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.

  • Sun Chaser Crochet Crop Top

    Booked the trip, packed the crochet, no further questions. This crochet crop top brings breezy texture, scalloped details, and an open-back design that was made for vacation photos and rooftop plans. Pair with the matching maxi skirt.

    Shop Matching Bottoms: Sun Chaser Crochet High Slit Maxi Skirt

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Scalloped trim
    • Sleeveless deep V-neckline
    • Tank shoulder straps
    • Open back, lower tie-back spaghetti straps
    • Ultra-cropped hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-000338

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sun Chaser Crochet High Slit Maxi Skirt

    Booked the trip, packed the crochet, no further questions. This crochet maxi skirt brings breezy texture, scalloped details, and a high-cut side slit that was made for vacation photos and rooftop plans. Pair with the matching crop top.

    Shop Matching Top: Sun Chaser Crochet Crop Top

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Scalloped hem
    • High-rise waist, tie-front detail
    • High-cut side slit
    • Midi-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000127

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Weekend Away Strapless Maxi Dress

    This chevron maxi dress hugs in all the right places with a sleek strapless neckline and leg-baring side slit that was practically made for resort dinners, sunset cocktails, and strolling the beachside town.

    Fit & Features

    • Chevron pattern, knit fabric
    • Strapless neckline
    • Side slit
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000595

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Meet Me At Sunset Floral Mini Dress

    Designed with a plunging halter neckline, dramatic open back, and flirty ruffle hem, this mini dress features an oversized floral print and cascading side sash made for vacations, going night, and flirty weekend looks.

    Fit & Features

    • Floral print, mesh fabric, knit lining
    • Plunge halter neckline, bar accent, tie straps
    • Curve-hugging fit
    • Ruffled side sash
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000969

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Rynlee Strapless Mermaid Formal Dress

    Special Occasion

    Made for the kind of evening that lingers long after the last dance, Rynlee slinky knit mermaid gown blends sleek glamour with striking detail. The strapless neckline, wooden hoop insert cutout bust, and flowing center front sash create a sculpted silhouette that feels equal parts polished and unforgettable.

    Fit & Features

    • Slinky knit fabric, knit lining
    • Strapless neckline
    • Wooden hoop insert, cutout, center front sash
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Destination weddings, engagement parties, vacations, honeymoons, resort getaways, cocktail parties, date nights, birthday dinners, formal celebrations

    Style Number/Barcode: 05002-001603

    Category Name: Vacation Looks

    Price: $69.90

    Availability: In Stock

    Available Color: SAGE

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

    Product Badge:
    • New Arrival
  • Rooftop In Santorini Maxi Dress

    The dress equivalent of a first class upgrade. With a plunging halter neckline, statement bead details, and a low open back, this maxi dress was made for resort dinners, oceanfront cocktails, and making every entrance feel a little more unforgettable.

    Fit & Features

    • Mesh fabric, knit lining
    • Plunge halter neckline
    • Open back design
    • Front colored stone button accents
    • Ruched drop waist panel
    • Side slit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001163

    Category Name: Vacation Looks

    Price: $48.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Ocean View Floral Beaded Mini Dress

    This is the dress that ends up in every vacation photo. With a draped cowl neckline, floral beading, and an open tie-back design, this bodycon mini dress was made for dinner reservations that turn into unforgettable nights.

    Fit & Features

    • Floral print, beaded mesh fabric, sewn-in knit lining
    • Cowl neckline
    • Spaghett straps
    • Open tie-back
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000830

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Dinner At Eight Floral Maxi Dress

    Some dresses get compliments. This one starts conversations. Featuring an elegant cowl neckline, an open-back halter design, and oversized floral artwork, this maxi dress was made for vacation dinners, wedding guest RSVPs, and every plan that deserves a dramatic entrance.

    Fit & Features

    • Tropical floral print, knit stretchy fabric
    • Cowl halter neckline
    • Open tie-back
    • Side slit
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000678

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Midnight Magic Halter Mini Dress

    A little sparkle and magic. Featuring a draped cowl neckline, open back halter design, and celestial-inspired sequin artwork, this sweater mini dress was made for cocktail parties, birthday dinners, and unforgettable entrances.

    Fit & Features

    • Sweater knit fabric
    • Cowl halter neckline
    • Open back with strap detail
    • Sequin-embellished sun
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000360

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Booked And Beachside Maxi Dress

    This is the dress you pack first and plan the trip around later. Featuring a statement hardware detail, dramatic front cutout, and leg-lengthening slit, this maxi dress was made for sunset dinners, oceanfront cocktails, and every photo op.

    Fit & Features

    • Smooth knit fabric, stretchy
    • Halter neckline, tie straps
    • Front hardware insert and cutout bodice
    • Ultra-high front slit
    • Flowy A-line maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000790

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Sunshine On Schedule Halter Romper

    Your vacation itinerary just found its outfit. This plunging halter romper brings all the resort energy with a vibrant abstract print, a cinched waist, and a flirty skater silhouette perfect for tropical resorts, sunny weekends, and beachside brunch.

    Fit & Features

    • Abstract print, knit fabric
    • Plunge halter neckline, tie straps
    • Open back design
    • Cinched waist
    • Flowy skater hem
    • Built-in shorts knit lining
    • Runs true to size

    Style Number/Barcode: 06503-000329

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Angelique Abstract Print Mermaid Formal Dress

    Special Occasion

    The Angelique formal dress is the kind of gown that makes every entrance feel mystical. Crafted from printed mesh in a sculpting mermaid silhouette, this floor-length dress features a plunging halter neckline, daring cutouts, and delicate beaded trim that catches the light from every angle.

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Halter V-neckline, spaghetti straps
    • Open tie-back and strappy accents
    • Cutout bodice with beaded-embellished straps
    • Mermaid floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Vacations, honeymoons, resort getaways, birthday dinners, cocktail parties, destination weddings, formal cruise events, and fashion-forward occasions.

    Style Number/Barcode: 05002-001579

    Category Name: Vacation Looks

    Price: $89.90

    Availability: In Stock

    Available Color: BLUE

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

    Product Badge:
    • Ships Free
  • Brunch Then Cocktails Midi Dress

    When the invite says casual chic, this is the dress you reach for first. The ribbed knit hugs in all the right places while the hardware detail and thigh-high slit give it that elevated, fashion-girl finish.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless tube neckline with hardware insert
    • High front slit
    • Form-hugging midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000369

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Endless Summer Abstract Maxi Dress

    This dress looks like it was made for golden hour by the water. Featuring a dreamy abstract print, draped cowl neckline, and beaded halter straps, it brings effortless vacation energy to every RSVP.

    Fit & Features

    • Abstract print, knit fabric
    • Square halter neckline, beaded tie straps
    • High side slit
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000811

    Category Name: Vacation Looks

    Price: $45.90

    Availability: In Stock

    Available Color: BLUE-2

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Make Them Stare Mesh Slit Maxi Dress

    This is the dress that captures all the attention on vacations and weekend escapes. Featuring a bold floral print, curve-hugging fit, and a leg-baring side slit, it's equal parts sultry and unforgettable.

    Fit & Features

    • Statement floral print, mesh-lined fabric
    • Strapless tube neckline
    • High side slit
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-001170

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

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

    Product Badge:
    • New Arrival
  • Daydreaming Floral Knit Dress

    Equal parts cozy and cute, this floral midi dress is made for brunch, weekend plans, and vacations. The oversized floral design gives it a playful statement feel, while the strapless silhouette keeps the look effortlessly polished.

    Fit & Features

    • Statement floral print, sweater knit fabric
    • Strapless tube neckline
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000417

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN-2

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Vacay Muse Floral Beaded Babydoll Top

    Booked the trip, packed the cute top. This floral beaded halter top features a floaty babydoll fit, shiny embroidered details, and an open back that was made for vacation photos and sunset dinners.

    Fit & Features

    • Chiffon fabric, no stretch
    • Floral beaded embroidery
    • Sleeveless deep V-neckline, small keyhole cutout
    • Halter spaghetti straps
    • Open back, lower tie-back spaghetti straps
    • Mid-length hem, babydoll fit
    • Runs true to size

    Style Number/Barcode: 06003-000367

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: MINT

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Bold Entrance One-Shoulder Mini Dress

    Consider this your excuse to make an entrance. This one-shoulder mini dress hugs in all the right places with an asymmetric cutout, ruched detailing, and a bold side sash that does all the talking.

    Fit & Features

    • Slinky knit fabric, high stretch
    • One-shoulder neckline, long fitted sleeve
    • Asymmetric waist cutout
    • Ruched detailing
    • Side sash accent
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000864

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Stacked To Perfection Bangle Bracelet Set

    The outfit looked good, then these showed up. This bangle bracelet set pairs a sleek resin bangle with a polished metal bangle for an effortless stacked look that works from coffee runs to dinner reservations.

    Fit & Features

    • Two-pack bangle bracelet set
    • Resin bangle
    • Metal bangle

    Style Number/Barcode: 07003-000258

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: NS

    Product Badge:
    • New Arrival
  • Trendy Mood Bangle Bracelet Set

    Proof that the right accessories can change the whole mood. This bangle bracelet set combines a sleek metal bangle with an asymmetric resin bangle for a stacked look that instantly pulls an outfit together.

    Fit & Features

    • Two-pack bangle bracelet set
    • One metal bangle
    • One asymmetric resin bangle

    Style Number/Barcode: 07003-000262

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

    Product Badge:
    • New Arrival
  • Chic On Schedule Thong Heels

    These are the heels you reach for when the outfit needs that final touch. With a sleek square toe, minimalist thong strap, and kitten heel, they pair effortlessly with every outfit.

    Fit & Features

    • 2.5" Kitten stiletto heel
    • Square toe
    • Thong strap
    • Cushioned insole
    • Glossy patent faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-000850

    Category Name: Vacation Looks

    Price: $28.90

    Availability: In Stock

    Available Color: PINK

    Available Size: 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • New Arrival
  • Caught Looking Cat-Eye Sunglasses

    Serving side glances and stealing attention without saying a word. These cat-eye sunglasses feature tinted lenses and a sleek retro-inspired shape that instantly pulls any outfit together, from coffee runs to rooftop plans.

    Fit & Features

    • Cat-eye shape
    • Plastic frame
    • Built-in nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000131

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: NS

    Product Badge:
    • New Arrival
  • Meet Me In Miami Halter Mini Dress

    From cocktails to beachside dinners, this is the dress that makes vacation photos look even better. This tropical mesh mini dress is serving destination energy with a draped cowl neckline, open-back detail, and a statement sash that moves with every step. 

    Fit & Features

    • Abstract print, mesh-lined fabric
    • Halter cowl neckline
    • Open back design
    • Curve-hugging silhouette
    • Ruffled trim mini-length hem with a cascading drape
    • Runs true to size

    Style Number/Barcode: 05103-001080

    Category Name: Vacation Looks

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • After Hours Aura Beaded Lace Bra Top

    All sparkle, no subtlety. This beaded lace bra top brings the drama with a halter neckline, pearl-inspired draping, and chain body detailing made for going out, festival fits, and photo-ready plans.

    Fit & Features

    • Lined lace fabrication
    • Beaded embellishments
    • Halter neckline with bra cups
    • Draped fringe trim and chain body detailing
    • Open back with adjustable tie closures
    • Runs true to size

    Style Number/Barcode: 06001-000564

    Category Name: Vacation Looks

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free