Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

  • Kiss And Shell Crochet Belt

    You'll fall for this crochet belt's beachy vibes to go with your weekend or vacation attire! The belt features round shells connected by crochet strings and has a self-tie closure. Complete the look in a tropical dress for your next escape.

    Fit & Features

    • Crochet belt
    • Round shell decorations
    • Self-tie closure

    Style Number/Barcode: 07301-1116

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bon Voyage Sweetheart Floral Chiffon Skater Dress

    Say bon voyage looking darling in this floral chiffon skater dress whether you're heading out on your honeymoon or a trip abroad! Made from an airy chiffon fabric showcasing an adorable ditsy floral print that will make you stand out in the crowd. The sweetheart neckline and bust tie add a touch of romance while the skater silhouette and ruffled hem give it a playful twist. Complete the look with luxe earrings.

    Fit & Features

    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5714

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Wanderer Wrap Waist Boho Flare Pants

    Escape in these boho pants to the desert for festivals or concerts! Dance the weekend away in these pants featuring a flattering wrap style high-rise waist, a hip-hugging fit, and a trendy flared hem on ultra-soft brushed knit fabric with a unique bohemian print. Complete the look in a graphic tee and cowboy hat!

    Fit & Features

    • Bohemian print
    • Brushed knit fabric, moderate stretch
    • High-rise wrap style waist
    • Hip-hugging, flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2458

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Pretty Ombre Butterfly Two-Piece Hair Clips

    Look as pretty as the sunset taming your tresses with this hair clip set featuring gorgeous ombre organza butterfly clips with pretty rhinestone embellished trim. Complete the look in lace-up sandals for any occasion!

    Fit & Features

    • Two-piece hair clip set
    • Ombre organza butterflies 
    • Rhinestone embellished trim
    • Metal clip

    Style Number/Barcode: 07006-0489

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweeten The Deal V-Neck Floral Chiffon Skater Dress

    Sweeten the deal for upcoming plans showing up in this floral chiffon skater dress for brunch, birthdays, or shower celebrations! Featuring a V-neckline, adjustable straps, and a waist tie to show off your figure, a layered ruffled short-length hem adds a playful touch to the floral printed chiffon fabric. Complete the look in sandals.

    Fit & Features

    • Floral print, chiffon fabric, woven lining
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3222

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Imagination Square Neck Eyelet Floral Bodysuit

    All of your outfits will be adorable when you style them with this floral bodysuit! Crafted from an eyelet floral printed knit fabric, this sleeveless bodysuit boasts a square neckline adorned with shoulder straps and a form-hugging fit. Complete the look with trendy distressed jeans and your favorite sneakers.

    Fit & Features

    • Eyelet knit fabric, floral print, sewn-in knit lining, stretchy
    • Shoulder straps
    • Form-hugging fit
    • Thong bottom, dual snap-button closures
    • Runs true to size

    Style Number/Barcode: 06001-5181

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go With The Flow Frayed Denim Bucket Hat

    Top off your look in this denim bucket hat for any casual hangs! It features a classic bucket hat design with cool fraying and a short brim to help shade from the sun. Complete the look in platform sneakers.

    Fit & Features

    • Denim material
    • Frayed design
    • Short brim
    • Classic bucket hat design

    Style Number/Barcode: 07302-1613

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sun-Soaked Adventure Woven Metallic Flat Sandals

    Let these faux leather flat sandals lead you on a sun-soaked adventure! The square toe and studded trim add edgy detail while the woven strap brings a touch of boho-chic. Plus, the metallic adjustable ankle strap ensures a comfortable fit. Perfect for beach days, city strolls, and vacations! Complete the look with a trendy tote bag and sunnies.

    Fit & Features

    • Flat faux leather sole
    • Square toe
    • Woven pattern strap
    • Studded trim
    • Metallic adjustable ankle strap, buckle closure
    • Runs true to size

    Style Number/Barcode: 07404-1193

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Decadent Charm Rhinestone Twist Hoop Earrings

    Elevate your look and feel effortlessly glamorous in these rhinestone twist hoop earrings for a stunning look. The twisted hoop design and rhinestone embellishments add a touch of elegance and sparkle to any outfit. Made with a sleek metal hoop and secure omega closure, these earrings are stylishly chic! Pair with a flirty off-the-shoulder dress for a date night!

    Fit & Features

    • Twisted hoop design
    • Rhinestone embellished hoop
    • Sleek metal hoop
    • Omega closure


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

    Style Number/Barcode: 07001-1963

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Minimalistic Elegance Square Ring Flat Sandals

    Indulge this season in these minimalistic faux leather flat sandals for an elegant and chic look! They feature a sleek square toe, a thong toe strap with a chunky square ring decor, and a cushioned footbed for all-day comfort. Complete the look with a trendy handbag.

    Fit & Features

    • Flat sole
    • Thong toe strap, chunky square ring
    • Cushioned footbed
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1206

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Escape Strapless Tropical Midi Dress

    Serve chic looks on your dreamy escape in this tropical print midi dress. The stretchy lined knit fabric showcases a detailed tropical print pattern on the figure-flaunting silhouette. The bodice features a strapless elasticized straight-across neckline, leading to a bodycon fit with a mid-length hem. Style with combat booties to add some edge!

    Fit & Features

    • Stretchy knit fabric with knit lining
    • Tropical print
    • Strapless elasticized straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5539

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oopsie Daisy Sleeveless A-Line Mini Dress

    Oopsie daisy this sleeveless mini dress must've caught you by a sweet surprise! Crafted from a soft brushed knit fabric with an adorable floral print, this dress is a must-have for spring and summer. Features a flattering V-neckline with an adjustable drawstring tie and an A-line silhouette. Complete the look with a denim jacket and sandals for a casual occasion!

    Fit & Features

    • Floral print, brushed knit fabric lined with knit
    • Adjustable drawstring neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5686

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Trendsetter Thong Strap Faux Leather Sandals

    These cute and trendy faux leather sandals are perf for leveling up your warm-weather looks! Made from a sleek faux leather material, these sandals feature a square-shaped toe with a wide thong strap. The slip-on-and-off design on the flat sole allows for effortless styling. Pair these sandals with an adorable tote bag.

    Fit & Features

    • Flat sole
    • Faux leather upper
    • Square toe
    • Wide thong strap design
    • Slip-on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1174

    Category Name: Vacation Looks

    Price: $4.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All About Floral Sweetheart Crepe Skater Dress

    Sweet and sassy, this floral skater dress is a must-have for your wardrobe! Featuring a trendy sweetheart neckline and adjustable spaghetti straps, this dress is perfect for any spring or summer occasion. Its skater silhouette and short-length hem will have you twirling all day, while the playful floral print will make you stand out in style! Complete the look with hoop earrings.

    Fit & Features

    • Floral print
    • Stretchy crepe fabric, knit lining at the bust
    • Sweetheart neckline
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3196

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Chic Straw Shoulder Bag

    Embrace a boho chic season by styling your fave 'fits with this adorable straw shoulder bag! Crafted with a trendy woven straw design, this bag features a small rectangular shape and a faux leather shoulder strap with sleek metal O-ring accents. Pair with the matching hat and heels!

    Shop Matching Hat: Boho Chic Tiered Floppy Straw Hat
    Shop Matching Tote Bag: Boho Chic Crossbody Straw Tote Bag
    Shop Matching Heels: Boho Chic Straw Platform Block Heels

    Fit & Features

    • Woven straw design
    • Small rectangular shape
    • Faux leather shoulder strap with metal O-ring accents
    • Snap-button closure
    • Spacious interior

      Style Number/Barcode: 07203-1947

      Category Name: Vacation Looks

      Price: $11.97 $24.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Slip Into Glam Rhinestone Strap Faux Leather Sandals

      Slip into glamour with these sleek rhinestone strap sandals for your next party! Designed with smooth faux leather material, they feature an open square-shaped toe, a wide banded strap embellished with all-over sparkling rhinestones, and a flat sole for comfortable wear. The open back offers effortless on-and-off styling. Pair with a fab rhinestone choker necklace.

      Fit & Features

      • Faux leather upper
      • Open square toe
      • Wide banded strap with rhinestones
      • Open back, flat sole
      • Luxe fit cushioned insole
      • On-and-off styling
      • Runs true to size

      Style Number/Barcode: 07404-1156

      Category Name: Vacation Looks

      Price: $12.97 $20.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Aviator Babe Cap Sleeve Utility Wide-Leg Jumpsuit

      Soar into this utility jumpsuit to take your style to new heights! Perfect for casual outings or travel, this twill-woven jumpsuit offers style and functionality with trendy cap sleeves, a collar neckline, button-down front closures, an adjustable tie-waist belt to snatch your figure, convenient front pockets to keep your things handy, and a flattering wide-leg silhouette. Complete the look in platform sneakers.

      Fit & Features

      • Twill woven fabric with stretch
      • Button-down front closures
      • Adjustable tie-waist belt, front pockets
      • Wide-leg silhouette
      • Runs true to size

      Style Number/Barcode: 06302-0824

      Category Name: Vacation Looks

      Price: $20.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Stay Sweet Flutter Sleeve Ditsy Floral Mini Dress

      Stay sweet in the cutest ditsy floral mini dress, perfect your for weekend plans! The stretchy brushed knit fabric features an adorable ditsy floral print for the prettiest vibe. The mini-length dress is shaped with a sweetheart neckline with flirty ruching and short flutter sleeves for an effortless look. The bodycon silhouette will flaunt your gorgeous figure. Style with hoop earrings and strappy sandals!

      Fit & Features

      • Ditsy floral print
      • Stretchy brushed knit fabric
      • Sweetheart neckline with ruching
      • Short flutter sleeves
      • Bodycon fit
      • Runs true to size

      Style Number/Barcode: 05102-5586

      Category Name: Vacation Looks

      Price: $9.97 $28.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Free Flowing Cutie V-Neck Ruffle Eyelet Maxi Dress

      Flattering and breezy come together on this charming eyelet lace maxi dress perfect for spring days and summer cuteness! This dreamy dress features a flattering V-neckline, adjustable spaghetti straps, and charming button accents. The cutout waist and flowy silhouette accentuate your figure, while the tiered ruffled maxi hem adds a whimsy touch. Complete the look in wedge sandals and a floppy hat!

      Fit & Features

      • Eyelet lace fabric lined with woven fabric
      • Adjustable spaghetti straps
      • Back zipper and hook-eye closure
      • Cutout waist
      • Ruffled maxi length hem
      • Runs true to size

      Style Number/Barcode: 05101-3286

      Category Name: Vacation Looks

      Price: $9.97 $54.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Meant To Last Square Toe Block Heel Mules

      These faux leather block heel mules are meant to last on rotation from season to season! Designed with a sleek square toe and a wide banded strap, these sandals have a cute block heel with a gold trim detail for some luxe. Complete the look with the matching bag for any occasion!

      Shop Matching Shoulder Bag: Made For You Faux Leather Shoulder Bag
      Shop Matching Crossbody Bag: Pretty Perfect Floral Strap Crossbody Bag

      Fit & Features

      • 3" Block heel with gold trim
      • Square toe
      •  Cushioned insole
      • Faux leather material
      • Runs true to size

        Style Number/Barcode: 07401-4710

        Category Name: Vacation Looks

        Price: $12.97 $26.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Boho Chic Crossbody Straw Tote Bag

        Mini and boho chic, this straw crossbody tote bag was made for fun under the sun! Pack this essential bag for vacations, weekend trips, or a beach day. It features a straw exterior with faux leather trim for a polished look, top handles, a detachable and adjustable crossbody strap to give you multiple ways to wear it, and a spacious interior to hold your things. Complete the look with the matching hat and heels!

        Shop Matching Hat: Boho Chic Tiered Floppy Straw Hat
        Shop Matching Shoulder Bag: Boho Chic Straw Shoulder Bag
        Shop Matching Heels: Boho Chic Straw Platform Block Heels

        Fit & Features

        • Straw material
        • Faux leather trim
        • Top handles
        • Detachable and adjustable crossbody strap
        • Zipper closure
        • Spacious interior, zipper pocket

        Style Number/Barcode: 07203-1946

        Category Name: Vacation Looks

        Price: $13.97 $28.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Dreamy Boho Paisley Satin Scarf

        Give off dreamy boho vibes with this sleek paisley satin scarf! Designed with a silky satin material with a trendy paisley pattern, this scarf offers multiple styling options. Wear it as a headwrap, a hair tie, or tie it around your neck for a chic accent! Pair with a layered charm necklace.

        Fit & Features

        • Non-stretch satin material
        • Paisley pattern

        Style Number/Barcode: 07305-0493

        Category Name: Vacation Looks

        Price: $5.97 $12.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Talking Sweet One-Shoulder Cutout Eyelet Lace Dress

        Dress to impress in this sweet one-shoulder cutout eyelet lace dress guaranteed to turn heads as the lovely bride-to-be or graduate! Made from eyelet lace fabric, this bodycon dress will hug your curves in all the right places. This stunning mini-length dress features a trendy one-shoulder neckline, a flirty puff sleeve, and a sultry side drawstring cutout so you can customize the look. Style this dress with sandals and a tote bag.

        Fit & Features

        • Eyelet lace fabric lined with stretchy knit
        • Drawstring side cut-out
        • Bodycon fit
        • Runs true to size

        Style Number/Barcode: 05102-5715

        Category Name: Vacation Looks

        Price: $9.97 $29.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Sweetest Allure Strapless Floral Eyelet Knit Midi Dress

        Give off the sweetest allure this summer season in this floral eyelet knit midi dress! The stretchy sheer eyelet knit fabric is detailed with an adorable ditsy floral print and includes a full knit lining for coverage. The mid-length dress features a strapless straight-across elasticized neckline and a bodycon silhouette to highlight your gorgeous figure. Style with espadrille wedges for weekend brunch!

        Fit & Features

        • Stretchy sheer eyelet knit fabric, full knit lining
        • Ditsy floral print
        • Strapless straight elasticized neckline
        • Bodycon silhouette
        • Runs true to size

        Style Number/Barcode: 05102-5488

        Category Name: Vacation Looks

        Price: $5.97 $30.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free