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.

  • Sunday Girl Floral Chiffon Skater Dress

    Look cute for Sunday brunch in this floral chiffon skater dress featuring three-quarter length puff sleeves, a square neck, and a pleated waistband on the skater silhouette. Showcase a peek of skin in the open-back design with tie closure and ruffled short-length hem. Composed of a chiffon floral lined fabric with no stretch. Perfect for styling with knee-high boots.

    Fit & Features

    • Three-quarter length puff sleeves, elastic cinched hems
    • Square neckline
    • Pleated waistband, skater silhouette
    • Ruffled short-length hem
    • Open-back, tie closure, back zipper, hook and eye closure
    • Chiffon floral lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-1706

    Category Name: Vacation Looks

    Price: $25.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Sweet Tie-Front Floral Top

    Keep it sweet in a floral top that brings major charm! The top features a sweetheart neckline, long sleeves, a tie-front hem, and a pretty floral print. The top is composed of a semi-sheer gauze fabric that offers a relaxed fit with minimal stretch. Complete the look with the matching shorts.

    Shop Matching Bottoms: Too Sweet High Waist Floral Shorts

    Fit & Features

    • Sweetheart neckline
    • Long bishop sleeves, elastic cinched hems
    • Tie-front hem 
    • Floral print 
    • Lined gauze knit fabric 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06003-1592

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Sweet High Waist Floral Shorts

    Keep it sweet in floral shorts that bring major charm! The shorts feature a high-rise fitted waist with a smocked back, a pretty floral print, and a wide-leg hem. The shorts are composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete the look with the matching tie front top.

    Shop Matching Top: Too Sweet Tie Front Floral Top

    Fit & Features

    • High-rise fitted waist
    • Smocked back 
    • Floral print
    • Wide-leg hem 
    • Lined gauze knit fabric
    • Minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06303-0162

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Endless Summer Fishnet Bikini Bottoms

    Spend endless days in your shades and these bikini bottoms for summer! It features a hipster style silhouette, side tie closures so you can customize the fit, and a fishnet overlay. Complete the look in the matching bikini top.

    Shop The Matching Bikini Top: Endless Summer Fishnet Bikini Top

    Fit & Features

    • Hipster style silhouette
    • Side tie closures
    • Cheeky coverage
    • Fishnet overlay
    • Fits true to size 

     

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

    Style Number/Barcode: 07105-0834

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Summer Fishnet Bikini Top

    Spend endless days in your shades and this bikini top for summer! It features triangle cups with fishnet overlay and dual tie-back closures so you can customize the fit. Complete the look in the matching bikini bottoms.

    Shop The Matching Bikini Bottoms: Endless Summer Fishnet Bikini Bottoms

    Fit & Features

    • Triangle cups
    • Fishnet overlay
    • Dual tie-back closures
    • Fits true to size

    Style Number/Barcode: 07104-0687

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist And Turn Hoop Earrings

    Don't sleep on it, these twisted metal hoop earrings will be gone before you know it! They feature an omega-back closure for a secure fit. Complete the look in a darling sweater dress.

    Fit & Features

    • Twisted design
    • Omega-back closure
    • Metal material

     

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

    Style Number/Barcode: 07001-1179

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Solstice Chiffon Tie Romper

    Bring on the warmer temps in this stylish chiffon romper perf for brunches! It features long sleeves, a collared v-neck, a surplice bodice with tie closure, and a snake pattern. Composed of non-stretch chiffon fabric with an inner knit lining. Style with lace-up heels.

    Fit & Features

    • Long sleeves, collared v-neck
    • Surplice bodice, tie-waist closure
    • Snake pattern
    • Chiffon fabric, inner knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 06303-0167

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fab And Wild Slip Dress

    Keep it fab with a slip dress that showcases your wild side! The dress features a snake print, a sleeveless cowl neckline, adjustable spaghetti straps that cross at the back, a tie-back accent, and a short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps, cross at back
    • Tie back ties
    • Snake print
    • Short length hem
    • Lined lightweight woven fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4345

    Category Name: Vacation Looks

    Price: $4.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Drink Guinness Graphic Tee

    This graphic tee is traditionally brewed to be everyone's favorite! It features classic short sleeves, a crew neck, and a front graphic script that reads, "Guinness Extra Stout" stamp, and a cut-off hem. Complete the look in distressed shorts for a cute look.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Front graphic script, "Guinness Extra Stout" stamp
    • Cut-off hem
    • Breathable cotton fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06002-1128

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playing For Keeps Tie-Front Top

    This tie-front top is definitely a keeper! It features long sleeves, a plunge v-neckline with a tied crop hem. Composed of stretchy soft knit fabric. Style with denim shorts for a trendy vibe.

    Fit & Features

    • Long sleeves
    • Plunge v-neckline
    • Tied front crop hem
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06202-0275

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Flare High-Rise Pants

    Create a flirty vibe in these flare high-rise pants featuring an elasticized waist and a form-fitting silhouette on slinky knit fabric. Complete the look in the matching top.

    Shop Matching Top: Flirty Flowy Sleeve Tie-Front Top

    Fit & Features

    • High-rise elasticized waist
    • Form-fitting silhouette
    • Flare hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0813

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Flowy Sleeve Tie-Front Top

    Create a flirty vibe in this flowy 3/4 sleeve crop top featuring a plunge v-neck with a tie-front on slinky knit fabric. Complete the look in the matching bottoms.

    Shop Matching Bottoms: Flirty Flare High-Rise Pants

    Fit & Features

    • Flowy 3/4 sleeves
    • Plunge v-neckline
    • Tie-front 
    • Cropped hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0297

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild But Cute Leopard Wrap Top

    Show your wild side in a cute way! This leopard wrap top features long sleeves, a v-neckline, and a wrap-style crop hem with self-tie closure on ribbed knit fabric. Complete the look with a lace bralette and jeans. 

    Fit & Features

    • Long sleeves
    • V-neckline
    • Wrap style crop hem
    • Self-tie closure
    • Leopard pattern
    • Ribbed knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4069

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Fabulous Cat-Eye Sunglasses

    These sleek cat-eye sunglasses will be forever fab and always on-trend! They feature a chic oversized cat-eye design crafted with a plastic frame and arms, built-in nose pads for support, and tinted lenses. Style these shades with hoop earrings.

    Fit & Features

    • Oversized cat-eye design
    • Plastic frame and arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1070

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All The Boho Vibes Maxi Skirt

    Bring all the boho vibes to your look with this chic printed maxi skirt. It features a high-rise waist, a thigh-high side slit, and a curve-hugging ankle-length silhouette. The brushed knit fabric showcases an all-over bohemian-inspired print. Style this skirt with a lightweight crop top and mules.

    Fit & Features

    • High-rise waist
    • Thigh-high slit
    • Form-fitting ankle-length silhouette
    • Bohemian-inspired print
    • Brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 06501-0651

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless And Breezy Crop Top

    Showcase an effortless and breezy look with this lightweight crop top. It features a collared V-neckline, long sleeves with buttons to cuff, a button-down front, and a chic wrap-front design at the cropped hem. Style this top with light wash denim shorts and strappy sandals.

    Fit & Features

    • Collared V-neckline
    • Long sleeves, dual buttons to cuff
    • Button-down front
    • Cropped hem, wrap-front design, elasticized back hem
    • Sheer woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1893

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Femme Floral Chiffon Sweetheart Top

    Florals are forever femme! Unleash your inner boho in this chiffon crop top featuring peasant long sleeves, a sweetheart neck with keyhole tie, and a smocked back. Complete the look in flare jeans perfect for a day date.

    Fit & Features

    • Peasant long sleeves
    • Sweetheart neck, keyhole tie
    • Cropped hem
    • Smocked back
    • Ditsy floral pattern
    • Chiffon-lined fabric
    • Fits true to size, no stretch

    Style Number/Barcode: 06003-1687

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Season Zebra Slit Maxi Skirt

    Create many wild memories! This sultry zebra maxi skirt features a high-rise waist and an eye-catching front slit to showcase some leg on the floor-length hem. Composed of lined fabric with no stretch. Style with the matching top.

    Shop The Matching Top: Wild Season Zebra Halter Top

    Fit & Features

    • High-rise waist
    • Front slit
    • Zebra pattern
    • Floor-length hem
    • Lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06501-0564

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Season Zebra Halter Top

    Create many wild memories! This sultry zebra halter top features an eye-catching strappy design with tie closure, open-back, and a front drawstring cutout atop an ultra-cropped hem. Composed of lined fabric with no stretch. Style with the matching skirt.

    Shop The Matching Bottoms: Wild Season Zebra Slit Maxi Skirt

    Fit & Features

    • Sleeveless, halter neckline, front drawstring cutout
    • Strappy design
    • Ultra-cropped hem
    • Open-back
    • Zebra pattern
    • Lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06001-3889

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gimme More Twist Cutout Bodysuit

    Elevate your basics in this long sleeve bodysuit featuring a crew neck and a sultry front cutout design with a twisted bodice, dual snap closure, and a thong cut bottom. Complete the look in faux leather pants.

    Fit & Features

    • Long fitted sleeves, crew neck
    • Front cutout design, twisted bodice
    • Dual snap closure
    • Thong-cut bottom
    • Soft knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-3979

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Paradise Floral Ruched Midi Dress

    Fly to paradise in this perfect floral midi dress featuring a sleeveless, square neck, spaghetti straps, bodycon fit, and a side ruche with a tie so you can customize the fit. Complete the look in stylish mules.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon fit
    • Midi-length hem
    • Side ruche with tie
    • Floral pattern
    • Stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05101-1362

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 90's Moment Rectangular Sunglasses

    Throw it back to the '90s in these trendy sunglasses featuring small plastic rectangular frames and arms with grommet insets. Complete the look in a faux leather blazer.

    Fit & Features

    • Small rectangular frames
    • Grommet insets on arms
    • Plastic material 

        Style Number/Barcode: 07008-0922

        Category Name: Vacation Looks

        Price: $3.97 $9.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Rays For Daze Square Oversized Sunglasses

        Shade your eyes from the rays in these edgy sunglasses! They feature oversized square frames and chain-link arms. Complete the look in a faux leather jacket for hanging with friends.

        Fit & Features

        • Oversized square frames
        • Chain-link arms
        • Nose pads

        Style Number/Barcode: 07008-0925

        Category Name: Vacation Looks

        Price: $5.97 $12.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Ready For My Vacay Mesh Kimono

        Be sure to pack this breezy mesh kimono for your island getaway! It features mid-length loose sleeves, a draped open front with a tie-front belt to stylishly cinch your waist, a flowy silhouette, and an all-over palm leaf print. Layer this lightweight kimono over your fave bikini for the perf beachside coverup.

        Fit & Features

        • Mid-length, loose kimono-style sleeves
        • Open front, tie-front belt
        • Flowy, relaxed fit
        • Palm leaf print
        • Sheer mesh fabric, moderate stretch
        • Runs true to size

        Style Number/Barcode: 06202-0263

        Category Name: Vacation Looks

        Price: $23.97 $36.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale