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.

  • Bohemian Babe Knit High-Rise Mini Skirt

    Channel a boho babe vibe in this sweater knit mini skirt featuring a high-rise waist and a short, curve-hugging fit. Style with the matching tube top for a chic and seamless look!

    Shop Matching Top: Bohemian Babe Knit Cutout Tube Top

    Fit & Features

    • Sweater knit fabric, ribbed hems, high stretch
    • High-rise waist
    • Mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000022

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Life Floral Chiffon Skater Dress

    Live the sweet life twirling in this floral chiffon dress at birthday parties or baby showers! Featuring an adorable off-the-shoulder neckline with ruffle trim, short-sleeve cuffs, a bust keyhole cutout with a tie accent, and a short skater silhouette. The dress is composed of a dainty floral print chiffon fabric with a knit lining. Complete the look in simple platform heels.

    Fit & Features

    • Off-the-shoulder neckline, ruffle trim
    • Short-sleeve cuffs, elasticized hems
    • Keyhole bust with tie, back zipper, hook and eye closure
    • Short skater silhouette
    • Dainty floral print
    • Sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2038

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Aren't I Grand Crepe Chiffon Romper

    Make an entrance in this crepe chiffon romper at your next chic soiree! Features a sleeveless V-neckline, adjustable spaghetti straps, wrap-around straps, and a ruffled layer short hem. Complete the look in colorful heels.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Wrap-around straps
    • Ruffled layer short hem
    • Crepe chiffon fabric, partial lining
    • Runs true to size

    Style Number/Barcode: 06403-0296

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Just A Crush Satin Pleated Top And Shorts Set

    It'll start out as just a crush, but you'll totally be smitten with this top and shorts set for all of your styling needs! The top features long sleeves, a collar neckline, a button-down front, and a flowy cropped hem. The shorts feature a high-rise elastic waist and a short-length hem. Each is composed of a satin pleated fabric. Complete the look in chic clear heels.

    Fit & Features

    • Satin pleated top and shorts set
    • Top, long sleeves, collar neckline
    • Button-down front, flowy cropped hem
    • Shorts, high-rise elastic waist
    • Short-length hem
    • Non-stretch fabric
    • Runs true to size

    Style Number/Barcode: 06503-1040

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cali Palms Smocked Mini Skirt

    Feel the breeze in Cali or wherever you vacay! Look cute in this mini skirt featuring a high-rise waist, smocked detail, bodycon silhouette, and a palm leaf print on woven fabric. Complete the look with the matching top.

    Shop Matching Top: Cali Palms Cap Sleeve Tie-Front Top

    Fit & Features

    • High-rise waist
    • Smocked detail
    • Bodycon silhouette
    • Mini-length hem
    • Palm leaf print
    • Runs true to size

    Style Number/Barcode: 06301-0112

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cali Palms Cap Sleeve Tie-Front Top

    Feel the breeze in Cali or wherever you vacay! Look cute in this tie-front top featuring puff cap sleeves, sweetheart neck, a smocked bodice, and a palm leaf print on woven fabric. Complete the look with the matching skirt.

    Shop Matching Bottoms: Cali Palms Smocked Mini Skirt

    Fit & Features

    • Puff cap sleeves
    • Sweetheart neck
    • Tie-front detail
    • Smocked bodice
    • Cropped hem
    • Palm leaf print
    • Runs true to size

    Style Number/Barcode: 06003-1683

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coastal Cute Linen Top And Shorts Set

    The perfect linen top and shorts set for your drive up the coast or beach cottage vacay! The oversized top features long sleeves with button cuffs, a collar neckline, a front pocket, and a button-down front. The matching shorts feature a smocked elastic high-rise waist. tie accent, side pockets, and a short-length hem. Complete the look in trendy sandals.

    Fit & Features

    • Linen top and shorts set
    • Oversized top, long sleeves, button cuffs
    • Collar neckline, front pocket
    • Button-down closures
    • Smocked elastic shorts, high-rise waist
    • Tie accent, side pockets, short hem
    • Runs true to size

    Style Number/Barcode: 06303-0227

    Category Name: Vacation Looks

    Price: $21.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch Date Floral Chiffon Skater Dress

    This adorable floral chiffon skater dress is perfect for brunch dates! The mini dress features a sleeveless square neckline, spaghetti straps, a smocked bust, a short skater skirt with a fit and flare silhouette, and a dainty floral print pattern, this dress is a must-have for the spring and summer seasons. Style with heeled sandals.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Smocked bust
    • Short skater skirt, fit and flare silhouette
    • Dainty floral print
    • Swiss dot chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2282

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Social Butterfly Mesh Corset Top

    Got plans? You'll adore this charming mesh corset top for festivals and parties! Featuring a sleeveless scoop neckline, adjustable spaghetti straps, a bust cutout accent with lattice trim, underwire cups, a fitted crop hem, and back hook and eye closures. Style with sleek faux leather leggings to complete the look!

    Fit & Features

    • Sleeveless scoop neckline, adjustable spaghetti straps
    • Bust cutout accent with lattice trim
    • Underwire cups, fitted crop hem
    • Back hook and eye closures
    • Butterfly appliques
    • Partially lined mesh fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4883

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pencil Me In Bandage Midi Skirt

    Add chic and sophisticated vibes by adding this bandage midi skirt to your closet! It features a smooth high-rise fit and is crafted from bandage-seamless knit fabric that offers a form-hugging fit and moderate stretch. Complete the look in a sultry corset top for a wine bar with the ladies! 

    Fit & Features

    • Smooth high-rise fit
    • Form-hugging
    • Midi-length hem
    • Bandage-seamless knit design
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0837

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Strike Again Marble Print Mini Dress

    Strike a stunning look every time you're in this knit mini dress at parties or nights out! It features a sleeveless one-shoulder neckline, dual spaghetti straps with a sultry cutout, a bodycon silhouette, and a trendy marble print on stretchy knit fabric. Complete the look in sandals.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Dual spaghetti straps
    • Cutout bust
    • Bodycon silhouette
    • Mini-length hem
    • Marble print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4932

    Category Name: Vacation Looks

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Made You Flirt Lace Skater Dress

    Make your crush flirt with how cute you'll be looking in this lace eyelet short dress perfect for birthday brunches or parties! Featuring a sleeveless scoop neck, ruffled straps, a ruched bust, and a fit-and-flare skater silhouette. Style with a chic bracelet and heels to complete the look.

    Fit & Features

    • Sleeveless scoop neck, ruffled straps
    • Ruched bust
    • Fit and flare skater silhouette
    • Short-length hem
    • Lace eyelet fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2155

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sandy Beaches Palm Bandeau Top

    Can't you imagine strolling the beach in this palm print bandeau top? Embrace vacay in this tropical stunner featuring a sleeveless, strapless neckline, tie-front closure, and a smocked bodice. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Sandy Beaches Palm Wide-Leg Pants

    Fit & Features

    • Sleeveless, strapless neckline
    • Tie-front closure
    • Smocked bodice
    • Cropped hem
    • Palm print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1809

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Desert Haze Paisley Flare Pants

    These boho-chic printed flare pants are perfect for a weekend getaway! They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, a flared hem, and a trendy paisley multi-print pattern. The knit fabric offers plenty of stretch. Style with a tie-front top and booties!

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Paisley multi-print pattern
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-0944

    Category Name: Vacation Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Muse Lace-Up Embroidered Crop Top

    Channel that boho babe vibe in this lace embroidered crop top with a trendy lace-up front design. Style with the matching mini skirt for festival season!

    Shop Matching Bottoms: Boho Muse Lace Embroidered Mini Skirt

    Fit & Features

    • Lined sheer mesh fabric with lace embroidery
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Front lace-up design
    • Smocked back, zipper closure
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2746

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sandy Beaches Palm Wide-Leg Pants

    Can't you imagine strolling the beach in these palm print pants? Embrace vacay in this tropical stunner featuring a high-rise waist, wide-leg silhouette, and back zipper closure. Complete the look with the matching top.

    Shop Matching Top: Sandy Beaches Palm Bandeau Top

    Fit & Features

    • High rise waist
    • Wide-leg silhouette
    • Back zipper closure
    • Palm print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0655

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oopsy Daisy Print Knit Mini Dress

    It's no mistake if this casual mini-dress makes its way into your cart! Perfect for weekend outings and day dates, this daisy print dress features a sleeveless V-neck, spaghetti straps, a center bust ruched seam for a cute scrunched look, and a bodycon silhouette. Complete the look in strappy platform sandals.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Center bust ruched seam
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy daisy print
    • Rib knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5041

    Category Name: Vacation Looks

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Timeless Love Rib Knit Maxi Dress

    You'll adore this rib knit maxi dress time and time again! Create your capsule wardrobe with this perfect dress featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry side slit. Complete the look in a statement crop jacket, hoop earrings, and your go-to sneakers!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Curve-hugging silhouette
    • Side slit
    • Maxi-length hem
    • Stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4916

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine State Of Mind Off-The-Shoulder Romper

    Perfect for soaking up the sun, this off-the-shoulder romper is an effortlessly stylish option for spring! It features puff short sleeves, a ruched bust with a faux wrap look and tie-back closure, and a flowy layered short hem. Complete your flirty outfit with platform sandals.

    Fit & Features

    • Puff short sleeves, off-the-shoulder
    • Ruched bust, faux wrap with tie-back closure
    • Back zipper and hook-eye closure
    • Flowy, layered short hem
    • Shorts-lining
    • Crepe woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0297

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Get That Glow Tank And Biker Shorts Set

    Get that glow in this bold seamless set that you can style up or down! It features a cropped tank with a V-neckline, spaghetti straps, and a fitted silhouette. The matching biker shorts feature a high-rise waist, a mid-thigh length hem, and a form-hugging fit. The ribbed knit fabric offers plenty of stretch. Style with a denim jacket and sneakers.

    Fit & Features

    • Matching tank and shorts set
    • Cropped tank, V-neckline, spaghetti straps
    • Biker shorts, high-rise waist, mid-thigh length, form-hugging fit
    • Seamless ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 07103-0919

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Diva Moment Cat Eye Sunglasses

    Have a total diva moment in these edgy-glam sunglasses! They feature an oversized cat eye design with a flat top and dark-tinted lenses. Style with a quilted clutch.

    Fit & Features

    • Oversized cat eye design
    • Flat top
    • Plastic frame, stud accents
    • Dark-tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-0989

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hidden Treasure Faux Pearl Slide Sandals

    You'll truly covet these faux pearl sandals all season long! They feature a square toe, a wide single strap with faux pearls, a quilted faux leather footbed, a flat sole, and slide-on-and-off styling. Complete the look in a trendy crossbody bag.

    Fit & Features

    • Square toe
    • Faux pearl wide single strap
    • Quilted faux leather footbed
    • Flat sole
    • Slide-on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1083

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Day To Night Chic Crossbody Bag

    This chic crossbody bag is perfect for transitioning from day to night! It features a mini design with a top handle strap, a fold-over design with a sleek metal trim and a snap-button closure, a diamond-shaped quilted faux leather exterior, a lined interior, and a thin chain-link shoulder strap. Style with a pair of strappy mules.

    Fit & Features

    • Mini design
    • Top handle strap
    • Fold-over design, metal trim, snap-button closure
    • Diamond quilted faux leather exterior
    • Woven lined interior
    • Chain-link shoulder strap

    Style Number/Barcode: 07203-1181

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Muse Butterfly Print Flare Pants

    You'll be a dreamy muse in these trendy and fab butterfly print flare pants! They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, and a flared hem. The sheer mesh fabric features an abstract butterfly print pattern, perf for festival season! Style with an embellished crop top and clear mules.

    Fit & Features

    • High-rise elasticized waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Butterfly print
    • Sheer mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2265

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale