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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Natural Romancer Crew Neck Lace Mini Dress
Indulge in the effortless romance of this lace mini dress perfect for bridal showers, rehearsal dinners, and parties! This stunning dress features short sleeves, a flattering crew neckline, and a bodycon silhouette that hugs your curves. The sheer lace fabric exudes romance, while the attached knit slip lining provides comfort and coverage. Complete the look with earrings and strappy sandals.
Fit & Features
- Sheer lace fabric with stretch
- Attached slip knit lining
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5548
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Ease Strapless Boho Print Wide-Leg Jumpsuit
The perfect strapless boho jumpsuit for every summer adventure that features a stretchy smocked bodice, a braided waist belt, and a flattering wide-leg fit. The sleek knit fabric offers plenty of stretch and a unique boho-print.
Fit & Fetaures
- Boho-print, sleek knit fabric, moderate stretch
- Strapless neckline
- Stretchy smocked bodice
- Braided waist belt
- Wide-leg fit
- Jumpsuit has a 12” front rise with a 29.5” inseam
- Runs true to size
Style Number/Barcode: 06502-2524
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sun-Soaked Halter Open Back Paisley Crop Top
Have a sun-soaked adventure in this paisley crop top this summer! Featuring a flattering halter V-neckline and spaghetti strap ties, along with an open back elasticized bar and a pointed crop hem to show off your figure. Complete the look in jean shorts and sunglasses.
Fit & Features
- Paisley print, knit fabric, minimal stretch
- Halter V-neckline, spaghetti strap ties
- Open back with elasticized bar
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2552
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Striped Halter Crochet Midi Dress
Stay stylish in this striped crochet midi dress for a sunny day by the beach or on vacation! It features a flattering halter neckline, adjustable spaghetti strap ties, and a bodycon fit that accentuates your curves along the midi-length hem. Complete the look with sunglasses and a tote bag!
Fit & Features
- Striped pattern, crochet fabric, short knit stretchy lining
- Halter neckline with spaghetti strap ties
- Bodycon fit
- Midi-length silhouette
- Runs true to size
Style Number/Barcode: 06005-2032
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Golden Hour Shell Toe Ring Set
Serving seaside glam with zero sand required. This 3-piece shell ring set brings the beach to your fingertips—literally. Stack 'em, mix 'em, or wear solo for a subtle flex.
Fit & Features
- Starfish, cowrie, and conch shell charms
- Coastal-inspired accents
- Pack includes three toe-rings
Style Number/Barcode: 07004-000032
Category Name: Vacation Looks
Price: $2.97 $6.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Versatile Dream Strappy Faux Leather Block Heels
A versatile pair of faux leather heels that can be styled with multiple outfits! They feature a sleek square toe, block heel, and a strappy design for a stylish touch. Complete the look with a trendy tote bag.
Fit & Features
- 3.5" Block heel
- Square toe
- Strappy design
- Faux leather material
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4904
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Match Short Sleeve Tie-Front Top
Flirt up your style in this crop top on vacation or weekend fun! The flowy short sleeves and cropped hem provide a flattering fit, while the tie-front design adds a touch of playful charm. Complete the look with the matching bottoms.
Shop Matching Bottoms: Flirty Match High-Rise Palazzo Pants
Fit & Features
- Woven fabric, no stretch
- Tie-front design
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1752
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strolls In The Sand V-Neck Tropical Skater Mini Dress
Getaway in this tropical skater mini dress to the beach or on vacay! Featuring adjustable spaghetti straps and a flattering V-neckline, this dress hugs your silhouette with an elasticized waist and side cutouts. Its skater silhouette and mini-length hem make it perfect for any daytime adventure. Complete the look in cute sandals.
Fit & Features
- Tropical print, woven fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline
- Elasticized waist with side cutouts
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5656
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Style Cowl Neck Slit Paisley Maxi Dress
Bask in the aesthetic perfection of this paisley mesh maxi dress whether you're on vacation or having a sunset dinner with friends! This form-hugging dress features a cowl neckline and spaghetti straps, highlighting your figure in all the right ways. The high-side slit and sheer maxi-length hem add a touch of allure to this must-have dress! Complete the look with a necklace and earrings.
Fit & Features
- Paisley print, partially lined mesh fabric
- Cowl neckline
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5694
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Times Long Sleeve Striped Button Down Top
Casually update your everyday look in this striped oversized top to pair with your favorite bottoms! It features a collar neckline, long sleeves with button cuffs, a button-down front, and a trendy oversized fit on poplin woven fabric for a polished look. Style this top with jean shorts, sandals, and sunglasses!
Fit & Features
- Striped print, poplin woven fabric, no stretch
- Collar neckline
- Button down front
- Oversized fit
- Runs true to size
Style Number/Barcode: 06003-2627
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Moves Ruffled Slit Knit Midi Skirt
Make major flirty moves and create an enticing aura in this ruffled slit midi skirt! Designed with a stretchy smooth knit fabric, it features a high-rise elasticized waist for comfortable wear, ruching down the side seam to accentuate your curves, a sultry high-cut side slit with a ruffled hem, and a bodycon fit along the midi-length silhouette. Style with the matching crop top for a girl's night out!
Shop Matching Top: Flirty Moves Ruffled Tie-Front Knit Crop Top
Fit & Features
- Stretchy smooth knit fabric
- High-rise elasticized waist
- Ruched side seam
- High side slit, ruffled hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1042
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Glowing Rhinestone Strap Sandals
Always glow in these rhinestone strap sandals to dress up your everyday look or date night dress!
Fit & Features
- Square toe
- Asymmetrical rhinestone straps
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1257
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Good V-Waist Smocked Flare Pants
Looking good will be effortless in these flare pants perfect for vacation or a hot night out! Made of smocked stretchy knit fabric, these pants offer comfort and a flattering silhouette. The cinched mid-rise V-waist and hip-hugging fit will accentuate your curves, while the flared hem adds a touch of flare to your outfit. Complete the look with the matching top.
Shop Matching Top: Looking Good Sweetheart Tie Front Crop Top
Fit & Features
- Stretchy smocked knit fabric
- Mid-rise V-waist with cinch
- Hip-hugging fit
- Flare hem
- Runs true to size
Style Number/Barcode: 06502-2495
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Kellie Strapless Ruffled Slit Lace Formal Dress
Special Occasion
A showstopping lace formal dress that exudes romance and modern elegance. Designed with a high strapless neckline, this long dress boasts a bodycon silhouette with flirty cascading ruffles and a sultry high-side slit. Complete the look with earrings and heels.
Unapologetically bold, this dress is all about confidence. Keep the luxe look going with our stunning strapless prom dresses or discover the perfect fit among our stylish wedding guest dresses.
Fit & Features
- Lace fabric lined with stretchy knit
- High strapless neckline, non-slip grip lining
- Side zipper and hook-eye closure
- High-side slit
- Bodycon silhouette
- Long-length hem
- Runs true to size
Style Number/Barcode: 05002-8961
Category Name: Vacation Looks
Price: $19.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Beach Three-Pack Anklet Set
Take a stylish stroll along the sandy beach wearing this three-pack anklet set. It features two dainty chain link anklets and one chain anklet with a seashell charm. Each has a lobster clasp closure. Complete the look in cute sandals.
Fit & Features
- Three-pack anklet set
- Two dainty chain link anklets
- One chain anklet with seashell charm
- Each has a lobster clasp closure
Style Number/Barcode: 07003-0554
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sassy Sweet Floral Strapless Mini Dress
This sassy sweet strapless mini dress was made for a vacay or weekend getaway! Designed with an abstract floral print, it features side ruching leading to a chic short slit and a flowy A-line silhouette.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract floral print
- Strapless straight neckline
- Side ruching, adjustable tie, short side slit
- Mini-length A-line silhouette, asymmetric hem
- Runs true to size
Style Number/Barcode: 05103-000094
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect In Paradise Floral One-Piece Swimsuit
Create a poolside look perfect for paradise in this one-piece swimsuit featuring a large floral print, a halter neckline with an alluring bust cutout, and a cheeky fit. Style with gold bangle bracelets and flat sandals.
Fit & Features
- Nylon-blend fabric, high stretch
- Large floral print
- Halter neckline, large bust cutout
- Tie-back halter straps, open lower back
- Cheeky fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000013
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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New Favorite Thong Strap Low-Block Heels
These simple yet stylish low-block heels will become your new fave go-to! Made with sleek faux leather material, they feature an open square-shaped toe with a thin thong strap design, thin adjustable ankle and heel straps for a customized fit, and a low block heel for comfort and a chic look. Pair with a mini handbag for your weekend plans!
Fit & Features
- 3" Low block heel
- Faux leather upper
- Square toe
- Thong strap design
- Adjustable ankle and heel straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4664
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Personality Button Up Crop Linen Shacket
An easygoing babe like you will appreciate this linen shacket for effortless styling! Featuring three quarter roll cuffed sleeves, a collar neckline, and button-up front closure, this shacket brings versatility to your wardrobe. With flap pockets and a cropped hem, this shacket adds a playful touch to any outfit. Complete the look in trendy boots.
Fit & Features
- Linen blend woven fabric, no stretch
- Collar neckline
- Button up front closures
- Flap pockets
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1784
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Step Into Summer Linen Wooden Platform Heels
Step into summer looking fabulous in these platform heels! These block heels feature a square toe with a wide strap, an adjustable ankle strap with buckle closure, and a lightweight wooden platform sole for a trendy finish. Complete the look with a cute handbag.
Fit & Features
- 3.5" Block Heel
- Square toe
- Adjustable ankle strap, buckle closure
- Lightweight wooden platform sole
- Luxe fit cushioned insole
- Linen material
- Runs true to size
Style Number/Barcode: 07401-4886
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Destined For Sun Tropical Mesh Tie Front Top
This tropical sheer mesh top is destined to go with you on the next sunny getaway! Featuring long sleeves with cuffs, a tie-front design, and a cropped hem to highlight your curves. Complete the look with the matching bottoms.
Shop The Matching Bottoms: Destined For Sun Tropical Mesh Mini Skirt
Fit & Features
- Tropical palm print, sheer mesh fabric, moderate stretch
- Long sleeves with cuffs
- Tie-front design
- Cropped hem
- Runs true to size
Style Number/Barcode: 06202-0452
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Chic Cutout Sandals
Bringing effortless energy wherever you go. These chic slide sandals are your no-brainer pick for sun-soaked strolls, coffee runs, and last-minute plans.
Fit & Features
- Square toe
- H-shaped band
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000038
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Trek Strappy Lace-Up Flat Sandals
Your trek to the farmer's market is looking cute in these statement flat sandals! They feature a square toe, a caged strappy design with knotted accents, and a trendy lace-up ankle that lets you customize the style on faux leather material. Complete the look with a trendy handbag.
Fit & Features
- Flat sole
- Square toe
- Strappy caged design with knotted accents
- Lace-up ankle
- Lightly cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1155
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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First Day Of Spring Puff Sleeve Smocked Romper
Embrace the beauty of spring in this adorable romper! Featuring delicate puff short sleeves and a tie-front bust, this romper flatters everyone. The stretchy smocked waist and flowy short-length hem provide ultimate comfort and style. Complete the look in cute sandals and sunnies for any casual outing!
Fit & Features
- Woven fabric lined with stretchy knit
- Tie-front bust
- Stretchy smocked waist
- Runs true to size
Style Number/Barcode: 06303-0265
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale