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.

  • Vacay Romance Floral Maxi Dress

    This is the dress that turns dinner plans into an occasion. Featuring a draped cowl neckline, open back, and oversized florals, it hugs in all the right places while serving effortless looks on vacations, weekend getaways, or date nights.

    Fit & Features

    • Floral tropical print, knit stretchy fabric
    • Cowl halter neckline, tie straps
    • Open back
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-001148

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: ORANGE

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

    Product Badge:
    • New Arrival
  • Gianna Striped Linen A-Line Formal Dress

    Special Occasions

    Effortlessly striking and made for sun-drenched celebrations, the Gianna dress brings together a softly textured striped linen fabric with a modern asymmetrical silhouette. The ruched bodice, side cutout detail, and flowing a-line skirt create beautiful movement, while the open tie-back design adds an unexpected finishing touch.

    Fit & Features

    • Striped pattern, subtle metallic threads, linen-blend fabric, sewn-in bodice lining
    • Asymmetrical neckline, spaghetti straps
    • Open tie-back detail, side zipper and hook-eye closure
    • Side cutout, ruched bodice accent
    • A-line silhouette, high side slit
    • Floor-length hem
    • Runs true to size

     

    Where to Wear:

    Outdoor weddings, vacations, honeymoons, resorts, birthday brunches, cocktail events, engagement parties, summer dinner parties, wineries

    Style Number/Barcode: 05002-001567

    Category Name: Vacation Looks

    Price: $99.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Ships Free
  • Ailith Metallic Striped Formal Dress

    Special Occasion

    Like a sunset slipping into evening, the Ailith metallic knit column gown catches the light with every step. The softly draped neckline and open cowl back with delicate tie detailing create an effortlessly polished silhouette that feels made for formal celebrations and unforgettable entrances.

    Fit & Features

    • Metallic striped knit fabric, smooth knit lining
    • Cowl neckline
    • Adjustable spaghetti straps
    • Open tie-back with draped accent
    • Column floor-length silhouette
    • Runs true to size

     

    Where to Wear:

    Outdoor weddings, galas, honeymoons, vacations, resorts, engagement parties, rehearsal dinners, cocktail events, formal milestone celebrations, date nights

    Style Number/Barcode: 05002-001738

    Category Name: Vacation Looks

    Price: $79.90

    Availability: In Stock

    Available Color: BLUE

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

    Product Badge:
    • Ships Free
  • City Escape Aviator Sunglasses

    These aviator sunglasses are the finishing touch for poolside selfies, coffee runs, and pretending you’re off the grid for the weekend.

    Fit & Features

    • Aviator silhouette
    • Clear tinted lenses
    • Lightweight frame
    • 100% UV protection

    Style Number/Barcode: 07008-000180

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: RED

    Available Size: NS

    Product Badge:
    • New Arrival
  • Resort Vacay Shell Chandelier Earrings

    The kind of earrings that make every outfit feel a little more expensive. These cascading shell chandelier earrings were made for vacation dinners, messy buns, and compliments from strangers.

    Fit & Features

    • Round sheel cascading design
    • Chandelier silhouette
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000350

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

    Product Badge:
    • New Arrival
  • Moonlit Escape Chiffon Poncho

    This sheer chiffon poncho drapes with an easy off-the-shoulder feel, while delicate lace trim adds just the right amount of detail. Toss it over swimwear, pair it with denim, or wear it whenever your outfit needs that extra little something.

    Fit & Features

    • Sheer chiffon fabric
    • Asymmetrical one-shoulder neckline
    • Relaxed poncho silhouette
    • Lace trim hem
    • Runs true to size

    Style Number/Barcode: 06204-000173

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS/S, M/L

    Product Badge:
    • New Arrival
  • Weekend Breeze Crop Top

    This top was made for sunny forecasts and spontaneous plans. The airy gauze fabric, soft hue, and trendy crop length make it look effortless.

    Shop Matching Bottoms: Weekend Breeze Maxi Skirt

    Fit & Features

    • Gauze woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Cinched crop-length hem
    • Runs true to size

    Style Number/Barcode: 06003-000352

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Everyday Luxe Square Sunglasses

    These oversized square sunglasses feature warm gradient lenses, sleek gold-tone details, and a polished silhouette that feels equally at home on vacation, at brunch, or running errands with an iced coffee in hand.

    Fit & Features

    • Oversized square frames
    • Rubber nose supports
    • Sleek metal arms with plastic trim
    • Tinted lenses

    Style Number/Barcode: 07008-000137

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: NS

    Product Badge:
    • New Arrival
  • Bright Side Bracelet Set

    This chunky bangle bracelet set mixes translucent and vibrant colorways for an easy statement that pairs perfectly with everything from vacation looks to casual denim days.

    Fit & Features

    • Two pack bracelet set
    • Colored resin material
    • Chunky silhouette

    Style Number/Barcode: 07003-000242

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: NS

    Product Badge:
    • New Arrival
  • Wild Side Zebra Print Tie-Front Top

    Serving confidence with a little bit of chaos. This zebra print mesh tie-front top brings all the drama with a deep neckline, flowy flare sleeves, and an ultra-cropped fit made for statement-making plans. Style with the matching maxi skirt.

    Shop Matching Bottoms: Wild Side Zebra Print High-Slit Maxi Skirt

    Fit & Features

    • Zebra print sheer mesh fabric, high stretch
    • Deep V-neckline
    • Tie-front design
    • Long flowy flare sleeves
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000116

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: ZEBRA

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Clear Choice Jelly Thong Strap Kitten Heels

    Minimal effort, maximum outfit payoff. These jelly thong strap kitten heels bring a barely-there look that pairs perfectly with everything from denim and cargos to your favorite vacation-ready dresses.

    Fit & Features

    • Kitten heel
    • Open square-shaped toe
    • Clear jelly thong straps, toe strap
    • Open back, on-and-off styling
    • Faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07401-000649

    Category Name: Vacation Looks

    Price: $30.90

    Availability: In Stock

    Available Color: NATURAL

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

    Product Badge:
    • New Arrival
  • Effortless Days Sheer Chiffon Poncho

    Floaty, effortless, and impossible to overlook. This sheer chiffon poncho drapes with an airy relaxed fit that instantly elevates everything from swimwear, mini skirts, and vacation-ready looks.

    Fit & Features

    • Sheer chiffon woven fabric, no stretch
    • Boat neckline
    • Long flowy sleeves
    • Cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-000174

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS/S, M/L

    Product Badge:
    • New Arrival
  • Plans Confirmed Strappy Wedges

    The kind of wedges that make every outfit feel cuter. With strappy details and a trendy cork platform sole, they're ready for everything from brunch reservations to wedding guest weekends.

    Fit & Features

    • 5" Wedge heel
    • Almond toe
    • Strappy design
    • Adjustable ankle strap with buckle closure
    • Cork platform sole
    • Runs true to size

    Style Number/Barcode: 07406-000062

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: WHITE, GOLD

    Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10, 11

    Product Badge:
    • New Arrival
  • Sunshine State Chiffon Babydoll Top

    The kind of top that makes saying yes to plans way too easy. This chiffon babydoll top features a plunging halter neckline, flowy pleated silhouette, and open back detail made for warm nights, weekend getaways, and last-minute plans.

    Fit & Features

    • Chiffon fabric, knit lining
    • Halter plunge neckline, tie straps
    • Open back with tie
    • Flouncy ruffled babydoll silhouette
    • Crop-length hem
    • Runs true to size

    Style Number/Barcode: 06003-000398

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Saltwater Chic Crochet Cardigan

    The cardigan that makes every swim look styled. Designed with an airy open-knit crochet, tie-front details, and shell-trimmed bell sleeves that catch the light with every step, this duster was made for pool parties, vacations, and weekend escapes. 

    Fit & Features

    • Sheer crochet fabric
    • Long bell sleeves with shell embellished trim
    • Dual tie-front closures
    • Open front design
    • Long-length hem
    • Runs true to size

    Style Number/Barcode: 06204-000153

    Category Name: Vacation Looks

    Price: $59.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Brunch Bound Espadrille Wedges

    Elevating every outfit without even trying. These espadrille wedges pair braided textures with an easy platform silhouette, making them the pair you'll reach for from brunch dates to vacation plans.

    Fit & Features

    • Espadrille wedge heel
    • Platform sole
    • Open round toe
    • Espadrille straps
    • Dual straps across the foot, adjustable ankle strap with buckle closure
    • Faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07406-000070

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: 6, 7, 8, 9, 10

    Product Badge:
    • New Arrival
  • Runway Route Square Sunglasses

    These rimless square sunglasses bring a sleek, trend-forward finish to every outfit, whether you're heading to work or weekend plans. These sunglasses make every car ride fashionable. 

    Fit & Features

    • Lightweight square frame silhouette
    • Sleek bar trim
    • Rubber nose supports
    • Metal arms with plastic trim
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000153

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: ROSE, GOLD

    Available Size: NS

    Product Badge:
    • New Arrival
  • Mermaid Hour Lurex Poncho

    Caught the light from every angle? Exactly the plan. This airy lurex poncho drapes effortlessly over swimwear, tops, and going-out looks, adding just the right amount of shimmer.

    Fit & Features

    • Shimmer knit lurex fabric, sheer design
    • Off-shoulder neckline
    • Flowy fit
    • Asymmetrical hem
    • Runs true to size

    Style Number/Barcode: 06202-000105

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: TEAL

    Available Size: XS/S, M/L

    Product Badge:
    • New Arrival
  • Chic On Arrival Metallic Espadrille Wedges

    These metallic espadrille wedges pair a leg-lengthening platform with sleek straps, making them an easy chic pick for weddings, vacations, rooftop dinners, and every RSVP in between.

    Fit & Features

    • Espadrille wedge heel
    • Open round toe
    • Metallic faux leather straps
    • Toe strap, adjustable ankle strap with buckle closure
    • Metallic faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07406-000063

    Category Name: Vacation Looks

    Price: $40.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: 6, 6.5, 7, 7.5, 8, 8.5, 9, 10, 11

    Product Badge:
    • New Arrival
  • Weekend Away Bow Thong Sandals

    Tiny bow details just make everything feel cuter. These faux leather sandals are the pair you pack for trips or any weekend plans.

    Fit & Features

    • Almond toe
    • Thong strap with bow
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-000077

    Category Name: Vacation Looks

    Price: $14.90

    Availability: In Stock

    Available Color: WHITE

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

    Product Badge:
    • New Arrival
  • Spritz O' Clock Kitten Striped Heels

    The shoes that make every outfit look like it came with a boarding pass. With a woven raffia finish and an easy slip-on design, these mule heels are ready for dinners, brunch reservations, and every sunny plan in between.

    Fit & Features

    • Kitten stiletto heel
    • Pointed toe
    • Curved band
    • Cushioned insole
    • Striped pattern, rafia material
    • Runs true to size

    Style Number/Barcode: 07401-000746

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: MULTI

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

    Product Badge:
    • New Arrival
  • Serving Looks Leopard Print Halter Top

    Serving looks without saying a word. This leopard print halter top hugs in all the right places with a draped cowl neckline and open-back detail that was made for plans worth getting dressed up for. Pair with the matching mini skort.

    Shop Matching Bottoms: Serving Looks Leopard Print Ruffle Mini Skort

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Abstract leopard print
    • Sleeveless cowl neckline, bar strap detail
    • Halter strap, partially open back
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000591

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Sparkly Fave Rhinestone Floral Ruffle Romper

    Straight to the favorites folder. This rhinestone floral ruffle romper pairs a plunging halter neckline with sparkling details and a flouncy layered hem that was made for birthday dinners, vacation nights, and every photo op in between.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Sleeveless deep V-neckline, rhinestone floral embellishments
    • Tie-back halter straps, partially open back
    • Ruched drop waist design
    • Tiered ruffled overlay with mini-length hem, A-line fit
    • Hidden built-in shorts
    • Runs true to size

    Style Number/Barcode: 06503-000321

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Weekend Breeze Maxi Skirt

    This skirt was made for sunny forecasts and spontaneous plans. The airy gauze fabric, soft hue, and flirty high front slit make it look effortless.

    Shop Matching Top: Weekend Breeze Crop Top

    Fit & Features

    • Gauze woven fabric
    • High-rise waist
    • Flowy tiered silhouette
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06301-000014

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set