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 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.
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Denim Diva Sleeveless Catsuit
Showcase your fashion diva side in this trendy denim catsuit! It features a sleeveless bodice, tank straps, a V neck and back, and a back zipper closure. The high waist leads to form-fitting pant legs, offering a curve-hugging style. The denim fabric offers moderate stretch. Complete your look with a chic necklace and heels.
Fit & Features
- Tank straps
- V neck and back
- Back zipper closure
- High waist
- Fitted pant legs
- Form-hugging fit
- Denim fabric with a moderate stretch
Style Number/Barcode: 06602-0088
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweet And Stylish Paper Bag Shorts
Show off your sweet style in these adorable paper bag shorts! They feature a high-rise waist with a tie-front belt, front pockets, a single back pocket, and a fitted silhouette. Pair these chic dressy woven shorts with a crop top and cute wedges.
Fit & Features
- High-rise paper bag waist
- Tie-front belt
- Front pockets
- Single back pocket
- Fitted silhouette
- Woven fabric
- Runs true to size
Style Number/Barcode: 06403-0144
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Walk In The Park Eyelet Lace-Up Espadrille Wedges
From brunch to a day at the park, these wedges will keep you comfortable and stylish all day long. Featuring a delicate eyelet design and a lace-up ankle strap, these espadrille wedges are perfect for adding a touch of cuteness to any outfit.
Fit & Features
- 4" Wedge heel
- Closed almond toe with eyelet inset
- Lace-up ankle strap
- Espadrille material
- Runs true to size
Style Number/Barcode: 07406-000012
Category Name: Vacation Looks
Price: $12.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gorgeous Getaway One-Piece Swimsuit
Look absolutely gorgeous for your weekend getaway in this adorable one-piece swimsuit! It features thin shoulder straps that lead to a backless design, a V neckline with a zipper front, open side details, a semi-cheeky fit, and an all-over tropical print. Layer on a flowy sheer duster and complete the look with strappy sandals.
Fit & Features
- Thin shoulder straps
- Open back
- V neckline with a zipper front
- Open sides
- Semi-cheeky fit
- Ribbed fabric with a tropical print
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0217
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Casual High Rise Frayed Cutoff Shorts
Keep it casual and laid back with shorts that channel those lowkey vibes. The shorts feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, and a frayed cutoff hem. Complete the look with a ruched crop top.
Fit & Features
- High rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Moderate destruction
- Frayed cutoff hem
- Form hugging fit with a moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0163
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit Twist Front Crop Top
Give your basic crop a trendy twist to nail your OOTD! The crop top features a V-neckline, a twist front bodice, long sleeves, and a cropped hem. The top is composed of a ribbed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with a denim mini skirt.
Fit & Features
- V-neckline
- Twist-front bodice
- Long sleeves
- Cropped hem
- Ribbed cotton knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3141
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Eyes On You Sunglasses
All eyes will be on you in these trendy-chic sunglasses. They feature a skinny hexagon-shaped design with a thin gold metal frame and green-tinted lenses. Pair these sunnies with your fave boho-inspired look and strappy sandals.
Fit & Features
- Skinny hexagon-shaped design
- Thin gold metal frame
- Green-tinted lenses
Style Number/Barcode: 07008-0808
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glamour Diva Large Hoops Three-Pack
Glam up your look with hoops that make a bold statement with your look. The pack includes three pairs of large hoops that vary in design. One pair features a sleek flat metal design, one pair features a textured design, and one pair features a geometric flat metal design. Complete look with a ruched mini dress and mules for a date night look.
Fit & Features
- Three pairs of large hoops
- Flat metal design
- Textured design
- Geometric design
- Omega closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-0758
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chasing The Sun Swim Bottoms
Soak up those sun rays as you lounge in the sand in these too cute swim bottoms! They feature a high rise banded waist, a semi-cheeky fit, and a striped pattern perf for the spring and summer months. Complete your beach-ready look with the matching swim top and some adorable sandals.
Shop Matching Swim Top: Chasing The Sun Swim Top
Fit & Features
- High rise banded waist
- Semi-cheeky fit
- Striped pattern
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0639
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chasing The Sun Swim Top
Soak up those sun rays as you lounge in the sand in this too cute swim top! It features tank-like shoulder straps, a square neckline, a banded hem, and a striped pattern perf for the spring and summer months. Complete your beach-ready look with the matching swim bottoms and some adorable sandals.
Shop Matching Swim Bottoms: Chasing The Sun Swim Bottoms
Fit & Features
- Tank-like shoulder straps
- Square neckline
- Banded hem
- Striped pattern
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0491
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning And Sultry Snake Print Swim Bottoms
Bring those stunning and sultry vibes to your poolside look in these snake print swim bottoms! They feature a high-cut design, thin strap details on each side, and a cheeky bottom with minimal coverage. Complete your fierce look with the matching swim top and a sheer mesh duster.
Shop Matching Swim Top: Stunning And Sultry Snake Print Swim Top
Fit & Features
- High-cut design
- Thin straps
- Cheeky bottom with minimal coverage
- Snake print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0697
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning And Sultry Snake Print Swim Top
Bring those stunning and sultry vibes to your poolside look in this snake print swim top! It features a triangle design with halter spaghetti straps and lower tie-back straps. Complete your fierce look with the matching swim bottoms and a sheer mesh duster.
Shop Matching Swim Bottoms: Stunning And Sultry Snake Print Swim Bottoms
Fit & Features
- Triangle design
- Halter spaghetti straps
- Lower tie-back straps
- Snake print
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0550
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glitter Goals Embellished Jelly Sandals
Elevate your glam status in these adorable glitter jelly sandals! They feature a T-strap design with a silver chrome strap, iridescent gemstone embellishment, an adjustable ankle strap, and a flat sole. Pair these trendy sandals with a skater dress and earrings for a pretty party look.
Fit & Features
- T-strap design
- Silver chrome straps
- Iridescent gemstone embellishment
- Adjustable ankle strap
- Flat sole
- Glitter PVC material
Style Number/Barcode: 07404-0682
Category Name: Vacation Looks
Price: $7.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish And Chic Ruched Mini Skirt
Show off your trendy-chic style in this adorable faux suede mini skirt! It features a high-rise waist, ruching on one side with a drawstring at the hem, and a short, curve-hugging silhouette. Pair this skirt with a flirty crop top and clear heels for a perfect date look.
Fit & Features
- High-rise waist
- Ruching on one side
- Drawstring at the hem
- Mini-length, form-fitting style
- Faux suede fabric
- Runs true to size
Style Number/Barcode: 06501-0378
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double Dose Of Glam Clear Mules
Bring double the glam with mules that slay! The mules feature an open back, a double row of clear straps, a square toe, and a clear lucite block heel. Complete the look with a ruffled mini dress.
Fit & Features
- Open back
- Double row of clear straps
- Square toe
- Clear lucite block heel
- Faux leather material
Style Number/Barcode: 07401-2703
Category Name: Vacation Looks
Price: $12.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Throwing Shade Square Frame Sunglasses
Throw some shade in sassy sunglasses that slay all your favorite looks. The sunglasses feature an oversized square frame, dark lenses, a tortoise-shell hued frame, and sleek arms. Complete look with a denim jumpsuit and wedges.
Fit & Features
- Oversized square frame
- Dark lenses
- Tortoise-shell
- Sleek arms
Style Number/Barcode: 07008-0829
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Day Bestie Crop Tube Top
Sunshine days call for a bestie like this cropped tube top! It's designed with a trendy decor insert and a fitted silhouette that flaunts your figure.
Fit & Features
- Smooth, stretchy knit fabric
- Strapless neckline, decor insert
- Fitted silhouette
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-000058
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hello Weekend Straw Tote Bag
Get all of those end of the week feels with this super cute tote bag! It features top handles, a front button closure, and a front velcro closure pouch with the script, "Hello Weekend." The bag is made of a woven straw-like material and is perfect for all of your upcoming summer outings! Complete look with sunnies and a floppy hat for those weekend getaway vibes!
Fit & Features
- Top handles
- Front-button closure
- Front velcro closure pouch
- "Hello Weekend" script
- Straw-like body
Style Number/Barcode: 07203-0511
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Babe Four-Pack Necklace Set
Showcase your trendy babe status by accessorizing with this chic necklace set! It features four choker necklaces with varying styles of chains, the longest necklace a dainty chain with a center rhinestone embellished heart charm. Pair this necklace pack with your basic everyday 'fit to effortlessly elevate your look.
Fit & Features
- Four choker necklaces
- Varying styles of chains
- Snake chain, flat chain, textured chain, and dainty chain
- Center rhinestone adorned heart charm on the longest layer
- Adjustable lobster clasp closures
Style Number/Barcode: 07002-0591
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Good Time High Rise Cutoff Shorts
Channel those good vibes with shorts that call for a laid-back kind of day. The shorts feature a high rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, moderate destruction, and a cutoff hem with frayed detail. Complete look with a ruched crop top and sneakers.
Fit & Features
- High rise waist
- Single-button with hidden zipper closure
- Traditional five-pocket with belt loop design
- Moderate destruction
- Cutoff hem with frayed detail
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0170
Category Name: Vacation Looks
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Straps One Piece Swimsuit
Keep it sleek with this stylish swimsuit that brings those chic vibes. The swimsuit features a plunging V-neckline with a lattice detail, a triple row spaghetti strap that leads to a criss-cross strap design, and a high cut with a lattice design at the hip. Complete look with sunglasses.
Fit & Features
- Plunging V-neckline with lattice detail
- Triple row spaghetti straps
- Criss-cross strap design
- High cut with lattice design at the hip
- Cheeky bottom
- Form hugging fit, moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0262
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brighter Days Cutout One Piece Swimsuit
Chase that glow with a swimsuit that radiates good vibes. The swimsuit features a plunging V-neckline, triangle-shaped cups, a cross strap design at the bust, a sexy midriff cutout, a high cut, and a thong bottom. Complete look with t-strap sandals and a floppy hat.
Fit & Features
- Plunging V-neckline
- Triangle-shaped cups, removable padding
- Cross-strap design at the bust
- Midriff cutout
- High cut, thong bottom
- Form-hugging fit
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07109-0258
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stacked On Basics Platform Sandals
Stack on the style with these cute platform sandals! Perfect for those warmer days spent at a weekend getaway or for a casual BBQ. The sandals feature an open almond toe, a single strap over the toe, an adjustable ankle strap, and a platform sole with a foam-like insole. Complete look with a ruffled mini dress.
Fit & Features
- Open almond-toe
- Single strap over the toe
- Adjustable ankle strap
- Platform sole
- Foam-like insole
- Faux leather material
Style Number/Barcode: 07404-0579
Category Name: Vacation Looks
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blooming Beauty Floral Crop Top
Let your beauty bloom in this stunning crop top! The top features a square neckline, a floral print, short puff sleeves with a ruffled trim, a cropped hem, and a sexy lower back keyhole with tie back straps. The top is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete your look with high waist shorts.
Fit & Features
- Square neckline
- Floral print
- Short puff sleeves with a ruffled trim
- Cropped hem
- Lower back keyhole with tie back straps
- Crepe fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3154
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale