee! It features a crew neckline with a cut notched front design, short sleeves, a motorcycle and wings graphic with the scripts "Full Throttle" and "Live To Ride, Ride To Live," and a form-hugging fit. The cotton-blend fabric offers a moderate stretch. Style with distressed denim.
Fit & Features
- Crew neckline, notched front design
- Short sleeves
- Motorcycle, wings, and flames graphic
- Script that reads "Full Throttle" and "Live To Ride, Ride To Live"
- Cropped hem, form-hugging fit
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1457
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cool Girl Cargo Skinny Pants
Show off your cool-girl style in these trendy cargo skinny pants. They feature a mid-rise waist, a button-front closure, faux cargo-style flap pockets, and a tapered, form-hugging fit. The woven cotton-blend fabric has no stretch. Style with a graphic tee and combat boots.
Fit & Features
- Mid-rise waist
- Belt loops
- Hidden zipper, button-front closure
- Front pockets, faux cargo-style flap pockets
- Skinny-leg silhouette, form-hugging fit
- Woven cotton-blend fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0700
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pour The Whiskey Graphic Crop Tee
Show off what kind of a girl you are! This graphic crop tee features cap sleeves, a crew neck, and front text that reads, "Whiskey Bent And Hell Bound" printed on soft and stretchy jersey knit fabric. Complete the look in trendy distressed jeans for happy hour!
Fit & Features
- Cap sleeves
- Crew neck
- Front text that reads, "Whiskey Bent And Hell Bound"
- Cropped hem
- Jersey knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1460
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Down To Business Ponte Leggings
Get your style down to business this season! These ponte knit leggings are designed for work or play in a sleek elasticized high-rise waistband, faux front zipper pockets, a skinny leg design, and tapered hem. Complete the look in a plaid vest and booties.
Fit & Features
- High-rise elasticized waistband
- Faux front zipper pockets
- Skinny-leg design
- Tapered hem
- Sculpting design
- Ponte knit fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06502-2226
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Scorpio Season Graphic Crop Tee
It's time to celebrate the season of the Scorpio! This graphic crop tee features cap sleeves, a crew neck, and a front script that reads, "It's The Scorpio In Me" printed on soft and stretchy jersey knit fabric. Complete the look in a faux leather mini skirt for a party!
Fit & Features
- Cap sleeves
- Crew neck
- Front script reads, "It's The Scorpio In Me"
- Cropped hem
- Soft and stretchy
- Jersey knit fabric
- Fits true to size
Style Number/Barcode: 06002-1475
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Romance Floral Lace-Up Maxi Dress
Evoke chic romance on date night in this gorgeous floral maxi dress designed with an open lace-up strappy back and floor-length form-hugging silhouette. Style with a sleek handbag and stiletto heels.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Large floral print
- Sleeveless deep V-neckline
- Spaghetti straps
- Open cross-back lace-up strappy design
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000111
Category Name: Vacation Looks
Price: $7.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute In Checkered Faux Sherpa Jacket
Achieve a cute streetwear style layering on this checkered hoodie jacket featuring long sleeves, an open-front design, hidden side pockets, oversized silhouette, crafted on faux sherpa-lined fabric. Complete the look in edgy booties.
Fit & Features
- Long sleeves
- Hoodie neckline
- Open-front design
- Hidden lined side pockets
- Oversized silhouette
- Checker pattern, faux sherpa fabric, lined, no stretch
- Runs true to size
Style Number/Barcode: 06201-0360
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cheer Spirit Ponte Pleated Skirt
Catch the stylish spirit of this ponte pleated skirt everyone will be cheering for! It features a high-rise waist, skater silhouette, and a short-length hem. Complete the look in a basic bodysuit.
Fit & Features
- High-rise waist
- Skater silhouette
- Pleating
- Short-length hem
- Ponte knit fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06501-0708
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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French Girl Wool Beret
Elevate your outfit to french girl status with this faux wool beret perfect for styling with a chic trench coat for a day out and about!
Fit & Features
- Beret style
- Wool material
Style Number/Barcode: 07302-1322
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rhinestone Star Beaded Beanie
Shine bright this holiday season with a cozy beanie that keeps it glam! This ribbed knit beanie features a fold-over hem with rhinestone embellishments in star designs and sparkly beaded detailing. Style with a sweater dress and a faux leather jacket.
Fit & Features
- Ribbed knit fabric
- Fold-over hem
- Rhinestone embellishments, star designs
- Beaded detailing
Style Number/Barcode: 07302-1323
Category Name: Vacation Looks
Price: $8.00 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Like Me Over The Knee Boots
Smooth and sultry, these over-the-knee boots are the ticket to an elevated style! They feature an almond toe, block heel, and side zipper closure, an adjustable drawcord at the top, and are composed of faux suede material. Complete the look in high-rise skinny jeans.
Fit & Features
- Almond toe
- Side zipper closure
- Block heel
- Over-the-knee shaft length
- Adjustable drawcord at the top
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0851
Category Name: Vacation Looks
Price: $12.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Peep This Chic Cutout Booties
Check out these chic nubuck booties and imagine all the ways you'd style them! They feature an almond peep toe, platform sole, stacked thin block heel, cutout sides, and an adjustable buckle strap and back zipper closure. Complete the look in a wide-leg jumpsuit for cocktail hour.
Fit & Features
- Almond peep toe
- Platform sole
- Stacked thin block heel
- Cutout sides
- Adjustable buckle strap and back zipper closure
- Nubuck material
- Runs true to size
Style Number/Barcode: 07403-1567
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale