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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Cool Cluster Cubic Zirconia Earring Pack
Keep all of your must-have classic styles on hand (and in-ear!) with this fab 5-pack! Includes five sets of different cluster-design mini cubic zirconia studs with post-back closure.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0074
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Buckled Strappy Platforms
Everyone needs a pair of simple flat platforms for those days you don't feel like wearing heels! These strappy platforms feature an open toe, and a double ankle strap that meets at a pin buckle closure with toned hardware. These sandals are composed of a faux leather material.
Style Number/Barcode: 07404-0070
Category Name: Vacation Looks
Price: $12.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Caged And Chic Block Heels
Step out and make each strut a chic one in these statement heels! They feature a closed zippered back, a double row buckle strap accent, a multi strap caged design, an open toe and a block heel. They are composed of a faux nubuck material.
Style Number/Barcode: 07404-0507
Category Name: Vacation Looks
Price: $16.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Catch Rays Shield Sunglasses
Catch rays, not feelings! These oversized sunglasses feature a flat top design, a large square frame, and semi-sheer brown lenses.
Style Number/Barcode: 07008-0515
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Especially Espadrille Platform Sandals
Take on the weekend in these especially cute Espadrille platform sandals! They feature an open toe with a wide strap, an adjustable ankle strap with a metal buckle, and a woven platform wedge heels that are adorned with a braided detail. Straps are composed of a faux suede material.
Style Number/Barcode: 07406-0019
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Call Of The Wild Sarong Cover Up
Wrap yourself in this wildly inspired sarong wrap! It features an all over leopard print and an asymmetrical hem. Cover up is composed of a semi-sheer knit fabric that offers a relaxed fit.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07305-0003
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Two Strap Double Buckle Sandals
For those days when a heel or platform simply won't do—get grounded and comfy in these chic sandals. They feature two thick buckle straps across the toe box and middle, a wider cork-style footbed, and a contrast traction sole. Shoes are made from a faux leather material.
Style Number/Barcode: 07404-0079
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet Summertime Wedges
Live easy in these sweet espadrille style platform wedges! They feature a thick single strap, a closed back heel and an adjustable ankle strap with a buckle closure. The wedge heel is composed of a braided rope material. Every day is one step closer to summer!
Style Number/Barcode: 07406-0223
Category Name: Vacation Looks
Price: $18.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Superb Woven Platform Sandals
Step out in style with these holographic platform sandals! Featuring two bands, one at the toe and one mid foot. The sandals have a holographic reflection, a woven espadrille platform, an easy grip sole, and a faux leather lining. These Sandals are easy to slide on and above all comfortable!Style Number/Barcode: 07404-0073
Category Name: Vacation Looks
Price: $17.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spotted in Leopard Flats
We spot a trend setter! These slide on leopard flats are so trendy, and we love it! Point toed, and an open back sets the vibe of an effortless cool. These flats are composed of a suede-like material as well as lined with a faux leather. Slip them on and step out for the day in style!Style Number/Barcode: 07405-0004
Category Name: Vacation Looks
Price: $13.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Slide Right In Sandal
Consider this ultra-chic flat your new warm-weather bestie. Sandals have a gold-tone buckle strap, crisscross strap across the toes, and toe loop. Sandals are made from a faux leather material and have a faux leather lining.Style Number/Barcode: 07404-0042
Category Name: Vacation Looks
Price: $12.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sassy Sling Back Espadrilles
Make each step a sassy and stylish one in these cute sling back espadrilles! They feature an open toe, faux suede double strap detailing, an around the ankle adjustable strap, an open heel, and an espadrille wedge heel with glitter woven throughout.
Style Number/Barcode: 07406-0013
Category Name: Vacation Looks
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone Fringe Belt
Never be afraid to bling ! This blingtastic belt adds all the sparkle to your ootd. With four rows of rhinestones at the belt, and adjustable lobster clasp closure this silver skirt is composed of rhinestone fringe. Twist and dazzle them all!Style Number/Barcode: 07301-0041
Category Name: Vacation Looks
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High-Rise Straight Cropped Jeans by Windsor Denim
Serve major style in these fabulous straight cropped jeans by Windsor Denim! They feature a flattering high-rise waist, a straight-leg silhouette, knee destruction accents, and a front cut-off style cropped hem. The medium-wash denim fabric offers a moderate stretch for comfortable wear. Complete the look in a cute corset top for a casual dinner!
Fit & Features
- High-rise waist
- Straight-leg silhouette, knee destruction accents
- Front cut-off cropped hem
- Front button, hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium-wash denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0416
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Making The Gradient Rimless Sunglasses
Soak up the sun—or beat the heat—in a pair of classically chic aviator-style sunnies. Glasses feature rimless gradient lenses and gold-tone temples, brow bar, and bridge.Style Number/Barcode: 07008-0655
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lovely Lace Up Espadrilles
These lovely lace up espadrilles are perf for your next brunch with the girls! They feature a closed woven toe and partially closed back, a woven strap that laces up the leg, and an espadrille wedge heel.
Style Number/Barcode: 07406-0015
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Gal Cat Eye Sunglasses
Girl, you'll look oh so glamorous in these flashy cat eye sunnies! The gold sunglasses feature a metal cat eye frame with small cut outs, gemstone accents on the sides, and brown tinted lenses.
Style Number/Barcode: 07008-0590
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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5 Row Swag Chain Belt
Yasss girl! Come through with plenty of confidence in this must have belt! The swag belt features 5 rows of draped chain links and an adjustable clasp closure.
Style Number/Barcode: 07301-0045
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boho Tassel Floral Earrings
Become a boho babe with these tassel earrings! They feature a floral rhinestone accent with post back closure anchored by swing-y, shoulder-grazing tassels.
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-4483
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Variety Pack Hair Scrunchies
Hold your locks in place with these basic scrunchies! Five piece set includes black, gray, beige, white, and pink colored hair scrunchies that are composed of a soft to the touch fabric.
Style Number/Barcode: 07006-0824
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Essential Braided T-Strap Sandals
These sandals will become your go-to for all your fave looks this season! They feature an open back, an adjustable ankle strap, a braided T-strap and a flat faux leather insole lining.
Style Number/Barcode: 07404-0087
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Espadrille Woven Mules
These slip on mules feature a square shaped open toe, as well as an open heel. They have two bands, one across the toes and a thicker one that crosses mid foot. The short heel and bands are composed of a knit woven material, and the inner lining is composed of a faux leather material. Pairs well with a day dress or your favorite pants! They are casually trendy
Style Number/Barcode: 07404-0063
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Drippin' In Rhinestones Swim Bottom
Girl, you'll be drippin' in rhinestones with these fab black swim bottoms! They feature a high rise waist band adorned with mini rhinestones and a partial coverage bottom. Complete your look with the matching swim top!Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0096
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Americana Swim Bottom
Rock some stars and stripes to show off your patriotic pride! These blue swim bottoms feature a hipster cut with cheeky bottom and contrasting white stars! Be sure to pick up the matching top to fully represent the USA!Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.Style Number/Barcode: 07105-0433
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free