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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Ruffle Realness Denim Cutout Maxi Dress
Sweet from the front, spicy from the back. With bold cutout accents, a hoop insert, and ruffled tiered flow, this maxi is bringing the drama in the cutest way possible.
Fit & Features
- Denim fabric, sewn-in knit lining
- Sweetheart neckline
- Adjustable spaghetti straps
- Cutout bodice design, hoop insert
- Stretchy smocked back panel, cutout accent, lower zipper and hook-eye closure
- Ruffled tiered maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000131
Category Name: Vacation Looks
Price: $30.97 $68.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Impression Open Back Mini Dress
Make a sultry impression with a mini dress that stuns with sexy details! The dress features a sleeveless scoop neckline with ruching at the bust, bungee spaghetti straps that lead to a cross-back detail, a backless design, and a mini-length silhouette. The dress is composed of smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with stilettos and statement earrings.
Fit & Features
- Sleeveless scoop neckline, ruching at the bust
- Bungee spaghetti straps, cross-back
- Backless
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4016
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Sweetheart Floral Mini Dress
Charm like the total sweetheart you are with a mini dress that brings the glam. The dress features an off-the-shoulder neckline, a padded sweetheart bust, long sleeves, a ruched body, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Off-the-shoulder neckline, padded sweetheart bust
- Long sheer sleeves, elastic cinched hems
- Ruched body
- Mini-length silhouette
- Floral print, sheer mesh fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1122
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Daze Linen Tie-Front Crop Top
Catch the breeze, catch the vibe. This linen tie-front crop top is made for sunny days and carefree moments—easy, airy, and ready for wherever the day takes you.
Shop Matching Bottoms: Sunny Daze Linen Mini Skort
Fit & Features
- Linen woven fabric
- Sleeveless V-neckline
- Tank shoulder straps
- Tie-front design
- Fitted ultra-cropped hem
- Runs true to size
Style Number/Barcode: 06204-000023
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Sale
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Casual Glam Ribbed Knit Maxi Dress
Keep it casually glam with a maxi dress that is perf to dress up or down for brunch! The dress features a sleeveless V-neckline, a cute tie-front, adjustable spaghetti straps, a button-down front, and a maxi-length silhouette accented with a high center slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a floppy hat.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, tie-front
- Button-down front
- Maxi-length silhouette, high center slit
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1347
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fiercely Fab Quilted Square Toe Mules
Keep it fab in these chic mules, a perfect option to elevate your everyday 'fit. They feature an on-trend square toe, a wide strap with a quilted design, an open back, and a thin block heel. Pair these mules with mom jeans and a cute crop top.
Fit & Features
- Square toe
- Wide strap
- Quilted design
- Open back
- Thin block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-2797
Category Name: Vacation Looks
Price: $7.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stars And Moon Charm Anklet
Channel a starry-inspired look with a cute anklet! The anklet features a two-row design with starburst charms and a crescent moon. Complete look with an LBD and mules.
Fit & Features
- Two-row design
- Starburst charms
- Crescent moon charm
- Lobster clasp closure
Style Number/Barcode: 07003-0266
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Chain Detail Jelly Slides
These on-trend jelly slides have a chic chain detail that will glam up your everyday outfit! The shoes feature an open round toe, a wide toe strap with a thick chain link design, and a flat sole. Style these slides with a casual dress and sleek hoop earrings.
Fit & Features
- Open round toe
- Wide toe strap
- Thick chain link design
- Flat sole
- Jelly material
- Runs true to size
Style Number/Barcode: 07404-0834
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual And Chill Strappy Sandals
Keep your everyday summer look casual and chill with these cute sandals. They feature an open round toe, a triple strap design with an adjustable ankle strap, and a comfortable flat rubber sole. Style these sandals with a basic tee and denim shorts.
Fit & Features
- Open round toe
- Triple strap design
- Adjustable ankle strap, buckle detail
- Flat rubber sole
- Runs true to size
Style Number/Barcode: 07404-0844
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glowing Glam Starburst Rhinestone Cuff Earring
Keep it glam with a cuff earring that adds the sparkle to your look! The cuff features a rhinestone embellished starburst charm and a fringe accent on post. Complete look with a matching top and skirt set.
Fit & Features
- Cuff design
- Starburst charm
- Rhinestones
- Fringe on post
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-0913
Category Name: Vacation Looks
Price: $0.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Vibes Faux Leather Strap Sandals
Channel those basic vibes to nail down a lowkey look! The sandals feature an open back, a wide adjustable ankle strap, an open almond toe with a wide strap over the toe, and composed of a faux leather material. Complete look with a romper and dainty rings.
Fit & Features
- Open back
- Adjustable ankle strap
- Open almond toe, strap over the toe
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-0863
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Boho Vibes Maxi Dress
Bring on the stunning boho vibes with this effortlessly chic maxi dress. It features a sleeveless V-neckline, spaghetti straps, a tie-front bust with a sexy waist cutout, and a curve-hugging floor-length silhouette with a sultry thigh-high side slit. Style this dress with trendy earrings and cute mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-front bust, waist cutout
- Floor-length, form-hugging fit
- High side slit
- Knit fabric, paisley print
- Runs true to size
Style Number/Barcode: 05102-4159
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild And Fab Snake Cork Wedges
Keep it wild and fab with wedges that make a one-of-a-kind statement! The wedges feature an open back, snake print straps, adjustable ankle strap, asymmetrical strap, an open almond toe with a strap over the toe, and a cork wedge with an espadrille trim. Complete look with a crop top and distressed jeans.
Fit & Features
- Open back
- Snake print
- Adjustable ankle strap
- Asymmetrical strap
- Open almond toe, strap over the toe
- Cork wedge, espadrille trim
- Runs true to size
Style Number/Barcode: 07406-0286
Category Name: Vacation Looks
Price: $7.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Style Triple Strap Sandals
Showcase your effortless style with sandals that are perf for your casual outfits! The sandals feature an open back, a wide adjustable ankle strap, a triple-row strap design, and an open almond toe. Complete look with a romper and dainty rings.
Fit & Features
- Adjustable ankle strap
- Triple-row strap design
- Open almond toe
- Rubber sole
- Runs true to size
Style Number/Barcode: 07404-0843
Category Name: Vacation Looks
Price: $7.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Glam Square Toe Sandals
Bring the romance with glam sandals that will make a charming impression! The sandals feature a slip-on design, an open almond toe, and a floral petal embellished strap over the toe. Complete look with a floral mini dress and a chunky chain link necklace.
Fit & Features
- Open back
- Slip-on design
- Open almond toe
- Floral petal embellished strap over the toe
Style Number/Barcode: 07404-0892
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Glam Espadrille Platform Sandals
Keep it casually glam with stylish sandals that are perf for keeping it lowkey! The sandals feature an open back, wide criss-cross ankle straps, an open almond toe with strap over the toe, and an espadrille platform. Complete look with a high-low floral dress and gold huggies.
Fit & Features
- Open back
- Wide criss-cross ankle straps
- Open almond toe, strap over the toe
- Espadrille platform
- Faux suede material
- Runs true to size
Style Number/Barcode: 07404-0922
Category Name: Vacation Looks
Price: $7.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Stylish Strappy Wedges
Hey babe, keep your summer look stylish and on-trend with these strappy wedges. They feature an open round toe, a thin asymmetrical strappy design with an adjustable heel strap, and a cork wedge with an espadrille trim detail. Pair these wedges with your fave sundress.
Fit & Features
- Open round toe
- Thin asymmetrical strappy design
- Adjustable heel strap, buckle detail
- Cork wedge, espadrille trim
- Runs true to size
Style Number/Barcode: 07406-0281
Category Name: Vacation Looks
Price: $16.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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You've Got Flare Halter Cutout Wide Leg Jumpsuit
Featuring a flattering halter neckline and playful cutout details, this jumpsuit combines trendiness with a touch of boldness. The wide-leg silhouette and ruffled accents create a flowy look that moves with you.
Fit & Features
- Woven fabric
- Halter plunge neckline, spaghetti strap tie
- Cutout bodice with drawstring tie
- Ruffled wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-000004
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summertime Chic Crop Top
Get a boho-chic look this summer season in this trendy crop top. It features a crew neckline, short sleeves, side ruched detailing, and a cropped, form-hugging fit. The brushed knit fabric has an all-over bohemian-inspired print. Style this top with the matching mini skirt and cool shades.
Shop Matching Bottoms: Summertime Chic Mini Skirt
Fit & Features
- Crew neckline
- Short sleeves
- Side ruched detailing
- Cropped fit
- Brushed knit fabric, plenty of stretch
- Boho-inspired print
- Runs true to size
Style Number/Barcode: 06001-3462
Category Name: Vacation Looks
Price: $5.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Essential Mesh Long Kimono
Bring it back to basics with cute layered looks with a flowy kimono! The kimono features a draped open front, long kimono sleeves, and a flowy long length. The kimono is composed of a sheer mesh fabric that offers a relaxed fit with a moderate stretch. Complete look with a swimsuit and sandals.
Fit & Features
- Draped open front
- Long kimono sleeves
- Flowy long length
- Sheer mesh fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0231
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Chic Crochet Crop Top
Keep it boho chic with a lace-up top that is perf for your next beach day! The top features a sleeveless V-neckline, spaghetti straps, a lace-up bodice, and a cropped hem. The top is composed of an unlined crochet knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with high waist shorts and sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Lace-up bodice
- Cropped hem
- Unlined crochet knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0971
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Sunsets Maxi Dress
Your dream vacation is calling! Pack this stunning tropical floral printed maxi dress for a gorgeous look. It features an off-the-shoulder square neckline, a fitted smocked bodice, short ruffled sleeves, a tie-front accent to highlight the waist, and a flowy, floor-length silhouette with a wrap-front design. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Off-the-shoulder square neckline
- Fitted smocked bodice
- Short ruffled sleeves
- Tie-front detail
- Flowy, floor-length silhouette, wrap-front design
- Woven fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-4068
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrapped In Florals Chiffon Skater Dress
Wrap yourself in a fab floral dress this season for your next brunch! The dress features a floral print, plunging V-neckline, ruffled cap sleeves, an open back with a tie-back strap, and a skater silhouette with an asymmetrical ruffled trim. The dress is composed of a semi-sheer chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with sandals and duster earrings.
Fit & Features
- Wrap V-neckline
- Ruffled cap sleeves
- Open back with tie back ties
- Skater silhouette
- Ruffle trim
- Floral print
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1103
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Getaway Mesh Mini Dress
Get ready for your island getaway in this adorable mesh mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing, a short, curve-hugging silhouette, and an all-over tropical palm leaf print. Style this dress with strappy sandals.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruching
- Mini-length, form-hugging fit
- Sheer mesh fabric, tropical palm leaf print, knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4133
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale