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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Catalyst Rhinestone Hoops
Create a spark with these breath-taking hoops! The have a thick hoop design adorned with multiple mini rhinestones that sparkle with every move. The thick hoops include an omega closure.
Style Number/Barcode: 07001-4195
Category Name: Vacation Looks
Price: $4.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sporty Chick High-Rise Nylon Skort
Show off your sporty style in this high-rise nylon skort, whether sitting on the sidelines or on the pickleball court! The skort is designed with an adjustable drawstring waist, convenient side pockets, and a sleek mini-length overlay with knit shorts lining. Pair with sneakers.
Fit & Features
- Nylon woven fabric, minimal stretch
- High-rise elasticized and adjustable drawstring waist
- Side pockets
- Mini-length overlay
- Stretchy knit shorts lining
- Skort in size small has a 10" front rise with a 1.5" inseam
- Runs true to size
Style Number/Barcode: 06303-0292
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Door Knocker Neon Earrings
They'll be knockin' on your door asking where those fab neon pink earrings are from! They feature a large, square, door-knocker design, a textured plastic material, and post back closures.
Style Number/Barcode: 07001-0036
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Level Up High Waist Shorts
Oasis by EuninaTake your look to the next level in these statement making shorts! They feature a high rise waist, a single button with zipper closure, a classic five pocket with belt loop design, light destruction and a frayed hem. Shorts are composed of a lightly faded black denim fabric with moderate stretch.
Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.Style Number/Barcode: 06603-0759
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Clearance
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All That Glitters Textured Earrings
Bring the glam in these dazzling gold hued earrings! They feature a a textured disc on post and an attached large textured O ring.
Style Number/Barcode: 07001-0028
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Distressed With Style Jean Shorts
Stylishly distress your look and add some edge with these classic jean shorts! They feature a high rise waist, the traditional five pocket and belt loop design, a front button down closure, and a distressed and frayed hem. The shorts are composed of a denim fabric with no stretch.
Style Number/Barcode: 06603-0776
Category Name: Vacation Looks
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Shine In Rhine Earrings
Shine in rhine with these gorgeously glam silver earrings! They feature a an open circular post connected to double hoops. The earrings are adorned with sparkling rhinestones and include a post back closure.
Style Number/Barcode: 07001-0001
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Don't Stress Denim Overalls
Let go of the stress and relax in these cute overalls! They have a small bib pocket and feature adjustable straps. The shorts feature a belt loop waist with button details and two basic front pockets. The jean overalls also feature a light distressed detail.Model is 5'7" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06603-0773
Category Name: Vacation Looks
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Add Some Edge Romper
Add some edge to your look with this trendy jean romper! It features a collar, a snap button down front, long sleeves with buttons to cuff, two front snap button pockets, two front pockets and two back pockets, and a majorly distressed hem. The romper is composed of a light wash denim fabric with no stretch.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06603-0772
Category Name: Vacation Looks
Price: $5.00 $72.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylishly Destructed Jean Shorts
These stylishly destructed jean shorts are a must have for sure! They feature a mid rise waist, the traditional five pocket and belt loop design, a single front button and zipper closure, and major distressing down the front with a frayed hem. The bermuda shorts are composed of a medium wash denim fabric that offers moderate stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06603-0767
Category Name: Vacation Looks
Price: $5.00 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute As A Button Down Jean Shorts
Because cute is your middle name! This must have pair of jean shorts feature a high waist, the traditional 5 pocket and belt loop design, a 5 button down front closure, rolled hems, slight destruction and a light wash.Model is 5'8 with a 32" bust, 24.5" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06603-0755
Category Name: Vacation Looks
Price: $28.90
Availability: Out of Stock
Product Badge:- Clearance
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Stylishly Distressed Shortalls
Stylishly distress your look with these cute jean shortalls! They feature a sleeveless bodice, adjustable shoulder straps with hook closures, a front kangaroo and mini pocket, belt loops, side buttons, two front and back pockets, slight destructed detailing, and a cuffed hem. The medium wash shortalls are composed of a denim fabric that offers moderate stretch.Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06603-0764
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Side Cut Out Jean Shorts
