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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.

  • Endless Summer O-Ring Ruffle Hem Mini Skirt

    Embrace the summer vibes in this flowy, boho mini skirt! Don't forget to add the matching crop top to complete the fit! 

    Shop Matching Top: Endless Summer O-Ring Ruffle Hem Crop Top 

    Fits & Features

    • High Rise Waist 
    • Side Zipper 
    • Faux Wrap Design With O-Ring Detail 
    • Mini Length I Ruffle-Trim Hem 
    • Woven Fabric I Fully Lined
    • Minimal Stretch 

    Style Number/Barcode: 06301-0066

    Category Name: Vacation Looks

    Price: $6.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Endless Summer O-Ring Ruffle Hem Crop Top

    Embrace the summer vibes in this flowy, boho crop top! Don't forget to add the matching mini skirt to complete the fit! 

    Shop Matching Bottoms: Endless Summer O-Ring Ruffle Hem Mini Skirt 

    Fits & Features

    • Elastic Plunging V Neckline I O-Ring Detail At Bust 
    • Long Sleeve 
    • Ruffle-Trim Cuffs & Crop Hemline 
    • Woven Fabric 
    • Plenty Of Stretch 

    Style Number/Barcode: 06003-0877

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Head Over Heels Bodysuit

    Fall head over heels in love with this gorg floral bodysuit! Paired with some denim and wedges, you'll have the perf brunch ready look!

    Fit & Fetatures

    • Long fitted cuffed sleeves
    • Wrap front V neckline
    • Thong bottom | Dual snap button closures
    • Floral print
    • Knit fabric | Plenty of stretch

    Style Number/Barcode: 06003-0735

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty In Floral Skater Dress

    Create an efforteless flirty look in pretty florals! This skater dress' flowy feel has a flattering figure.

    Fit & Features

    • Adjustable spaghett straps
    • Wrap front V neckline
    • Square back | Zipper and hook and eye closure
    • High waist seam
    • Flowy layered skater skirt | Knit lining
    • All over floral print
    • Sheer chiffon fabric | No stretch

    Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0114

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Burst Ruffle Mini Dress

    Burst into the season with fab florals bby! Pair this charming print with fab wedges and pop of color to complete a brunch-ready look! 

    Fit & Features 

    • Sweetheart Neckline | Drawstring
    • Short Puff Sleeves
    • Mid-Drift Cut Out 
    • Ruched Side Seam | Drawstring 
    • Floral Print 
    • Lined Chiffon 
    • Relaxed Fit | Minimal Stretch 


    Style Number/Barcode: 05102-0676

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fine In Florals High Neck Maxi Dress

    Florals are DEF your color, bb girl! Show off your curves in our Fine In Florals maxi dress! 

    Fits & Features

    • Spaghetti Straps That Cross & Lace-Up At The Back 
    • High Neckline 
    • Maxi Length Silhouette 
    • Dual Side Slits 
    • Smooth Jersey Knit Fabric 
    • Form Hugging Fit I Ample Stretch 

    Style Number/Barcode: 05102-0277

    Category Name: Vacation Looks

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Chic Wavy Striped Crochet Midi Skirt

    Wrap yourself in the retro chic wavy striped crochet midi skirt. With a high-rise waist and back slit, it's perfect for flaunting your style. Pair it with the matching top for a fab look!

    Fit & Features

    • Unlined crochet knit fabrication, short knit stretchy lining
    • High-rise waist
    • Wavy striped pattern
    • High center slit at back of hem
    • Midi length hem
    • Runs true to size

     

    Shop Matching Top: Retro Chic Wavy Striped Crochet Tube Top

    Style Number/Barcode: 06501-1107

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smocked Sweetheart Gingham Mini Dress

    Yes girl, it's the perfect daytime date dress! Perfectly pair the look with some clean white sneakers or heeled sandals! 

    Fits & Features

    • Elastic Sweetheart Neckline & Cuffs 
    • Tie Design & Cut Out At The Bust
    • Woven Short Sleeves I Can Be Worn Off Shoulder
    • Smocking Throughout 
    • Mini Length Hemline With Ruffle Trim 
    • Gingham Print Design 
    • Form Hugging Fit I Plenty Of Stretch 

    Style Number/Barcode: 05102-0688

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Purrfectly Fierce Smocked Mini Dress

    Look purrfectly fierce in this so of the moment leopard printed mini dress! Its smocked detailing will flatter your curves.

    Fit & Features

    • Strapless sweetheart neckline
    • Tie front detail
    • Front cut out
    • Stretchy smocked body
    • Short, form hugging fit
    • Leopard print

    Style Number/Barcode: 05102-0682

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Girly In Gingham Smocked Mini Dress

    Look oh so gorgeous and girly in this gingham smocked mini dress babe! Pair with some cute wedges and you'll have a spring ready look!

    Fit & Features

    • Tie shoulder spaghetti straps
    • Notched V neckline | Ruffle trim
    • Stretchy smocked body
    • Short, form hugging fit
    • All over gingham print

    Style Number/Barcode: 05102-0683

    Category Name: Vacation Looks

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Beauty Eyelet Mini Dress

    You've got that effortless beauty babe! Wear this gorg eyelet mini dress and have the perfect spring time look!

    Fit & Features

    • Adjustable spaghetti straps
    • Wrap front V neckline
    • Hidden back zipper | Hook and eye closure
    • Side tie detail
    • Wrap front skirt
    • Eyelet detail woven fabric | No stretch

    Style Number/Barcode: 05102-0686

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pick Of The Bunch Floral Chiffon Skater Dress

    It's finally spring and that means adding more floral additions to your wardrobe! Brighten up your look with these fresh prints!

    Fits & Features

    • Adjustable Shoulder Straps 
    • V Neckline I Back Zip With Hook & Eye Closure 
    • Mini Length Hem I Skater Style Silhouette
    • Lined Chiffon Fabric I Floral Prints Throughout 
    • Form Hugging Fit

     

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0313

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tag Me Square Skinny Sunglasses

    These sunnies will have you feelin' so  that you'll b making sure you get tagged in allll da photoz! The brown lenses give a vintage vibe that will pair well with an over-sized button up & sneaks!

    • Skinny rectangular design
    • Brown lenses
    • Double bar arms
    • 100% UV protection

    Style Number/Barcode: 07008-0769

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Best Yet Sleeveless Crew Neck Slit Maxi Dress

    The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!

    Fit & Features

    • Soft knit fabric, short lining, plenty of stretch
    • Sleeveless crew neckline
    • Tank straps
    • Side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5588

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bein' Cute Ain't Easy Acrylic Box Clutch

    Being cute ain't easy, but accessorizing can be when you have this clear box purse by your side!

    • Medium rectangular structure
    • Golden trim | Snap closure
    • Detachable acrylic chain link strap
    • Clear acrylic design

    Style Number/Barcode: 07203-0233

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Livin' My Best Life Cheeky Swim Bottoms

    Live your best life on the beach in a strappy black swimsuit babe! Perfectly style with a black sheer kimono and oval shades! Don't forget to pick up the matching swim top!

    Shop Matching Swim Top: Livin' My Best Life Lace Up Swim Tank

    Fit & Features

    • Mid-rise fit
    • Cheeky bottom
    • Self-tie hip detail
    • Moderate stretch

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0506

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Livin' My Best Life Lace Up Swim Tank

    Live your best life on the beach in a strappy black swimsuit babe! Perfectly style with a black sheer kimono and oval shades! Don't forget to pick up the matching swim bottoms!

    Shop Matching Bottoms: Livin' My Best Life Cheeky Swim Bottoms

    Fit & Features

    • Tank straps
    • Scoop neckline
    • Lace detail center bust
    • Non-padded
    • Wrap around criss cross waist straps

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0355

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk On The Wild Side Tiger Print Swim Bottoms

    Take a walk on the wild side in a sassy tiger print swimsuit! Don't forget to pick up the matching top, and top it all off with a red lippy!

    Shop Matching Top: Walk On The Wild Side Tiger Print Swim Top

    Fit & Features

     

    • Mid-rise fit
    • High hip
    • Cheeky bottom
    • Tiger print pattern
    • Fully lined

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0457

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk On The Wild Side Tiger Print Swim Top

    Take a walk on the wild side in a sassy tiger print swimsuit! Don't forget to pick up the matching bottoms, and top it all off with a red lippy!

    Shop Matching Bottoms: Walk On The Wild Side Tiger Print Swim Bottoms

    Fit & Features

    • Wired swim top
    • Non-padded
    • Adjustable spaghetti straps
    • Bar hook closure
    • Tiger print pattern
    • Fully lined

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0300

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Lovin' High Waist Swim Bottoms

    Get in the summer lovin' state of mind in a sweet and simple swimsuit! Don't forget to pick up the matching bandeau swim top to complete your look!

    Shop Matching Top: Summer Lovin' Bandeau Swim Top

    Fit & Features

    • Banded high waist fit
    • Cheeky bottom
    • Fully lined
    • Moderate stretch

    Style Number/Barcode: 07105-0559

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Lovin' Bandeau Swim Top

    Get in the summer lovin' state of mind in a sweet and simple swimsuit! Don't forget to pick up the matching bottoms to complete your look!

    Shop Matching Bottoms: Summer Lovin' High Waist Swim Bottoms

    Fit & Features

    • Bandeau tube top design
    • Non-padded
    • Fully lined
    • Moderate stretch

    Style Number/Barcode: 07104-0411

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Groovy Gal Striped Cutout Mini Dress

    When your dress is the moment, this one’s got that groovy energy! The bold bell sleeves and plunging neckline were made for concerts, bright lights, and dance floors.

    Fit & Features

    • Striped texture knit fabric, soft stretchy knit lining
    • Plunging V-neckline with half hoop insert
    • Bell long sleeve
    • Side cutouts and open back
    • Bodycon silhouette, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000118

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Vibes Straw Tote Bag

    Set it off this weekend with a beach day or a getaway with the squad with this supes cute tote! 

    • Canvas Handles 
    • Rectangular Body 
    • Single Button Closure 
    • Straw Body 
    • Large Exterior Pocket 
    • "Weekend Vibes" Graphic

    Style Number/Barcode: 07203-0223

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine Like A Boss Rhinestone Belt

    Shine bright like the diamond that you are when you a add this sparkling belt atop your swim suit or festival wear bby!

    Fit & Features

    • Adjustable lobster clasp closure
    • Gold chain detailing
    • Double swag drop at the thigh
    • Rhinestone embellished

    Style Number/Barcode: 07301-0170

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale