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.

  • Chiffon Sweetheart Smocked Mini Dress

    Whether you're brunching with your girls or got a date scheduled, finding the right dress can be difficult. Look no further, this pretty chiffon mini dress is your perfect go-to! 

    Fits & Features 

    • Sweetheart Neckline
    • Puff Accent Shoulders I Long Sleeves
    • Empire Waist
    • Smocked Skirt & Cuffs
    • Fully Lined I Chiffon Composition 
    • Mini Length, Ruffle Trim Hemline
    • Zipper Not Included 

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

    Style Number/Barcode: 05102-0449

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leopard Print Surplice Smocked Mini Dress

    If you're on the hunt for a fierce print and body-flattering dress, look no further than this!

    Fits & Features

    • Plunging V Neckline With Surplice Design
    • Cuffed Long Sleeves
    • Smocked Skirt With Merrow Edge Trim Hem
    • Leopard Print Design
    • Form Hugging Fit I Plenty Of Stretch At Bottom 
    • Zipper Not Included 

     

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

    Style Number/Barcode: 05102-0428

    Category Name: Vacation Looks

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fur-Ever Fab Slides
    Keep it fab girl with these fashionista-approved slides! They feature an easy slip on design, a round toe, a single wide band with a faux fur detailing and a flat sole.

    Style Number/Barcode: 07408-0025

    Category Name: Vacation Looks

    Price: $8.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Chiffon Blouson Mini Dress
    Get an effortlessly beautiful look in this floral printed chiffon blouson dress! The mini features a ruffle mock neckline, long sheer puffed sleeves with elastic cinched wrists, and a stretchy smocked dress with a short hem. The all over floral print gives a pretty touch to the dress.

    Style Number/Barcode: 05102-0508

    Category Name: Vacation Looks

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready For It Mini Dress
    Get ready to have a total trendy look with this cute little mini! It features a slight sweetheart neckline, long sheer chiffon puffed sleeves with smocked cuffs, and a stretchy, smocked dress with a short, mid-thigh length hem with a front drawstring.

    Style Number/Barcode: 05102-0507

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Add Some Flair Ruffle Detail Midi Dress

    Add some flirty flair to your look with this gorgeous ruffle detail midi dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back strap design, a sultry ruffled front slit to show some leg, and a midi-length, sleek, curve-hugging silhouette. The dress is composed of a crepe fabric that offers a moderate stretch. Style the look with eye-catching strappy heels for the perfect date night outfit.

    Shop Long Crepe Version: Tiffany Sleeveless High Slit Formal Dress

    Shop Satin Midi Version: Ravishing Ruffles High Slit Midi Dress

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Strapless or adhesive bra recommended
    • Cross-back strap design, front slit, ruffled hem
    • Midi-length silhouette
    • Crepe fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-0885

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bella High Rise Skinny Ankle Jeans

    Oasis by Eunina

    Our Bella skinny jeans are a necessity for your closet! They feature a super high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, slight destructed detailing down the front, skinny pant legs, and a raw cut ankle hem. The denim fabric offers moderate stretch for comfortable wear.

     Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small. 

    Style Number/Barcode: 06602-0033

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Clara High Rise Destructed Skinny Crop Jeans

    Oasis by Eunina

    Our Clara high rise skinny jeans are perfect in creating a stylish 'fit! They feature the traditional five pocket and belt loop design, a front button and hidden zipper closure, super destructed detailing down the front, skinny pant legs, and a cropped hem. The denim fabric offers moderate stretch for comfortable wear.

    Style Number/Barcode: 06602-0035

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Snake Print Moment O-Ring Purse

    Have yourself a moment with a snake print purse! Hand held or cross-body for the girl on the go!

    • O-Ring handle
    • Structured rectangular shape
    • Brown toned snake print pattern
    • Detachable shoulder strap
    • Faux leather
    • Inner zipper pocket | Open pocket

    Style Number/Barcode: 07203-0165

    Category Name: Vacation Looks

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dainty Rhinestone Bands Variety Pack

    Keep it dainty and chic with a sparkling band to match your mani! This pack includes 5 rings adorned with a rhinestone embellishments. Easily stack or wear alone.

     

    Style Number/Barcode: 07004-0034

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • You're My Butterfly Pendant Necklace

    Take it back to the days when you were obsessed with butterfly everything, oh wait, we never gave that up! Butterflies are making a come back and we are so here for it!

    • Dainty chain
    • Large rhinestone butterfly pendant
    • Lobster clasp closure

    Style Number/Barcode: 07002-0193

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Newsgirl Cabby Hat
    Extra, extra, read all about your stylish new hat! This newsboy-inspired cap features braided trim with button detail.

