Vacation Looks

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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.

  • Sunkissed Chic Cutout Crochet Maxi Dress

    Resort plans just got a plot twist. This beaded crochet maxi dress serves sculpted curves with a sweetheart neckline, waist cutout, and chic bead details made for walking in and turning heads.

    Fit & Features

    • Crochet knit fabric with knit lining, moderate stretch
    • Sleeveless sweetheart neckline, U-wired metal insert, beaded fringe design
    • Padded bust, waist cutout
    • Adjustable spaghetti straps
    • Back zipper with hook-eye closure
    • Maxi-length hem, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001474

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Low Key Drama Open Back Plunge Dress

    A dramatic neckline and an open back make this one an instant standout. This flowing dress pairs a plunging front with airy draped sleeves and a side-tie detail for an effortlessly elevated look with beautiful movement. Perfect for vacations, dinner dates, and special occasions where an unforgettable entrance is part of the plan.

    Fit & Features

    • Silky satin fabric, sewn-in woven lining
    • Plunging V-neckline
    • Open-back design, adjustable strap, lower zipper and hook-eye closure
    • Draped long sleeves with side tie accents
    • Curve-hugging mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001334

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Paradise In Floral Midi Dress

    The RSVP practically sends itself. This tropical floral midi dress features a breezy asymmetric hem and flattering halter neckline that was made for destination weddings, dinners, and vacation photos.

    Fit & Features

    • Abstract floral print, mesh-lined fabric
    • Halter V-neckline
    • Spaghetti straps
    • Ruffled trim
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000813

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: PINK-2

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Amara Mesh Halter A-Line Formal Dress

    Special Occasion

    Easy, alluring, and made for warm-weather RSVPs, the Amara mesh A-line gown brings a breezy kind of drama to every step. A ruched halter bodice, front cutout, and double-slit skirt create movement that feels effortless, polished, and just a little unforgettable.

    Fit & Features

    • Lined mesh fabric
    • Halter neckline, tie straps
    • Open tie-back design
    • Thigh-high front slit
    • Flowy A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Destination weddings, beach weddings, honeymoons, vacations, resorts, birthday dinners, cocktail events, bachelorette weekends, sunset celebrations, yacht parties

    Style Number/Barcode: 05002-001671

    Category Name: Vacation Looks

    Price: $69.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Bead Side Halter Maxi Dress

    Minimal effort, major impact. This textured knit maxi dress brings a halter neckline, curve-skimming fit, and side cutouts with bead accents for dinner plans, vacations, and every invite that calls for something sleek.

    Fit & Features

    • Texture knit fabric
    • Halter neckline
    • Side cutouts with beaded straps
    • High center back slit
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001472

    Category Name: Vacation Looks

    Price: $56.90

    Availability: In Stock

    Available Color: BROWN-2

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Flirt First Flutter Sleeve Crop Top

    A little flounce, a lot of attitude. This flutter sleeve crop top brings the cinched tie-front detail and shoulder-baring fit your jeans have been waiting for.

    Fit & Features

    • Gauze woven fabric
    • Sweetheart neckline
    • Cinched tie-front design
    • Short flutter sleeves, can be worn off-the-shoulder
    • Smocked back
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000065

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Shore Thing Statement Earrings

    These iridescent shell drop earrings pair luminous shine with textured metal accents for a look that feels equal parts beach treasure and polished statement.

    Fit & Features

    • Textured accent
    • Iridescent shell drop silhouette
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged

    Style Number/Barcode: 07001-000405

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • New Arrival
  • Bloom Snap Flower Hair Clips

    Your quick hair fix just got way cuter. This two-pack flower hair clip set brings a glossy petal design with claw clip closures for easy updos and half-up styles.

    Fit & Features

    • Two-pack hair clip set
    • Tropical flower designs
    •  Claw clip closure

    Style Number/Barcode: 07006-000139

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: NS

    Product Badge:
    • New Arrival