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.

  • Effortless Era Woven A-Line Midi Dress

    Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.

    Fit & Features

    • Poplin smooth cotton woven fabric with full-length woven lining
    • Sleeveless square neckline, adjustable spaghetti straps
    • Stretchy smocked bodice
    • V-shaped waist
    • Pleating, hidden side pockets
    • Midi-length flowy A-line silhouette, high side slit
    • Runs true to size

    Style Number/Barcode: 05102-000001

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Classic Fold-Over Ribbed Knit Beanie

    This cute classic ribbed knit beanie is a winter must-have! It features a thick ribbed knit material with a fold-over design and offers moderate stretch. Style this adorable beanie with a fuzzy faux sherpa jacket.

    Fit & Features

    • Thick ribbed knit material
    • Fold-over design
    • Moderate stretch

    Style Number/Barcode: 07302-1514

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Perfection Bodycon Striped Mini Dress

    With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!

    Fit & Features

    • Striped pattern, texture knit fabric, moderate stretch
    • Spaghetti straps
    • Square neckline with twist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5675

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Babe Button Up Linen Vest

    A sleek fit with tailored details, this sleeveless linen vest is essential for spring-to-summer wear! The vest is designed with a flattering V-neckline, button-up front closures, and a curved cropped hem to flaunt your figure. Complete the look with the matching pants.

    Shop Matching Bottoms: Cutest Babe Wide Leg Linen Trouser Pants

    Fit & Features

    • Lined linen fabric
    • Button up front closures
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1737

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Babe Tie-Back Crochet Mini Dress

    Channel a beachy babe vibe in this trendy crochet mini dress! Designed with a sheer crochet fabric with a boho-inspired woven design, the short dress includes a stretchy knit lining for coverage. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, an adorable tie-back design, a flirty lower back cutout that peaks out on both sides, and a form-hugging fit to flaunt your figure. Style with espadrille sandals.

    Fit & Features

    • Crochet fabric with woven design, stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Tie back straps, back cutout
    • Hidden side zipper with hook and eye closure
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5780

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Icon Striped Crochet Halter Top

    You'll be a cool summer icon in this striped crochet crop top featuring a plunging V-neckline with tie-back halter straps and a fitted, cropped hem. Style with cutoff denim shorts!

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Striped pattern
    • Sleeveless plunge V-neckline
    • Tie-back halter straps, partially open back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000070

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

  • Bri High-Rise Flare Jeans by Windsor Denim

    Keep your casual everyday 'fits trendy with the Bri high-rise flare jeans. This pair by Windsor Denim features a fitted high-rise waist, destructed detailing at the knees, and a fab flare hem. The denim fabric offers a moderate stretch for comfortable wear. Style with a bodysuit and mules.

    Fit & Features

    • High-rise waist
    • Destructed detailing at the knees
    • Fitted silhouette, flare hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0354

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All This Love Cowl Halter Crop Top

    A sweet crop top with a sultry open back and cowl halter neckline that dresses up your favorite jeans.

    Fit & Features

    • Smooth knit stretchy fabric
    • Cowl halter neckline, spaghetti strap tie
    • Open back
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000087

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Instant Fave Disty Floral Short Sleeve Midi Dress

    This adorable disty floral midi dress will be an instant fave of yours for the summer season. It features a crew neckline, short fitted sleeves, a small top keyhole cutout at the back with a button closure, a larger lower back cutout, a high waist seam, a midi-length hem with a high front slit, and a form-hugging silhouette. The floral printed brushed knit fabric offers plenty of stretch. Style with espadrille sandals.

    Fit & Features

    • Crew neckline, short sleeves
    • Small back keyhole cutout, button closure
    • Larger lower back cutout, high waist seam
    • Midi-length hem, front slit, form-hugging fit
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5184

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love's In The Air Floral Chiffon A-Line Dress

    Slip into the romantic vibes of this floral chiffon mini dress for day dates to shower celebrations! The dress flaunts a pretty corset bodice and lace-up back that turns heads, while the A-line silhouette flatters your figure.

    Fit & Features

    • Dainty floral print, chiffon fabric, stretchy knit lining
    • Sweetheart neckline
    • Wide shoulder straps
    • Underwire bust, tie front, side zipper and hook-eye closure
    • Corset-trim bodice, lace-up back design
    • A-line silhouette, short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4046

    Category Name: Vacation Looks

    Price: $9.97

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Touch Faux Wool Beret

    This beret will add a chic touch to all of your 'fits this season! It features a classic beret design and is composed of a faux wool material. Style with an oversized blazer and ankle booties for a city trip!

    Fit & Features

    • Classic beret design
    • Faux wool material
    • Moderate stretch

    Style Number/Barcode: 07302-1486

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Curves Keyhole Maxi Dress

    Serving curves and confidence—this dress eats every time. The keyhole cutout and body-hugging silhouette? A certified head-turner for nights that don’t end early.

    Fit & Features

    • Stretchy textured knit fabric
    • Scoop neckline with spaghetti straps
    • Front keyhole cutout at bust
    • Form-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000166

    Category Name: Vacation Looks

    Price: $35.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M

  • Effortless Influence Strapless Bodycon Midi Dress

    Achieve a stylish rep in this strapless midi dress wherever you go! With a flattering bodycon fit and trendy stone metal insert, this dress will enhance your natural silhouette and captivate any room you enter.

    Fit & Features

    • Stretchy knit fabric
    • Strapless neckline, stone metal insert
    • bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000062

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Softest Style Plaid Frayed Scarf

    This plaid frayed scarf will be the softest style in your lineup! Perfect for wearing around your neck or shoulders, the styling possibilities are endless. Complete the look in cute boots.

    Fit & Features

    • Plaid pattern
    • Frayed edge trim
    • Ultra-soft knit material

    Style Number/Barcode: 07305-0459

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Escape Cropped Halter Top

    Shop Matching Bottoms: Coastal Escape High Rise Ruched Midi Skirt

    Fit & Features

    • Smooth knit fabrication
    • Sleeveless halter neckline
    • Halter neck ties
    • Cutouts
    • Beaded detailing
    • Cropped hem
    • Runs true to size 

    Style Number/Barcode: 06001-5672

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cold Weather Luxe Faux Fur Trim Gloves

    Enter into the cold season with luxe style with these faux fur gloves! They feature a fitted design made from soft faux suede material with chic faux fur cuffs. Complete your cute cold-weather 'fit with a rhinestone-embellished beanie!

    Fit & Features

    • Fitted design
    • Faux suede fabric
    • Faux fur cuffs

    Style Number/Barcode: 07304-0047

    Category Name: Vacation Looks

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Bold Floral Mesh Strapless Maxi Dress

    Be a bold babe in this airy mesh maxi dress designed with a large floral print pattern to turn heads. Featuring ruching at the bust, a high-cut side slit, and a form-hugging silhouette, style with wedges for a sunset dinner.

    Fit & Features

    • Sheer mesh fabric with full-length brushed knit lining, high stretch
    • Large floral print
    • Strapless straight-across neckline
    • Ruched bust
    • Thigh-high side slit
    • Maxi-length hem, form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000098

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: CORAL

    Available Size: XS

    Product Badge:
    • Sale
  • My Lane Corduroy Faux Sherpa Collar Crop Jacket

    Take a walk down style lane in this corduroy crop jacket essential for the chilly season ahead! It features long sleeves with button cuffs, a faux sherpa collar, button-down front and flap pockets, and a back elasticized cinch hem. Layer over a basic top and currently trending cargo pants.

    Fit & Features

    • Long sleeves, button cuffs
    • Faux sherpa collar
    • Button down front, flap pockets
    • Cropped hem
    • Back elasticized cinch hem
    • Corduroy fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1690

    Category Name: Vacation Looks

    Price: $15.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute But Chill A-Line Mini Dress

    Looks like a serve, feels like a chill day 'fit. This nylon mini dress comes through with a flattering silhouette and hidden shorts, so you can dance, lounge, or do your thing without a second thought.

    Fit & Features

    • Smooth nylon fabric, moderate stretch
    • Sleeveless square neckline
    • Spaghetti straps
    • Short front slit
    • Mini-length hem, hidden shorts
    • Fitted A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000031

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Sweet Like Summer Crochet Bralette Top

    Sweet like summer, this crochet bralette top was made to flirt. With a plunging V-neck, scalloped trim, and open tie-back design, it's your new go-to for coastal vibes. Style with the matching maxi skirt.

    Shop Matching Bottoms: Sweet Like Summer Crochet Maxi Skirt

    Fit & Features

    • Crochet knit fabric, moderate stretch
    • Sleeveless plunge V-neckline
    • Tank shoulder straps
    • Scalloped trim
    • Open back, tie-back spaghetti straps
    • Fitted ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000052

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Daydream Chiffon Crop Top

    You'll look like such a daydream in this airy chiffon crop top! It features a subtle sweetheart neckline, a ruched bust, long sheer bishop sleeves, a cropped hem with a wrap-front detail, and a stylish tie-back design. Complete the look with cute denim and clear mules.

    Fit & Features

    • Sheer chiffon fabric, front knit lining, minimal stretch
    • Sweetheart neckline
    • Ruched bust
    • Long sheer bishop sleeves, elastic cinched hems
    • Cropped hem, wrap-front detail
    • Tie-back design
    • Runs true to size

    Style Number/Barcode: 06003-2301

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Repeat Flat Over-The-Knee Boots

    These must-have flat over-the-knee boots will be styled on repeat all season long. They feature a fitted over-the-knee design, an inner zipper closure that runs down the length of the boot, an almond-shaped toe, and a flat sole with a short block heel. The boots have a trendy design of sleek faux leather at the front with smooth spandex at the back. Pair with a sweater dress for such a chic winter look.

    Fit & Features

    • Fitted over-the-knee design
    • Complete inner zipper closure
    • Almond toe
    • Flat sole, short block heel
    • Half faux leather material
    • Half lycra material
    • Runs true to size

    Style Number/Barcode: 07402-0980

    Category Name: Vacation Looks

    Price: $11.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Getaway Tropical Print Crop Top

    This alluring tropical print crop top will create a gorgeous getaway look! Designed with a trendy tropical print pattern on the airy mesh fabric, it features a sleeveless plunging V-neckline, halter spaghetti straps, a tie-front design under the bust, and a cropped, ruffled, babydoll hem with a flowy fit. Style with the matching maxi skirt for your next destination vacay!

    Shop Matching Bottoms: Gorgeous Getaway Tropical Print Maxi Skirt

    Fit & Features

    • Sleeveless plunging V-neckline
    • Halter spaghetti straps
    • Tie-front design
    • Cropped, ruffled, babydoll hem, flowy fit
    • Tropical print
    • Sheer mesh fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-5074

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Bohemian Babe Knit Cutout Tube Top

    Channel a boho babe vibe in this sweater knit tube top featuring a strapless straight neckline, dual bust cutouts with a beaded trim, and a front slit accent. Style with the matching mini skirt for a chic and seamless look!

    Shop Matching Bottoms: Bohemian Babe Knit High-Rise Mini Skirt

    Fit & Features

    • Sweater knit fabric, ribbed hems, high stretch
    • Strapless straight-across neckline
    • Dual bust cutouts, beaded trim
    • Front slit design
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000031

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free