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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Butterfly Kisses Ring 10 Pack
Keep the style going down to your finger tips! This set includes a variety of ten multi sized rings. They showcase chain link designs, a heart midi ring, and butterflies! Layer them up for a boho glam look!Style Number/Barcode: 07004-0029
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Satin Tie Front Kimono
Designed with a satin fabric, a deep V neckline, quarter sleeves, and a cropped hem, this kimono tie front top is feeling like a new closet staple! Offering a relaxed fit, this satin blouse adds style to your look. Pair with high waist pants and you are good to go!
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06204-0165
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fierce Leopard Sleeveless Midi Dress
Get spotted in this sleek midi dress to make a fierce statement! It features sleeveless bodice, a cowl neckline, adjustable straps and a midi length silhouette. The all over leopard print is all you need to stay on trend. Dress is composed of a lined semi-sheer lightweight woven fabric that offers a relaxed fit with a minimal stretch. Includes a back zipper closure.
Style Number/Barcode: 05101-0352
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Print Wrap Front Midi Dress
You're quite the fierce fashionista, so this leopard print midi suits you! The dress features a sleeveless bodice, adjustable spaghetti straps, a wrap front V neckline, a V back with a hidden zipper closure, a high waist seam with a wrap front skirt with a faux tie detail, and a mid-length, flowy fit. Dress is comosed of a sheer textured woven fabric with a short woven lining.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0396
Category Name: Vacation Looks
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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F*ck You Next Cap
Ummmm NEXT! Send a straight forward message in a cap designed for a baddie. This baseball cap that features front embroidered text and an adjustable back buckle closure.Style Number/Barcode: 07302-0117
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Textured Knit Cabby Hat
Style Number/Barcode: 07301-0078
Category Name: Vacation Looks
Price: $5.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rainbow Marquise Rhinestone Hair Pins
Add a pop of color to that updo lady! This pack includes two hair pins that are bobby style and are varied shaped of marquise stones and circular stones.Style Number/Barcode: 07006-0100
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shell Choker Necklace
This adorable shell choker is totally beach babe approved! The necklace features a row of seashells woven together with a single gold accent shell, and includes a gold adjustable chain and lobster clasp closure.Style Number/Barcode: 07002-0252
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake Print Ruffle Mini Dress
Ruffle up the style game with this on trend snake print mini dress. It features a sleeveless bodice, adjustable spaghetti straps that lead to a halter back, a deep V neckline, and a high waist seam with a tiered, ruffled flowy skirt. The dress is composed of a chiffon fabric with a woven lining and has no stretch.Style Number/Barcode: 05101-0386
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Call Of The Wild Cross Body
Answer the call as you slay with this fierce cross body! It features an envelope design with snap button closure, a large zippered compartment and a detachable shoulder chain strap. The body is composed of a faux suede material. The interior is composed of a nylon material and includes card slots.
Style Number/Barcode: 07201-0001
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Rise Slit Skinny Jeans
Take on the day with these must have skinny jeans! They feature a high rise waist, a traditional five pocket with belt loop design, a single button with zipper closure, knee slit accents and a skinny leg fit with tapered leg. Jeans are composed of a stretchy denim fabric that offer a curve hugging fit.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06602-0050
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bejeweled Headband
Add some jewels to your look! This open ended headband features a knot accent at the center and is composed of a satin material. Headband is structured and has multi colored, multi sized stones throughout!Style Number/Barcode: 07006-0063
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pearl Embellished Headband
Add a little to your look with a headband! This open ended band is composed of a knit material that sheen finish and has a sweet pearl accent off center with little touches of rhinestone.Style Number/Barcode: 07006-0062
Category Name: Vacation Looks
Price: $12.90
Availability: Out of Stock
Product Badge:- Ships Free
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Parisian Girlie Wool Beret
Add a pinch of Parisian chic to your wardrobe in this classic beret – ooh la la! Crafted from a soft and luxe wool-blend material with a classic beret design, this hat offers lasting beauty and warmth. Complete the look in a cute faux leather jacket for your next trip to Europe or inspired cafe!
Fit & Features
- Classic beret design
- Wool-blend material
- Soft and comfortable
Style Number/Barcode: 07302-1540
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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High Waist Destructed Shorts
Oasis by EuninaFreshen up your spring wardrobe with this pair of high waist destructed shorts! The white denim bottoms feature a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, distressed detailing down the front, and a cuffed hem. The shorts offer moderate stretch and a form-fitting style.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.Style Number/Barcode: 06603-0761
Category Name: Vacation Looks
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tortoise Shell Hair Clips
Step up your hair accessory game with these trendy tortoise shell hair clips! The set features two alligator style clips, one with an open accent.Style Number/Barcode: 07006-0070
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take Me To The Edge Cropped Jeans
Give your look an edge of attitude with these must have jeans! They feature a high rise waist, a single button with zipper closure, a traditional belt loop with five pocket design, and a skinny leg fit with heavy distressed detailing and slits throughout. Jeans are composed of a denim fabric that offers a curve hugging fit with a moderate stretch.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06602-0046
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wrap Around My Heart Dress
You're looking like hot stuff this evening, babes! This dress has a wrap bodice with a deep V neckline, spaghetti straps, and ruching on the side. A wrap skirt creates an asymmetrical hemline for a party perfect ensemble. Dress is composed of an unlined crepe fabric that offers a moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-3609
Category Name: Vacation Looks
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snake Print Long Sleeve Crop Top
Strut in snake print! This crop top features a deep v neckline, long sleeves that puff at the wrist and a tie front closure. It is composed of a semi sheer chiffon material that showcases a neutral snake print design. Top offers a relaxed fit.
Model is 5'9" with a 32" bust, 24.5" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06204-0247
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On A Mission Bikini Bottom
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.You're on a mission to kick it beachside! This swim bottom features a high rise fit, open sides with large gold metal grommets and tie straps, and a full coverage bottom.
Model is 5'9 with a 33" bust, a 24" waist, and 35.5" hips. She is wearing a size small.Style Number/Barcode: 07105-0022
Category Name: Vacation Looks
Price: $15.87 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Don't Cross Me Anklet Set
This set includes two sleek designed toe rings that are open ended, as well as a dainty chain anklet with two rows and cross charms that dangle and reflect with the help of the dazzling rhinestones! Anklet has a lobster clasp closure and is adjustable in size.
Style Number/Barcode: 07003-0028
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Buttoned Beauty Ribbed Mini Dress
Button up in this cute mini for the perfect day out! It features an off the shoulder neckline, a multi button down front, fitted long sleeves and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a curve hugging fit with a moderate stretch.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0272
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Josie Mid Rise Skinny Jeans
Oasis By Eunina
Introducing your new favorite skinnies. These jeans feature a high waist, zip fly, 5-pocket styling and light destruction detail. They're made of a stretchy denim and have a body-hugging fit.
Style Number/Barcode: 06602-0004
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Staple Strap Sandals
Make these sandals a staple to your closet! The simple design features a single strap as well as an adjustable ankle strap with a gold hued buckle closure. They also feature a chain detailing around the edge of the foot. They are composed of a faux leather material that makes them work with any outfit!
Style Number/Barcode: 07404-0026
Category Name: Vacation Looks
Price: $12.97
Availability: Out of Stock
Product Badge:- Ships Free