    Style Number/Barcode: 07302-0091

    Category Name: Vacation Looks

    Price: $15.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dainty Cross Pendant Necklace

    Add a subtle touch from heaven above bb. This sweet dainty necklace is real cute, amen.

    • Dainty gold chain
    • Cross pendant
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07002-0229

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Chic Everyday Hoops

    Consider these simply chic hoop earrings an essential to your everyday outfit! With their sleek stylish design, you can easily take them from workwear to a night-out look. Their medium size and post-back closure make for easy wear. Pair with a curve-hugging pencil skirt and trendy heels.

    Fit & Features

    • Slim design
    • Medium-sized
    • Post-back closure

     

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

    Style Number/Barcode: 07001-0115

    Category Name: Vacation Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist Knot Headband

    Give your tresses a twist with this pretty head band! It features a twist knot top accent, and is composed of a smooth knit material that is designed over a structured headband. 

    Style Number/Barcode: 07006-0027

    Category Name: Vacation Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Large Rhinestone Hoops

    Go for a glam vibe whenever you're feeling a little extra in these attention garnering earrings!

    • Large dainty design
    • Encrusted in rhinestones
    • Omega closure

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

    Style Number/Barcode: 07001-4330

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tassel On Hoops

    Keep calm and tassel on in these cute hoops! They feature a gold hoop, an attached fringe tassel and a fish hook back.

     

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

    Style Number/Barcode: 07001-4125

    Category Name: Vacation Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cute And Chic Block Heels

    Keep it cute and chic with these classic white faux leather block heels! They feature an open toe with a single strap, an adjustable ankle strap, a closed back, and a short block heel.

    Style Number/Barcode: 07401-0737

    Category Name: Vacation Looks

    Price: $20.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leopard Print Weekender Duffle Bag
    Show up to your weekend vacay in style! This leopard duffle features a gold zipper opening, large handles, and a sturdy textured body. The woven lined interior includes an open pocket and zippered pocket as well as an included shoulder strap to hook on. The exterior of the bag is composed of a faux leather material that showcases our fav leopard print pattern!

    Style Number/Barcode: 07203-0144

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cubic Zirconia Teardrop Necklace And Studs

    This sophisticated cubic zirconia necklace and stud earrings set will dazzle up the room. The necklace's dainty chain leads to a center teardrop charm. The pack also comes with gorgeous matching teardrop stud earrings so you can wear them together for a beautiful look. Accessorize with this set for brunch with the girls! Pair with a flirty floral dress and cute wedges.

    Fit & Features

    • Dainty chain with teardrop charm
    • Adjustable lobster clasp closure
    • Cubic zirconia embellishment
    • Matching teardrop stud earrings
    • Post-back closures

     

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

    Style Number/Barcode: 07002-4752

    Category Name: Vacation Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Rise Paper Bag Skinny Jeans

    Change up your everyday denim with this cute pair of paper bag skinny jeans!  They have a high rise waist, a traditional five pocket and belt loop design, a removable tie belt, a button down front, and skinny, form-fitting pant legs. The denim offers moderate stretch for super comfortable wear.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size 3.

    Style Number/Barcode: 06602-0063

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Classy Affair Mini Faux Leather Purse
    For the days you feel like being a classy lady, this adorable mini purse completes your oh so put together look! Designed with a mini handle, a detachable matching cross body strap, and a snap fold over closure with a gold bar detailing. Purse is composed of a saffiano faux leather that has a textured matte finish.

    Style Number/Barcode: 07203-0201

    Category Name: Vacation Looks

    Price: $14.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Luxe Dainty Bar Necklace Set

    Layer up with luxe pieces! This set features three necklaces that can be worn alone or layered to create a unique look! They feature a dainty chain, a rectangular shaped charm and a vertical bar charm.

     

    Style Number/Barcode: 07002-0205

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • LA Splash x Windsor Collab Faux 3-D Mink Lashes

    LA Splash x Windsor Collab

    Give your lashes an extra pop with fluttery lashes! This set includes eight pairs of 100% hand made 3-D faux mink material and adhesive band to easily place near lash line for dramatic effect. The set includes a variety of wispy, dramatically bold and natural styles to match your look! Lashes are 100% Hand Made and are Vegan-Friendly!

    Fashion tape, adhesive bras, adhesive panties, pasties, hosiery, cosmetics and lingerie are considered final sale merchandise FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07307-0020

    Category Name: Vacation Looks

    Price: $15.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free