Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Autumn Chill Crochet Wide-Leg Pants

    You'll love styling these crochet knit pants on chill autumn days! They feature a flattering high-rise elasticized waistband, a wide-leg silhouette, and ribbed cuffs. Complete the look in a basic top, cozy jacket, and slippers! 

    Fit & Features

    • High-rise elasticized waistband
    • Wide-leg silhouette
    • Ribbed cuffs
    • Crochet knit fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06502-2392

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Frolic In Floral Tie Midi Dress

    Frolic all over town in this floral midi dress perfect for an afternoon tea with the girls! It features a sleeveless V-neck, spaghetti straps, a knot tie bust, a curve-hugging silhouette, and a flirty front slit. The dress is designed with a ditsy floral bud print on stretchy knit fabric. Complete the look in trendy wedge sandals.

    Fit & Features

    • Sleeveless V-neck
    • Spaghetti straps
    • Knot tie bust
    • Curve-hugging silhouette
    • Front slit, midi-length hem
    • Ditsy floral bud print, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4865

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stop And Flare Smocked Skater Dress

    Stroll on by making everyone stop and stare at you in this flirty skater dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a cutout bust accent, a stretchy smocked bodice, and a flattering skater short-length hem. Complete the look in statement sandals for a brunch or day date!

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Cutout bust accent
    • Stretchy smocked bodice
    • Skater silhouette, short-length hem
    • Cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5337

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Something Special Lace Satin Tie Skater Dress

    Look and feel like something special in this lace skater dress and enter your romance era! The dress features a sweetheart neckline with a satin ribbon tie, an underwire bust for support, adjustable satin spaghetti straps, and a satin ribbon tie waist that leads to the flattering skater silhouette and ruffled short-length hem. Complete the look in sparkly sandals for a day date or party!

    Fit & Features

    • Sleeveless sweetheart neckline, satin ribbon tie
    • Underwire bust, adjustable satin spaghetti straps
    • Back zipper and hook-eye closure
    • Satin ribbon tie waist
    • Skater silhouette, ruffled short-length hem
    • Delicate sheer lace, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5336

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Caught On-Trend Basic V-Neck Midi Dress

    Get caught on trend always in this basic midi dress for casual slays! It features cap sleeves, a V-neckline, a flattering bodycon silhouette, and a midi-length hem on soft modal knit fabric with a stretchy mesh lining. Complete the look with a ring set and heels.

    Fit & Features

    • Cap sleeves
    • V-neckline
    • Bodycon silhouette
    • Midi-length hem
    • Soft modal knit fabric, stretchy mesh lining
    • Runs true to size

    Style Number/Barcode: 05102-5306

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serious Chills Velour Cargo Joggers

    Sit back and chill or go on a coffee run in these trendy velour joggers! It features a flattering mid-rise elasticized waist with hidden side pockets for keeping your hands warm, a relaxed fit, cargo flap pockets, and elasticized cuffs. The ultra-soft velour fabric has a moderate stretch. Complete the look with the matching jacket and your favorite sneakers!

    Shop Matching Jacket: Serious Chills Velour Zip Up Hoodie Jacket

    Fit & Features

    • Mid-rise elasticized waist
    • Hidden side hip pockets
    • Cargo flap pockets, velcro closures
    • Relaxed fit
    • Elasticized cuffs
    • Soft velour fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0973

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Colorful Sensation Abstract Print Maxi Dress

    Be the colorful sensation in whatever room you walk into wearing this abstract print midi dress! It features a sleeveless square neckline, spaghetti straps, a bodycon silhouette, and an adjustable ruched drawstring atop a sultry slit. Complete the look with a chic handbag for an art gallery opening or sunset cocktails!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Adjustable ruched drawstring, high slit
    • Maxi-length hem
    • Abstract print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5279

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Dreamer One Shoulder Abstract Maxi Dress

    Dreaming of an artsy wardorbe? Look no further than this abstract print maxi dress perfect for an art show or gallery opening! It features a sleeveless one-shoulder neckline, tank strap, a bodycon silhouette, and a side ruched seam atop a sultry high slit to show some skin. Complete the look with a rhinestone bracelet and heels.

    Fit & Features

    • Sleeveless one-shoulder neckline, tank strap
    • Bodycon silhouette
    • Side ruched seam, high side slit
    • Maxi-length hem
    • Abstract print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5258

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine All Way Metallic Woven Skater Dress

    Shine all way to and from the party in this breezy skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a stretchy smocked waist, and a flattering skater silhouette with a ruffled short-length hem. The dress is crafted from an airy woven fabric with shimmering metallic threads and has a stretchy knit lining. Complete the look in stiletto heels.

    Fit & Features

    • Sleeveless V-neck
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Skater silhouette
    • Ruffled short-length hem
    • Metallic threads, airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5405

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Standout Marble Print Satin Midi Dress

    You'll be a stunning standout in this silky-satin marble print midi dress! It features a sleeveless sweetheart neckline with a sultry bust seam outline, adjustable spaghetti straps, waist cutouts on each side that lead to an open lower back, and a midi-length hem with a flowy A-line silhouette. The sleek satin-woven fabric features a multi-colored marble print pattern for an eye-catching vibe. Complete your look for happy hour with stilettos.

    Fit & Features

    • Sleeveless sweetheart neckline, bust seam outline
    • Adjustable spaghetti straps, stretchy smocked back panel
    • Dual waist cutouts, lead to an open lower back
    • High waist, hidden side zipper, hook and eye closure
    • Midi-length hem, flowy A-line silhouette
    • Marble print, silky satin-woven fabric, top knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2892

    Category Name: Vacation Looks

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carpe Denim Platform Block Heels

    Seize the day in these majorly trendy denim platform heels! They feature an almond toe, crisscross straps, a chunky platform sole and block heel, and an adjustable ankle strap with buckle closure. Complete the look with a chic mini handbag for a party.

    Fit & Features

    • Almond toe
    • Crisscross straps
    • Chunky platform sole and block heel
    • Adjustable ankle strap, buckle closure
    • Denim material
    • Runs true to size

    Style Number/Barcode: 07401-4516

    Category Name: Vacation Looks

    Price: $12.96 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ray Of Beauty Ruffled Short Skater Dress

    You'll be a bright ray of beauty in this adorable ruffled short skater dress! It features a V-neckline with a cute tie-front design, a front keyhole cutout, short puff sleeves with a ruffled trim, a high-rise stretchy smocked waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight sheer chiffon fabric includes a partial woven lining. Style with hoop earrings and clear mules for a day date!

    Fit & Features

    • V-neckline, tie-front design, front keyhole cutout 
    • Short puff sleeves, ruffled trim
    • High-rise stretchy smocked waist
    • Short skater skirt, tiered ruffled design
    • Fit and flare silhouette
    • Sheer chiffon fabric, partial woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5392

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Picking Daisies Chiffon Strappy Skater Dress

    The perfect dress you'll want to pluck from the garden! This dreamy skater dress features adorable puff short sleeves, a square neckline, and pleated bust, a cutout strappy front and back with ties, and a short-length hem on daisy printed chiffon fabric. Complete the look in cute sandals for a family party!

    Fit & Features

    • Puff short sleeves
    • Square neckline, pleated bust
    • Cutout strappy front and back, tie closure
    • Back hidden zipper and hook-eye closure
    • Skater-silhouette, short-length hem
    • Dainty printed chiffon fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5389

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Basic Crew Neck Slit Midi Dress

    Forever your basic midi dress with head-turning detail! It features classic cap sleeves, a crew neckline, a flirty cutout back accent, a flattering bodycon silhouette, and a midi-length hem with a high front slit. The soft brushed knit fabric has plenty of stretch. Complete the look with a glam ring set for a family party or casual date!

    Fit & Features

    • Cap sleeves
    • Crew neckline
    • Cutout back accent
    • Bodycon silhouette
    • Midi-length hem, high front slit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5334

    Category Name: Vacation Looks

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Contemporary Art Hoop Earrings

    Elevate your contemporary style with these artsy hoop earrings for the perfect finishing touch! They feature a sleek metal hoop frame with a U-shaped dip and horizontal lines from side to side. Complete the look with a sleek choker necklace for brunch or a theatre show!

    Fit & Fetaures

    • Sleek metal frame
    • Hoop design
    • U-shaped dip
    • Horizontal lines from side-to-side
    • Fish hook-clasp closure

     

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

    Style Number/Barcode: 07001-1670

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Work Or Play Ruffle Strap Button Skater Dress

    Work or play, this cotton skater dress is a charming choice for a stroll downtown or a coffee date! It features a sleeveless V-neckline, adorable ruffled straps, a stretchy smocked bodice, a button-down front, and a flattering short-length hem. Complete the look in strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Ruffled straps
    • Stretchy smocked bodice
    • Button-down front
    • Skater silhouette, short-length hem
    • Lightweight cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5369

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheer Elegance Mesh Tie Front Kimono

    Layer on sheer elegance to your look with this mesh kimono perfect for a beach day or weekend escape! It features three-quarter length sleeves, a V-neckline, tie-front closure, and a cropped hem on sheer mesh fabric. Complete the look in chunky sandals.

    Fit & Features

    • Three-quarter length sleeves
    • V-neckline
    • Tie-front closure
    • Cropped hem
    • Sheer mesh fabric
    • Runs true to size

    Style Number/Barcode: 06202-0311

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Divine Darling Square Neck Ruffle Mini Dress

    Breeze in looking so darling in this sleeveless mini dress for a day date or dinner party! It features a square neckline, adjustable spaghetti straps, an eye-catching tie-back closure, and a flattering wrap hem with ruffle trim. The dress is composed of an airy woven fabric with a stretchy knit lining. Complete the look with strappy block heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Tie-back closure
    • Wrap mini-length hem, ruffle trim
    • Airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2860

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Chill Crew Neck Knit Dress

    You'll feel effortlessly chill in this basic midi dress perfect for looking cute on the go! It features short sleeves, a crew neck, a bodycon silhouette, a side slit accent, and a knee-length hem. The dress is composed of a soft hacci rib knit fabric with plenty of stretch. Style with trendy flat sandals for grabbing coffee!

    Fit & Features

    • Short sleeves
    • Crew neck
    • Bodycon silhouette
    • Side slit accent
    • Knee-length hem
    • Hacci rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5190

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Flow High-Rise Wide-Leg Pants

    Flowy and effortless! These wide-leg pants are perfect for everyday styling. They feature a flattering high-rise banded waist, a wide-leg silhouette, and are designed on a textured knit fabric. Complete the look in a crop top and heels for dinner and drinks with friends!

    Fit & Features

    • High-rise banded waist
    • Wide-leg silhouette
    • Textured knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2382

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sassy Slit Strapless Midi Sweater Dress

    This comfy midi sweater dress is the perfect blend of cozy and cute! It features a trendy strapless straight-across neckline with an elastic banded hem, ensuring a secure and comfortable fit. The high front slit on the midi-length hem adds a flirty touch to your look. Its form-hugging silhouette enhances your natural curves, while the sweater knit fabric with moderate stretch keeps you snug all day. Complete your look with a pair of sandals for a fabulous and playful outfit.

    Fit & Features

    • Strapless straight-across neckline, elasticized hem
    • Midi-length hem
    • High front slit
    • Form-hugging silhouette
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1708

    Category Name: Vacation Looks

    Price: $3.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Loving Basics V-Neck Bodycon Tank Dress

    Every girl loves her basics and this sleeveless tank dress is perfect for day or night styling! It features a sleeveless notch V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look in a layered choker necklace for a backyard dinner party or casual hang!

    Fit & Features

    • Sleeveless notch V-neckline
    • Bodycon silhouette
    • Fitted mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5176

    Category Name: Vacation Looks

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Caught In The Midi Crew Neck Tank Dress

    A midi dress you wouldn't mind being spotted in! The dress features a sleeveless crew neck, a bodycon silhouette, and a fitted midi-length hem on stretchy rib knit fabric. Complete the look in a sleek layered necklace for lunch with friends!

    Fit & Features

    • Sleeveless crew neck
    • Bodycon silhouette
    • Fitted midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5242

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Somewhere Sweet Mesh Tie Front Crop Top

    Let this mesh crop top take you somewhere sweet to show it off! The top features sheer peasant long sleeves, a plunge V-neckline, and a flirty tie-front hem. Style with sassy high-waist pants for a wine night with the girls!

    Fit & Features

    • Sheer peasant long sleeves
    • Plunge V-neckline
    • Tie-front cropped hem
    • Sheer mesh fabric
    • Runs true to size

    Style Number/Barcode: 06202-0259

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free