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.

  • Mood Board Stone Charm Necklace

    Your jewelry stack just found its favorite plus one. This stone charm necklace mixes gemstone details with dainty heart and flower charms for the kind of layered look that makes even a basic tank feel fully styled.

    Fit & Features

    • Dainty chain-link design
    • Stone beaded charms
    • Gemstone charms
    • Flower and heart charms
    • Lobster clasp closure with extender

    Style Number/Barcode: 07002-000453

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: NS

  • Beachy Charm Puka Shell Belly Chain

    This puka shell belly chain brings the perfect mix of beachy charm and low-rise styling for bikinis, mini skirts, and every last-minute getaway 'fit.

    Fit & Features

    • Chain-link design
    • Puka shell accents
    • Lobster clasp closure with extender
    • Adjustable fit

    Style Number/Barcode: 07002-000458

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Vacation Flirting Halter Tunic Top

    A little daring, a little vacation-coded, and fully worth the stare. This halter tunic top brings flowy movement, a dramatic open front, and an abstract print that makes even simple plans feel expensive.

    Fit & Features

    • Abstract print, sheer mesh fabric, bust lining
    • Sweetheart halter neckline, tie straps, hoop insert
    • Center front high slit opening
    • Flowy long-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000695

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • Kristen Printed Rhinestone Formal Dress

    Special Occasion

    The Kristen mermaid gown brings together sculpted ruching, a dramatic plunge neckline, and shimmering rhinestone detailing for a look that feels unforgettable from every angle. The lace-up back and curve-skimming silhouette make it the perfect plus-one for every RSVP that calls for going all in.

    Fit & Features

    • Printed mesh-lined fabric
    • Sculpted strapless neckline
    • Open lace-up back
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Destination weddings, vacations, summer galas, cocktail soirees, formal celebrations, birthday dinners

    Style Number/Barcode: 05002-001442

    Category Name: Vacation Looks

    Price: $79.90

    Availability: In Stock

    Available Color: RED

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

    Product Badge:
    • Ships Free
  • Second Glance Beaded-Trim Halter Midi Dress

    The kind of dress that gets a second glance before you even say a word. This beaded-trim halter midi dress hugs in all the right places with a textured knit feel, open lace-up sides, and an open back that makes every entrance look intentional.

    Fit & Features

    • Textured knit fabric, high stretch
    • Sleeveless V-neckline, beaded bar strap accent
    • Tie-back halter spaghetti straps, beaded accents
    • Open back, lower tie-back spaghetti straps, back zipper closure
    • Open lace-up side design
    • Midi-length hem, back slit detail, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000627

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Espresso Martini Beaded Mini Dress

    This beaded mesh mini dress brings a sculpted bodycon fit, flirty halter neckline, and shimmer details that catch every dim light, dance floor selfie, and “one more drink?” invite.

    Fit & Features

    • Beaded pattern, mesh fabric, lined
    • Cowl halter neckline, tie straps
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000818

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Bright Side Striped Hot Shorts

    Serving sunshine, shopping days, and spontaneous plans all in one look. The bold chevron striped pattern brings instant vacation energy, while the form-hugging fit keeps it playful, flirty, and ready for wherever the day takes you.

    Shop The Matching Top: Bright Side Striped Halter Top

    Fit & Features

    • Chevron striped pattern, knit fabric
    • Mid-rise waist
    • Form-hugging fit
    • Cheeky hem
    • Runs true to size

    Style Number/Barcode: 06503-000277

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Bright Side Striped Halter Top

    Serving sunshine, shopping days, and spontaneous plans all in one look. The bold chevron striped pattern brings instant vacation energy, while the halter silhouette keeps it playful, flirty, and ready for wherever the day takes you.

    Shop The Matching Bottoms: Bright Side Striped Hot Shorts

    Fit & Features

    • Chevron striped pattern, knit fabric
    • High halter neckline, tie straps
    • Fitted crop-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000359

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Table For Two Lace Maxi Dress

    The kind of dress that keeps the compliments coming before you’ve even made it to dinner. This lace maxi dress hugs in all the right places with a curve-skimming fit and strappy open back that feels equal parts effortless and unforgettable.

    Fit & Features

    • Lace fabric
    • Sweetheart neckline
    • Spaghetti straps
    • Open strappy back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001131

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Double Take Animal Print Mini Dress

    The outfit equivalent of being impossible to forget. This animal print halter mini dress hugs in all the right places with a plunging cowl neckline, statement hardware, and a flirty ruffled hem made for plans that deserve a little extra attention.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Abstract animal print
    • Sleeveless plunging cowl neckline, flower hardware accent
    • Halter strap
    • Lower back cutout, ruched detailing
    • Mini-length ruffled hem, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-001050

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

  • Paradise Found Halter Mini Dress

    Straight into the vacation outfit folder. This textured knit mini dress features playful side cutouts and cascading bead details that bring just the right amount of drama to beach cabanas, tropical dinners, and every photo-worthy plan.

    Fit & Features

    • Texture knit fabric
    • High halter neckline, tie straps
    • Open tie-back
    • Side cutouts with beaded fringe trim
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000628

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Take Me Somewhere Maxi Dress

    Currently accepting compliments and vacation invitations. This halter maxi dress hugs in all the right places with a plunging neckline and open back that feels made for dinners, destination weddings, and packed itineraries.

    Fit & Features

    • Stitched striped pattern, knit fabric
    • Plunge halter neckline
    • Open back
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000643

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

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

  • Brunch Booked Floral Mini Dress

    Serving vacation mood before you've even packed a bag. This floral tube mini dress features a flattering A-line fit that feels effortless for brunch, parties, and every warm-weather plan that pops up.

    Fit & Features

    • Floral print, knit fabric
    • Strapless tube neckline
    • A-line mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000581

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Chasing Sunlight Cutout Maxi Dress

    For the girl who packs the outfit before she books the reservation. With dreamy florals, statement cutouts, and a leg-baring ruffle slit, this maxi dress was made for sunset dinners, oceanfront cocktails, and every vacation photo worth posting.

    Fit & Features

    • Floral pattern, mesh-lined fabric
    • Sweetheart bra top, underbust detail
    • Bodice cutout
    • Open tie-back design
    • Center ruffled trim and slit accent
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000917

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Flirting In Positano A-Line Mini Dress

    Meet the dress equivalent of booking the flight before asking questions. With its dreamy coastal print and easy strapless fit, this mini dress was made for European getaways, brunch, and sunny day plans.

    Fit & Features

    • Multi-print design, linen-blend woven fabric, woven lining
    • Strapless neckline, non-slip grip lining
    • Side hidden zipper and hook-eye closure
    • Bar back accent and cutout
    • A-line fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000561

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

  • Ocean Air Mood Halter Maxi Dress

    This is the kind of dress that makes every plan feel a little more exciting. The soft hue, textured fabric, and waist cutouts bring just the right amount of drama for beachside dinners, cocktails, and those nights that somehow turn into your favorite memories.

    Fit & Features

    • Texture knit fabric
    • Sweetheart halter neckline, tie strap
    • Hoop insert and cutout bodice and back
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000714

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S, M, L

  • Salt Air Breeze Crochet Maxi Skirt

    This is the skirt that makes every vacation outfit look intentional. With its breezy crochet texture, leg-baring slit, and flowy fit, it's made for beachside strolls and cocktails in the cabana.

    Shop The Matching Top: Salt Air Breeze Bandeau Tube Top

    Fit & Features 

    • Texture crochet woven fabric
    • Mid-rise waist with tassel ties
    • Thigh-high slit
    • Flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06301-000012

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

  • Extra Confident Cowl Neck Ruffle Romper

    The group chat said “be casual,” but this cowl neck romper clearly had other plans. With a plunging neckline, playful ruffle details, and a flirty silhouette, it’s made for vacation dinners, rooftop cocktails, and every RSVP that calls for a little extra confidence.

    Fit & Features

    • Knit fabric, high stretch
    • Sleeveless plunging cowl neckline
    • Halter strap, open back, lower tie-back spaghetti straps
    • Ruched drop waist
    • Tiered ruffled mini-length overlay with A-line fit
    • Hidden built-in shorts
    • Runs true to size

    Style Number/Barcode: 06503-000287

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

  • Flash Warning Metallic Romper

    All eyes stayed exactly where they were supposed to. This metallic knit romper brings the perfect mix of daring and glam with a plunge halter neckline, ruched sides, and a layered ruffle hem that moves with every step.

    Fit & Features

    • Metallic foil knit fabric, built-in shorts lining
    • Plunge halter neck, tie straps
    • Open back
    • Ruched side seams
    • Fitted drop waist seam
    • Layered ruffle mini hem
    • Runs true to size

    Style Number/Barcode: 06503-000297

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: EMERALD

    Available Size: XS, S, M, L

  • Salt Air Breeze Bandeau Tube Top

    This is the tube top that makes every vacation outfit look intentional. With its breezy crochet texture, tie-back design, and bandeau-style look, it's made for beachside strolls and cocktails in the cabana.

    Shop The Matching Bottom: Salt Air Breeze Crochet Maxi Skirt

    Fit & Features 

    • Texture crochet woven fabric
    • Strapless sweetheart neckline
    • Cinched bust
    • Tie-back design
    • Bandeau-silhouette
    • Runs true to size

    Style Number/Barcode: 06003-000323

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Untamed Charm Stone Beaded Maxi Dress

    The kind of dress that changes the whole mood the second you walk in. With textured zebra burnout fabric, statement stone beaded straps, and a leg-baring front slit, this maxi dress was made for destination dinners, cocktail hour, and plans that call for a little extra confidence.

    Fit & Features

    • Burnout velvet zeubra striped pattern, mesh-lined fabric
    • V-neckline
    • Stone beaded spagehtti straps and back strap accent
    • Open back design
    • High front slit
    • Flowy maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05002-001400

    Category Name: Vacation Looks

    Price: $69.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Weekend Repeat Striped Midi Dress

    The kind of dress that makes outfit decisions feel way too easy. This striped halter midi dress hugs comfortably with a bodycon feel, making it the one you'll reach for on coffee dates, weekend plans, and vacations.

    Fit & Features

    • Striped knit fabric
    • Halter neckline
    • Bodycon fit
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000389

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Coast To Cocktails Halter Midi Dress

    With textured crochet-inspired detailing, a halter neckline, and a body-hugging fit, this midi dress is ready for vacation dinners, bridal events, and every RSVP that calls for something elevated.

    Fit & Features

    • Texture crochet knit fabric
    • High halter neckline
    • Form-hugging fit
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000352

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Brunch Bound Tie-Front Cropped Vest

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

    Shop Matching Bottoms: Brunch Bound Ruffle High-Low Maxi Skirt

    Fit & Features

    • Lightweight woven fabric
    • Sleeveless V-neckline
    • Tie-front design
    • Fitted, ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-000135

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set