Vacation Looks

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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.

  • Sleek And Sparkle 24 Rings Pack

    The more, the merrier, with this pack of 24 rings that give off sleek and sparkle vibes! The set includes 24 bands of both classic sleek rings and rhinestone encrusted rings. The pack includes regular and midi sized bands so they can be stylishly stacked.

    Style Number/Barcode: 07004-0960

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hustlin' Rhinestone Frame Sunglasses

    There's many ways show you are a hustler, and it starts with a pair of bomb af pair of rhinestone sunglasses!

    • Straight brow bar
    • Rhinestone frame
    • Dainty arms with rhinestone detail
    • Cut out center
    • 100% UV protection

    Style Number/Barcode: 07008-0684

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Danya Scuba Floral A-Line Dress

    Special Occasion

    Sway and sashay your way around the dance floor with our beautiful Danya! Her delicate floral prints add a flirty feminine touch.

    Fits & Features

    • Spaghetti Straps 
    • Plunging V Neckline I Princess Seams 
    • Zipper With Hook & Eye Closure At The Back 
    • A-Line, Floor Length Hem I High Slit At The Front
    • Smooth Scuba Knit Fabric With Floral Prints Throughout 
    • Form-Hugging Fit I Moderate Stretch

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0355

    Category Name: Vacation Looks

    Price: $19.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hammered Heart Faux Leather Belt

    We know the way to your heart is a statement belt girrrl! Dress up that denim, or even your go-to mini skirt with this simple yet still makes a statement belt!

    • Large hammered heart accent
    • Ball point buckle closure
    • Faux leather
    • Belt loop

    Style Number/Barcode: 07301-0098

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Holographic Trim Clear Mini Purse

    You always roll up with the best purse in hand! And you ain't stoppin' now!

    • Holographic Trim Mini Purse 
    • Clear design
    • Silver turn lock closure
    • Chain holographic shoulder strap
    • Rectangular structure

    Style Number/Barcode: 07203-0185

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Ready Faux Wool Panama Hat

    Be ready to channel your inner boho with this picture worthy panama hat that we are loving right now! Pair with a simple tee & jeans for an effortlessly trendy vibe!

    • Faux wool
    • Braided matching belt
    • Medium brim

    Style Number/Barcode: 07302-0126

    Category Name: Vacation Looks

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • I'm Busy Cat Eye Sunglasses

    Sometimes ur too busy. Sometimes you need to just throw on some shades and go, and we are feelin' this sassy pair for you babe!

    • Skinny frames
    • Cat eye design
    • Dark shading 
    • 100% UV Protection

    Style Number/Barcode: 07008-0682

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Moment Bow Block Heels

    These playful floral block heels are giving garden party glam with a cute bow—perfect for twirls, toasts, and turning heads at your next event!

    Fit & Features

    • Block heel
    • Square toe
    • Wide strap with bow
    • Adjustable ankle strap with buckle closure
    • Floral print
    • Faux leather padded insole
    • Runs true to size

    Style Number/Barcode: 07401-000362

    Category Name: Vacation Looks

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • H8 On This Rimless Rhinestone Sunglasses

    Try and h8 on me, you can't. You're too busy wondering where these fire shades came from!

    • Brow bar design
    • Rhinestone detailing
    • Rimless Lenses
    • Nose pads
    • Light shade
    • Solid arms
    • 100% UV Protection

    Style Number/Barcode: 07008-0683

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Gemstone Statement Necklace Set

    Make a statement with a beautiful floral gemstone necklace, composed of the most stunning fuchsia tone that compliments all skin tones!

    • Large gemstone design
    • Leafy style detailing
    • Matching earrings
    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07002-0285

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • It's A Vibe Chain Necklace Set

    Layer up with gold chains girl, it's a vibe!

    • Set of two necklaces 
    • Gold chain design 
    • Pendant accent
    • Lobster clasp closure

    Style Number/Barcode: 07002-0279

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babygirl Layered Necklace Set

    We know you love to layer as much as we do babygirl! An array of multi- layered necklaces can bring life to the simplest outfits!

    • Set of five separate necklaces
    • Various lengths
    • Variety of charms: Heart | Coin | Babygirl script
    • Lobster clasp closures 

    Style Number/Barcode: 07002-0270

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • You Are Stunning Floral Tassel Earrings

    You are already stunning, why not highlight your beauty with a little something sparkly!

    • Intricate floral post design
    • Rhinestone detailing
    • Drop tassel fringe
    • Post back closure

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0244

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mini Pearl Door Knocker Earrings

    Baby all you need is a small finishing touch and these cutie little pearl door knockers are just the thing!

    • Square design
    • Pearl detailing
    • Post back closure
    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0298

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Layered Pendant Necklace

    When you're looking to finish your sleek look the finishing touch is a simple layered gold necklace of course!

    • Single necklace | Two layers
    • Drop bar pendant
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07002-0256

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Picture Purrfect Mini Skirt

    You'll look picture purrfect in this trendy spotted mini skirt babe! Pair with the matching crop top for an on point look.

    Shop Matching Top: Picture Purrfect Crop Top

    Fit & Features

    • High rise waist
    • Stretchy smocked back
    • Animal print | Woven fabric
    • Short, curve hugging fit
    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06401-0161

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Picture Purrfect Crop Top

    You'll look picture purrfect in this trendy spotted crop top babe! Pair with the matching mini skirt for an on point look.

    Shop Matching Skirt: Picture Purrfect Mini Skirt

    Fit & Features

    • Off the shoulder sweetheart neckline
    • Short puffed sleeves
    • Tie front with keyhole cut out
    • Stretchy smocked back
    • Ruffle trim | Cropped
    • Animal print | Woven fabric
      Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 06003-0622

      Category Name: Vacation Looks

      Price: $9.97 $26.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Skinny Double O-Ring Belt

      Whether you're adding a little touch to a flowy dress, or amping up your denim with a skinny belt, you are making the right moves bb!

      • Skinny design
      • Double O-ring buckle
      • Adjustable closures

      Style Number/Barcode: 07301-0101

      Category Name: Vacation Looks

      Price: $5.97 $12.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Babes Day Out Panama Hat

      It's babes day out, grab your gals and go on an adventure in the city! Don't forget to throw on a panama hat to finish off that look!

      • Faux wool
      • Curved top
      • Braided belt accent 

      Style Number/Barcode: 07302-0127

      Category Name: Vacation Looks

      Price: $7.97 $15.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Glam AF Hair Clip Set

      Whether you cut your bangs too short or ur feelin' a like a lil' extra dose of glam, this set of hair clips will get ur look glammed the eff out!

      • Set of two
      • Large over-sized design
      • Rectangular structure
      • Snap closure

      Style Number/Barcode: 07006-0097

      Category Name: Vacation Looks

      Price: $5.97 $12.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Cubic Zirconia Butterfly Ring Set

      That style has our hearts fluttering girrrl! Finish your look the right way with a set of simply dainty butterfly rings!

      • Set of five rings
      • Three butterflies | Two sleek finish
      • Closed design 
      • Larger rings: size 7
      • Midi rings: size 4

      Style Number/Barcode: 07004-0049

      Category Name: Vacation Looks

      Price: $6.97 $13.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Smooth Moves PU High-Rise Shorts

      Oh-so-contemporary and sleek, these smooth faux leather shorts feature a high-rise waist, front snap-button, hidden zipper closure, side pockets, seam detailing, and a fitted cheeky hem. The lined faux leather fabric has minimal stretch. Complete the look in a basic tee and boots for an edgy vibe.

      Fit & Features

      • High-rise waist
      • Front snap-button and hidden zipper closure
      • Side pockets
      • Seam detailing
      • Fitted, cheeky hem
      • Faux leather lined fabric, minimal stretch
      • Runs true to size

      Style Number/Barcode: 06403-0241

      Category Name: Vacation Looks

      Price: $29.90

      Availability: In Stock

      Available Color: BLACK

      Available Size: S, M, L, XS

    • Sleek Faux Leather Corset Belt
      Level up your look with a corset belt! Designed to fit perfectly below the cups, with a stretchy elastic backing and four metal snap button closures. Belt is thick and composed of faux leather.

      Style Number/Barcode: 07301-0107

      Category Name: Vacation Looks

      Price: $7.97 $15.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Justina Floral Velvet Burnout Chiffon Dress

      Special Occasion

      Get swept away in this dreamy floral dress! 

      Fits & Features

      • Plunging V Neckline I Empire Waist
      • Adjustable Spaghetti Straps That Cross At The Back 
      • Zipper With Hook & Eye Closure At Back
      • A-Line, Floor Length, Flowy Fit Skirt 
      • Chiffon Fabric With Velvet Burnout Floral Detailing I Fully Lined 
      • Moderate Stretch 

       

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05002-0452

      Category Name: Vacation Looks

      Price: $9.97 $124.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free