Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Romantic Roots Floral Chiffon Short Dress

    Get back to your romantic roots this season in this breezy ditsy floral chiffon dress perfect for baby showers to Sunday brunch! It features a sleeveless V-neck with a flirty bust tie, adjustable spaghetti straps, a stretchy smocked back, and a flattering skater short-length silhouette. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Sleeveless V-neck, bust tie, adjustable spaghetti straps
    • Stretchy smocked back, padded bust
    • Skater silhouette
    • Short-length hem
    • Ditsy floral print
    • Chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4939

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Midi Sweater Dress

    This adorable retro print sweater dress is giving major weekend getaway vibes! It features a sleeveless scoop neckline, a front O-ring accent with a small keyhole cutout, tank shoulder straps, a scoop-back design, a midi-length hem, and a form-hugging silhouette. The sweater knit fabric features a trendy retro-inspired multi-print pattern. Style with espadrille sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Front O-ring accent, small keyhole cutout
    • Tank shoulder straps, scoop-back design
    • Midi-length hem, form-hugging fit
    • Retro-inspired multi-print pattern
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1642

    Category Name: Vacation Looks

    Price: $6.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On The Move High-Rise Cargo Denim Shorts

    If you're a girl on the move these denim shorts are for you! They feature a high-rise waist, a relaxed silhouette, side cargo detail straps, and a short-length hem. Complete the look in a cute basic tank top for a casual day out!

    Fit & Features

    • High-rise waist, relaxed silhouette
    • Side cargo detail straps
    • Short-length hem
    • Front button and hidden zipper closure
    • Four-pocket styling, belt loop accents
    • Premium denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0348

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dainty Floral Dot Tie-Front Top

    Embrace sun-soaked days in the most perfect crop top! Featuring puff sleeves, a sweetheart neck with a tie-front and keyhole cutout, smocked back panel, crafted from gauze woven-lined fabric. Complete the look in denim shorts for strolling the pier.

    Fit & Features

    • Puff sleeves, sweetheart neck
    • Tie-front and keyhole cutout
    • Smocked back panel
    • Cropped hem
    • Dainty floral dot print
    • Gauze woven lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1826

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hampton Vacay Crochet Trim Duster

    Head out to the Hamptons in this effortlessly stylish duster featuring flowy short sleeves, open-front design, crochet trim, tie-front closure, and a long-length hem on gauze-woven fabric. Complete the look with a chic hat and oversized sunglasses.

    Fit & Features

    • Flow short sleeves
    • Open-front design
    • Crochet trim
    • Tie-front closure
    • Long-length hem
    • Gauze woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1582

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On My Mind Side Slit Maxi Skirt

    Perfect for the girl on the go, this knit maxi skirt can be styled in multiple ways for your everyday occasions and weekend plans! It features a high-rise waist, a hip-hugging fit, and a sultry high-side slit along a relaxed hem. The lined brushed knit fabric offers plenty of stretch. Complete the look with a statement handbag and jacket.

    Fit & Features

    • High-rise elasticized waist
    • Hip-hugging fit
    • High side slit
    • Maxi-length silhouette
    • Relaxed hem
    • Lined brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0842

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heat Wave Gauze Wrap Tie Crop Top

    Bring the heat in this gauze woven crop top perf for flaunting some skin! It features peasant long sleeves, a surplice V-neckline, and a wrap-tie design. Complete the look in a denim skirt and heels.

    Fit & Features

    • Peasant long sleeves, elastic cinched hems
    • Surplice V-neckline
    • Wrap-tie design
    • Cropped hem
    • Gauze woven fabric, lined, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1637

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Cutie Denim Tube Dress

    Keep it chic with a tube dress that is perf to dress up for your next brunch date! The dress features a sleeveless square neckline, belt loops, side pockets, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with a faux leather belt and mules. 

    Fit & Features

    • Sleeveless square neckline
    • Belt loops
    • Side pockets
    • Mini length silhouette
    • Denim fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4128

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cruise Control Rectangular Frame Sunglasses

    Roll the windows down and cruise so everyone can see you in these trendy rectangular sunglasses! They feature wide, smokey plastic frames with tinted lenses and UV protection from the sun's rays. Complete the look with a ring set for your stylish drive down the coast!

    Fit & Features

    • Rectangular shape
    • Wide, smokey plastic frames
    • Tinted lenses
    • UV 400 protection

    Style Number/Barcode: 07008-0993

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Legend Lace-Up Graphic Short Dress

    Everyone will make way for you, a major legend walking through! This graphic short dress flaunts your edgy-cool girl style featuring a sleeveless scoop neckline, spaghetti straps, dual side lace-up plackets that reveal some skin, a short bodycon fit, and a front script that reads, "Legend" with graphic detailing. Complete the look with a chain choker necklace and earrings.

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Dual side lace-up plackets, cutouts
    • Short bodycon fit
    • Front script reads, "Legend", graphic details
    • Mini-length hem
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1525

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Carefree Cutie Low-Rise Pleated Denim Skirt

    Stay on trend like the carefree cutie you are in this micro mini denim skirt perfect for casual weekend plans! It features a sleek low-rise waist, front pleating, and a frayed cut-off micro mini-length hem. Style with a basic sleeveless top and sandals.

    Fit & Features

    • Low-rise waist
    • Front pleating
    • Frayed cut-off mirco mini-length hem
    • Front button and hidden zipper closure, belt loop accents
    • Medium-wash denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06601-0083

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Precious In Faux Pearl Flat Sandals

    Look and feel precious in these chic flat sandals perfect for slipping on while getting ready for a formal wedding or styling for a dressy date! They feature a square toe, and a wide strap with faux pearl insets, and are composed of an ultra-soft faux suede material. Complete the look with a hair clip to create a cute updo!

    Fit & Features

    • Square toe
    • Wide strap with faux pearl insets
    • Flat sole
    • Ultra-soft faux suede material
    • Runs true to size

    Style Number/Barcode: 07404-1136

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendsetting Style Chain Strap Mini Dress

    Show off your trendsetting style in this sleeveless bodycon mini dress! It features a scoop neckline, adjustable spaghetti straps with chunky chain-link accents, a mini-length hem, and a curve-hugging fit. The ribbed knit fabric offers plenty of stretch. Complete the look in this short dress with a mini handbag and clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, chain-link accents
    • Mini-length hem
    • Form-hugging fit
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4917

    Category Name: Vacation Looks

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pristine Chic Bandage Midi Skirt

    Keep your style pristine and chic in this must-have bandage midi skirt featuring a smooth high-rise fit and a bodycon silhouette. The skirt is designed with a specialty bandage-seamless knit fabric that hugs your body like a glove! Complete the look in a lace-bustier and oversized blazer for dinner and drinks.

    Fit & Features

    • Smooth high-rise fit
    • Bodycon silhouette
    • Midi-length hem
    • Bandage-seamless knit design
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0839

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Cotton V-Neck Crop Top

    Let the sunshine on your shoulders in this cotton crop top for your next vacay! It features a sleeveless V-neckline, adjustable spaghetti straps, a center front drawstring along the cropped hem, and a back smocked panel. Complete the look in a mini skirt and sandals.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Center front drawstring
    • Cropped hem
    • Back smocked panel
    • Lined cotton fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1905

    Category Name: Vacation Looks

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Biker Chick Cropped Graphic Tee

    Edge up your look with this trendy cropped graphic tee! It features a crew neckline with a notched front, short sleeves, a tie-front design, a skull and wings graphic with the script, "Motorcycle," and a fitted cropped hem. Complete your biker chick look with a fringe skirt and cowboy boots.

