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.

  • Wild Card Chiffon Halter Mini Dress

    This chiffon halter dress combines a bold mixed animal print, open back, and flowing hanky hem for a look that feels equal parts daring and unforgettable. Style with sandals for vacations, date nights, or parties.

    Fit & Features

    • Animal print chiffon fabric, lined
    • Halter neckline, hardware insert, tie straps
    • Open back design
    • Flowy A-line silhouette
    • Hanky mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001177

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Set The Mood Abstract Print Halter Maxi Dress

    Some dresses complete the outfit. This one sets the entire mood. This abstract print halter maxi dress combines a dramatic plunging cowl neckline, sculpting ruching, and a fluid front sash for a look that feels both gallery opening and late-night dinner reservation.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Abstract print
    • Sleeveless plunging cowl neckline, bar strap detail
    • Tie-back halter straps, open back, lower back spaghetti straps
    • Front sash accent, ruched detailing
    • Maxi-length hem, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001173

    Category Name: Vacation Looks

    Price: $56.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L, XL

    Product Badge:
    • New Arrival
  • Shay Tropical Printed Bead Mini Dress

    Special Occasion

    Made for the nights when blending in simply isn't on the itinerary, the Shay mini dress brings bold glamour to every RSVP. This beaded mesh dress features a sculpted strapless silhouette, intricate tropical-inspired print, and a twisted sweetheart neckline that catches attention from every angle.

    Fit & Features

    • Printed tropical design, beaded embellishments, mesh-lined fabric
    • Strapless sweetheart neckline,
    • Bodycon mini-length silhouette
    • Runs true to size

     

    Where to Wear:

    Bachelorettes, birthday dinners, date nights, cocktail parties, fashion-forward events, vacations, honeymoons, resort getaways

    Style Number/Barcode: 05001-000783

    Category Name: Vacation Looks

    Price: $89.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XXS, XS, S, M, L

    Product Badge:
    • Ships Free
  • Island Intentions Satin Mini Dress

    The dress to pack in your suitcase. Designed with a tropical-inspired print, beaded straps, and a lace-up open back, this satin mini dress was made for oceanfront dinners and resort cocktails.

    Fit & Features

    • Silky satin woven fabric
    • Subtle tropical print
    • Square neckline
    • Beaded spaghetti straps
    • Lace-up open back
    • Curve-hugging, mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000596

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Destination Glam Abstract Print Halter Top

    Booked, busy, and dressed like the destination. This abstract print halter top features a plunging neckline and ruched fit that hugs in all the right places for rooftop dinners, resort nights, and every plan in between. Pair with the matching maxi skirt.

    Shop Matching Bottoms: Destination Glam Abstract Print Maxi Skirt

    Fit & Features

    • Sleek knit fabric, high stretch
    • Abstract print
    • Sleeveless deep V-neckline
    • Tie-back halter straps, partially open back
    • Ruched bodice
    • Mid-length hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000687

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Garden Glow Flower Statement Earrings

    These dimensional acrylic flower earrings feature vibrant petals and a rhinestone-embellished center, making them the perfect finishing touch for vacations, brunch, and every outfit that could use a playful pop.

    Fit & Features

    • Dimensional flower
    • Mini rhinestone embellished center
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000384

    Category Name: Vacation Looks

    Price: $13.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: NS

    Product Badge:
    • New Arrival
  • Sunny Side Up Aviator Sunglasses

    These colored aviator sunglasses bring a retro-inspired feel with an effortless cool factor that works from beach days to city strolls.

    Fit & Features

    • Square-shaped aviator silhouette
    • Rubber nose supports
    • Tinted lenses
    • 100% UV protection
    • Lightweight frame

    Style Number/Barcode: 07008-000160

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: NS

    Product Badge:
    • New Arrival
  • Pretty Please Flower Earrings

    Cute from every angle and impossible to overlook. These flower earrings feature delicate petal studs with dangling gem charms that add the prettiest finishing touch to looks for brunch, parties, or vacations.

    Fit & Features

    • Flower designs, mini rhinestone embellished center
    • Dainty chain fringe
    • Teardrop rhinestone charm
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000479

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

    Product Badge:
    • New Arrival
  • Tropical Flair Four-Pack Hair Clips Set

    Your messy bun just booked a one-way ticket somewhere tropical. These tropical flower clips add the cutest little finishing touch to beach days, dinner plans, and every photo you almost didn’t post.

    Fit & Features

    • Four-pack hair clips set
    • Tropical flowers
    • Clip closure

    Style Number/Barcode: 07006-000134

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

    Product Badge:
    • New Arrival
  • Weekend Worthy Tropical Floral Tube Top

    One top, endless outfit screenshots. This tropical floral tube top combines a sleek strapless silhouette with adjustable drawstring details for a look that's effortlessly on-trend.

    Fit & Features

    • Knit fabric, high stretch
    • Large tropical floral print
    • Strapless straight-across neckline
    • Ruched side seams, adjustable drawstrings
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000619

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Packed And Polished Hair Claw Clip

    Your updo just booked a vacation. This clear embellished tropical flower hair claw clip adds a playful finishing touch to messy buns, sleek twists, and every warm-weather outfit in between.

    Fit & Features

    • Hair claw clip silhouette
    • Tropical flower design
    • Embellished detailing
    • Clip closure

    Style Number/Barcode: 07006-000150

    Category Name: Vacation Looks

    Price: $8.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: NS

    Product Badge:
    • New Arrival
  • Desert Disco Beaded Bra Top

    Made for head-turning stares. With intricate beadwork, cascading draped strands, and an open back silhouette, this statement bra top brings a festival-luxe feel that looks straight off a designer runway.

    Fit & Features

    • Beaded embellishments, knit fabric
    • Halter neckline, tie straps
    • Open back with tie
    • Cascading beaded front drape
    • Bra top silhouette
    • Runs true to size

    Style Number/Barcode: 06001-000623

    Category Name: Vacation Looks

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Glam Abstract Print Maxi Skirt

    Booked, busy, and dressed like the destination. This abstract print maxi skirt features a ruched waist and high-cut side slit that creates a flowy fit for rooftop dinners, resort nights, and every plan in between. Pair with the matching halter top.

    Shop Matching Top: Destination Glam Abstract Print Halter Top

    Fit & Features

    • Sleek knit fabric, high stretch
    • Abstract print
    • High-rise waist, ruched detailing
    • High-cut side slit
    • Maxi-length hem
    • Flowy A-line silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000180

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Vacay Slay Shell-Trim Crochet Mini Skirt

    The kind of skirt that instantly creates a vacay slay. This crochet mini skirt pairs a barely-there open knit with shell-trim details for a look that was made for beach clubs, oceanside strolls, and spontaneous getaway plans. Style with the matching crop top.

    Shop Matching Top: Vacay Slay Shell-Trim Crochet Crop Top

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Mid-rise waist
    • Mini-length hem, shell trim fringe
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000146

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Vacay Slay Shell-Trim Crochet Crop Top

    The kind of top that instantly creates a vacay slay. This crochet crop top pairs a barely-there open knit with shell-trim details for a look that was made for beach clubs, oceanside strolls, and spontaneous getaway plans. Style with the matching mini skirt.

    Shop Matching Bottoms: Vacay Slay Shell-Trim Crochet Mini Skirt

    Fit & Features

    • Crochet knit fabric, lined bust, moderate stretch
    • Sleeveless deep V-neckline
    • Halter spaghetti straps
    • Partially open back
    • Cropped hem, shell trim fringe
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-000373

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Poolside Priority Tie Front Top

    This top practically comes with a boarding pass. Featuring a flirty tie front crop top, flutter sleeves, and a crop length, it's the kind of look that belongs at pool parties, vacations, and every photo op in between.

    Shop The Matching Skirt: Poolside Priority Slit Maxi Skirt

    Fit & Features

    • Stretchy knit fabric
    • Tie-front neckline
    • Flutter short sleeves
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000110

    Category Name: Vacation Looks

    Price: $22.90

    Availability: In Stock

    Available Color: YELLOW-2

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Poolside Priority Slit Maxi Skirt

    This skirt practically comes with a boarding pass. Featuring a flirty mid-rise waist, curve-hugging fit, and a leg-baring high-front slit, it's the kind of look that belongs at pool parties, vacations, and every photo op in between.

    Shop The Matching Top: Poolside Priority Tie Front Top

    Fit & Features

    • Stretchy knit fabric
    • Mid-rise waist
    • High front slit
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000157

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Katana Abstract A-Line Formal Dress

    Special Occasion

    Float through the evening like you already belong on the best-dressed list in The Katana, a sweeping statement made for unforgettable arrivals. The abstract print mesh fabric, plunge halter V-neck, and open back bring a striking contrast to the soft movement of the A-line floor-length silhouette and front slit.

    Fit & Features

    • Abstract print, mesh fabric, knit stretchy lining
    • Plunge halter V-neckline with tie straps, padded bra cups
    • Open back, lower zipper and hook-eye closure
    • Side ruched seams
    • Front slit
    • A-line floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Weddings, galas, engagement parties, art galleries, cocktail soirees, birthday dinners, vacations, destination celebrations

    Style Number/Barcode: 05002-000879

    Category Name: Vacation Looks

    Price: $79.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free