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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.

  • Summer Romance Floral Chiffon Skater Romper

    Find your summer love in this charming floral chiffon skater romper! It features a square neckline with a dainty tie-front design, short puff sleeves with ruffled trims, dual high waist seams, and a fit and flare silhouette with flowy shorts and a short skater skirt overlay with ruffled hems. The all-over blooming floral print on the airy chiffon fabric is perfect for the season. Style with butterfly charm earrings.

    Fit & Features

    • Square neckline, tie-front design
    • Short puff sleeves, ruffled trims
    • Dual high waist seams, fit and flare silhouette
    • Flowy shorts, short skater skirt overlay, ruffled hems
    • Blooming floral print
    • Sheer chiffon fabric, knit bust lining and skirt lining
    • Runs true to size

    Style Number/Barcode: 06403-0319

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Dreams Linen Tropical Wide Leg Pants

    Your next getaway calls for these linen tropical pants to look stunning on vacay! They feature an elasticized high-rise waist, a flowy wide-leg silhouette, and a palm leaf print on lightweight linen woven fabric. Complete the look in a casual crop top for sipping a marg by the beach!

    Fit & Features

    • High-rise elasticized waist
    • Flowy wide-leg silhouette
    • Palm leaf tropical print
    • Lightweight linen woven fabric
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06302-0776

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shade Shift Leopard Square Sunglasses

    Block the rays, not the slay. These square sunglasses serve retro energy with a modern edge—aka your new go-to for every vibe.

    Fit & Features

    • Leopard pattern
    • Square frame
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000080

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Style Strappy Back Midi Dress

    Simple yet so alluring, you'll love the sultry style of this strappy back midi dress. It features a sleeveless V-neckline, spaghetti straps that lead to an open back with cross-back lace-up straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Complete your look with clear heels and a chic handbag.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Open back, cross-back lace-up straps, tie closure
    • Midi-length hem
    • Bodycon silhouette
    • Ribbed knit fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4835

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stand Out Marble Print Cutout Midi Dress

    Stand out this season and have all eyes on you in this marble print midi dress perfect for weekend getaways or sunset cocktails! The dress features a sleeveless square neck, spaghetti straps, a cutout bodice, and side ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker necklace.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cutout bodice
    • Side ruched seams, bodycon silhouette
    • Midi-length 
    • Marble print, smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5235

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living In Color Chiffon Halter Maxi Dress

    Live life in color! Easy and breezy, this chiffon maxi dress is perfect for all of your summer activities. It features a sleeveless halter V-neckline, a unique braided neck strap with tie closure, a stretchy smocked back, and a flowy silhouette. The dress is designed with an airy chiffon fabric showcasing a watercolor print and a woven lining. Complete the look with a sleek arm cuff bracelet.

    Fit & Features

    • Sleeveless halter V-neckline
    • Braided neck strap, tie closure
    • Stretchy smocked back
    • Flowy silhouette
    • Maxi-length hem
    • Airy chiffon fabric, watercolor print, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5269

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Simple Smooth Knit Mini Dress

    This chic and simple smooth knit mini dress is the elevated basic you need! It features a sleeveless mock neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The buttery-soft and smooth double-lined knit fabric offers plenty of stretch. Style with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps
    • Mini-length hem
    • Bodycon silhouette
    • Soft and smooth double-lined knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5198

    Category Name: Vacation Looks

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miss. Fashion Strapless Marble Print Mini Dress

    They'll call you Miss. Fashion when you step out in this mesh mini dress! It features a strapless neckline, a bodycon silhouette, an adjustable side drawstring that lets you customize the style, a slit accent, and an asymmetrical hem. Style with lucite heels for a seamless-chic look!

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Adjustable side drawstring, slit accent
    • Asymmetrical mini-length hem
    • Marble print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5268

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Cute Things Layered Charm Neckalce

    Adorn your look with all the cute things this Y2K layered necklace has to offer! It features a three-layered design, one beaded heart charm layer, one dainty chain butterfly charm layer, and one dainty chain flower charm layer. Complete the look with statement earrings for a party!

    Fit & Features

    • Three-layered necklace design
    • One beaded heart charm layer
    • One dainty chain butterfly charm layer
    • One dainty chain flower charm layer
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07002-1508

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Free Wanderer Butterfly Lariat Necklace

    Enchant your vacation outfits with this lovely lariat necklace to bring those wanderlust vibes! It features a choker chain with an attached dainty chain with a rhinestone butterfly charm. Complete the look in sleek hoop earrings.

    Fit & Features

    • Choker chain
    • Attached dainty lariat chain
    • Rhinestone butterfly charm

    Style Number/Barcode: 07002-1509

    Category Name: Vacation Looks

    Price: $2.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Art Of Style Abstract Print Midi Dress

    Show everyone how it's done! This sleeveless midi dress features a square neck, spaghetti straps, a side ruched seam that accentuates your curves along the bodycon silhouette, and a high side asymmetrical slit. The dress is designed with an artsy abstract print on smooth knit fabric. Complete the look with earrings for an art gallery opening!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Side ruched seam, bodycon silhouette
    • High side asymmetrical slit
    • Midi-length hem
    • Abstract print, smooth knit fabric, moderate stretch
    • Bust lining
    • Runs true to size

    Style Number/Barcode: 05102-5206

    Category Name: Vacation Looks

    Price: $5.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Remy High-Rise Frayed Hem Denim Shorts by Windsor Denim

    Level up your casual summer outfits with the Remy frayed hem denim shorts by Windsor Denim. They feature a high-rise waist, a color-faded design for a vintage look, and a cute frayed hem with side slit accents. Includes a five-pocket and belt loop design. Style with a basic bodysuit and slip-on sandals.

    Fit & Features

    • High-rise waist
    • Color-faded design
    • Frayed hem, side slit accents
    • Five-pocket and belt loop design
    • Button-front and hidden zipper closure
    • Denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06603-0341

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Dolled Up Strappy Back Maxi Dress

    This maxi dress gives you a reason to get all dolled up! It features a sleeveless square neckline, adjustable spaghetti straps, an open strappy back with a lower ruched seam atop a sultry high slit, and a bodycon silhouette on slinky knit-lined fabric. Complete the look in rhinestone strappy heels for a cocktail party.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Open strappy back, lower ruched seam, high slit
    • Bodycon silhouette
    • Maxi-length hem
    • Slinky knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2414

    Category Name: Vacation Looks

    Price: $9.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Here To Play Satin Strapless Pleated Jumpsuit

    Play up your sassy style in this satin pleated jumpsuit for going out with the ladies! Featuring a strapless neckline, an elasticized high-rise waistband, and a flowy wide-leg silhouette. Complete the look with a chic choker necklace.

    Fit & Features

    • Strapless neckline
    • Elasticized high-rise waistband
    • Flowy wide-leg silhouette
    • Satin pleated fabric 
    • Smooth and stretchy satin lining
    • Runs true to size

    Style Number/Barcode: 06502-2351

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Enchanting Entrance Chiffon Floral Maxi Dress

    Make an enchanting entrance into a tropical destination wedding in this effortless chiffon floral maxi dress! It features a sleeveless V-neckline, flirty ruffled spaghetti straps, a stretchy smocked back, a ruched bust, and a flowy tiered ruffled silhouette with a flattering front slit. Complete the look with a dainty layered choker necklace and heels.

    Fit & Features

    • Sleeveless V-neckline, ruffled spaghetti straps, adjustable
    • Stretchy smocked back, ruched bust
    • Flowy tiered ruffled silhouette, front slit
    • Maxi-length hem
    • Tropical floral print
    • Airy chiffon fabric, short smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5270

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun And Fun Sleek Rectangle Sunglasses

    These sunglasses were made for fun under the sun! They feature a plastic rectangular frame, tinted lenses, and gold metal detailing along the arms. Style with a trendy distressed denim jacket for a beach day!

    Fit & Features

    • Plastic rectangular frames
    • Tinted lenses
    • Gold metal detailing along the arms
    • Polycarbonate blocks 100% UV

    Style Number/Barcode: 07008-1009

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Luxe With No Limits Halter Midi Dress

    Quiet luxury, but she still turns heads! With a flattering halter neckline, cutout back, and a sneaky little slit, this midi keeps it classy with just the right amount of edge.

    Fit & Features

    • Pointelle knit fabric
    • Halter neckline, tie straps
    • Cutout back
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000010

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun Ready Strapless High Slit Maxi Dress

    If sandy beaches are what you seek this maxi dress is ready for fun under the sun! It features a strapless neckline, a side O-ring metal insert atop the sexy high slit, and a flowy long hem on slinky knit fabric. Complete the look in strappy sandals and sunglasses!

    Fit & Features

    • Strapless neckline
    • Side O-ring insert, high side slit
    • Flowy maxi silhouette
    • Long hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5263

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drinks Please Satin Pleated Tie-Front Top

    The perfect satin crop top to hit up a rooftop lounge and post all over your social! It features peasant long sleeves, a plunge V-neckline, and a flirty tie-front design on satin pleated fabric. Complete the look in boyfriend jeans and heels.

    Fit & Features

    • Peasant long sleeves
    • Plunge V-neckline
    • Tie-front design
    • Cropped hem
    • Satin pleated fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1603

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tropical Destination High Waist Palazzo Pants

    Heading somewhere tropical? These palazzo pants will keep you cute during your stay! They feature a flattering high-rise waist, and a wide-leg silhouette, and are composed of smooth and stretchy knit fabric with an all-over palm leaf print that showcases major summer vibes. Complete the look with the matching top.

    Shop Matching Top: Tropical Destination Twist Crop Top

    Fit & Features

    • High rise waist
    • Wide-leg silhouette
    • Palm leaf print all-over
    • Smooth and stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2352

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Destination Twist Crop Top

    Heading somewhere tropical? This crop top will keep you cute during your stay! It features a sleeveless sweetheart neckline, spaghetti straps, and a twisted bust accent, and is composed of smooth and stretchy knit fabric with an all-over palm leaf print that showcases major summer vibes. Complete the look with matching bottoms.

    Shop Matching Bottom: Tropical Destination High Waist Palazzo Pants

    Fit & Features

    • Sleeveless sweetheart neck
    • Spaghetti straps
    • Twisted bust accent
    • Ultra cropped hem
    • Palm leaf print all-over
    • Smooth and stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4886

    Category Name: Vacation Looks

    Price: $4.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Frill Of The Moment Ruffle Tank Crop Top

    This tank crop top deserves a moment to admire its cuteness! Featuring a sleeveless mesh ruffle trim sweetheart neckline, bungee spaghetti straps, a flirty front bust tie with a keyhole accent, and a mesh ruffled trim hem on stretchy rib knit fabric. Complete the look in high-rise jeans and mules for a coffee meet-up!

    Fit & Features

    • Sleeveless mesh ruffle trim sweetheart neckline
    • Bungee spaghetti straps
    • Front bust tie, keyhole accent
    • Mesh ruffled trim crop hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1621

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Current Mood Striped Halter Sweater Top

    Flaunt your best style this summer in this halter crop top perf for a beach day or pool party! Featuring a sleeveless plunge halter V-neckline with a wide strap, a striped design, and a tie-back closure. Complete the look in trendy denim shorts.

    Fit & Features

    • Sleeveless plunge halter V-neckline, wide strap
    • Striped design
    • Cropped hem
    • Tie-back closure
    • Stretchy sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1714

    Category Name: Vacation Looks

    Price: $4.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The 'It' Knit Sleeveless Maxi Dress

    Take your trendsetting status to chic summer style with this sleeveless knit maxi dress perfect for styling over your swimsuit! It features a scoop neckline, tank shoulder straps, a form-hugging fit, and a flirty high-side slit on crochet-style knit fabric with a short stretchy lining. Complete the look in sunglasses and sandals!

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Form-hugging fit
    • High side slit
    • Maxi-length hem
    • Crochet-style knit fabric, short stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5207

    Category Name: Vacation Looks

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free