    Fit & Features

    • Crew neckline, notched front
    • Short sleeves
    • Tie-front design
    • Skull and wings graphic, script that reads, "Motorcycle"
    • Fitted cropped hem
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1516

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • GNO Denim Corset

    Step out for GNO in a stunning corset that stuns! The corset features a sleeveless sweetheart neckline, adjustable shoulder straps, padded demi-cups, flexible boning, and a hook and eye front closure. The corset is composed of a lined denim fabric that offers a form hugging fit with a moderate stretch. Complete look with a wrap skirt.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Padded demi cups
    • Flexible boning
    • Hook and eye front closure
    • Cropped hem
    • Lined denim fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06003-1684

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Find Balance Ying Yang Graphic Crop Tee

    Find your balance with this graphic tee to add to your weekly rotation! It features short sleeves, a crew neck, a front ying yang graphic, and a raw-cut cropped hem on cotton fabric. Complete the look in denim shorts for a casual hang with friends!

    Fit & Features

    • Short sleeves, crew neck
    • Front ying yang graphic
    • Raw-cut, cropped hem
    • Relaxed fit
    • Soft and stretchy cotton fabric
    • Runs true to size

    Style Number/Barcode: 06002-1509

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet And Chic Paperbag Shorts

    Sweet and chic, these dressy paperbag shorts will elevate your everyday looks. They feature a high-rise waist, a tie-front belt, front pockets, and a relaxed fit. Style with a basic bodysuit or a cute cropped blouse.

    Fit & Features

    • High-rise elasticized paperbag waist
    • Tie-front belt
    • Front pockets, single faux back pocket
    • Relaxed fit
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0287

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Nail The Trend Swirl Print Sweater Dress

    Make heads turn in this on-trend sweater dress to show off your new spring style! It features a sleeveless square neck, adjustable spaghetti straps, a bodycon silhouette, and a midi-length hem on swirl print knit fabric. Complete the look in sandals for a backyard party!

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Swirl print
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1671

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Starstruck Glitter Mesh Mini Dress

    You'll leave them starstruck by your beauty in this glitzy glitter mesh mini dress! It features a sleeveless V-neckline with a dainty ruffled trim, spaghetti straps, all-over ruching, a mini-length ruffled hem with a front adjustable drawstring, and a curve-hugging silhouette. The sheer glitter mesh fabric includes a full knit lining. Style with metallic heels.

    Fit & Features

    • Sleeveless V-neckline, ruffled trim
    • Spaghetti straps
    • All-over ruching
    • Mini-length ruffled hem, front adjustable drawstring
    • Curve-hugging fit
    • Sheer glitter mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1873

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Free Spirited Paisley Tie-Back Crop Top

    Calling all free-spirited babes! This crop top is perfect for festivals and your warm-weather closet. It features adorable puff short sleeves, a scoop neck, and a flirty tie-back on woven fabric with a boho paisley-floral print. Complete the look in trendy denim shorts.

    Fit & Features

    • Puff short sleeves
    • Scoop neck
    • Cropped hem
    • Tie-back design
    • Paisley-floral print
    • Non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-1924

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty And Bold Floral Jelly Sandals

    Pretty and bold, these floral jelly sandals add a casual-chic vibe. They feature a square-shaped toe, a wide toe strap with a floral pom design, an open back for easy on-and-off styling, and a flat sole for comfortable wear. Style with a mini handbag.

    Fit & Features

    • Square-shaped toe
    • Wide toe strap
    • Floral pom design, faux leather material
    • Open back
    • Flat sole
    • PVC material
    • Runs true to size

    Style Number/Barcode: 07404-1126

    Category Name: Vacation Looks

    Price: $8.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In Spring Floral Block Heel Mules

    Get in the spring of things in these fresh and flirty floral mules to elevate every outfit this season! They feature a square toe, dual straps with floral accents, and a block heel, and are composed of faux leather material. Complete the look in a cute short dress for a graduation ceremony or birthday!

    Fit & Features

    • Square toe
    • Dual straps with floral accents
    • Block heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4134

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale