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.

  • Off The Shoulder Floral Peplum Top

    Spring forward with your wardrobe in this adorable floral printed peplum top! Pair with some light wash denim for a fresh look.

    Fit & Features

    • Off the shoulder elastic banded neckline
    • Long sleeves | Elastic banded hems
    • High rise elastic banded waist
    • Wrap front peplum hem
    • Lighweight, semi-sheer woven fabric
    • All over floral print

    Style Number/Barcode: 06003-0733

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Love The Lace Up Satin Crop Top

    We know, we all are in LOVE with this lace up satin crop top! Pair with some denim for an effortless yet so trendy look!

    Fit & Features

    • Slight sweetheart neckline
    • Long puff sleeves | Single buttons to cuff
    • Lattice lace up front
    • Cropped
    • Sleek satin-like fabric
    • Minimal stretch

    Style Number/Barcode: 06003-0744

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Falling For It Ruffled Chiffon Leopard Print Dress

    Have them all falling for you when you step out in this flirty chiffon ruffled mini dress! Easily style with a pair of black mules and sweet pearl hoops!

    Fit & Features

    • Ruffle trim mock neckline
    • Long sleeves with a ruffled wrist
    • Relaxed bodice
    • Stretchy smocked waist line
    • Tired ruffled skirt
    • Mini hemline | Lined at the skirt
    • Slip on fit | No closures

    Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0513

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Girl Next Door Strapless Denim Mini Dress

    Create a trendy girl next door vibe in this denim cargo mini dress! Made with a stretchy cotton-blend denim fabric, this dress features a strapless straight-across neckline, a secure back zipper closure, faux chest pockets, and large cargo-style flap pockets at the waist. The form-hugging silhouette will flaunt your gorgeous figure. Style this mini-length dress with cowboy boots for a country concert!

    Fit & Features

    • Cotton-blend denim fabric, moderate stretch
    • Strapless straight neckline, front no-slip strip
    • Back zipper with hook and eye closure
    • Faux chest pockets
    • Cargo flap pockets
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5524

    Category Name: Vacation Looks

    Price: $11.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shady Business Square Oval Sunglasses

    Keep it shady with this classic pair of shades that literally goes with everything!

    • Square oval design
    • Dainty arms
    • Textured gold hardware
    • 100% UV protection

    Style Number/Barcode: 07008-0694

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • With Love Heart Sunglasses

    Hey there miss mod! Throw on your heart shaped shades, and some red lipstick cause you're a modern day pinup doll!

    • Heart shaped frame
    • Cat eye corners
    • Dark lenses
    • 100% UV Protection

    Style Number/Barcode: 07008-0695

    Category Name: Vacation Looks

    Price: $4.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Later Hater Square Cat Eye Sunglasses

    Peace out haterrrr, we got our shades on and we cant b bothered!

    • Square cat eye design
    • Ombre effect
    • Golden hardware
    • Skinny arms
    • 100% UV protection

    Style Number/Barcode: 07008-0693

    Category Name: Vacation Looks

    Price: $5.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heart Eyez Rimless Sunglasses

    Do you have heart eyes for me or is it just your cute shades?

    • Rimless design
    • Rose gold hardware
    • Heart shaped lenses
    • 100% UV protection
    • Ombre effect

    Style Number/Barcode: 07008-0696

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flower Child Rhinestone Tassel Earrings

    Feeling a little boho, feeling a little glam? We got u boo! These versatile tassel earrings can be paired with nearly all looks! 

    • Gold flower designed post
    • Rhinestone embellished
    • 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: 07001-0315

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wide Brim Belted Panama Hat

    This adorable belted panama hat screams brunch! Get totally weekend ready with this trendy hat.

    • Wide brim
    • Curved top
    • Belted accent

    Style Number/Barcode: 07302-0131

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walks Through The Park Slide On Sandals

    Whether you are walking through the park, or taking a walk on the beach these goes-with-everything slides are the perfect fit!

    • Open almond toe
    • Slide on design
    • Narrow fit
    • Faux leather
    • Single band

    Style Number/Barcode: 07404-0537

    Category Name: Vacation Looks

    Price: $9.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paisley and Playful Halter Skater Dress

    Flirty, floaty, and made for dancing under the sun. With a smocked bust and ruffled skater fit, this halter mini dress is your go-to for festivals, vacays, or just looking way too good for no reason.

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline, spaghetti strap tie
    • Stretchy smocked bust
    • Open tie-back detail
    • Flowy skater silhouette
    • Ruffled trim short hem
    • Runs true to size

    Style Number/Barcode: 05102-000065

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Ready Platform Sandals

    Get ready to take on the weekend in these absolutley ADORABLE platform sandals! Wear them to shop, brunch, and hang with your squad!

