Vacation Dresses & Outfits

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STYLE SPOTLIGHT

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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.

  • Stunning Favorite Strapless Cutout Floral Maxi Dress

    Create a stunning aurora in this floral maxi dress for summer cocktail hours! The strapless neckline and side cutout provide a flattering silhouette, while the form-hugging fit accentuates your curves, and the high side slit offers a show of leg. Complete the look in strappy stiletto heels.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Strapless neckline
    • Side cutout
    • Form-hugging fit
    • High side slit
    • Runs true to size

    Style Number/Barcode: 05101-3278

    Category Name: Vacation Dresses & Outfits

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfectly Glam Rhinestone Butterfly Spiral Strap Sandals

    Create a perfectly glam vibe with these rhinestone butterfly strappy sandals! Designed with sleek faux leather, they feature an almond-shaped toe, a dual toe strap and trendy spiral strap design, mini rhinestone embellishments for that glitzy shine, and organza butterfly accents with rhinestone detailing. They include a flat sole with a padded insole for comfortable wear. Style with a summer party dress!

    Fit & Features

    • Faux leather upper
    • Almond toe
    • Dual toe strap and spiral strap design
    • Mini rhinestones
    • Sheer organza butterfly accents with rhinestones
    • Flat sole, padded insole
    • Runs true to size

    Style Number/Barcode: 07406-0362

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Adorable Puff Sleeve Cutout Crop Top

    Simply adorable, this puff sleeve cutout crop top will effortlessly elevate your casual 'fits. The smooth knit fabric offers a lightweight feel and plenty of stretch. The top features a ruched V-neckline, short puff sleeves with elasticized hems, and a bold front cutout below the bust. The open lower back is accented with an adorable tie-back design. Style this fitted top with high-rise jeans and strappy mules.

    Fit & Features

    • Stretchy knit fabric, double-lined front
    • Ruched V-neckline
    • Short puff sleeves
    • Front cutout
    • Open lower back, tie-back design
    • Cropped, fitted
    • Runs true to size

    Style Number/Barcode: 06001-5329

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stackable Style Seven Pack Ring Set

    The perfect seven-pack ring set to achieve stackable style! This set features an assortment of various designs and styles with glitzy rhinestone embellishments that bring some sparkle to your look. Complete the look with a chic handbag for any occasion!

    Fit & Features

    • Seven-pack ring set
    • Rhinestone embellishments
    • Various designs and styles

    Style Number/Barcode: 07004-0399

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crusin' The Tropics Lace-Up Tropical Mini Dress

    Cruise the tropics in this stylish tropical mini dress! Designed with a tropical palm print on knit fabric, this dress is sure to stand out on the island and boat. Featuring a V-neckline and spaghetti straps, a lace-up back that lets you customize the style, and a flattering bodycon fit. Complete the look with sunglasses.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, sewn-in lining
    • Spaghetti straps
    • V-neckline
    • Lace-up back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5549

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Outside The Lines Tie Back Slit Marble Maxi Dress

    Color outside the lines and rock this chic marble print maxi dress for dressy showers or summer events! With a square neckline and spaghetti straps, this dress flatters your figure with a form-hugging fit. The tie-back design adds a touch of unique style while the front slit showcases your legs along the maxi-length hem. Complete the look with earrings and heels.

    Fit & Features

    • Marble print, smooth knit fabric with stretchy lining
    • Spaghetti straps
    • Square neckline
    • Tie back design
    • Form-hugging fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3455

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Constant Sensation V-Neck Corset Satin Skater Dress

    Always be a constant sensation when you step out in this satin skater dress at parties or soirees! With a flirty V-neckline, comfortable shoulder straps, and a flattering corset-seam bodice, this dress has a playful skater silhouette and a short-length hem. The abstract print adds a touch of fun to the satin fabric. Complete the look with bracelets and a clutch!

    Fit & Features

    • Abstract print, satin fabric, woven lining, no stretch
    • V-neckline, shoulder straps
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3291

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine On My Mind Strapless Tropical Skater Dress

    This tropical skater dress will inspire sunshine on your mind! Perfect for vacations or a beach day, this strapless dress features a stretchy waist leading to the skater silhouette and a flirty ruffled mini-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Tropical palm print, gauze woven fabric, bust lining
    • Strapless neckline
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5744

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Silhouette Rosette Ruffled Knit Mini Dress

    The knit mini dress features a sleeveless scoop neckline accented with a dainty rosette detail for an adorable touch. The tiered ruffled mini-length hem and bodycon fit add a flirty feel while highlighting your curves.

    Fit & Features

    • Ribbed knit fabric with knit lining, plenty of stretch
    • Scoop neckline with rosette detail
    • Spaghetti straps
    • Tiered ruffled mini-length hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5846

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blissful Afternoons Corset A-Line Midi Dress

    Enjoy an afternoon of bliss looking so sweet in this A-line midi dress at showers or semi-formal weddings! The sweetheart neckline and adjustable spaghetti straps accentuate your figure while the corset bodice with built-in padded underwire bust provides support. The flowy A-line silhouette and midi-length hem add elegance to your look. Complete the look in strappy heeled sandals.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Corset bodice, built-in padded underwire bust
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3309

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Undeniable Halter V-Neck Crop Top

    All you need is your undeniable sass and this crop top for an adorable style! It features a sultry halter V-neckline and a fitted pointed crop hem that flatters your figure on mineral wash stretchy rib knit fabric. Complete the look in jeans and sandals.

    Fit & Features

    • Mineral wash stretchy rib knit fabric
    • Halter V-neckline
    • Pointed crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1880

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Happy Hour Ruffled Skater Dress

    This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.

    Fit & Features

    • Sleeveless V-neckline
    • Halter tie-back straps, open back
    • Stretchy smocked high waist
    • Short skater skirt, tiered ruffled design
    • Fit and flare silhouette
    • Twill fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5531

    Category Name: Vacation Dresses & Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: YELLOW, WHITE-2, WHITE

    Available Size: XS, M, L, XXS, XL

  • Catch A Cutie Short Sleeve Cutout Eyelet Skater Dress

    Catch yourself a cutie wearing this eyelet skater dress to day parties this season! With playful puff sleeves and a flirty cutout. The sweetheart neckline and bust drawstring add a touch of romance, while the skater silhouette and tiered ruffled hem keep it fun and flirty. Complete the look in wedge sandals.

    Fit & Features

    • Eyelet fabric lined with stretchy knit
    • Sweetheart neckline
    • Adjustable bust drawstring, cutout
    • Skater silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5430

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Twist Cutout Knit Midi Dress

    Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Knit fabric, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • Twist back cutout
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1950

    Category Name: Vacation Dresses & Outfits

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Scene Mock Neck Abstract Mini Dress

    Indulge in the artsy scene in this mock neck abstract mini dress for downtown art walks! This sleeveless dress boasts a figure-flattering bodycon silhouette with side ruching, while the mini-length hem adds a flirty touch. The abstract print adds a bold and unique touch to this must-have dress. Complete the look in edgy boots and a shoulder bag.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5630

    Category Name: Vacation Dresses & Outfits

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Office One Shoulder Tropical Maxi Dress

    This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!

    Fit & Features

    • Tropical palm leaf print, stretchy knit fabric
    • One-shoulder neckline
    • Knotted shoulder strap
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5695

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Legendary Style Western Buckle Faux Leather Sandals

    It's impossible not to make an iconic fashion statement in these faux leather sandals! Featuring a sleek square toe, a flat sole, and a Western-inspired buckle along the strap for added flair. Complete the look with a trendy denim jacket.

    Fit & Features

    • Square toe
    • Flat sole
    • Western-inspired buckle on strap
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1239

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laid Back Fave Crew Neck Tank Maxi Dress

    Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies!

    Fit & Features

    • Rib-knit stretchy fabric
    • Crew neck
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5573

    Category Name: Vacation Dresses & Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Done In One Ribbed Knit Bodycon Midi Dress

    Be ready in a flash with this done-in-one bodycon midi dress perfect for styling up or down! Made with stretchy ribbed knit fabric, it's also soft and comfortable to wear all day. It features a flattering scoop neckline and tank shoulder straps for a comfortable and stylish fit. With a bodycon silhouette and midi-length hem, this dress will hug your curves! Complete the look in a crop denim jacket and sandals.

    Fit & Features

    • Ribbed knit fabric, sewn-in knit lining, moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5666

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girlycore Off-The-Shoulder Ruffled Skater Dress

    Embrace a girly-core coquette aesthetic in this skater dress perfect for sunny days! The sweetheart neckline and cutout waist add a flirty touch, while the stretchy smocked bodice hugs your curves, and the ruffled tier short-length hem adds a feminine flair. Complete the look in wedge sandals.

    Fit & Features

    • Airy woven fabric with lining
    • Stretchy smocked bodice with bust tie
    • Cutout waist
    • Ruffled tier skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3054

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cherry On Top Lace Trim V-Neck Mesh Mini Dress

    This mesh mini dress is the cherry on top of your perfect summer! Featuring delicate lace trim V-neckline, adjustable spaghetti straps, and a cherry print on mesh fabric, this mini-length bodycon dress will hug your curves and flaunt your style. Complete the look in platform heels.

    Fit & Features

    • Cherry print, mesh fabric, stretchy knit lining
    • Lace trim V-neckline
    • Adjustable spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5798

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pick Me Halter Floral Eyelet Crop Top

    Pick this floral crop top for the sweetest look! This halter crop top features a flattering V-neckline with a spaghetti strap tie for a perfect fit, while a sweet bow detail adds a touch of charm. The fitted crop hem and floral printed eyelet fabric give off a playful, summertime vibe. Complete the look in high-rise jeans for any casual plans!

    Fit & Features

    • Floral printed eyelet fabric, minimal stretch
    • Halter V-neckline, spaghetti strap tie
    • Bow along the bust
    • Fitted crop length
    • Runs true to size

    Style Number/Barcode: 06001-5365

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Highly Favored Triangle Rhinestone Lariat Necklace

    This lariat necklace will be highly favored over the rest! It features a dainty chain adorned with rhinestone charms leading to a sleek triangle charm with rhinestone trim and a single fringe chain with a rhinestone. Complete the look in a sultry cocktail dress for a rehearsal dinner or reception!

    Fit & Features

    • Dainy chain lariat necklace
    • Rhinestone charms
    • Triangle charm with rhinestone trim
    • Single fringe chain with rhinestone
    • Lobster clasp closure

    Style Number/Barcode: 07002-1872

    Category Name: Vacation Dresses & Outfits

    Price: $2.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

  • Confident Flirty Strappy One-Shoulder Crop Top

    Make your crush stop and stare at you in this sleeveless crop top! It boasts a flirty strappy one-shoulder neckline, and a fitted crop hem, and is made from a stretchy rib knit fabric. Complete the look in a denim mini skirt for any casual plans!

    Fit & Features

    • Stretchy rib knit fabric
    • Strappy one-shoulder neckline
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1878

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale