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.

  • Favorite Fleur V-Neck Floral Chiffon Skater Dress

    Give them a twirl in this adorable floral chiffon skater dress at birthdays or graduation parties! Featuring puff short sleeves, a tie front bust, and a stretch smocked empire waist, this dress will hug your curves in all the right places. The skater silhouette and ruffled hem add a playful touch to this flowy chiffon dress. Complete the look with teardrop earrings.

    Fit & Features

    • Floral print, chiffon fabric lined with stretchy knit
    • V-Neckline, tie front
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3135

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Seas The Day Shell Stud Earrings

    A little coastal charm, a lot of main character energy. These seashell studs are the perfect vibe for vacay fits, beach days, or cute mermaid moments.

    Fit & Features:

    • Mini seashell design with polished finish
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000126

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Energy Halter Cut Out Wide Leg Jumpsuit

    Bring the sunny energy in this halter cut-out wide leg jumpsuit wherever you go! This sultry texture knit jumpsuit features a halter spaghetti strap with tie closure for a perfect fit, along with a cutout bust design to show some skin, and a flattering wide-leg silhouette for an easy, breezy style. Complete the look with sunnies and sandals!

    Fit & Features

    • Texture knit stretchy fabric
    • Halter spaghetti strap
    • Cut out bust
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2472

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Chic Floral Embroidered Chiffon Skater Dress

    This breezy chic floral chiffon skater dress is perfect for your summer parties! The airy sheer embroidered chiffon fabric is detailed with a dainty floral print and includes a stretchy full-length knit lining. The short dress features a sleeveless sweetheart neckline, a bustier-style bodice with a padded bust and structured underwire, and ruched cups. The adjustable spaghetti straps lead to a partially smocked back design for added stretch with a secure back zipper closure. The front faux buttons lead to a high waist seam flowing out to a short skater skirt with a flirty fit and flare A-line silhouette. Complete your look with strappy sandals.

    Fit & Features

    • Sheer embroidered chiffon fabric, floral print, stretchy knit lining
    • Sweetheart neckline, bustier bodice, padded bust with underwire, ruching
    • Adjustable spaghetti straps
    • Partial stretchy smocked back, zipper with hook and eye closure
    • Front faux buttons, high waist seam
    • Fit and flare A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3009

    Category Name: Vacation Looks

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance That Wows Large Blossom Floral Maxi Dress

    Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!

    Fit & Features

    • Large blossoming floral print
    • Mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3343

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be My Forever Ribbon Bow Bodycon Mini Dress

    Flattery will get you everywhere in this sleeveless mini dress perfect for boasting an adorable look! The scoop neckline is adorned with delicate lace and charming bow detail, while the tank shoulder straps give a flirty touch. The bodycon silhouette and mini-length hem finish this flawless dress. Complete the look in platform high heels for a party.

    Fit & Features

    • Woven fabric with minimal stretch
    • Scoop neckline, lace and ribbon trim, bow
    • Back zipper and hook-eye closure
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5817

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Presence Abstract Floral Mini Dress

    Make a sultry impression in this abstract floral mini dress with an alluring cutout and a ruffled slit design perfect for grabbing cocktails on vacation!

    Fit & Features

    • Abstract floral print, mesh-lined fabric
    • Cowl halter neckline
    • Cutout bodice with hoop insert
    • Bodycon silhouette
    • Ruffled slit design, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000038

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Artsy Flair Strapless Cutout Abstract Mini Dress

    Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Side cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5693

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sure To Love Floral Woven Puff-Sleeve Skater Dress

    You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.

    Fit & Features

    • Floral print
    • Woven fabric with smooth woven lining
    • Ruched scoop neckline with tie-front detail
    • Short puff sleeves with elastic cinched hems
    • Stretchy smocked high waist
    • Fit-and-flare silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5716

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Vibes Halter Crop Top

    This halter crop top will serve major stunning vibes for cocktails and dinner! It is designed with ruched side seams and a fitted crop hem that accentuates your figure.

    Fit & Features

    • Sheen knit fabric, sewn-in knit lining, high stretch
    • Halter plunge neckline with tie closure
    • Side ruched seams
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000176

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: IVORY, MOCHA, WINE, BROWN, OLIVE, EMERALD

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • Garden Of Romance Tie Back Rose Floral A-Line Dress

    Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.

    Fit & Features

    • Rose floral print, chiffon fabric lined with stretchy knit
    • Square neckline
    • Adjustable spaghetti straps
    • A-Line silhouette
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3257

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Signature Stripes Strapless A-Line Maxi Dress

    Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.

    Fit & Features

    • Striped pattern, cotton woven fabric, no stretch
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5802

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Aesthetic Pairing Three-Pack Bracelet Set

    Elevate any look with this three-pack bracelet set featuring a paperclip chain-link bracelet and two stretchy beaded bracelets. Complete the look with a cute crossbody bag for any occasion!

    Fit & Features

    • Three-pack bracelet set
    • One paperclip chain-link bracelet, adjustable lobster clasp closure
    • Two stretchy beaded bracelets

    Style Number/Barcode: 07003-0561

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Catch Attention Cowl Neck Abstract Floral Maxi Dress

    Catch everyone's attention in this abstract floral maxi dress at cocktail hour! The cowl neckline adds a touch of sophistication while the adjustable spaghetti straps provide a perfect fit. The form-hugging silhouette flatters your figure and the maxi-length hem offers a chic finish. Complete the look with a clutch and heels.

    Fit & Features

    • Abstract floral print, mesh fabric lined with stretchy knit
    • Cowl neckline
    • Adjustable spaghetti straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3323

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fluttering Elegance Rhinestone Butterfly Earrings

    These charming earrings add a whimsical style to your look! They feature butterflies with mini rhinestone embellishments, linear chains with bar trim, and a post-back closure. Complete the look with a trendy denim jacket.

    Fit & Features

    • Butterflies with mini rhinestone embellishments
    • Linear chains with bar trim
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2057

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Appeal Puff Sleeve Chiffon Skater Dress

    Swiss dots add whimsical appeal to this charming chiffon skater dress perfect for birthdays, graduations, or showers! With sheer puff sleeves, a sweetheart neckline, and a tiered ruffled skater silhouette, this dress is both playful and flattering. Its short-length hem adds a touch of flirty charm. Complete the look in mules and a trendy purse!

    Fit & Features

    • Swiss dot chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2999

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Impact Toggle Chain Bracelet

    Perfectly bold and trendy, this toggle chain bracelet adds something unique to every look!

    Fit & Features

    • Toggle closure
    • Chunky chain link

    Style Number/Barcode: 07003-0698

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Way She Moves Striped Midi Skirt

    This striped midi skirt has entered the girl's vacay chat! Boasting a sexy bodycon silhouette and mid-rise waist, you'll be the hit of the trip. Pair with the matching top to complete the look!

    Shop Matching Top: Way She Moves Striped Bra Top

    Fit & Features

    • Striped print, scalloped trim, stretchy knit fabric
    • Mid-rise waist
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0743

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Style Bow Detail Polka Dot Mesh Mini Dress

    Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.

    Fit & Features

    • Polka dot printed sheer mesh fabric with knit lining
    • Plenty of stretch
    • V-neck and back, tank shoulder straps
    • Mini bow detail, eyelet trim
    • Tie-back straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5828

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Allure Floral Mesh High-Slit Maxi Skirt

    Giving goddess vibes with a flirty twist. This floral mesh maxi skirt brings all the drama with its flowy fit and daring high-cut side slit.

    Shop Matching Top: Blooming Allure Floral Mesh Cutout Tube Top

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Large floral print
    • High-rise fitted waist
    • High-cut side slit
    • Maxi-length hem, flowy silhouette
    • Flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000066

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • A Little Wild One-Shoulder Zebra Print Maxi Dress

    Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.

    Fit & Features

    • Zebra printed knit fabric, plenty of stretch
    • One-shoulder neckline, spaghetti strap
    • Side drawstring cutout
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5821

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Feels Off-The-Shoulder Sweater Mini Dress

    Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.

    Fit & Features

    • Sweater knit fabric, moderate stretch
    • Off-the-shoulder neckline
    • Bodycon fit
    • Mini-length
    • Runs true to size

    Style Number/Barcode: 06005-1947

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Babe Floral Woven Puff Sleeve Skater Dress

    Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.

    Fit & Features

    • Dainty floral print
    • Woven fabric
    • V-neckline, tie-front detail
    • Short puff sleeves, ruffled trims
    • Back zipper closure, high waist seam
    • Short skater skirt, fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3466

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clear Obsession PVC Flat Sandals

    You'll be obsessed with these flat sandals perfect for styling on rotation! They feature an almond toe, a clear PVC strap, and a flat sole with edge trim on faux leather material. Complete the look with a trendy crossbody purse.

    Fit & Features

    • Almond toe
    • Clear PVC strap
    • Flat sole with edge trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1233

    Category Name: Vacation Looks

    Price: $12.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free