    • Open rounded toe
    • Thick toe strap
    • Adjustable around the ankle strap
    • Open back
    • Cork platform
    • Textured rubber flat sole
    • Faux leather straps and insole lining

    Style Number/Barcode: 07404-0540

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step It Up Block Heeled Sandals

    We've found it - the it girl sandal of the season to step up your shoe game. Add to cart now, and thank us later 

    • Open almond toe
    • Thick toe strap
    • Adjustable around the ankle strap
    • Open back
    • Short block heel
    • Faux leather straps and insole lining

    Style Number/Barcode: 07404-0536

    Category Name: Vacation Looks

    Price: $14.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hear Meow-Out Leopard Midi Dress

    Fiercely command a room with this bold mini dress! They'll be listening to every fashion tip you got 

    Fits & Features

    • Adjustable Spaghetti Straps Cross At Back 
    • Cowl Neckline I Back Zip 
    • Midi Length Silhouette I Side Slit 
    • Woven Fabric I Leopard-Inspired Print 
    • Relax Fit I Minimal Stretch

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

    Style Number/Barcode: 05102-0371

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lucky Feather Mini Hoop Earrings

    Wear a pair of lucky feathers this season, whether your're at a festival, or you just feel like making a statement, these earrings are a boho dream!

    • Small hoop with omega closure
    • Drop bar
    • Dangling large black feather 

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

    Style Number/Barcode: 07001-0355

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Five Pack Ombre Stone Bobby Pins

    Add some glam to your pretty tresses with this five pack of ombre stone bobby pins!

    • Five pack of gold bobby pins
    • Differing hued stones 
    • Ombre effect when all worn together
    • Mauve + Clear stones
    • Slide on fit

    Style Number/Barcode: 07006-0108

    Category Name: Vacation Looks

    Price: $3.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine Is On Your Side Rhinestone Teardrop Barrettes

    We know you love a good sparkle. Show your shine in these rhinestone barettes! 

    • Set Of Three
    • Wide Teardrop-Style Barette
    • Adorned With Sparkling Rhinestones 

    Style Number/Barcode: 07006-0110

    Category Name: Vacation Looks

    Price: $2.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Attention Please High-Rise Cargo Mini Skirt

    Functional fashion meets a flattering silhouette with this cargo mini skirt perfect for hangs! Featuring a high-rise waist and bodycon fit, this skirt accentuates your curves. The side flap pockets and faux back pockets add a touch of utility-chic style to the twill woven fabric. Complete the look in a short sleeve tee and sneakers.

    Fit & Features

    • Twill woven fabric, no stretch
    • High rise waist
    • Front button and hidden zipper closure
    • Side flap pockets, faux back pockets
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06301-0183

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Collared Button Down Shirt Dress

    This classic, chic button-down shirt dress can be worn as a sexy dress or layered over an edgy 'fit!

    Fit & Features

    • Collared
    • Long sleeves | Dual buttons to cuff
    • Button down front
    • Slight cinched waist
    • Relaxed fit
    • Woven fabric

    Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0549

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ur On My Mind Clear Banded Mules

    Every lil' thing you do, ur on my mind! Especially when you walk out in these trendsetting mules bb!

    • Open almond toe
    • Double clear bands
    • Short block heel
    • Faux nubuck material
    • Slide on design 

    Style Number/Barcode: 07401-0586

    Category Name: Vacation Looks

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Step By Step Wrap Sandals

    Peep that pedi babe! Even though sandals are more casual, this unique design brings a little life to your everyday look! Pair with high waist shorts and a graphic tee to complete your look!

    • Open almond toe
    • Single band over the toe
    • Strappy wrap around lace up detail
    • Flat sole

    Style Number/Barcode: 07404-0107

    Category Name: Vacation Looks

    Price: $12.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Oh My Heart Rhinestone Barrette

    You are just a lil' sweetheart ain't ya? This rhinestone barrette is the cutest addition to your hair do! Simply tease your hair a little bit and then set barrette on top!

    • Medium sized
    • Heart outline design
    • Rhinestone embellished 
    • Snap ball closure

    Style Number/Barcode: 07006-0111

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Live Your Coziest Life Slipper Socks

    Live your coziest life in a pair of comfy slipper socks boo!

    • Faux fur lining
    • Woven knit design
    • Over the ankle fit
    • Non-slip grip
    • Pom-Pom accents

    Style Number/Barcode: 07306-0033

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Sale