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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.

  • Spring It On Me Floral Mini Skirt

    Embrace floral vibes by adding this flirty mini skirt into your weekly lineup! The woven skirt features a classic high-rise waist, back zipper closure, a form-hugging silhouette, and a front slit accent. Complete the look in a crop top for a day at the beach!

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Form-hugging
    • Front slit accent
    • Ditsy floral print
    • Woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06301-0132

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sent With Love Swiss Dot Sleeveless Dress

    Send love from where ever you go in this swiss dot sleeveless dress whether it's a trip to Tuscany or a destination dinner with the girls! It features a sleeveless surplice V-neckline, a button-back closure with a keyhole slit detail, side ruched seams, and a bodycon silhouette with a flirty ruffled short hem. Complete the look in rhinestone mules.

    Fit & Features

    • Sleeveless surplice V-neckline
    • Button-back closure, keyhole slit detail
    • Back zipper and hook-eye closure
    • Side ruched seams, bodycon silhouette
    • Ruffled short-length hem
    • Swiss dot chiffon fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2107

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Weekend Vibes Floral Mini Dress

    Give off those effortless weekend vibes in this adorable floral mini dress! It features a V-neckline with a twist-front design, a front keyhole cutout under the bust, adjustable spaghetti straps, a smocked design down the back and body of the dress, a mini-length hem with a form-hugging silhouette, and a ditsy floral print pattern. The woven fabric offers a moderate stretch. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Keyhole cutout under the bust, adjustable spaghetti straps
    • Smocked design down the back and body of the dress
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4920

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everlasting Bliss Ditsy Floral Mini Dress

    You'll be blissful all season with this ditsy floral mini dress in your closet! Blossom into florals for spring bridal showers, graduations, and casual parties. Featuring a sleeveless square neck, adjustable spaghetti straps, and side ruched seams to accentuate your natural curves along the bodycon silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti traps
    • Side ruched seam
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Lined knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5046

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Challis Boho Slit Midi Skirt

    Show off some skin this spring! Create an effortless look in this casual midi skirt featuring a high-rise waist, back zipper closure, and a flirty front slit on challis boho print fabric. Complete the look in lace-up heels for a daytime outing.

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Front slit
    • Midi-length hem
    • Challis boho-inspired print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0149

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Beauty Ikat Surplice Top

    Breeze in looking like beauty in this chiffon top featuring peasant long sleeves, a surplice plunge neckline, and a lower back keyhole with tie closure. Complete the look in a basic cami top and midi skirt.

    Fit & Features

    • Peasant long sleeves
    • Surplice plunge neckline
    • Lower back keyhole, tie closure
    • Ikat print
    • Sheer chiffon fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1857

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Boho Vibes Scarf Top

    Bring the effortless boho vibes with this lightweight woven scarf top. It features a sleeveless halter neckline, a completely open back with a tie-back strap design, an asymmetrical front hem, and an all-over paisley print. Style this top with high-rise mom jeans and cute sandals.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
    • Open back
    • Tie-back strap design
    • Asymmetrical front hem, cropped fit
    • Paisley print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1727

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Moves Eyelet Lace Mini Dress

    The perfect sundress for bridal showers or outdoor parties! It features adorable puff short sleeves, a square neck, side ruched seams along the bodice, and a bodycon silhouette with a mini-length hem. Complete the look in trendy espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Square neck
    • Side ruched seams on bodice
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4874

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swirl Of Attraction Printed Flare Pants

    Draw all the attraction onto you in these stylish printed flare pants at festivals or summer concerts! They feature a flattering high-rise elasticized waistband, a hip-hugging fit, and a flared hem on swirl print knit fabric. Complete the look in a cute corset top.

    Fit & Features

    • High-rise elasticized waistband
    • Hip-hugging fit
    • Flared hem
    • Swirl print
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2284

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Just Slayin' High Rise Cut Off Denim Shorts

    You'll be slayin' in these must-have denim shorts perfect for adding to your weekly rotation! They feature a flattering super high-rise waist, a form-hugging fit, and cut-off style hems with distressing on washed premium denim fabric with color fading. Complete the look in a graphic tee and sandals.

    Fit & Features

    • Super high-rise waist
    • Form-hugging fit
    • Cut off style hem, distressing
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Washed premium denim fabric, color fading, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0323

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bri High-Rise Lace-Up Flare Jeans By Windsor Denim

    Give them something to talk about when you exit the room in the Bri jeans by Windsor Denim! They feature a flattering high-rise waist with a lace-up placket, a hip-hugging fit, and a flared hem on premium denim fabric. Complete the look in a cute crop top for a concert or happy hour!

    Fit & Features

    • High-rise waist
    • Lace-up placket
    • Hip-hugging fit
    • Flared hem
    • Five-pocket styling, belt loop accents
    • Premium denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0403

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vineyard Gal Floral Linen Skater Dress

    Perfect for vineyard weddings, wine tasting, and daytime soirees! This vintage-inspired floral linen dress features adorable puff short sleeves, a sweetheart neck with a bust tie, a lace-up back design, and a tiered fit and flare skater silhouette with a short hem. Complete the look in on-trend espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, bust tie
    • Lace-up back design
    • Tiered fit and flare skater silhouette
    • Short-length hem
    • Vintage floral print, linen fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4919

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Roots Floral Chiffon Short Dress

    Get back to your romantic roots this season in this breezy ditsy floral chiffon dress perfect for baby showers to Sunday brunch! It features a sleeveless V-neck with a flirty bust tie, adjustable spaghetti straps, a stretchy smocked back, and a flattering skater short-length silhouette. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Sleeveless V-neck, bust tie, adjustable spaghetti straps
    • Stretchy smocked back, padded bust
    • Skater silhouette
    • Short-length hem
    • Ditsy floral print
    • Chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4939

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Sultry Strapless Bodycon Midi Dress

    Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down!

    Fit & Features

    • Brushed knit double-lined stretchy knit fabric
    • Strapless neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000186

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: WINE, RED, BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Weekend Getaway Midi Sweater Dress

    This adorable retro print sweater dress is giving major weekend getaway vibes! It features a sleeveless scoop neckline, a front O-ring accent with a small keyhole cutout, tank shoulder straps, a scoop-back design, a midi-length hem, and a form-hugging silhouette. The sweater knit fabric features a trendy retro-inspired multi-print pattern. Style with espadrille sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Front O-ring accent, small keyhole cutout
    • Tank shoulder straps, scoop-back design
    • Midi-length hem, form-hugging fit
    • Retro-inspired multi-print pattern
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1642

    Category Name: Vacation Looks

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On The Move High-Rise Cargo Denim Shorts

    If you're a girl on the move these denim shorts are for you! They feature a high-rise waist, a relaxed silhouette, side cargo detail straps, and a short-length hem. Complete the look in a cute basic tank top for a casual day out!

    Fit & Features

    • High-rise waist, relaxed silhouette
    • Side cargo detail straps
    • Short-length hem
    • Front button and hidden zipper closure
    • Four-pocket styling, belt loop accents
    • Premium denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0348

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dainty Floral Dot Tie-Front Top

    Embrace sun-soaked days in the most perfect crop top! Featuring puff sleeves, a sweetheart neck with a tie-front and keyhole cutout, smocked back panel, crafted from gauze woven-lined fabric. Complete the look in denim shorts for strolling the pier.

    Fit & Features

    • Puff sleeves, sweetheart neck
    • Tie-front and keyhole cutout
    • Smocked back panel
    • Cropped hem
    • Dainty floral dot print
    • Gauze woven lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1826

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hampton Vacay Crochet Trim Duster

    Head out to the Hamptons in this effortlessly stylish duster featuring flowy short sleeves, open-front design, crochet trim, tie-front closure, and a long-length hem on gauze-woven fabric. Complete the look with a chic hat and oversized sunglasses.

    Fit & Features

    • Flow short sleeves
    • Open-front design
    • Crochet trim
    • Tie-front closure
    • Long-length hem
    • Gauze woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1582

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On My Mind Side Slit Maxi Skirt

    Perfect for the girl on the go, this knit maxi skirt can be styled in multiple ways for your everyday occasions and weekend plans! It features a high-rise waist, a hip-hugging fit, and a sultry high-side slit along a relaxed hem. The lined brushed knit fabric offers plenty of stretch. Complete the look with a statement handbag and jacket.

    Fit & Features

    • High-rise elasticized waist
    • Hip-hugging fit
    • High side slit
    • Maxi-length silhouette
    • Relaxed hem
    • Lined brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0842

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Wave Gauze Wrap Tie Crop Top

    Bring the heat in this gauze woven crop top perf for flaunting some skin! It features peasant long sleeves, a surplice V-neckline, and a wrap-tie design. Complete the look in a denim skirt and heels.

    Fit & Features

    • Peasant long sleeves, elastic cinched hems
    • Surplice V-neckline
    • Wrap-tie design
    • Cropped hem
    • Gauze woven fabric, lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1637

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Cutie Denim Tube Dress

    Keep it chic with a tube dress that is perf to dress up for your next brunch date! The dress features a sleeveless square neckline, belt loops, side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with a faux leather belt and mules. 

    Fit & Features

    • Sleeveless square neckline
    • Belt loops
    • Side pockets
    • Mini length silhouette
    • Denim fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4128

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cruise Control Rectangular Frame Sunglasses

    Roll the windows down and cruise so everyone can see you in these trendy rectangular sunglasses! They feature wide, smokey plastic frames with tinted lenses and UV protection from the sun's rays. Complete the look with a ring set for your stylish drive down the coast!

    Fit & Features

    • Rectangular shape
    • Wide, smokey plastic frames
    • Tinted lenses
    • UV 400 protection

    Style Number/Barcode: 07008-0993

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Legend Lace-Up Graphic Short Dress

    Everyone will make way for you, a major legend walking through! This graphic short dress flaunts your edgy-cool girl style featuring a sleeveless scoop neckline, spaghetti straps, dual side lace-up plackets that reveal some skin, a short bodycon fit, and a front script that reads, "Legend" with graphic detailing. Complete the look with a chain choker necklace and earrings.

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Dual side lace-up plackets, cutouts
    • Short bodycon fit
    • Front script reads, "Legend", graphic details
    • Mini-length hem
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1525

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Carefree Cutie Low-Rise Pleated Denim Skirt

    Stay on trend like the carefree cutie you are in this micro mini denim skirt perfect for casual weekend plans! It features a sleek low-rise waist, front pleating, and a frayed cut-off micro mini-length hem. Style with a basic sleeveless top and sandals.

    Fit & Features

    • Low-rise waist
    • Front pleating
    • Frayed cut-off mirco mini-length hem
    • Front button and hidden zipper closure, belt loop accents
    • Medium-wash denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06601-0083

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance