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 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: In Stock

    Available Color: WHITE

    Available Size: S, M

  • Stunning Silhouette High Slit Maxi Dress

    Show off your stunning silhouette in this curve-hugging high-slit maxi dress! It features a sleeveless square neckline, tank shoulder straps, a partially open back with a twist-back design and a lower back cutout, a maxi-length hem with a trendy thigh-high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch and has a sewn-in knit lining. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Partially open back, twist-back design, lower back cutout
    • Maxi-length hem, thigh-high side slit
    • Bodycon silhouette
    • Ribbed knit fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4875

    Category Name: Vacation Looks

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Unwind Tropical Slit Midi Dress

    Take time to relax and unwind on your next vacation...in this stylish tropical midi dress! It features a sleeveless square neck, spaghetti straps, a bodycon fit, and a front slit accent on slinky knit-lined stretchy fabric. Complete the look in cute platform wedges.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Bodycon fit
    • Front slit accent, midi-length hem
    • Tropical palm leaf print
    • Slinky knit fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5177

    Category Name: Vacation Looks

    Price: $5.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catching Flights O-Ring Halter Midi Dress

    Catch flights not feelings! This halter midi dress is bringing those getaway vibes. It features a sleeveless halter neckline with a tank strap, an O-ring bust insert with a cutout accent and a form-hugging silhouette. Complete the look in cute flat sandals for a sunset cocktail hour!

    Fit & Features

    • Sleeveless halter neckline, tank strap
    • O-ring bust insert, cutout accent
    • Form-hugging silhouette
    • Midi-length hem
    • Stretchy rib knit fabric, knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5002

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can't Go Without Cargo Twill Shorts

    Don't let your closet be without these twill shorts to give your closet the perfect refresh! They feature a flattering high-rise elasticized waist, dual-side cargo flap pockets, and a fitted hem. Complete the look in cute flat sandals for a casual style.

    Fit & Features

    • High-rise elasticized waist
    • Dual side-flap cargo pockets
    • Fitted short hem
    • Front button and hidden zipper closure
    • Belt loop accents
    • Twill woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0239

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bloom With Beauty Flower Duster Earrings

    Bloom with beauty with these gorgeous flower duster earrings that will elevate your summer looks. They feature a linear drop design with three flower-shaped accents. Style with a tropical print maxi dress and strappy sandals.

    Fit & Features

    • Linear drop design
    • Three flower-shaped accents
    • Textured metal material
    • Post-back closure, rubber stopper


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

    Style Number/Barcode: 07001-1597

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Time To Be Bold Oversized Round Sunglasses

    This summer, it's time to be bold with your trendy 'fits! Style up these glam oversized shades for your iconic looks. The sunglasses feature an oversized round shape with a plastic frame, gold metal detailed accents with mini rhinestones, and tinted lenses. Pair with large hoop earrings.

     Fit & Features

    • Oversized round shape
    • Plastic frame, gold metal detailed accents, mini rhinestones
    • Tinted lenses
    • Polycarbonate blocks 100% UV

    Style Number/Barcode: 07008-1010

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Moves Flat-Top Oversized Sunglasses

    Make trendy moves when you accessorize your 'fits with these oversized shades! The sunglasses feature a rectangular flat-top shape with thin metal arms, ombre-tinted lenses, and rubber nose pads for support. Style with sleek hoop earrings.

    Fit & Features

    • Oversized design
    • Rectangular flat-top shape
    • Thin metal arms
    • Ombre-tinted lenses
    • Rubber nose pads

    Style Number/Barcode: 07008-1016

    Category Name: Vacation Looks

    Price: $3.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Plans Rib Knit Bodycon Maxi Dress

    Casual plans? Look amazing in this sleeveless maxi dress for everything on your social calendar! It features a square neckline, spaghetti straps, a bodycon silhouette, and a fitted long hem on stretchy rib knit fabric. Complete the look in cute flower earrings and sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Maxi, fitted long-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5195

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slice Of Summer V-Neck Tank Maxi Dress

    Break yourself off a slice of this summer-ready rib knit maxi dress you'll love taking on vacation or around town! It features a sleeveless plunge V-neckline, tank shoulder straps, a form-hugging slim silhouette, and a sexy high-side slit. Complete the look with statement earrings and sandals.

    Fit & Features

    • Sleeveless plunge V-neckline
    • Tank shoulder straps
    • Form-hugging, slim silhouette
    • High side slit
    • Maxi-length hem
    • Soft and stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5080

    Category Name: Vacation Looks

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coolness In Check Oversized Chain Sunglasses

    Keep your coolness in check with these oversized sunglasses perfect for everyday styling! They feature square-shaped plastic frames, tinted lenses, and chain-link accented arms. Complete the look in sleek large hoop earrings.

    Fit & Features

    • Square-shaped oversized plastic frames
    • Tinted lenses
    • Chain-link accented arms

    Style Number/Barcode: 07008-1014

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Trendy Charm Choker Necklace Set

    Layer on these trendy charm choker necklaces for a casual glam look this summer! The set features three separate choker necklaces with varying designs including faux pearl beading, a faux pearl beaded flower accent, and mini-hanging coin charms. Includes back adjustable chains and lobster clasp closures. Style with a cute ring pack.

    Fit & Features

    • Three-pack choker necklace set
    • Faux pearl beading
    • Faux pearl beaded flower accent
    • Mini-hanging coin charms
    • Adjustable chains, lobster clasp closures

    Style Number/Barcode: 07002-1505

    Category Name: Vacation Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Swept Away Gauze Tie-Front Top

    Let this tie-front top sweep you away somewhere sweet this summer! It features peasant long sleeves, a plunging neckline, a tie-front closure, and a cropped hem on leaf-printed gauze woven fabric. Complete the look with a boho necklace.

    Fit & Features

    • Peasant long sleeves
    • Plunging neckline
    • Tie-front closure
    • Cropped hem
    • Leaf print
    • Gauze woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1581

    Category Name: Vacation Looks

    Price: $4.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dream Big Butterfly Chain Belt

    Build your dream look by accessorizing with this statement chain belt featuring an eye-catching butterfly design with a back adjustable chain and a lobster clasp closure. Style with a flirty ruffled romper for a summer party!

    Fit & Features

    • Butterfly design
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07301-0634

    Category Name: Vacation Looks

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom With A View Floral Tube Top

    Wherever your travels take you, this floral tube top is here to make your view that much prettier! Designed to flatter, this top has a sleek strapless neckline and fitted crop hem that highlights your figure. Pair with the matching skirt to complete the look.

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining, moderate stretch
    • Strapless tube neckline
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Skirt: Bloom With A View Floral Mini Skirt

    Style Number/Barcode: 06001-000140

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Drive Linen Wide-Leg Cargo Pants

    The cute and casual vibes of these linen-blend wide-leg cargo pants are perfect for a drive up the coast! They feature a high-rise waist with a back elastic waistband, front pockets, large cargo-style side pockets, a wide-leg silhouette with a cuffed hem, and an overall relaxed fit. Style with a crop top and sandals.

    Fit & Features

    • High-rise waist, back elastic waistband
    • Belt loops, hidden front zipper, button closure
    • Dual front pockets, dual large cargo-style side pockets
    • Wide-leg silhouette, cuffed hem
    • Relaxed fit
    • Linen-blend fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06302-0779

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Weekend Style Denim Skort

    Level up your casual summer weekend style with this on-trend denim skort. It features a high-rise waist, a short asymmetric wrap-front overlay with button detailing, front and back pockets, and a fitted silhouette. Pair with a basic bodysuit and strappy sandals.

    Fit & Features

    • High-rise waist
    • Short asymmetric wrap-front overlay
    • Button detailing
    • Belt loops
    • Dual front and back pockets
    • Denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0339

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Darling Ditsy Floral Flowy Shorts

    Create a sweet look that is oh-so-darling with these ditsy floral printed shorts! They feature a high-rise waist, a back zipper closure, and a flowy, relaxed silhouette. The lightweight woven fabric features an adorable dainty ditsy floral print pattern. Style with the matching crop top for the perfect brunch outfit.

    Shop Matching Top: So Darling Ditsy Floral Puff Sleeve Crop Top

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Flowy, relaxed fit
    • Ditsy floral print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0225

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance