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.

  • On Your Radar Aviators

    Stay on their radar this Halloween with these classic aviators! These statement-ready sunglasses are ready to throw some shade with a wire, aviator frame and gradient lenses. Pair these shades with our Miss Officer look for the a sexy Halloween costume! 

    Style Number/Barcode: 07008-0294

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twice Upon A Rhine Choker

    You're looking fine in a necklace and earrings set that brings the fire to your next outfit! Make your fashion dreams come true in a necklace set that features a double-row rhinestone choker with a lobster clasp closure for easy wear. It also includes matching rhinestone stud earrings with post-back closures. Perfect to dress up your going-out look, pair with an off-the-shoulder top and some clear mules.

    Fit & Features

    • Double row rhinestone choker necklace
    • Lobster clasp closure
    • Stud rhinestone earrings
    • Post-back closures

     

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

    Style Number/Barcode: 07002-4871

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cubic Zirconia Buttery Pendant Layered Necklace

    Dainty and effortless, this pretty butterfly pendant necklace is sure to flutter some hearts!

    • Two rows of layered chain links
    • Longer row showcases small butterfly pendant
    • Embellished with cubic zirconia stones

    Style Number/Barcode: 07002-0323

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Change Of Heart Rhinestone Hoop Earrings

    You give us heart eyes bby!! These rhinestone earrings are a cute and unique way to change up your everyday hoop to somethin' a lil' more glam!

    • Open ended
    • Heart shaped design
    • Pave encrusted rhinestones
    • Post back closure

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

    Style Number/Barcode: 07001-0328

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Falling In Love With Matte Jelly Cross-Body Purse

    Fall in love with a matte finish! It's sleek and elegant, and gives a high end finish to all looks!

    • Rectangular structure
    • Turn lock closure
    • Chain shoulder strap
    • Matte quilted design
    • Inner divider
    • Golden hardware

    Style Number/Barcode: 07203-0216

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blessed Long Rhinestone Cross Necklace

    BB you are blessed! Everyday is a blessed day when you look that gorgeous! Don't forget to finish off your look with a sparkling dainty necklace!

    • Long dainty chain necklace
    • Rhinestone cross pendant
    • Adjustable lobster clasp closure

    Style Number/Barcode: 07002-0225

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dust It Off Drop Earrings
    Dust off all ya problem with these chic earrings. Featuring beaded detail and flirty fringe, these statement earrings add a pop of high fashion to any 'fit. Topped with post back closures.

    Style Number/Barcode: 07001-0149

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cubic Zirconia Floral Stud Earrings

    This pair of earrings show major class with the design of a beautiful blooming flower. They have a post back closure and are composed of cubic zirconia rhinestones which have more sparkle and gleam than the average stone!

     

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

    Style Number/Barcode: 07001-0200

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Butterfly Baby Rhinestone Hair Clips
    Come out of your cocoon baby-girl! This set includes two barrettes that have a ball snap closure, and showcase a beautiful butterfly structure that is embellished with rhinestones!

    Style Number/Barcode: 07006-0054

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Extra Large Sleek Hoops

    These extra large hoop earrings are a must-have for your jewelry collection. With their sleek finish, they add the perfect amount of glam to any outfit. The omega closure is great for easy wear. Accessorize with them for a day date with your bae! Pair with a basic tee and your favorite mom jeans to elevate the look.

    Fit & Features

     

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

    Style Number/Barcode: 07001-0111

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gold Rush Textured Door Knocker Earrings

    You don't shy away from big and bold—so go for the gold with this door knocker style! Earrings are made made from an eye-catching textured gold metal and feature an oversize, open square shape attached to a solid gold oval with post back closure.

     

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

    Style Number/Barcode: 07001-0033

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Draped 3 Row Chain Belt

    Level up your festival wear with this chain belt! It features three rows of chains that drape across your hip, and an adjustable single back chain with a lobster clasp closure. 

    Style Number/Barcode: 07301-1050

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oh La La Wool Beret
    Oh la la, this wool beret is oh so chic! It features a rounded classic floppy look, and is perfect for the fall season!

    Style Number/Barcode: 07302-0030

    Category Name: Vacation Looks

    Price: $6.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleek And Sultry Halter Jumpsuit

    This halter jumpsuit brings the drama with a front twist cutout, curve-loving fit, and wide-leg silhouette made to stun on sight. Wear it to turn every room into your runway.

    Fit & Features

    • Halter neckline with multiple ways to style
    • Cutout bodice, partially open back 
    • Straight leg fit with a flared hem 
    • Form-hugging fit 
    • Moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06502-0531

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Take A Bow Clutch

    This adorable bow detail clutch gives off such a classic chic vibe!

    • Foldover design with metal front bow detail
    • Magnetic snap button closure
    • Two interior compartments with mutiple card slots
    • Zippered pouch
    • Included detachable wristlet and chain shoulder strap
    • Faux leather material

    Style Number/Barcode: 07201-0010

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Diva Alert Sunglasses

    Major diva alert. These sunnies will give you that much needed glam factor.

    • Square plastic frame with gold metal arms
    • Dark tinted lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0689

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basically Beautiful Swim Top

    Look like a total beauty in this basic swim top that will have all eyes on you! Pair with the matching bikini bottoms for an all together gorg look.

    Shop Matching Bottoms: Basically Beautiful Swim Bottoms

    Fit & Features

    • Adjustable spaghetti straps
    • Square neck and back
    • Nylon | Moderate stretch

     

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

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

    Style Number/Barcode: 07104-0330

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basically Beautiful Bikini Bottoms

    Look like a total beauty in these basic bikini bottoms that will have all eyes on you! Pair with the matching swim top for an all together gorg look.

    Shop Matching Top: Basically Beautiful Swim Top

    Fit & Features

    • Side tie closures
    • Cheeky bottom
    • Nylon | Moderate stretch

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

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

          Style Number/Barcode: 07105-0483

          Category Name: Vacation Looks

          Price: $8.97 $16.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Seas The Day Cut Out One Piece Bathing Suit

          Seas the day in a sexy cut out bathing suit! This sexy one piece will have those daiquiris delivered to you before you even order them!

          Fit & Features

          • One piece
          • Adjustable spaghetti straps
          • Scoop neckline
          • Hip cut out
          • High waist cheeky fit
          • Moderate stretch
          • No padding included 

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

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

          Style Number/Barcode: 07109-0136

          Category Name: Vacation Looks

          Price: $9.97 $42.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Mauve Tonez Satin Headband 2 Pack

          Keep the romantic vibes going with a sweet pair of headbands that will add a feminine touch to all of your looks!

          • Set of two head bands
          • Twist front design
          • Satin finish
          • Mauve + Light pink
          • Elastic stretchy back

          Style Number/Barcode: 07006-0112

          Category Name: Vacation Looks

          Price: $5.97 $12.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Pretty In Pastel Satin Scrunchy 5 Pack

          Keep it cute with every mood! We are loving the look of a day dress with a cute messy bun with a scrunchy to finish it all off!

          • Set of five scrunchies
          • Satin finish
          • Elastic with stretch
          • Lavender | Beige | Copper | Grey purple | Dusty blue

          Style Number/Barcode: 07006-0113

          Category Name: Vacation Looks

          Price: $5.97 $12.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Cubic Zirconia Lariat Double Row Necklace

          Wearing a deep v dress or blouse? A dainty lariat necklace is the best way to accessorize and amp up that decolletage!

          • Dainty chain design
          • Double row
          • Lariat drop pendant
          • Adjustable lobster clasp closure
          • Cubic zirconia stones

          Style Number/Barcode: 07002-0263

          Category Name: Vacation Looks

          Price: $6.97 $13.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Vibrant Stones Door Knocker Earrings

          Finish your look with a pop of color! This rhinestone door knockers are a chic way to compliment an all black outfit, and a low bun!

          • Door knocker design
          • Multi shape stones
          • Multi colored stones
          • Post back closure

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

          Style Number/Barcode: 07001-0337

          Category Name: Vacation Looks

          Price: $6.97 $13.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Sale
        • Ready Or Not Ruched Bodysuit

          Ready or not, you'll come at them with the fiercest style in this ruched bodysuit!

          Fit & Features

          • Bungee spaghetti straps
          • Sweetheart neckline | Sheer mesh ruffle trim
          • Lattice lace up front
          • All over ruched detailing
          • Cheeky bottom | Triple snap button closures
          • Sheer mesh fabric | Knit lining
          • Plenty of stretch | Form hugging fit

          Style Number/Barcode: 06003-0748

          Category Name: Vacation Looks

          Price: $6.97 $34.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance