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.

  • Blooming Romance Floral Satin Mini Dress

    Your special someone won't be able to take their eyes off of you in this blooming floral mini dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, subtle pleating at the waist, and a mini-length hem with a form-hugging silhouette. The smooth satin-knit fabric showcases a bold floral print pattern for a romantic vibe. Style with strappy stilettos for date night.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Pleating at the waist
    • Mini-length hem, form-hugging silhouette
    • Large floral print
    • Satin-knit fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2017

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On My Street High-Rise Cargo Pants

    Level up your street style in these nylon cargo pants perfect for hitting your favorite spots downtown! They feature a high-rise adjustable drawstring waistband, front hip flap pockets with snap-button closures and lower flap pockets, a wide-leg silhouette with four snap-button closures along the hem, and faux back pockets. Complete the look in a trendy corset top and heels.

    Fit & Features

    • High-rise adjustable drawstring waistband
    • Front hip flap pockets with snap-button closures
    • Lower flap pockets
    • Wide-leg silhouette, four snap-button closures on hem
    • Faux back pockets
    • Non-stretch nylon fabric
    • Runs true to size

    Style Number/Barcode: 06302-0707

    Category Name: Vacation Looks

    Price: $21.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Country Babe Pearl Detailed Western Booties

    Show off a chic strut in these western booties that will have you giving off country babe vibes! They feature an above-the-ankle fit, pull tabs on each side for easy on-and-off styling, a pointed toe, a stacked block heel, a western-inspired embroidered design, and mini faux pearl embellishments. Style with a denim jacket for a music festival.

    Fit & Features

    • Above-the-ankle fit
    • Pull tabs for easy on-and-off styling
    • Pointed toe
    • Stacked block heel
    • Faux leather material, embroidered design
    • Faux pearl embellishments
    • Runs true to size

    Style Number/Barcode: 07403-1622

    Category Name: Vacation Looks

    Price: $4.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Prowlin' Cutie Leopard Crepe A-Line Dress

    Look cute for your daytime prowls in this leopard print crepe dress! It features long bell sleeves, a scoop neck with a ruched tie-front bust, halter straps with self-tie closure, and a flattering A-line silhouette and dual side slit accents. Complete the look in sassy sandals!

    Fit & Features

    • Long bell sleeves
    • Scoop neck, ruched tie-front bust
    • Halter straps, self-tie closure
    • A-line silhouette
    • Short-length hem with dual side slit accents
    • Leopard print, crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4959

    Category Name: Vacation Looks

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild One Chiffon Surplice Bodysuit

    Unleash your wild side in this chiffon bodysuit perf for bringing the heat on girl's night! It features long peasant sleeves, a surplice v-neck, dual snap-button closure, a thong bottom, and a fierce leopard and chain-link print design. Complete the look in high-rise jeans.

    Fit & Features

    • Long peasant sleeves
    • Surplice v-neck
    • Dual snap-button closure, thong bottom
    • Leopard and chain-link print
    • Sheer chiffon fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1670

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Midnight Floral Mesh Mini Dress

    Play up florals on a summer night out in this mesh mini dress featuring a sleeveless, square neck, tank shoulder straps, all-over ruching, and a form-hugging fit. Complete the look in chic PVC strap heels.

    Fit & Features

    • Sleeveless, square neck
    • Tank shoulder straps
    • Back zipper closure
    • All-over ruching
    • Form-hugging, mini-length hem
    • Floral print, mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1683

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Deets Lace-Up Corset Top

    You'll love the sultry details of this chic lace-up corset top. It features a sleeveless sweetheart neckline, underwire cups with a built-in padded bust, adjustable spaghetti straps, and a lace-up with tie closure on an angled cropped hem. Pair this top with trendy vintage-style jeans.

    Fit & Features

    • Sweetheart neckline, adjustable spaghetti straps
    • Underwire, built-in padded bust
    • Lace-up with tie closure
    • Flexible boning, back hook-eye closures
    • Cropped angle hem
    • Crepe fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1866

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Isn't She Lovely Floral Midi Skirt

    Everyone will be thinking how lovely you look strolling by in this floral midi skirt perfect for wearing on a sunny day! It features a high-rise waist, a center front ruched seam to accentuate your curves atop the flirty slit accent, and a bohemian-inspired floral print pattern. The lightweight woven fabric includes a mini-length knit lining. Complete the look in a chic corset top and heels.

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Center front ruched seam and slit accent
    • Midi-length hem
    • Bohemian floral print
    • Woven fabric, mini-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06401-0568

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Renaissance Me Tie Front Corset Top

    Get swept off your feet looking like a modern princess in this crop corset top to bring the romantic allure to your favorite bottoms! Featuring peasant long sleeves, an off-the-shoulder neckline with a tie-front keyhole, a ruched bust, flexible boning, and front hook and eye closures. Complete the look in boyfriend jeans for a casual day date.

    Fit & Features

    • Peasant long sleeves
    • Off-the-shoulder neckline, tie-front keyhole
    • Ruched bust
    • Flexible boning inserts
    • Front hook and eye closures
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-1993

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chain To Chain Three Earrings Set

    You'll be on the edge of style with this three-pack earring set! It features one pair of statement chain link earrings, one pair of twist chain earrings, and one pair of blockchain earrings. Each has a post-back closure. Style with a sleek faux leather jacket.

    Fit & Features

    • Three-pack earrings set
    • One pair of statement chain link earrings
    • One pair of twist chain earrings
    • One pair of blockchain earrings
    • Each has a post-back closure and rubber stopper

     

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

    Style Number/Barcode: 07001-1468

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Breezy Vibes Lace Mini Skirt

    Show off a breezy chic vibe in this airy lace mini skirt featuring a high-rise waist and a short form-hugging fit. Style with the matching tie-front top for a weekend getaway.

    Shop Matching Top: Breezy Vibes Lace Tie-Front Top

    Fit & Features

    • Sheer lace fabric with lining
    • High-rise waist, eyelet lace trim
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-000004

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

    Product Badge:
    • Sale
  • What The Heart Wants Belly Ring

    Showcase your heart for glamour with this belly ring featuring a sleek metal design, a rhinestone stud accent, and a rhinestone-embellished heart charm. Style with a crop top to flaunt your new bling!

    Fit & Features

    • Sleek metal frame
    • Rhinestone stud accent
    • Rhinestone heart charm

     

    Belly button rings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07004-0326

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slip Into Comfort Puff Slide Sandals

    Slip into these comfy and casual slide sandals perfect for your off-duty days! They feature a round toe, a wide textured puff strap, and a comfort foam sole. Style with a cute and cuddly shacket for lounging at home or a coffee run! 

    Fit & Features

    • Round toe
    • Wide textured puff strap
    • Comfort foam sole
    • Runs true to size

    Style Number/Barcode: 07404-1110

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance For One Rose Tie-Front Dress

    Romance yourself! Look sweet in this rose print casual dress on a day date or brunch. It features a sleeveless sweetheart neck, spaghetti straps, bust tie-front, and keyhole, side ruched seams to accentuate your figure along the mini, bodycon silhouette. Style with a denim jacket to complete the look!

    Fit & Features

    • Sleeveless sweetheart neck, spaghetti straps
    • Bust tie-front and keyhole
    • Side ruched seams
    • Bodycon silhouette, mini-length hem
    • Ditsy rose print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4929

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step Out And Shine Chrome Sandals

    Step out and shine in these trendy chrome sandals! They feature an open round toe, a wide banded toe strap, an open back for easy on-and-off styling, a flat sole, and a fab chrome sheen. Pair these sandals with hoop earrings.

    Fit & Features

    • Open round toe
    • Wide banded toe strap
    • Open back
    • Flat sole
    • Chrome sheen
    • Faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-1097

    Category Name: Vacation Looks

    Price: $9.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Magic In Metallic Rhinestone Sandals

    Every step is magical in these metallic flat sandals perfect for gaming up your outfit! They feature a sleek square toe, a wide strap with colored rhinestones, and a flat sole. Complete the look in trendy skinny jeans.

    Fit & Features

    • Square toe
    • Wide strap with colored rhinestones
    • Flat sole
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07404-1100

    Category Name: Vacation Looks

    Price: $5.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Maybelle Formal Floral Chiffon A-Line Dress

    Special Occasion

     Delicate floral blooms transform the Maybelle formal dress into a dream for bridesmaids and spring fling dances! She enchants in adorable short puff sleeves, an elasticized square neckline with a keyhole tie-front, a lightly padded bust, and a fitted bodice. Her flattering a-line silhouette effortlessly creates the illusion of a smaller waistline as it flares out into a floor-sweeping hem with a sultry wrap high-cut front slit. The formal dress is composed of a floral printed airy chiffon fabric with a sewn-in knit lining and no stretch. Style with platform lace-up heels to complete the look!

    Fit & Features

    • Short puff sleeves, elasticized square neckline
    • Keyhole tie-front, lightly padded bust, fitted bodice
    • Back zipper and hook-eye closure
    • A-line silhouette, high-cut wrap front slit, floor-length hem
    • Delicate floral print, chiffon fabric, sewn-in knit lining, no stretch
    • Bra optional
    • Runs true to size

    Style Number/Barcode: 05002-7053

    Category Name: Vacation Looks

    Price: $19.97 $68.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Diva Vibes Ruched Rhinestone Sandals

    Live your best life and give off diva vibes in these glam rhinestone sandals! They feature an open square toe, a ruched toe strap with mini rhinestone embellishments, a thin adjustable heel and ankle strap, and a flat sole. Style with a mini dress and hoop earrings.

    Fit & Features

    • Open square toe
    • Ruched toe strap
    • Mini rhinestones
    • Thin adjustable heel and ankle strap
    • Flat sole
    • Faux suede material, faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-1106

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stay Trendy Strappy Platform Sandals

    These strappy platform sandals will keep your casual 'fits trendy and cute! They feature an open round toe, a double-banded strap design, an adjustable heel strap, and a platform sole. Style with a cropped denim jacket.

    Fit & Features

    • Open round toe
    • Double-banded strap design
    • Adjustable heel strap, buckle detail
    • Platform sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1107

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Follow Your Heart Hoop Earrings

    Follow your heart and add some glamour to your look with these adorable hoop earrings! They feature a layered design of three heart-shaped metal outlines with textured detailing. Style with a flirty cropped blouse and a satin midi skirt.

    Fit & Features

    • Layered design
    • Three heart-shaped metal outlines
    • Textured detailing
    • Omega closure, rubber stopper


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

    Style Number/Barcode: 07001-1472

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Edgy Faux Pearl Chain Layer Necklace

    Pretty and edgy! This layered necklace is sure to give your outfit an eye-catching detail. It features three layers with one faux pearl and chain layer, one statement chain link layer, and one snake chain layer each with lobster clasp closures. Complete the look in a ring set.

    Fit & Features

    • Three layered necklace
    • One faux pearl and chain layer
    • One statement chain link layer
    • One snake chain layer
    • Each has lobster clasp closures

    Style Number/Barcode: 07002-1374

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Total Trendsetter Chunky Platform Sandals

    Show off your trendsetting style in these of-the-moment chunky platform sandals. They feature an open almond-shaped toe, a wide banded toe strap with a cushioned fabric for comfort, an open back for easy on-and-off styling, and a platform and thick low block heel with a lug sole. Style these faux leather sandals with hoop earrings.

    Fit & Features

    • Open almond-shaped toe
    • Wide banded toe strap, cushioned fabric
    • Open back
    • Platform, thick low block heel, lug sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1109

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Chic Strappy Sandals

    These on-trend strappy sandals will give off major bohemian chic vibes! They feature a round toe with a criss-cross strappy design, wrap-around adjustable heel and ankle straps, and a flat sole with a subtle cushioned insole. Style with a flowy printed midi dress.

    Fit & Features

    • Round toe
    • Criss-cross strappy design
    • Wrap-around adjustable heel and ankle straps, buckle detail
    • Flat sole, subtle cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1111

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Daisy Floral Print Sandals

    Oh-so-darling, these daisy floral print sandals will create a cute springtime look. They feature a round toe, a wide woven strap with a bow design and an adorable daisy print floral pattern, an open back for easy on-and-off styling, and a flat sole with an espadrille trim. Style with a casual dress.

    Fit & Features

    • Round toe
    • Wide woven strap, bow design
    • Daisy print floral pattern
    • Open back
    • Flat sole, espadrille trim
    • Faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-1104

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale