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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Checked In Lace Shorts
Booked, packed, and already thinking about the vacation photos. These lace shorts pairs a form-hugging fit with a flirty low-rise waist for an effortlessly styled getaway look.
Shop Matching Top: Checked In Lace Crop Top
Fit & Features
- Lace-lined fabric
- Low-rise waist, hoop insert belt accent
- Form-hugging fit
- Cheeky bottom
- Runs true to size
Style Number/Barcode: 06503-000335
Category Name: Vacation Looks
Price: $29.90
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Bloom Flower Arm Cuff
The outfit was cute, but the flower arm cuff made it unforgettable. Designed with sculptural floral details and a wrapped silhouette, this statement piece brings an elevated finish to dresses, swim looks, and vacation outfits alike.
Fit & Features
- Metal wrap-around design
- Resin flower accents
Style Number/Barcode: 07003-000247
Category Name: Vacation Looks
Price: $14.90
Availability: In Stock
Available Color: GREEN
Available Size: NS
Product Badge:- New Arrival
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Center Of Attention Floral Maxi Dress
This is the dress that gets the double-take. Designed with a curve-hugging mermaid silhouette and oversized floral print, it brings major romance with a little bit of drama.
Fit & Features
- Statement floral print, stretchy knit fabric
- Strapless tube neckline
- Curve-hugging, mermaid fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000593
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: XS, S, M, L, XL
Product Badge:- New Arrival
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Packing This First Mini Dress
This dress belongs in a photo with palm trees in the background. Featuring a body-hugging sweater knit and an oversized tropical flower, it's the kind of mini dress that makes vacation packing easy.
Fit & Features
- Sweater knit fabric with stretch
- Strapless tube neckline
- Tropical flower print
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000416
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Vacay-Coded Tropical Floral Print Maxi Skirt
Vacation-coded, curve-hugging, and not here to blend in. This tropical floral print maxi skirt brings a high-rise waist, a high-cut side slit, and ruched shaping that’s ready for rooftop reservations, vacation dinners, and every “where did you get that?” moment. Pair with the matching halter top.
Shop Matching Top:
Fit & Features
- Knit fabric with lining, high stretch
- Large tropical floral print
- High-rise waist
- High-cut side slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06501-000169
Category Name: Vacation Looks
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Part of a Set
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Resort Reserved Tropical Print Halter Jumpsuit
Vacation photos are about to have some competition. This tropical print halter jumpsuit pairs a draped cowl neckline with a striking beaded open back and flowy wide-leg silhouette that looks polished with almost zero effort.
Fit & Features
- Tropical printed woven fabric
- Sleeveless cowl neckline, halter strap
- Open back, beaded strappy design, lobster clasp closures
- Lower back zipper closure
- High waist seam
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-000036
Category Name: Vacation Looks
Price: $69.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
Product Badge:- New Arrival
- Tropical printed woven fabric
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Coconut Coast Cutout Maxi Dress
Booked the trip and packed this tropical maxi dress that brings vacay vibes with a smocked fit, breezy skirt, and just the right amount of skin-baring detail. Pair with sandals and sunnies.
Fit & Features
- Tropical palm print, gauze-woven fabric
- Strapless sweetheart neckline
- Ruched drawstring tie-front bodice
- Cutout accent
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000601
Category Name: Vacation Looks
Price: $59.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
Product Badge:- New Arrival