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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Sun Chaser Crochet Crop Top
Booked the trip, packed the crochet, no further questions. This crochet crop top brings breezy texture, scalloped details, and an open-back design that was made for vacation photos and rooftop plans. Pair with the matching maxi skirt.
Shop Matching Bottoms: Sun Chaser Crochet High Slit Maxi Skirt
Fit & Features
- Crochet knit fabric, moderate stretch
- Scalloped trim
- Sleeveless deep V-neckline
- Tank shoulder straps
- Open back, lower tie-back spaghetti straps
- Ultra-cropped hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-000338
Category Name: Vacation Looks
Price: $32.90
Availability: In Stock
Available Color: GOLD
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Sun Chaser Crochet High Slit Maxi Skirt
Booked the trip, packed the crochet, no further questions. This crochet maxi skirt brings breezy texture, scalloped details, and a high-cut side slit that was made for vacation photos and rooftop plans. Pair with the matching crop top.
Shop Matching Top: Sun Chaser Crochet Crop Top
Fit & Features
- Crochet knit fabric, moderate stretch
- Scalloped hem
- High-rise waist, tie-front detail
- High-cut side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-000127
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: GOLD
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Weekend Away Strapless Maxi Dress
This chevron maxi dress hugs in all the right places with a sleek strapless neckline and leg-baring side slit that was practically made for resort dinners, sunset cocktails, and strolling the beachside town.
Fit & Features
- Chevron pattern, knit fabric
- Strapless neckline
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000595
Category Name: Vacation Looks
Price: $46.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Meet Me At Sunset Floral Mini Dress
Designed with a plunging halter neckline, dramatic open back, and flirty ruffle hem, this mini dress features an oversized floral print and cascading side sash made for vacations, going night, and flirty weekend looks.
Fit & Features
- Floral print, mesh fabric, knit lining
- Plunge halter neckline, bar accent, tie straps
- Curve-hugging fit
- Ruffled side sash
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000969
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Rynlee Strapless Mermaid Formal Dress
Special Occasion
Made for the kind of evening that lingers long after the last dance, Rynlee slinky knit mermaid gown blends sleek glamour with striking detail. The strapless neckline, wooden hoop insert cutout bust, and flowing center front sash create a sculpted silhouette that feels equal parts polished and unforgettable.
Fit & Features
- Slinky knit fabric, knit lining
- Strapless neckline
- Wooden hoop insert, cutout, center front sash
- Mermaid floor-length silhouette
- Runs true to size
Where to Wear:
Destination weddings, engagement parties, vacations, honeymoons, resort getaways, cocktail parties, date nights, birthday dinners, formal celebrations
Style Number/Barcode: 05002-001603
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: SAGE
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Rooftop In Santorini Maxi Dress
The dress equivalent of a first class upgrade. With a plunging halter neckline, statement bead details, and a low open back, this maxi dress was made for resort dinners, oceanfront cocktails, and making every entrance feel a little more unforgettable.
Fit & Features
- Mesh fabric, knit lining
- Plunge halter neckline
- Open back design
- Front colored stone button accents
- Ruched drop waist panel
- Side slit
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-001163
Category Name: Vacation Looks
Price: $48.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Ocean View Floral Beaded Mini Dress
This is the dress that ends up in every vacation photo. With a draped cowl neckline, floral beading, and an open tie-back design, this bodycon mini dress was made for dinner reservations that turn into unforgettable nights.
Fit & Features
- Floral print, beaded mesh fabric, sewn-in knit lining
- Cowl neckline
- Spaghett straps
- Open tie-back
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000830
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Dinner At Eight Floral Maxi Dress
Some dresses get compliments. This one starts conversations. Featuring an elegant cowl neckline, an open-back halter design, and oversized floral artwork, this maxi dress was made for vacation dinners, wedding guest RSVPs, and every plan that deserves a dramatic entrance.
Fit & Features
- Tropical floral print, knit stretchy fabric
- Cowl halter neckline
- Open tie-back
- Side slit
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000678
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Midnight Magic Halter Mini Dress
A little sparkle and magic. Featuring a draped cowl neckline, open back halter design, and celestial-inspired sequin artwork, this sweater mini dress was made for cocktail parties, birthday dinners, and unforgettable entrances.
Fit & Features
- Sweater knit fabric
- Cowl halter neckline
- Open back with strap detail
- Sequin-embellished sun
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 06005-000360
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Booked And Beachside Maxi Dress
This is the dress you pack first and plan the trip around later. Featuring a statement hardware detail, dramatic front cutout, and leg-lengthening slit, this maxi dress was made for sunset dinners, oceanfront cocktails, and every photo op.
Fit & Features
- Smooth knit fabric, stretchy
- Halter neckline, tie straps
- Front hardware insert and cutout bodice
- Ultra-high front slit
- Flowy A-line maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000790
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: HUNTER
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Sunshine On Schedule Halter Romper
Your vacation itinerary just found its outfit. This plunging halter romper brings all the resort energy with a vibrant abstract print, a cinched waist, and a flirty skater silhouette perfect for tropical resorts, sunny weekends, and beachside brunch.
Fit & Features
- Abstract print, knit fabric
- Plunge halter neckline, tie straps
- Open back design
- Cinched waist
- Flowy skater hem
- Built-in shorts knit lining
- Runs true to size
Style Number/Barcode: 06503-000329
Category Name: Vacation Looks
Price: $49.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
Product Badge:- New Arrival