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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Cheetah Daze One Shoulder Bikini Top
Add some spice to your swimwear with this cheetah bikini top featuring a one-shoulder neckline, asymmetrical strap with cutout detail, removable padding on lined fabric. Complete the look in the matching bikini bottoms.
Shop The Matching Bikini Bottoms: Cheetah Daze Cutout Bikini Bottoms
Fit & Features
- Sleeveless, one-shoulder neckline
- Asymmetrical strap, cutout detail
- Removable padding
- Cheetah print
- Lined fabric
- Runs true to size
Style Number/Barcode: 07104-0636
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pool Party High Waist Swim Bottoms
Get the cutest look for all your summer pool parties with these trendy high waist swim bottoms! They feature cutout details on the sides and a semi-cheeky fit. Style with the matching swim top and cool shades.
Shop Matching Top: Pool Party One-Shoulder Swim Top
Fit & Features
- High-rise waist
- Side cutouts
- Semi-cheeky fit
- Moderate stretch
- Runs true to size
RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07105-0784
Category Name: Vacation Looks
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pool Party One-Shoulder Swim Top
Get the cutest look for all your summer pool parties with this trendy one-shoulder swim top! It features an asymmetrical dual strap design with a front cutout detail and removable padding. Style with the matching swim bottoms and cool shades.
Shop Matching Bottoms: Pool Party High Waist Swim Bottoms
Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetrical dual strap design, spaghetti strap, tank strap
- Front cutout detail
- Removable padding
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0637
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Metallic Moment Bikini Top
Have your moment under the sun! Stun in this sultry bikini top featuring a deep V-neckline, shoulder straps, and a wide bust band. Complete the look in the matching bikini bottoms.
Shop Matching Bikini Bottoms: Metallic Moment Bikini Bottoms
Fit & Features
- Deep V-neckline, shoulder straps
- Wide bust band
- Metallic fabric
- Slip-on/off styling
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0630
Category Name: Vacation Looks
Price: $4.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Charm Coin Drop Earrings
These charming boho earrings feature a filigree design, drop accent, and coin charm detailing. Complete the look in a sleek bustier for a night out.
Fit & Features
- Filigree design
- Drop accent
- Coin charm detailing
- Push closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1265
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Top Down Square Sunglasses
Cruise with the top down in these fab square sunglasses featuring a rose gold trim, oversized tortoise plastic frames, and gradient lens. Complete the look in a sultry casual dress for a day out.
Fit & Features
- Oversized tortoise plastic frames
- Rose gold trim at the top
- Gradient lens
- 100% UV protection
Style Number/Barcode: 07008-0956
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Together Pleat Wide-Leg Pants
Get together with the girls in these cute high-rise pants for an ocean brunch! They feature pleat front detailing, a wide-leg silhouette, and hidden side pockets to keep your hands warm. Complete the look in the matching top.
Shop Matching Top: Get Together Smocked Crop Top
Fit & Features
- High-rise waist, side zipper closure
- Hidden side pockets
- Pleat front detailing
- Wide-leg silhouette
- Linen woven-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0649
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Soak Up The Sun Square Sunglasses
Enjoy a sunny day out in these square sunglasses that offer UV protection and a stylish look with your fit!
Fit & Features
- Square frames
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000016
Category Name: Vacation Looks
Price: $2.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Together Smocked Crop Top
Get together with the girls in this cute crop top for an ocean brunch! It features a sleeveless, one-shoulder neckline with a shoulder strap and an all-over smocked bodice. Complete the look in the matching pants.
Shop Matching Pants: Get Together Pleat Wide-Leg Pants
Fit & Features
- Sleeveless, one-shoulder neckline
- Shoulder strap
- All-over smocked bodice
- Cropped hem
- Runs true to size
Style Number/Barcode: 06003-1787
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Social Butterfly Duster Earrings
Have plans? Of course, you do! Keep your outfit on point in these butterfly duster earrings featuring rhinestone embellishments, a dainty linear chain-link, and a post-back closure. Complete the look in an oversized denim jacket.
Fit & Features
- Rhinestone butterfly charms
- Dainty linear chain-link
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1226
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gone On Vacay Espadrille Cork Wedges
Take a vacay from your heels and slip on these trendy espadrille wedges! They feature an almond toe, platform cork sole, criss-cross toe strap, and a buckle ankle strap. Complete the look in a flowy maxi dress and Panama hat.
Fit & Features
- Almond toe
- Platform cork sole
- Criss-cross toe strap, buckle ankle strap
- Espadrille trim
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07406-0301
Category Name: Vacation Looks
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Statement Rhinestone Chain Bra
Make a glam statement with this rhinestone chain bra to elevate your babe status! It features a plunge v-neck, triangle-shaped cups, and an adjustable lobster clasp closure. Complete the look in a panama hat for a trendy festival vibe.
Fit & Features
- Plunge v-neck
- Triangle-shaped cups
- Lobster clasp closure
- Rhinestone chain design
Style Number/Barcode: 07107-0750
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rise And Stun Cutout Bikini Top
Rise and stun in this bikini top perf for a day spent under the sun. It features a square neck, adjustable spaghetti straps, and a cutout caged design. Complete the look in the matching bikini bottoms.
Shop The Matching Bikini Bottoms: Rise And Stun String Bikini Bottoms
Fit & Features
- Square neck
- Adjustable spaghetti straps
- Cutout caged design
- Lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0705
Category Name: Vacation Looks
Price: $4.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Layers Of Rhine Necklace
This layered rhinestone necklace is perfect for dressing up an outfit! It features a five-row design with a mix of snake chains and rhinestones with a lobster clasp closure. Complete the look in a sultry cocktail dress.
Fit & Features
- Five-row layered design
- Snake chains
- Rhinestones
- Lobster clasp closure
Style Number/Barcode: 07002-1173
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Throw It Back Rhine Wedge Sandals
Throw it back to the early 2000s in these stunning sandals! They feature a rounded almond toe, wedge sole, and rhinestone thong straps on a comfort foam footbed. Complete the look in a crop top and flared pants.
Fit & Features
- Rounded almond toe
- Wedge sole
- Rhinestone thong straps
- Comfort foam footbed
- Runs true to size
Style Number/Barcode: 07406-0314
Category Name: Vacation Looks
Price: $8.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Remy High-Rise Distressed Shorts
The Remy distressed denim shorts are a classic staple for casual everyday looks. They feature a high-rise waist, subtle destructed detailing, and a raw-cut hem. The shorts offer a semi-cheeky fit with a moderate stretch. Style with a crop top and sandals.
Fit & Features
- High-rise waist
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Subtle distressing, raw-cut hem
- Semi-cheeky fit
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0301
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Desert Queen Boho Flare Pants
You're the queen of the desert in these boho flare pants featuring an elasticized high-rise waist and a form-fitting silhouette. Complete the look in the matching top for the perf music festival outfit!
Shop The Matching Top: Desert Queen Boho Halter Top
Fit & Features
- High-rise elasticized waist
- Form-fitting silhouette
- Flare hem
- Boho-inspired print
- Pull-on/off styling
- Fits true to size
Style Number/Barcode: 06502-0717
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Desert Queen Boho Halter Top
You're the queen of the desert in this boho top featuring a sleeveless, halter neck, cropped hem, and a partial open with cross strap detail. Complete the look in the matching bottoms for the perf music festival outfit!
Shop The Matching Bottoms: Desert Queen Boho Flare Pants
Fit & Features
- Sleeveless, halter neck, spaghetti straps
- Cropped hem
- Partial open back with cross straps
- Boho-inspired print
- Fits true to size
Style Number/Barcode: 06001-3757
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Bound Bandeau Halter Top
Pack this adorable bandeau top in your carry-on before you jet set off on your vacay! It features a sleeveless halter neckline with a cross-front strap design, a center cutout at the bust, and a majorly cropped, form-hugging fit. The lightweight woven fabric offers minimal stretch. Complete the look with the matching mini skirt.
Shop Matching Bottoms: Vacay Bound Ruched Mini Skirt
Fit & Features
- Sleeveless halter neckline
- Spaghetti straps, cross-front design, tie closure at back of the neck
- Center cutout at the bust
- Ruched detailing
- Cropped, form-hugging fit
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1757
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Bound Ruched Mini Skirt
Slip into this mini skirt to nail those vacay shots on the perfect getaway! The skirt features a high-rise waist, a ruched body, a center drawstring, and a mini-length hem. The skirt is composed of a lined lightweight knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with the matching bandeau halter top.
Shop Matching Top: Vacay Bound Bandeau Halter Top
Fit & Features
- High-rise waist
- Ruched body
- Center drawstring
- Mini length hem
- Lined knit fabric
- Hidden back zipper closure with hook and eye
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06301-0117
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty Flair Crepe Faux Wrap Dress
Short, sweet, and extra flirty this mini dress is just what you need for every occasion! It features a sleeveless, square neck, spaghetti straps, princess seams on the bodice, and a faux wrap asymmetrical skirt with side pleating. Complete the look in platform heels.
Fit & Features
- Sleeveless, square neck
- Spaghetti straps
- Princess seams on bodice
- Faux wrap asymmetrical skirt
- Side pleating
- Crepe fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05103-4241
Category Name: Vacation Looks
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cut It Out Babe Midi Dress
Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.
Fit & Features
- Stretchy rib knit fabric, contrast trim
- Square neck, tank shoulder straps
- Cutout bodice
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000045
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Clear View PVC Espadrille Wedges
You might want to get a clear view of these chic wedges! They feature a square toe, espadrille sole, dual PVC clear straps, and a faux leather footbed. Complete the look in a trendy skater dress for brunch with the girls.
Fit & Features
- Square toe
- Espadrille sole
- Dual PVC clear straps
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07406-0312
Category Name: Vacation Looks
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Open Season Caged Comfort Sandals
It's open-toe season and these sandals are here for it! They feature a round toe, comfort foam sole, and a caged strap design with adjustable buckle closure. Complete the look in a casual sundress for a picnic lunch.
Fit & Features
- Round toe
- Comfort foam sole
- Caged strap design
- Adjustable buckle closure
- Runs true to size
Style Number/Barcode: 07404-1024
Category Name: Vacation Looks
Price: $12.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale