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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.

  • Do Whats Best 4 U Jelly Cross-body Purse

    Always do whats best for you even if that means treating yourself to a creamy colored jelly purse!

    • Jelly handle
    • Jelly rectangular structure
    • Smooth shiny finish
    • Push clasp closure
    • Golden hardware
    • Detachable chain shoulder strap
    • Matte jelly inside

    Style Number/Barcode: 07203-0222

    Category Name: Vacation Looks

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Babe Lace Hanky Hem Maxi Skirt

    Live out your boho era in this airy sheer lace maxi skirt with a mini-length lining for a chic look. The long flowy silhouette will create that effortlessly cool vibe.

    Fit & Features

    • Sheer lace fabric with mini-length knit lining
    • High-rise waist
    • Hip-hugging fit
    • Maxi-length hanky hem
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06501-1131

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cut Out For It Strappy Block Heels

    If anyone is cut out for the job its you doll! These strappy heels are everything and more! Pair them with high waist dress pants, or a pair of dressy linen shorts!

    • Open almond toe
    • Strappy caged detailing
    • Zip back detailing
    • Block heel

    Style Number/Barcode: 07401-2138

    Category Name: Vacation Looks

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Anytime Anywhere Oval Sunglasses

    We love a staple pair of sunglasses like these! They work anytime, anywhere, and with every 'fit!

    • Oval design
    • Double bar arms
    • Gold framing
    • 100% UV protection

    Style Number/Barcode: 07008-0712

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Laced Up and Ready One Piece Swimsuit

    Babe get laced up and ready to hit the waves in this stunning one piece!

    Fit & Features

    • Plunging V-neckline
    • Tank straps
    • Lace up detail down the center bodice
    • Lace up side detailing
    • Low scoop back
    • Cheeky bottom
    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.    

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

    Style Number/Barcode: 07109-0155

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catch Your Eye Sparkling Fringe Shawl

    Catch some glances when you style your going out attire with a shimmering fringe shawl! Styled in many ways, you can wrap over your swim for a bronzed goddess vibe, or style over your special occasion dress for a sparkling finish!

    Fit & Features

    • Woven with silver glitter reflects
    • Fringe ends
    • Golden champagne tones

    Style Number/Barcode: 07305-0080

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Off Shoulder Lattice Back Romper

    Ruffle up your look with this chic and cute romper! Wear your hair in soft curls, slip into some heels, and you got yourself a date night look! 

    Fits & Features

    • Spaghetti Straps 
    • Off Shoulder Sleeves I Ruffle-Trim Neckline 
    • Lattice Lace-Up Back 
    • Wide Leg Shorts 
    • Crepe Fabric I Unlined 
    • Moderate Stretch

    Style Number/Barcode: 06503-0110

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty Floral Tie Front Crop Top

    Bring the flirty vibes in this adorable floral tie front crop top! Perf for spring time, the top can easily be paired with denim and sandals for a casual, cute vibe.

    Fit & Features

    • Short puff sleeves | Tie details
    • Wrap front V neckline | Ruffle hem
    • Tie front
    • Cropped
    • Small floral print
    • Sheer woven fabric | No stretch

    Style Number/Barcode: 06003-0881

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flower Thru It Tie Front Crop Top

    Attend any spring soiree looking sweet and dreamy in this floral tie front crop top! Don't forget to pick up the matching skirt to complete the outfit!

    Shop Matching Bottoms: Flower Thru It Mini Skirt 

    Fits & Features

    • Roomy Long Sleeves
    • Elastic Cuffs & Shoulders
    • Plunging V Neckline I Tie Front
    • Smocked Back
    • Crop Hemline 

    Style Number/Barcode: 06003-0879

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flower Thru It Mini Skirt

    Attend any spring soiree looking sweet and dreamy in this floral mini skirt! Don't forget to pick up the matching top to complete the outfit!

    Shop Matching Top: Flower Thru It Tie Front Crop Top 

    Fits & Features

    • High Rise Waist
    • Back Zipper With Hook & Eye Closure
    • Woven Fabric I Fully Lined 
    • Mini Length Silhouette I Front Slit 
    • Form Hugging Fit I Minimal Stretch 

    Style Number/Barcode: 06401-0232

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Confident Moves Crew Neck Ruffled Mini Dress

    Get ready to make confident moves in this sleeveless mini dress perfect for office days and after work play! Featuring a crew neckline and bodycon fit, this dress will have you feeling fabulous. The tiered ruffled mini-length hem adds a playful touch that will have heads turning. Complete the look in stiletto pumps and a blazer.

    Fit & Features

    • Smooth double-lined knit fabric, moderate stretch
    • Crew neck
    • Bodycon fit
    • Tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5792

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tie Waist Button Front Twill Shorts

    Every girl needs a pair of comfy yet oh so stylish shorts in their closet! Wear these with a chic blouse and some cute wedges.

    Fit & Features

    • High rise waist
    • Partial button down front
    • Tie front belt
    • Lightweight twill woven fabric
    • No stretch

    Style Number/Barcode: 06303-0048

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mini Matte Snake Textured Purse

    Mini purses, they hold the essentials, and also our hearts because they are so darn cute!

    • Mini rectangle structure
    • Matching handle
    • Matte faux leather
    • Snake texture
    • Detachable matching shoulder strap
    • Snap closure

    Style Number/Barcode: 07203-0262

    Category Name: Vacation Looks

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lil Miss Sunshine Smocked Tube Top

    Nothing but good vibes in our Lil Miss Sunshine set! Brighten up any room as you walk in bringing the fun! 

    Shop Matching Top: Lil Miss Sunshine Smocked Tube Top 

    Fits & Features

    • Ruffle-Trim Strapless Neckline & Hem 
    • All Over Smocking 
    • Tie Design At Center Front 
    • Plenty Of Stretch 

    Style Number/Barcode: 06003-0530

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flow With It Linen High Low Tunic

    Go with the flow of this absolutley gorg linen tunic! Its high low feature makes for a statement making look.

    Fit & Features

    • Adjustable spaghetti straps
    • V neck twist front
    • Hidden back zipper
    • Cropped
    • Flowy high low hem
    • Linen gauze fabric | No stretch

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0486

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flower Move Tie Front Off Shoulder Crop Top

    Strike them with a pose! Make all your best moves in this fun and flirty crop top! We love seeing this teamed up with a pair of jeans and heels! 

    Fits & Features

    • Sweetheart Neckline I Padded Bust I Center Front Tie
    • Ruffle-Trim, Off Shoulder Short Sleeves & Neck 
    • Smocked Back 
    • Crop Hemline 
    • Woven Fabric I Lined At The Front 
    • Minimal Stretch 

    Style Number/Barcode: 06003-0540

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Out Of Town Striped Mini Dress

    Head out of town in this stylish striped mini dress for an effortlessly cute look everywhere! Designed with a trendy twisted bust and a bodycon mini-length silhouette that perfectly flaunts your figure. Style with sandals!

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Twist sweetheart strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000029

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Vibes Skater Dress

    Give off major flirty vibes and capture some hearts in this adorable double layered skater dress! Keep it casual with some white sneakers or dress it up with some wedges!

    Fit & Features

    • Adjustable spaghetti straps
    • Square neckline
    • Open back | Tie closure
    • High waistband
    • Double layered skater skirt
    • Flowy fit
    • Woven fabric

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.

      Style Number/Barcode: 05101-0747

      Category Name: Vacation Looks

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Denim Doll Puff Sleeve Mini Dress

      Spring is right around the corner and you'll want to bust out those wedges and sandals to complement this cute denim dress! 

      Fits & Features

      • Puff Shoulder Short Sleeves I Elastic Cuffs
      • Sweetheart Neckline 
      • Square Back I Zipper Closure 
      • Mini Length Silhouette 
      • Denim Fabric 
      • Curve Hugging Fit I Plenty Of Stretch

      Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

      Style Number/Barcode: 05102-0426

      Category Name: Vacation Looks

      Price: $9.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Dreamy Meadow Chiffon Ruffle Maxi Dress

      Look like a dreamy meadow in this flowy and sweet midi dress! Slip into some block heels and you'll be ready for your spring soiree! 

      Fits & Features

      • Adjustable Spaghetti Straps
      • Surplice V Neckline I V Back 
      • Back Zipper 
      • Maxi Length Silhouette I Ruffle-Trim Hem I Partial Lining
      • Adjustable Drawstring & Ruching At Front Side 
      • Chiffon Fabric I Floral & Botanical Prints 
      • Minimal Stretch 

      Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

      Style Number/Barcode: 05101-0769

      Category Name: Vacation Looks

      Price: $21.97 $54.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Be Amazed Ruched Off Shoulder Mini Dress

      Not your typical LBD. They're going to be amazed once they see you strutting in with this mini dress! Dust your neckline with some sparkling rhinestone accents to go for that extra glow! 

      Fits & Features

      • Off Shoulder Neckline I Elastic Interior Band 
      • Fitted Long Sleeves
      • Drawstring Bust 
      • Back Zipper With Hook & Eye Closure 
      • Mini Length Silhouette I Mesh Lined Fabric 
      • Ruching Throughout I Ruffle Trim Neckline & Hem 
      • Form Hugging Fit I Moderate Stretch 

      Style Number/Barcode: 05101-0767

      Category Name: Vacation Looks

      Price: $9.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • All The Stripe Moves Chevron Straight Leg Pants

      We are lovin' this groovy vibe you got! Make sure you pick up the matching crop top to complete this retro-inspired ensemble! 

      Shop Matching Top: All The Stripe Moves Chevron Tube Top 

      Fits & Features

      • High Rise Waistband 
      • Straight Leg Silhouette
      • Colorful Knit Chevron Pattern I Fully Lined 
      • Form Hugging Fit 
      • Moderate Stretch
      • Matching Top Sold Separately 

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

      Style Number/Barcode: 06302-0086

      Category Name: Vacation Looks

      Price: $6.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • All The Stripe Moves Chevron Tube Top

      We are lovin' this groovy vibe you got! Make sure you pick up the matching crop top to complete this retro-inspired ensemble! 

      Shop Matching Bottoms: All The Stripe Moves Chevron Straight Leg Pants

      Fits & Features

      • Strapless
      • Sweetheart Neckline
      • Colorful Knit Chevron Pattern 
      • Form Hugging Fit 
      • Moderate Stretch
      • Matching Bottoms Sold Separately 

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

      Style Number/Barcode: 06003-0481

      Category Name: Vacation Looks

      Price: $6.97 $18.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Keep On Keepin' On Distressed Denim Mini Skirt

      Keep on keepin' on, and look cute on an everyday basis of course! This distressed mini has us daydreaming of summer day adventures, farmers markets, and coffee dates!

      Fit & Features

      • High waist fit
      • Button + Zipper closure
      • Raw hemline
      • Distressed detailing
      • Traditional pockets + Belt loops
      • Short hemline
      • Medium wash denim | Slight stretch

      Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.  

      Style Number/Barcode: 06601-0011

      Category Name: Vacation Looks

      Price: $11.97 $29.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance