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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Glam Goals Flat Top Sunglasses
Reach your goals to get glam with these flat-top sunglasses featuring rhinestone embellished trim, curved gradient lens, and plastic nose and arm support. Complete the look in a sultry bustier and jeans.
Fit & Features
- Flat-top design
- Rhinestone embellished trim
- Curved gradient lens
- Plastic nose and arm support
Style Number/Barcode: 07008-0923
Category Name: Vacation Looks
Price: $6.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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New Look Round Metal Sunglasses
Rock a new look in these round sunglasses featuring a metal frame, gradient lens, and rubber nose support. Complete the look in a cool moto jacket.
Fit & Features
- Round metal frame
- Gradient lens
- Rubber nose support
Style Number/Barcode: 07008-0929
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beach Side Longline Bikini Top
Sitting beachside and looking so fine in this longline bikini top! It features a square neck, detachable spaghetti straps, removable padding, and a bandeau-style silhouette. Complete the look in the matching bikini bottoms.
Shop The Matching Bottoms: Beach Side Hipster Bikini Bottoms
Fit & Features
- Squareneck
- Detachable spaghetti straps
- Removable padding
- Longline hem
- Bandeau-style silhouette
- Lined knit fabric
- Fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0673
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Calabasas Caged Bikini Top
Spend time under the sun in this caged bikini top featuring a plunge v-neck with strap detail, removable padding, and a caged-back design. Complete the look in the matching bikini bottoms.
Shop The Matching Bikini Bottoms: Calabasas Lattice Bikini Bottoms
Fit & Features
- Plunge v-neck, strap detail
- Removable padding
- Caged-back design
- Lined knit fabric
- Fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0674
Category Name: Vacation Looks
Price: $4.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutie Alert Cap Sleeve Swim Top
Cutie alert! All eyes on you at the pool in this cap sleeve swim top featuring a scoop neck, removable padding, adjustable side ties, and a cropped hem on lined knit fabric. Complete the look in the matching swim bottoms.
Shop The Matching Bottoms: Cutie Alert String Bikini Bottom
Fit & Features
- Cap sleeves
- Scoop neck
- Removable padding
- Adjustable side ties
- Cropped hem
- Lined knit fabric
- Fits true to size
RETURNS ARE ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Style Number/Barcode: 07104-0672
Category Name: Vacation Looks
Price: $8.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Radar Lace-Up Flat Sandals
Your glam radar is coming in hot! Create a sparkly look with these lace-up sandals featuring a round toe, rhinestone embellished straps, adjustable buckle closure, and a flat sole. Complete the look in a sleek satin dress.
Fit & Features
- Round toe
- Rhinestone embellished straps
- Lace-up design
- Adjustable buckle closure
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-0975
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Catch Feels Dual Buckle Sandals
Catch feels for these comfy and stylish sandals! They feature an open almond toe with strap, dual buckle strap design, and a slide-on styling. Complete the look in trendy denim shorts.
Fit & Features
- Open almond toe with toe strap
- Dual buckle strap design
- Slide-on/off styling
- Runs true to size
Style Number/Barcode: 07404-1034
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Forward Espadrille Flat Sandals
Season's change and so should your shoe game! Slide into these espadrille sandals featuring a slightly square toe, single band, and a flat sole. Complete the look in a cute sundress for the farmer's market.
Fit & Features
- Slight square toe
- Single-band
- Flat sole
- Espadrille trimming
- Slide-on/off design
- Runs true to size
Style Number/Barcode: 07404-1059
Category Name: Vacation Looks
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachside Beauty Tie-Front Top
Showcase effortless vibes in this breezy tie-front top that is perfect for a beachside vacay. It features three-quarter length flowy sleeves, a tie-front design creating a V-neckline, and a cropped fit. Style with your favorite high waist bottoms and cute sandals.
Fit & Features
- Three-quarter length flowy sleeves
- Tie-front
- V-neckline
- Cropped
- Rayon gauze fabric, crinkle detailing
- Runs true to size
Style Number/Barcode: 06204-1190
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Retro Chic Wavy Striped Crochet Tube Top
Fit & Features
- Unlined crochet knit fabrication
- Sleeveless sweetheart neckline
- Keyhole cutout at the bust
- Wavy striped pattern
- Cropped hem
- Runs true to size
Shop Matching Skirt: Retro Chic Wavy Striped Crochet Midi Skirt
Style Number/Barcode: 06005-2189
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beach Cottage Striped Linen Top
This striped linen top is perfect for a beach vacay! It features cuffed dolman short sleeves, a collared neckline, a button-down front with a pocket, and a flirty tie-knot cropped hem. Complete the look in denim shorts.
Fit & Features
- Cuffed dolman short sleeves
- Collared neckline
- Button-down front
- Front pocket
- Tie-knot cropped hem
- Striped pattern
- Linen woven fabric, no stretch, fits true to size
Style Number/Barcode: 06003-1796
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy-Chic Style Halter Midi Dress
Showcase your trendy-chic status in this of-the-moment midi dress! It features a sleeveless halter neckline, spaghetti straps that lead to a cross-back lace-up strappy design, a sleek front O-ring accent, a midi-length, curve-hugging silhouette, and an all-over geometric striped pattern. Style this dress with heeled mules.
Fit & Features
- Sleeveless halter neckline, spaghetti straps
- Open back, strappy cross-back lace-up design, tie closure
- Front O-ring detail
- Midi-length, form-fitting silhouette
- Geometric striped pattern
- Knit fabric, partial front knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4411
Category Name: Vacation Looks
Price: $4.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Speed Racer Graphic Lace-Up Tee
Get in it to win it wearing this graphic tee featuring short sleeves, a square neck, and a front lace-up placket with exposed seam detail and a cropped hem. Complete the look in skinny jeans for a cute look.
Fit & Features
- Short sleeves
- Square neck
- Lace-up placket
- Graphic detail
- Exposed seams, cropped hem
- Cotton blend fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06002-1163
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Palm Beach Linen Crochet Kimono
Imagine yourself in this linen kimono walking the beach under the palm trees! It features 3/4 length sleeves, an open front design with tie waist, side slits, and crochet trim. Complete the look in a cute floppy straw hat.
Fit & Features
- 3/4 length sleeves
- Open-front design
- Tie waist, side slits, crochet trim
- Mid-calf length hem
- Linen fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1415
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy And Chic Sheer Crop Top
Breezy and chic, this sheer woven crop top will bring effortless vibes to your look. It features a sweetheart neckline, long bishop sleeves, an adorable tie-back design, a cropped fit, and an all-over swiss dot pattern. Style this top with denim shorts and sandals.
Fit & Features
- Sweetheart neckline
- Long bishop sleeves, elastic cinched hems
- Tie-back design
- Cropped
- Swiss dot pattern
- Sheer woven fabric, partial front knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1653
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Current Mood Denim Belted Mini Skirt
With this denim mini skirt, you'll always be in the mood to create fab looks! It features a high-rise waist, button, and hidden zipper closure, an adjustable belt with belt loops, front and back pockets on stretchy denim fabric. Complete the look in a bodysuit and knee-high boots.
Fit & Features
- High-rise waist
- Button and hidden zipper closure
- Adjustable belt and belt loops
- Front and back pockets
- Mini-length hem
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0066
Category Name: Vacation Looks
Price: $8.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plaid On Babe Pleated Skort
Keep it chic in a plaid skort for a fab day out! The skort features a plaid print, a high-rise elastic waist, a pleated skirt overlay, and a pair of wide-leg shorts. The skort is composed of a woven fabric that offers a relaxed fit with a minimal stretch. Complete look with a bustier and sandals.
Fit & Features
- Plaid print
- Elastic high rise waist
- Pleated skirt overlay
- Wide leg shorts
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06303-0201
Category Name: Vacation Looks
Price: $32.90
Availability: Out of Stock
Product Badge:- Clearance
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Blissful Blooms Crepe Floral Kimono
Feel the bliss of these floral blooms! Step out for spring in this crepe kimono featuring three-quarter length sleeves, an open front, and a flowy longline hem. Complete the look in a casual bodycon dress.
Fit & Features
- Three-quarter length sleeves
- Open front
- Flowy longline hem
- Floral pattern
- Crepe fabric, no stretch
Style Number/Barcode: 06204-1423
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ditsy Floral Off-Shoulder Crop Top
Create a cute look in this disty floral off-the-shoulder crop top featuring short puff sleeves, dual drawstrings on the front, and pleat detail on stretchy knit fabric. Complete the look in high-rise jeans.
Fit & Features
- Off-the-shoulder
- Short puff sleeves
- Dual drawstrings on the front
- Pleat detail, cropped hem
- Ditsy floral pattern
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06001-4284
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On A Roll Denim Mom Shorts
Dang fashionista! You're on a stylish roll in these denim mom shorts featuring an on-trend high-rise waist, distressed accents, slight color fading effect, and a front side rolled hem on medium wash denim fabric. Complete the look in a cute crop top.
Fit & Features
- High-rise waist
- DIstressed accents, front side rolled hem
- Slight color fading effect
- Mom-style silhouette
- Front button and hidden zipper closure
- Five-pocket design, belt loop accents
- Fits true to size
Style Number/Barcode: 06603-0284
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Cutie High Rise Mom Shorts
Flaunt your cuteness in these high-rise mom shorts featuring trendy distressed details, a raw cut hem, and cool color fading on medium wash denim fabric with minimal stretch. Complete the look in a bodysuit and sneakers.
Fit & Features
- High-rise waist
- Mom style
- Distressed details, color fade effect
- Raw cut hem
- Front button and hidden zipper closure
- Five-pockets, belt loop accents
- Medium wash denim, minimal stretch, fits true to size
Style Number/Barcode: 06603-0283
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Fling Flowy Sleeve Kimono
This three-quarter length sleeve kimono is in for the long haul! It features an open-front, side slit accents, and a floral pattern on gauze woven fabric. Complete the look in a chic midi dress and booties.
Fit & Features
- Three-quarter length sleeves
- Open front
- Side slit accents
- Floral pattern
- Gauze woven fabric, no stretch
Style Number/Barcode: 06204-1425
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Comfort Level Criss-Cross Sandals
Reach the perfect level of comfort in these criss-cross sandals featuring an almond toe, platform sole, and an adjustable ankle buckle closure. Complete the look in cute loungewear set for a chill day.
Fit & Features
- Almond toe
- Platform comfort sole
- Criss-cross strap design
- Adjustable ankle buckle closure
Style Number/Barcode: 07404-1038
Category Name: Vacation Looks
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Whispered Secrets Floral Mesh Maxi Dress
Soft girl meets siren vibes. With delicate lace trim and a mesh maxi flow, this floral dress brings that effortlessly undone energy to every room.
Fit & Features
- Floral print, mesh fabric lined with stretch knit
- Lace trim V-neckline
- Spaghetti straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000230
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free