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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Vacay Romance Floral Maxi Dress
This is the dress that turns dinner plans into an occasion. Featuring a draped cowl neckline, open back, and oversized florals, it hugs in all the right places while serving effortless looks on vacations, weekend getaways, or date nights.
Fit & Features
- Floral tropical print, knit stretchy fabric
- Cowl halter neckline, tie straps
- Open back
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-001148
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Gianna Striped Linen A-Line Formal Dress
Special Occasions
Effortlessly striking and made for sun-drenched celebrations, the Gianna dress brings together a softly textured striped linen fabric with a modern asymmetrical silhouette. The ruched bodice, side cutout detail, and flowing a-line skirt create beautiful movement, while the open tie-back design adds an unexpected finishing touch.
Fit & Features
- Striped pattern, subtle metallic threads, linen-blend fabric, sewn-in bodice lining
- Asymmetrical neckline, spaghetti straps
- Open tie-back detail, side zipper and hook-eye closure
- Side cutout, ruched bodice accent
- A-line silhouette, high side slit
- Floor-length hem
- Runs true to size
Where to Wear:
Outdoor weddings, vacations, honeymoons, resorts, birthday brunches, cocktail events, engagement parties, summer dinner parties, wineries
Style Number/Barcode: 05002-001567
Category Name: Vacation Looks
Price: $99.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- Ships Free
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Ailith Metallic Striped Formal Dress
Special Occasion
Like a sunset slipping into evening, the Ailith metallic knit column gown catches the light with every step. The softly draped neckline and open cowl back with delicate tie detailing create an effortlessly polished silhouette that feels made for formal celebrations and unforgettable entrances.
Fit & Features
- Metallic striped knit fabric, smooth knit lining
- Cowl neckline
- Adjustable spaghetti straps
- Open tie-back with draped accent
- Column floor-length silhouette
- Runs true to size
Where to Wear:
Outdoor weddings, galas, honeymoons, vacations, resorts, engagement parties, rehearsal dinners, cocktail events, formal milestone celebrations, date nights
Style Number/Barcode: 05002-001738
Category Name: Vacation Looks
Price: $79.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L, XL
Product Badge:- Ships Free
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City Escape Aviator Sunglasses
These aviator sunglasses are the finishing touch for poolside selfies, coffee runs, and pretending you’re off the grid for the weekend.
Fit & Features
- Aviator silhouette
- Clear tinted lenses
- Lightweight frame
- 100% UV protection
Style Number/Barcode: 07008-000180
Category Name: Vacation Looks
Price: $12.90
Availability: In Stock
Available Color: RED
Available Size: NS
Product Badge:- New Arrival
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Resort Vacay Shell Chandelier Earrings
The kind of earrings that make every outfit feel a little more expensive. These cascading shell chandelier earrings were made for vacation dinners, messy buns, and compliments from strangers.
Fit & Features
- Round sheel cascading design
- Chandelier silhouette
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000350
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
Product Badge:- New Arrival
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Moonlit Escape Chiffon Poncho
This sheer chiffon poncho drapes with an easy off-the-shoulder feel, while delicate lace trim adds just the right amount of detail. Toss it over swimwear, pair it with denim, or wear it whenever your outfit needs that extra little something.
Fit & Features
- Sheer chiffon fabric
- Asymmetrical one-shoulder neckline
- Relaxed poncho silhouette
- Lace trim hem
- Runs true to size
Style Number/Barcode: 06204-000173
Category Name: Vacation Looks
Price: $19.90
Availability: In Stock
Available Color: BLACK
Available Size: XS/S, M/L
Product Badge:- New Arrival
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Weekend Breeze Crop Top
This top was made for sunny forecasts and spontaneous plans. The airy gauze fabric, soft hue, and trendy crop length make it look effortless.
Shop The Matching Skirt: Weekend Breeze Maxi Skirt
Fit & Features
- Gauze woven fabric
- Square neckline
- Adjustable spaghetti straps
- Cinched crop-length hem
- Runs true to size
Style Number/Barcode: 06003-000352
Category Name: Vacation Looks
Price: $26.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Everyday Luxe Square Sunglasses
These oversized square sunglasses feature warm gradient lenses, sleek gold-tone details, and a polished silhouette that feels equally at home on vacation, at brunch, or running errands with an iced coffee in hand.
Fit & Features
- Oversized square frames
- Rubber nose supports
- Sleek metal arms with plastic trim
- Tinted lenses
Style Number/Barcode: 07008-000137
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: BROWN
Available Size: NS
Product Badge:- New Arrival
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Bright Side Bracelet Set
This chunky bangle bracelet set mixes translucent and vibrant colorways for an easy statement that pairs perfectly with everything from vacation looks to casual denim days.
Fit & Features
- Two pack bracelet set
- Colored resin material
- Chunky silhouette
Style Number/Barcode: 07003-000242
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: BLUE
Available Size: NS
Product Badge:- New Arrival