Change up your denim game with these side cut out jean shorts! They feature a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, a frayed hem, and cut outs with bar accents along the sides. The acid wash jean shorts are composed of a denim fabric that offers a form-fitting style with moderate stretch.Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 06603-0757
Category Name: Vacation Looks
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Distressed Diva High Waist Shorts
Take your look to the next level with these shorts to give you that extra boost! They feature a high rise waist, a multi button down front, a traditional five pocket design, distressed detailing and a frayed cut-off style hem. They are composed of a light-medium wash and offer a form hugging fit with a slight stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06603-0750
Category Name: Vacation Looks
Price: $10.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lulu High Waist Frayed Shorts
Oasis by Eunina
These frayed jean shorts are so cute, you'll want to wear them all day, everyday! They feature a high rise fit, the traditional five pocket and belt loop design, a front button closure, slight distressed detailing, and a frayed hem. The shorts are composed of a denim fabric with a form-fitting style.Style Number/Barcode: 06603-0741
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Easily Gorgeous Strapless Cable Knit Midi Dress
Flaunt your gorgeous curves in this chic cable knit midi dress for brunch or a casual party. The dress boasts a flattering bodycon silhouette and a center back slit for movement.
Fit & Features
- Cable knit design, soft stretchy knit lining
- Strapless neckline
- Bodycon silhouette
- Center back slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5898
Category Name: Vacation Looks
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lexi Mid Rise Cuffed Jean Shorts
Oasis by Eunina
Get ready for the new season in these distressed and cuffed jean shorts! They feature a mid rise waist, the traditional five pocket and belt loop design, a front button and zipper closure, slight destructed detailing, and a rolled, cuffed hem. The shorts are composed of a medium denim fabric that offers moderate stretch.
Style Number/Barcode: 06603-0742
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Girl Next Door Cuffed Overalls
Keep it low key and cute in these must have overalls! They have a small bib pocket and feature adjustable straps. The shorts feature a belt loop waist with button details and two basic front pockets. Overalls are composed of a medium wash denim fabric that offers a form hugging fit.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small
Style Number/Barcode: 06603-0012
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cuffed Up For Summer Denim Shorts
Oasis by EuninaGet on that summer romance with these super cute blue denim jean shorts. They feature a mid-rise waist, the traditional five-pocket and belt loop design, moderate distressing and cuffed raw hems. Shorts offer a form hugging fit with a moderate stretch.
Model is 5'7" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.Style Number/Barcode: 06603-0009
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Fling Denim Shorts
Have some fun this summer in these cute denim jean shorts! They feature a high waist, the traditional five pocket and belt loop design, a single button and zipper closure, and raw hems. 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: 06603-0007
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Break Away Destructed Shorts
Break away from average in these edgy black jean shorts! They feature a high waist, a standard five pocket and belt loop design, a front zipper and button closure, and a frayed, rough cut hem. Shorts are composed of a black, denim jean fabric that offer a form hugging fit with a moderate stretch.Model is 5'8 with a 32" bust, 23" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 06603-0010
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Clearance
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Low Rise Distressed And Cuffed Jean Shorts
These distressed and cuffed jean shorts are perf for the summer season! They feature a low rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, slight distressed detailing, and a raw cut cuffed hem. The light wash jean shorts are composed of a denim fabric with moderate stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06603-0005
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rural Chic Button Front Overalls
Mix that rural style with your city chic for a super cute look! These dark blue denim jean overalls feature a below the bust bib, traditional overall straps, a button down front and a skinny leg. Overalls are composed of a denim fabric with moderate stretch.Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06602-1634
Category Name: Vacation Looks
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy And Striped Skater Romper
Make your look sassy and stylish with this adorable black and white striped skater romper! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a high waist seam, fitted shorts, and a flowy skater skirt overlay with a front slit. The romper is composed of a textured knit fabric with moderate stretch.Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06503-0942
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance