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.

  • Brunch Bound Ruffle High-Low Maxi Skirt

    Light, airy, and ready for wherever the day decides to go. This ruffle maxi skirt brings an effortless, breezy feel with its lightweight woven fabric and high-low flowy fit that's made for weekend brunch with your girls. Style with the matching cropped vest.

    Shop Matching Top: Brunch Bound Tie-Front Cropped Vest

    Fit & Features

    • Lightweight woven fabric
    • High-rise waist
    • Maxi-length hem with flowy high-low silhouette
    • Ruffled design
    • Runs true to size

    Style Number/Barcode: 06301-000011

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Palm Breeze Beaded Halter Top

    The kind of top that makes every destination feel a little more glamorous. Designed with a curve-skimming fit, halter neckline, and beaded chain detail, this top brings effortless drama to beach dinners, resorts, and every plan in between.

    Shop The Matching Skirt: Palm Breeze Beaded Maxi Skirt

    Fit & Features

    • Slinky knit double-lined stretchy fabric
    • Halter neckline with beaded straps
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000522

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Palm Breeze Beaded Maxi Skirt

    The kind of skirt that makes every destination feel a little more glamorous. Designed with a curve-skimming fit, thigh-high slit, and beaded chain detail, this maxi skirt brings effortless drama to beach dinners, resorts, and every plan in between.

    Shop The Matching Top: Palm Breeze Beaded Halter Top

    Fit & Features

    • Slinky knit double-lined stretchy fabric
    • High-rise waist with detachable beaded swag chain
    • Thigh-high slit
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000135

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Villa Nights Halter Crop Top

    The kind of outfit that makes every entrance stunning. This halter crop top features a plunging neckline, open back, and beaded accents that effortlessly go from vacation dinners to special occasion plans.

    Shop The Matching Skirt: Villa Nights High Slit Maxi Skirt

    Fit & Features

    • Slinky knit double-lined knit stretchy fabric
    • Plunge halter neckline, beaded accents, tie straps
    • Open back
    • Fitted crop hem, side ruched seams
    • Runs true to size

    Style Number/Barcode: 06001-000688

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Charming Sweet Polka Dot Mini Dress

    This polka dot mini dress was for the kind of getaway where your camera roll fills up before noon. With a draped halter neckline, and flirty sash details, this dress is ready for hotel brunches and strolling downtown.

    Fit & Features

    • Polka dot print, mesh fabric, smooth lining
    • V-neckline
    • Form-hugging fit
    • Sash detailing
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000723

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Checking In Chiffon Mini Dress

    This ruffle chiffon mini dress was made for resorts, celebrations, and every vacation photo that somehow becomes your favorite. Just add sandals and oversized sunnies.

    Fit & Features

    • Chiffon fabric, smooth lining
    • Square neckline
    • Spaghetti straps
    • Ruffled A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001178

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Villa Nights High Slit Maxi Skirt

    The kind of outfit that makes every entrance stunning. This maxi skirt features a beaded cinch waist accent, thigh-high slit, and flowy fit that effortlessly goes from vacation dinners to special occasion plans.

    Shop The Matching Top: Villa Nights Halter Crop Top

    Fit & Features

    • Slinky knit double-lined knit stretchy fabric
    • High-rise waist with beaded cinch accent
    • Thigh-high front slit
    • Flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000181

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Analia Chiffon Halter Cutout A-Line Dress

    Special Occasion

    Designed for the kind of entrance that lingers long after you leave, the Analia dress brings effortless drama to every formal occasion. This airy chiffon A-line dress features a striking halter neckline, plunging cutout detail, open back, and flowing skirt that moves beautifully from cocktail hour to the last dance.

    Fit & Features

    • Sheer chiffon fabric with full-length lining
    • Sleeveless high halter neckline, plunging front cutout
    • Tie-back halter spaghetti straps, open back, lower zipper with hook-eye closure
    • Pleated waist
    • Floor-length hem with high-cut front slit
    • Flowy A-line silhouette
    • Runs true to size

     

    Where to Wear:

    Vacation dinners, engagement parties, bridal showers, rehearsal dinners, black-tie galas, evening dinners, and rooftop parties.

    Style Number/Barcode: 05002-001451

    Category Name: Vacation Looks

    Price: $74.90

    Availability: In Stock

    Available Color: RUST, IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Island Glow Metallic Mini Dress

    Serving vacation plans, nights out, and spontaneous photo ops all in one look. This metallic halter mini dress brings the drama with a plunging cowl neckline, strappy open back, and tiered ruffle skirt that moves with every step.

    Fit & Features

    • Metallic sheen knit fabric, knit lining
    • Cowl halter neckline, hardware insert, tie straps
    • Open strappy back
    • Form-hugging fit
    • Layered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000904

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: MINT, PINK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Take Me There Tube Top

    Mentally somewhere with better weather. This tropical island graphic top brings vacation vibes to your everyday lineup with an easy strapless fit that pairs perfectly with denim, linen, and a mai tai.

    Fit & Features

    • Cotton-blend stretchy knit fabric
    • Tube strapless neckline
    • Airbrush tropical island graphic
    • Fitted cro phem
    • Runs true to size

    Style Number/Barcode: 06002-000625

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Party Starter Beaded Mini Skort

    This skort understood the assignment and then went a little further. With beaded embroidery, swishy fringe detailing, and a flirty mini silhouette, it's made for concerts, bachelorettes, birthdays, and every plan that deserves a standout outfit.

    Fit & Features

    • Beaded embellished pattern, woven fabric
    • Mid-rise waist
    • Form-hugging silhouette
    • Fringe trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 06403-000154

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Off The Record Shield Sunglasses

    These shield sunglasses feature tinted frames and chain braided detail for a polished finish that makes even the simplest outfit look intentional.

    Fit & Features

    • Tinted frames
    • Oversized shield silhouette
    • 100% UV protection
    • Metal arms with chain braided detail

    Style Number/Barcode: 07008-000134

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: NS

    Product Badge:
    • New Arrival
  • Boardwalk To Beach Printed Romper

    Booked the trip or just dressing like it? This printed romper brings all the vacation-day charm with beaded straps, trendy side pockets, and an easy fit that makes getting ready feel effortless.

    Fit & Features

    • Printed design, woven fabric
    • Sleeveless V-neckline
    • Beaded shoulder straps
    • Open tie-back detail
    • Side pockets
    • Runs true to size

    Style Number/Barcode: 06303-000057

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: S, M, L

    Product Badge:
    • New Arrival
  • Gilded Goddess Halter Mini Dress

    The kind of dress that makes every entrance feel a little more unforgettable. With a plunging halter neckline, open back, and floaty hanky hem, this chiffon mini dress was made for rooftop hotel bars, vacations, and spontaneous photo ops.

    Fit & Features

    • Chiffon fabric, lined
    • Plunge halter neckline, tie straps
    • Open back
    • Waist sash hardware accent
    • Flowy mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000927

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: CHARTREUSE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Dress Code Destination Midi Dress

    RSVP secured, outfit handled. This floral mesh midi dress brings sweeping ruffles, an open back, and a halter neckline together for the kind of entrance that gets compliments before you even reach your table.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Plunge halter neckline, tie straps
    • Open back
    • Form-hugging fit
    • Asymmetrical ruffled midi hem
    • Runs true to size

    Style Number/Barcode: 05102-000675

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: PINK

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

    Product Badge:
    • New Arrival
  • Tropic Temptation Mesh Mini Dress

    This floral and animal print mesh mini dress brings all the playful drama with a sweetheart neckline, flirty ruffle tiers, and cascading side sash details made for beach clubs, birthday trips, and late-night dancing.

    Fit & Features

    • Floral and animal print, mesh-lined fabric
    • Strapless cutout neckline
    • Ruched bodycon silhouette
    • Side ruffled drapes
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000745

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Love At First Text Lace Top

    The kind of top that changes the whole outfit. With its delicate lace, plunge neckline, and barely there feel, this flyaway halter is made for concerts and spontaneous plans.

    Fit & Features

    • Lace woven fabric, lined
    • Plunge halter neckline, bar accent, tie straps
    • Open back
    • Ruffled split crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000332

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Resort Crush Beaded Fringe Halter Top

    Serving vacation photos before you even leave the house. This printed halter top features a plunging neckline and a beaded fringe hem that brings playful movement to every rooftop party, beach getaway, and girls' night out.

    Fit & Features

    • Stretch knit fabrication
    • Sleeveless v-neckline
    • Fitted halter top silhouette
    • Abstract mix animal and floral print
    • Cropped hem
    • Beaded fringe
    • Runs true to size

    Style Number/Barcode: 06001-000730

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Tropic Crush Flower Hair Clip Set

    A little flower moment goes a long way. This vibrant three-piece hair clip set brings instant vacation vibes to any look, whether you're heading to brunch, a beach day, or just trying to make a simple hairstyle look cute.

    Fit & Features

    • Three-piece hair clip set
    • Tropical flowers
    • Metal clip closure

    Style Number/Barcode: 07006-000158

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: NS

    Product Badge:
    • New Arrival
  • Jungle After Hours Ruffle Romper

    This halter romper brings together bold tropical blooms, a striking zebra-inspired print, and cascading ruffle details for a look that was made to turn heads. With its plunging halter neckline, open back, and built-in shorts underneath, it's perfect for nights out.

    Fit & Features

    • Floral, zebra print, mesh fabric, knit lining
    • Cowl halter neckline, tie straps
    • Open back
    • Form-hugging fit
    • Layered ruffle mini-length hem, side cascading ruffles
    • Built-in knit shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000320

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: ZEBRA

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Paradise Found Floral Mini Dress

    Found it: the dress that makes every plan feel like a getaway. With a dreamy tropical print, a plunging halter neckline, and playful tiered ruffles, this dress was made for beach clubs, sunset cocktails, and dinner with a show.

    Fit & Features

    • Tropical floral print, mesh-lined fabric, built-in panty lining
    • Halter plunge neckline, tie straps, hardware accent
    • Open back
    • Form-hugging fit
    • Layered ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000945

    Category Name: Vacation Looks

    Price: $40.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Sunkissed Stroll Knit Poncho

    The poncho that makes every outfit feel a little more effortless. With its airy open-knit design, soft drape, and relaxed silhouette, this throw-on poncho is made for layering over tops and swimsuits for that perfect summer lovin' vibe.

    Fit & Features

    • Sheer open knit fabric
    • Asymmetrical neckline
    • Relaxed silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000364

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Warm Breeze One Shoulder Poncho

    The kind of striped poncho that makes even the simplest denim look styled. Designed with a relaxed one-shoulder silhouette, airy drape, and subtle lurex shimmer woven throughout, this statement poncho brings effortless vacation vibes wherever you're headed.

    Fit & Features

    • Striped pattern
    • Lurex shimmer knit fabric
    • One-shoulder neckline
    • Relaxed poncho silhouette
    • Runs true to size

    Style Number/Barcode: 06202-000114

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: XS/S, M/L

    Product Badge:
    • New Arrival
  • Seashell Dreams Striped Mini Dress

    The kind of dress that makes packing for vacation feel easy. With a shimmering striped knit, plunging halter neckline, and open-back silhouette, it brings effortless beach club energy whether you're heading to dinner by the water or chasing golden hour plans.

    Fit & Features

    • Striped pattern, lurex knit fabric
    • Halter neckline, tie straps
    • Open back
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001253

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival