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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Charmed And Cute Polka Dot Chiffon Skater Dress
Envoke a charmed and cute style in this polka dot skater dress perfect for showers or graduates! Show off your curves with the sweetheart neckline and skater silhouette, while adding a touch of cuteness with the short puff sleeves. The tie-back adds a flirty detail and the short-length hem is perfect styling with trendy sneakers for a casual vibe.
Fit & Features
- Polka dot, chiffon fabric, woven lining, no stretch
- Sweetheart neckline
- Padded bra cups
- Back zipper hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3289
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Queen Tropical Floral Mesh Maxi Skirt
Slay your next vacay in this gorg tropical floral mesh maxi skirt with a mini-length lining and a high-cut side slit. Style with the matching crop top for a sultry vibe!
Shop Matching Top: Vacay Queen Tropical Floral Mesh Tie-Front Top
Fit & Features
- Sheer mesh fabric with mini-length knit lining, high stretch
- Large tropical floral print
- Mid-rise waist
- Hip-hugging fit
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000030
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All The Cozy Feels Faux Fur Knit Beanie
Keep your winter 'fit cozy with this adorable knit beanie! It features a ribbed fold-over hem, a cable knit design, an ultra-plush faux fur lining to keep you warm, and a top fuzzy faux fur pom detail. Style this cute beanie with your favorite sweater.
Fit & Features
- Ribbed fold-over hem
- Cable knit design
- Soft faux fur lining
- Faux fur pom
Style Number/Barcode: 07302-0988
Category Name: Vacation Looks
Price: $4.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Era Woven A-Line Midi Dress
Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.
Fit & Features
- Poplin smooth cotton woven fabric with full-length woven lining
- Sleeveless square neckline, adjustable spaghetti straps
- Stretchy smocked bodice
- V-shaped waist
- Pleating, hidden side pockets
- Midi-length flowy A-line silhouette, high side slit
- Runs true to size
Style Number/Barcode: 05102-000001
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Classic Fold-Over Ribbed Knit Beanie
This cute classic ribbed knit beanie is a winter must-have! It features a thick ribbed knit material with a fold-over design and offers moderate stretch. Style this adorable beanie with a fuzzy faux sherpa jacket.
Fit & Features
- Thick ribbed knit material
- Fold-over design
- Moderate stretch
Style Number/Barcode: 07302-1514
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Babe Button Up Linen Vest
A sleek fit with tailored details, this sleeveless linen vest is essential for spring-to-summer wear! The vest is designed with a flattering V-neckline, button-up front closures, and a curved cropped hem to flaunt your figure. Complete the look with the matching pants.
Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants
Fit & Features
- Lined linen fabric
- Button up front closures
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1737
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Perfection Bodycon Striped Mini Dress
With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!
Fit & Features
- Striped pattern, texture knit fabric, moderate stretch
- Spaghetti straps
- Square neckline with twist
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5675
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachy Babe Tie-Back Crochet Mini Dress
Channel a beachy babe vibe in this trendy crochet mini dress! Designed with a sheer crochet fabric with a boho-inspired woven design, the short dress includes a stretchy knit lining for coverage. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, an adorable tie-back design, a flirty lower back cutout that peaks out on both sides, and a form-hugging fit to flaunt your figure. Style with espadrille sandals.
Fit & Features
- Crochet fabric with woven design, stretchy knit lining
- Square neckline
- Adjustable spaghetti straps
- Tie back straps, back cutout
- Hidden side zipper with hook and eye closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5780
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Vibes Floral Halter Crop Top
Your plus-one to every fun night out. This floral halter crop top drapes effortlessly with a flirty cowl neckline and beaded accents that bring the perfect chic touch.
Fit & Features
- Sheer mesh fabric with brushed knit lining, high stretch
- Floral print
- Sleeveless cowl neckline
- Halter tie-back spaghetti straps, beaded accents
- Open back, lower tie-back spaghetti straps, beaded accents
- Cropped hanky hem
- Runs true to size
Style Number/Barcode: 06001-000262
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bri High-Rise Flare Jeans by Windsor Denim
Keep your casual everyday 'fits trendy with the Bri high-rise flare jeans. This pair by Windsor Denim features a fitted high-rise waist, destructed detailing at the knees, and a fab flare hem. The denim fabric offers a moderate stretch for comfortable wear. Style with a bodysuit and mules.
Fit & Features
- High-rise waist
- Destructed detailing at the knees
- Fitted silhouette, flare hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0354
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Instant Fave Disty Floral Short Sleeve Midi Dress
This adorable disty floral midi dress will be an instant fave of yours for the summer season. It features a crew neckline, short fitted sleeves, a small top keyhole cutout at the back with a button closure, a larger lower back cutout, a high waist seam, a midi-length hem with a high front slit, and a form-hugging silhouette. The floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.
Fit & Features
- Crew neckline, short sleeves
- Small back keyhole cutout, button closure
- Larger lower back cutout, high waist seam
- Midi-length hem, front slit, form-hugging fit
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5184
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love's In The Air Floral Chiffon A-Line Dress
Slip into the romantic vibes of this floral chiffon mini dress for day dates to shower celebrations! The dress flaunts a pretty corset bodice and lace-up back that turns heads, while the A-line silhouette flatters your figure.
Fit & Features
- Dainty floral print, chiffon fabric, stretchy knit lining
- Sweetheart neckline
- Wide shoulder straps
- Underwire bust, tie front, side zipper and hook-eye closure
- Corset-trim bodice, lace-up back design
- A-line silhouette, short-length hem
- Runs true to size
Style Number/Barcode: 05101-4046
Category Name: Vacation Looks
Price: $9.97
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Touch Faux Wool Beret
This beret will add a chic touch to all of your 'fits this season! It features a classic beret design and is composed of a faux wool material. Style with an oversized blazer and ankle booties for a city trip!
Fit & Features
- Classic beret design
- Faux wool material
- Moderate stretch
Style Number/Barcode: 07302-1486
Category Name: Vacation Looks
Price: $6.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Influence Strapless Bodycon Midi Dress
Achieve a stylish rep in this strapless midi dress wherever you go! With a flattering bodycon fit and trendy stone metal insert, this dress will enhance your natural silhouette and captivate any room you enter.
Fit & Features
- Stretchy knit fabric
- Strapless neckline, stone metal insert
- bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000062
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Softest Style Plaid Frayed Scarf
This plaid frayed scarf will be the softest style in your lineup! Perfect for wearing around your neck or shoulders, the styling possibilities are endless. Complete the look in cute boots.
Fit & Features
- Plaid pattern
- Frayed edge trim
- Ultra-soft knit material
Style Number/Barcode: 07305-0459
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coastal Escape Cropped Halter Top
Shop Matching Bottoms: Coastal Escape High Rise Ruched Midi Skirt
Fit & Features
- Smooth knit fabrication
- Sleeveless halter neckline
- Halter neck ties
- Cutouts
- Beaded detailing
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5672
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cold Weather Luxe Faux Fur Trim Gloves
Enter into the cold season with luxe style with these faux fur gloves! They feature a fitted design made from soft faux suede material with chic faux fur cuffs. Complete your cute cold-weather 'fit with a rhinestone-embellished beanie!
Fit & Features
- Fitted design
- Faux suede fabric
- Faux fur cuffs
Style Number/Barcode: 07304-0047
Category Name: Vacation Looks
Price: $7.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feelin' Bold Floral Mesh Strapless Maxi Dress
Be a bold babe in this airy mesh maxi dress designed with a large floral print pattern to turn heads. Featuring ruching at the bust, a high-cut side slit, and a form-hugging silhouette, style with wedges for a sunset dinner.
Fit & Features
- Sheer mesh fabric with full-length brushed knit lining, high stretch
- Large floral print
- Strapless straight-across neckline
- Ruched bust
- Thigh-high side slit
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05101-000098
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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My Lane Corduroy Faux Sherpa Collar Crop Jacket
Take a walk down style lane in this corduroy crop jacket essential for the chilly season ahead! It features long sleeves with button cuffs, a faux sherpa collar, button-down front and flap pockets, and a back elasticized cinch hem. Layer over a basic top and currently trending cargo pants.
Fit & Features
- Long sleeves, button cuffs
- Faux sherpa collar
- Button down front, flap pockets
- Cropped hem
- Back elasticized cinch hem
- Corduroy fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1690
Category Name: Vacation Looks
Price: $15.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Escape Floral Slit Maxi Skirt
Giving off total romantic vibes, this floral maxi skirt is flirty without trying too hard. With a high-rise waist, curve-hugging fit, and a high side slit detail, it’s the perfect blend of dreamy and effortless.
Fit & Features
- Floral print, mesh-lined fabric
- High-rise waist
- Curve-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06501-000065
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Daydream Chiffon Crop Top
You'll look like such a daydream in this airy chiffon crop top! It features a subtle sweetheart neckline, a ruched bust, long sheer bishop sleeves, a cropped hem with a wrap-front detail, and a stylish tie-back design. Complete the look with cute denim and clear mules.
Fit & Features
- Sheer chiffon fabric, front knit lining, minimal stretch
- Sweetheart neckline
- Ruched bust
- Long sheer bishop sleeves, elastic cinched hems
- Cropped hem, wrap-front detail
- Tie-back design
- Runs true to size
Style Number/Barcode: 06003-2301
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On Repeat Flat Over-The-Knee Boots
These must-have flat over-the-knee boots will be styled on repeat all season long. They feature a fitted over-the-knee design, an inner zipper closure that runs down the length of the boot, an almond-shaped toe, and a flat sole with a short block heel. The boots have a trendy design of sleek faux leather at the front with smooth spandex at the back. Pair with a sweater dress for such a chic winter look.
Fit & Features
- Fitted over-the-knee design
- Complete inner zipper closure
- Almond toe
- Flat sole, short block heel
- Half faux leather material
- Half lycra material
- Runs true to size
Style Number/Barcode: 07402-0980
Category Name: Vacation Looks
Price: $11.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bohemian Babe Knit Cutout Tube Top
Channel a boho babe vibe in this sweater knit tube top featuring a strapless straight neckline, dual bust cutouts with a beaded trim, and a front slit accent. Style with the matching mini skirt for a chic and seamless look!
Shop Matching Bottoms: Bohemian Babe Knit High-Rise Mini Skirt
Fit & Features
- Sweater knit fabric, ribbed hems, high stretch
- Strapless straight-across neckline
- Dual bust cutouts, beaded trim
- Front slit design
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 06005-000031
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gimme The Flare Denim Jumpsuit
Give your closet a trendy upgrade in this essential denim jumpsuit perfect for hitting up the farmer's market or grabbing brunch with friends! It features short sleeves, a collar neckline, button-down front closures, four-pocket styling, belt loop accents, and a hip-hugging flare-leg silhouette. Complete the look in peep toe booties.
Fit & Features
- Short sleeves
- Collar neckline
- Button-down front closures
- Four-pocket styling, belt loop accents
- Hip-hugging, flare-leg silhouette
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0366
Category Name: Vacation Looks
Price: $6.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance