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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Scene Set Statement Earrings
Polished with a little bite. These statement earrings bring glossy teardrop stones and textured metal trim for a sleek finish that elevates a simple outfit.
Fit & Features
- Statement drop earrings
- Glossy teardrop stone design
- Textured metal trim
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000439
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Sleek Strike Square Sunglasses
Lowkey dangerous in the best way—these were made to add a little attitude. The sleek square sunglasses shape keeps it polished, while the snake-inspired arms wrap things up with just the right amount of edge.
Fit & Features
- Square-shaped design
- Tortoisehell arms with snake design
- Thin metal nose bridge
- Adjustable rubber nose pads
- Tinted lenses, small studded side details
- 100% UV protection
Style Number/Barcode: 07008-000244
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: TORTOISE
Available Size: NS
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Soft Launch Square Frame Sunglasses
Giving It Girl taste with zero effort required. These square frame sunglasses are the pair you throw on for vacation mornings, coffee dates, and every “wait, take another pic” moment.
Fit & Features
- Lightweight plastic frame
- Chunky square silhouette
- Tinted lenses
Style Number/Barcode: 07008-000230
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: IVORY
Available Size: NS
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Running Late Flat Top Sunglasses
The outfit came together in five minutes but somehow still looks chic. These flat top sunglasses bring that cool girl off-duty feel with oversized coverage and sleek metal details that go with literally everything.
Fit & Features
- Lightweight metal frame
- Oversized flat top silhouette
- Rimless gradient lenses
- Slim arms with tortoiseshell-inspired detail
Style Number/Barcode: 07008-000231
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
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Just Add Sandals Midi Skirt
The outfit came together the second this skirt showed up. A hanky midi skirt with a ruched mid-rise waistband and flowy A-line fit, it's the effortless piece that works for brunch, vacations, and every plan in between.
Fit & Features
- Smooth knit fabric, knit lining, high stretch
- Mid-rise ruched waistband
- A-line flowy fit
- Hanky midi-length hem
- Runs true to size
Style Number/Barcode: 06501-000195
Category Name: Vacation Looks
Price: $29.90
Availability: In Stock
Available Color: BLUE
Available Size: M, L
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Sleek Attitude Oval Sunglasses
Serving sleek attitude with every glance. These oval sunglasses bring a chic, lightweight feel with just enough edge for everyday plans, from coffee runs to last-minute invites.
Fit & Features
- Oval-shaped design
- Thin metal arms, metal side accents
- Thin metal nose bridge
- Adjustable rubber nose pads
- Lightly tinted lenses
Style Number/Barcode: 07008-000248
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
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Seen At Sunset Cat Eye Sunglasses
The kind of sunglasses that make even a basic tank and denim feel planned. These cat eye sunglasses bring a sleek retro vibe that works from pool days to late lunch plans without missing a beat.
Fit & Features
- Lightweight plastic frame
- Narrow cat eye silhouette
- Tinted lenses
- Rounded edge detailing
Style Number/Barcode: 07008-000240
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: CLEAR
Available Size: NS
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Sweet Tea Flirt Mini Dress
This is the kind of dress that accidentally becomes your whole personality for the summer. Between the tiny floral print, smocked waist, and floaty skater fit, it’s basically made for farmers market mornings, brunch, and daytime celebrations.
Fit & Features
- Delicate floral print, woven fabric
- Square neckline
- Wide shoulder straps
- Stretchy socked bodice
- Ruffled skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001479
Category Name: Vacation Looks
Price: $62.90
Availability: In Stock
Available Color: IVORY
Available Size: S, M, L
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Picnic Flirt Eyelet Mini Dress
Sweet, but with a little attitude—just how we like it. This eyelet skater dress shapes you with a corset bodice and flexible boning, while the flutter sleeves and lace-up back keep it playful for every dressy event.
Fit & Features
- Eyelet woven fabric, woven lining
- Sweetheart neck, ruffle trim, bust tie
- Flutter short sleeves
- Lace-up back, zipper and hook-eye closure
- Corset bodice, flexible boning
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05101-001431
Category Name: Vacation Looks
Price: $56.90
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
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Wild Card Sheer Mesh Poncho Top
Throw it on and suddenly your outfit has something to say. This abstract animal print sheer mesh poncho top layers effortlessly for nights out, last-minute plans, or whenever your look needs a little edge.
Fit & Features
- Abstract animal print
- Sheer mesh fabric
- Relaxed poncho silhouette
- Crop-length hem
- Runs true to size
Style Number/Barcode: 06001-000704
Category Name: Vacation Looks
Price: $27.90
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
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Easy Plans Button Romper
From vacation mornings or weekend plans, it's the romper you'll keep reaching for when you want to look effortlessly chic. This sleeveless romper serves polished allure with a tailored button-front bodice and breezy shorts that are ready for everything on your calendar.
Fit & Features
- Linen-like woven fabric
- Square neckline
- Wide shoulder straps
- Button front accents
- Flowy shorts hem
- Runs true to size
Style Number/Barcode: 06303-000059
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, M, L
Product Badge:- New Arrival
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Chic Upgrade Stone Hand Chain
Your bracelet stack just got a chic upgrade. This three-row hand chain connects from wrist to ring with stone and rhinestone embellishments for a glam finish that does all the accessorizing for you.
Fit & Features
- Hand chain silhouette connecting bracelet to ring
- Three-row design
- Stone and rhinestone embellishments
- Lobster clasp closure with extender
- Adjustable fit
Style Number/Barcode: 07003-000266
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival