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.

  • 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
  • Vacay State Of Mind Tropical Slit Maxi Skirt

    Enter into a vacay state of mind with this tropical maxi skirt on your next trip! It features a flattering high-rise elasticized waist, a sensational high-front slit, and a flowy silhouette. Style with an adorable crop top and strappy sandals.

    Fit & Features

    • High-rise elasticized waist
    • High front slit
    • Flowy silhouette
    • Maxi-length hem
    • Tropical palm leaf print, stretchy knit fabric
    • Panties-style lining
    • Runs true to size

    Style Number/Barcode: 06501-0850

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Playful Prints Satin Pleated Skater Dress

    Play up your colorful side in this satin skater dress perfect for summer! It features a sleeveless V-neckline, adjustable spaghetti straps, a ruched tie-front bust, a stretchy smocked back, a flirty cutout, and a pleated short-length hem. The dress is designed with a multi-colored geometric print on smooth woven satin fabric. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruched tie-front bust, stretchy smocked back
    • Cutout accent, skater silhouette
    • Pleated short-length hem
    • Multi-colored geometric print
    • Smooth woven satin fabric, no stretch, bust lining
    • Runs true to size

    Style Number/Barcode: 05102-5284

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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

    Let your legs say hello to the sunshine in the edgy-cute Remy shorts by Windsor Denim! They feature a flattering high-rise waist, front and back distressed accents, and a frayed cut-off style hem. The jean shorts are composed of premium denim fabric with minimal stretch that offers a form-hugging fit. Complete the look in a trendy tie-front top for a casual backyard bbq dinner!

    Fit & Features

    • High-rise waist
    • Front and back distressed accents
    • Frayed cut-off style hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Premium denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0333

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Electric Love Chiffon Floral Maxi Dress

    Look absolutely electric in this 70s-inspired chiffon maxi dress at parties and vacations! It features a sleeveless V-neckline, adjustable spaghetti straps that cross along the open back, an empire waist, and a flowy maxi-length silhouette on floral print chiffon fabric with a smooth woven lining. Complete the look with a sleek arm cuff bracelet and heels.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross-open back
    • Empire waist
    • Flowy maxi-length silhouette
    • Floral print
    • Airy chiffon fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5264

    Category Name: Vacation Looks

    Price: $5.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Throwback Blues Denim Print Mini Dress

    Let this printed denim mini dress cure your throwback blues! It features a sleeveless square neckline, tank shoulder straps, a bodycon silhouette, and a mini-length hem on smooth and stretchy knit fabric. Complete the look with classic hoop earrings.

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Printed denim, smooth, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5229

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tag You're Knit Bodycon Midi Dress

    Tag you're it to rock this casually cute midi dress all over town! It features a sleeveless scoop neck, spaghetti straps, a flirty bust tie, and a figure-hugging bodycon silhouette with a side slit accent on stretchy rib knit fabric. Complete the look in sparkly teardrop earrings for an outdoor dinner party.

    Fit & Features

    • Sleeveless scoop neck
    • Bust tie, spaghetti straps
    • Bodycon silhouette
    • Side slit accent
    • Midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5138

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ibiza Graphic Fishnet Tank Top

    This graphic tank top is destined to be your plus one on vacations! It is designed in sheer fishnet fabric with a trendy graphic and script that reads "Ibiza."

    Fit & Features

    • Sheer fishnet fabric
    • Crew neckline
    • Graphic and script that reads "Ibiza.
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000036

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free