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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Dreamy And Chic Tie-Front Top
Style this boho-inspired tie-front top for a dreamy and chic look! It features three-quarter length kimono-style sleeves, a plunging V neckline, a tie-front, and a wide sheer lace trim. Pair this top with a denim mini skirt and strappy sandals.
Fit & Features
- Three-quarter length kimono-style sleeves
- Deep V neckline
- Tie-front
- Wide sheer lace trim
- Woven fabric, relaxed fit
- Runs true to size
Style Number/Barcode: 06204-0911
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sun Soaked Espadrille Strappy Wedges
Step into sunny style with these espadrille wedges in a strappy design that elevates any look!
Fit & Features
- Wedge heel
- Square toe
- Criss cross straps
- Closed ankle, back zipper closure
- Espadrille material
- Runs true to size
Style Number/Barcode: 07406-000011
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Medallion Marvel Strapless Jumpsuit
Make them marvel with a jumpsuit that channels a retro feel! The jumpsuit features a strapless square neckline, a medallion print, hidden side pockets, and a fitted straight leg. Complete the look with hoops and platform wedges for a gorge outfit.
Fit & Features
- Strapless square neckline
- Medallion print
- Hidden side pockets
- Fitted straight leg
- Knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0551
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island It Girl One-Shoulder Cutout Maxi Dress
Giving tropical baddie with a side of luxury, this one-shoulder maxi brings the heat with a bold leaf print, cutout waist, and gold hardware that says, "I didn’t come to play." It's made for vacation slays, beach weddings, or poolside parties!
Fit & Features
- Tropical leaf print, smooth stretchy knit fabric, short lining
- One-shoulder neckline with hardware trim
- Side cutout bodice
- High side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000082
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Getaway Mesh Duster
Look like you're jetting off to a tropical getaway in this chic mesh duster! It features long fitted sleeves, an open front, and a long, flowy silhouette. The sheer mesh fabric showcases an all-over neutral palm leaf print. Style this duster as a lightweight layer over a bodysuit and denim, and pair the look with heels.
Fit & Features
- Long fitted sleeves
- Open front
- Long, flowy silhouette
- Sheer mesh fabric
- Neutral palm leaf print
- Runs true to size
Style Number/Barcode: 06202-0159
Category Name: Vacation Looks
Price: $13.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Charmer Ditsy Floral Mini Dress
Charm them all with a mini dress that makes a sweet impression! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1895
Category Name: Vacation Looks
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Passion Gauze Knit Kimono
Unleash your passion for florals with a kimono that radiates beauty and style. The kimono features a drape open front, short kimono sleeves, a floral print, and a flowy long length. The kimono is composed of a gauze knit fabric that offers a relaxed fit with a minimal stretch. Complete look with a crop top and cutoff shorts.
Fit & Features
- Draped open front
- Floral print
- Kimono sleeves
- Flowy long length
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0886
Category Name: Vacation Looks
Price: $16.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropics Queen Swim Coverup
Head off to the tropics with a swim coverup that instantly transports you to paradise! The cover-up features a tropical palm leaf print and composed of a sheer mesh fabric. Complete outfit with a swimsuit and sunnies.
Fit & Features
- Tropical palm leaf print
- Mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 07305-0291
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Embraced In Beauty Chiffon Floral Duster
Embrace yourself with florals in a pretty duster to layer over outfits. The duster features a draped open front, a floral print, long sleeves, and a flowy long length. The duster is composed of a sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with a crop top and button-up shorts.
Fit & Features
- Draped open front
- Long sleeves
- Floral print
- Flowy long length
- Sheer chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0898
Category Name: Vacation Looks
Price: $16.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Spirit Flared Pants
Channel your bohemian spirit with flared pants that showcase your indie side! The pants feature a high-rise waist, a bohemian-inspired print, and a flared wide-leg. The pants are composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with a crochet top.
Fit & Features
- High rise waist
- Bohemian-inspired print
- Flared wide-leg hem
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-0573
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Florals On My Mind Tie Front Top
Keep florals on your mind with a pretty top that keeps it frilly and flirty. The top features a plunging tie-front bodice, ruffled quarter-length sleeves, a ditsy floral print, and a cropped hem. Complete look with high waist shorts and earrings.
Fit & Features
- Plunging V-neckline
- Ditsy floral print
- Ruffled 3/4 sleeves
- Cropped hem
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-0817
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Stunner Tie-Front Romper
You'll be such a stylish stunner in this pretty printed romper! It features flowy kimono-style sleeves, a wrap-front V neckline, a tie-back accent at the neck, a high waist with a tie-front belt, and flowy shorts. The woven fabric has a chic all-over bohemian-inspired print. Complete the look with gold hoop earrings and strappy sandals for the perfect summer outfit.
Fit & Features
- Kimono-style sleeves
- Wrap-front V neckline
- Tie-back detail at the neck
- High waist, tie-front belt
- Flowy shorts
- Woven fabric, bohemian-inspired print
- Runs true to size
Style Number/Barcode: 06303-0113
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Romance Ditsy Floral Mini Dress
Fall in love with this adorable ditsy floral mini dress that is perfect for summer date nights. It features short puff sleeves, a sweetheart neckline with a center criss-cross bust detail, and a mini-length, curve-hugging silhouette. Complete the outfit with a charm necklace and clear heels.
Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Center criss-cross bust detail
- Short, form-hugging fit
- Knit fabric, ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-2103
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Love Double-Layer Skater Dress
Fall head over heels for this pretty floral skater dress! It features a sleeveless square neckline, adjustable spaghetti straps, a back bow accent and lower back cutout, a fitted bodice with a high waist, and a flirty double-layered skater skirt with a flared-out silhouette. Style this dress with sleek hoop earrings and cute wedges for a summer date night.
Fit & Features
- Square neckline
- Adjustable spaghetti straps
- Back bow accent, lower back cutout
- Fitted bodice, high waist
- Double-layered skater skirt
- Crepe fabric, floral print
- Runs true to size
Style Number/Barcode: 05101-0653
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Beauty Crochet Crop Top
You'll look like a total boho beauty in this cute crochet crop top! It features a crew neckline, short cap sleeves, a trendy lattice back design, and a cropped, form-hugging fit. Pair this sheer crochet top with denim shorts and strappy sandals for an effortlessly stylish outfit.
Fit & Features
- Crew neckline
- Cap sleeves
- Lattice back design
- Cropped, form-hugging fit
- Crochet fabric, no stretch
- Runs true to size
Style Number/Barcode: 06005-0951
Category Name: Vacation Looks
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Darling Ditsy Floral Mini Skirt
Achieve that sweet darling look that's trendy for summertime with this adorable mini skirt! It features a high-rise waist, a mini-length, curve-hugging silhouette, a ruffle hem, and an all-over ditsy floral print. Pair this skirt with the matching crop top and strappy sandals.
Shop Matching Top: Sweet Darling Ditsy Floral Crop Top
Fit & Features
- High-rise waist
- Short, form-hugging fit
- Ruffle hem
- Ditsy floral print
- Smocked woven fabric
- Runs true to size
Style Number/Barcode: 06401-0310
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ladies' Night Abstract Floral Crop Top
This stunning abstract floral crop top will turn heads with every wear on your next ladies' night!
Fit & Features
- Abstract floral print, mesh fabric, sewn-in knit lining
- Adjustable drawstring shoulder straps
- Plunge neckline
- Side ruched seams
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000137
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Darling Ditsy Floral Crop Top
Achieve that sweet darling look that's trendy for summertime with this adorable crop top! It features a strapless neckline with a tie-front accent, a cropped, form-hugging fit, and an all-over ditsy floral print. Pair this top with the matching mini skirt and strappy sandals.
Shop Matching Bottoms: Sweet Darling Ditsy Floral Mini Skirt
Fit & Features
- Strapless neckline
- Tie-front
- Cropped, form-hugging fit
- Ditsy floral print
- Smocked woven fabric
- Runs true to size
Style Number/Barcode: 06003-1296
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sealed With Glam Tie Front One Piece Swimsuit
Seal your look with a glam swimsuit that brings the style! The swimsuit features a sleeveless sweetheart neckline, a cute tie front accent, adjustable spaghetti straps, a sexy cutout at the midriff, and a cheeky fit bottom. Complete look with slides and sunnies.
Fit & Features
- Sleeveless sweetheart neckline, padded cups
- Adjustable spaghetti straps
- Tie-front accent
- Cutout
- Cheeky fit bottom
Style Number/Barcode: 07109-0267
Category Name: Vacation Looks
Price: $15.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Faux Leather Double Band Slides
Slip on these stylish sandals to keep it basic and cute! The sandals feature an easy slip-on design, an open almond toe with a double band design, and a flat footbed. Complete look with a basic tee shirt and cutoff shorts.
Fit & Features
- Slip-on design
- Open almond toe
- Double-band design
- Flat footbed
- Faux leather material
Style Number/Barcode: 07404-0690
Category Name: Vacation Looks
Price: $12.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Vibes Cutoff Denim Shorts
Get those lowkey effortless vibes with these high-rise denim shorts. They feature a traditional five-pocket and belt loop design, a front button closure, destructed detailing, and a frayed cutoff hem. Complete the look with a cute bodysuit and strappy sandals.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button closure
- Destructed detailing
- Frayed cutoff hem
- Denim fabric
- Runs true to size
Style Number/Barcode: 06603-0216
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Distressed To Impress Cutoff Denim Shorts
These majorly distressed denim shorts will have your whole squad impressed with your style. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button closure, destructed detailing, and a cutoff hem. Complete the look with a graphic tee and sneakers.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button closure
- Destructed detailing
- Cutoff hem
- Denim fabric
- Runs true to size
Style Number/Barcode: 06603-0210
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fab And Frayed Cutoff Denim Shorts
Get a fab everyday look in these on-trend casual denim shorts. They feature a high-rise waist, a traditional five-pocket and belt loop design, a front button closure, destructed detailing, and a cutoff frayed hem. Style these shorts with your fave swimsuit and sandals for a summer beach trip with your squad.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button closure
- Destructed detailing
- Cutoff frayed hem
- Denim fabric
- Runs true to size
Style Number/Barcode: 06603-0209
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Must-Have Denim Shorts
These high-rise denim shorts are a must-have for achieving that casual and laidback summertime look. They feature a traditional five-pocket and belt loop design, a front button and hidden zipper closure, slight distressed detailing, and a frayed hem. Complete the outfit with a cute crop top and sneakers.
Fit & Features
- High-rise waist
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
- Subtle distressed detailing
- Frayed hem
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0189
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free