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.

  • Sunset Audience Paisley Wrap Crop Top

    Groove until sunset at the concert or party in this paisley crop top perfect summertime fun! It features retro bell long sleeves, a V-neckline, and a customizable wrap-tie hem on stretchy knit fabric. Complete the look in sleek faux leather shorts.

    Fit & Features

    • Bell long sleeves
    • V-neckline
    • Wrap-tie cropped hem
    • Paisley print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4724

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fit Check Strapless Denim Jogger Jumpsuit

    The denim jumpsuit you'll be wearing on rotation! It features a strapless elasticized neckline, hidden side pockets, a high-rise drawstring elasticized waist, and a relaxed jogger-style leg silhouette with elasticized cuffs. Complete the look in clear lucite heels and earrings for happy hour!

    Fit & Features

    • Strapless elasticized neckline
    • Hidden side pockets
    • High-rise drawstring elasticized waist
    • Relaxed, jogger-style leg silhouette
    • Elasticized cuffs
    • Light wash denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06602-0334

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Gem Of The Sea Faux Pearl Denim Shorts

    These statement denim shorts are truly the gem of the sea! They feature a flattering high-rise waist, front distressed accents and faux pearl embellishments, and a raw frayed cut-off hem with distressing. The jean shorts are composed of non-stretch medium wash denim with a color fade effect. Complete the look in a satin tie-front top for an haute night on the town!

    Fit & Features

    • High-rise waist
    • Front distressed and faux pearl embellishments
    • Raw frayed cut-off hem, distressing, slim, curve-hugging fit
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim fabric, no stretch, color fade effect
    • Runs true to size

    Style Number/Barcode: 06603-0326

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 70s Groove Floral Tie-Back Skater Dress

    Get into the groove of this 70s-inspired printed floral dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering skater short-length silhouette. Complete the look in rhinestone mules for a dressy date!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Skater silhouette
    • Short-length hem
    • 70s-inspired floral print
    • Woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5053

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Love For Chic Style Heart Hoop Earrings

    Show off your love for all things chic with these heart-shaped hoops. The metal earrings feature a bamboo-style texture with a click-top closure. Complete the look with a mini handbag.

    Fit & Features

    • Metal hoop earrings
    • Heart-shaped design
    • Bamboo-style texture
    • Click-top omega closure

     

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

    Style Number/Barcode: 07001-1616

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Soak Up The Sun Tropical Print Maxi Dress

    You'll be ready for those relaxing beachside strolls in this gorgeous tropical print maxi dress. It features a sleeveless V-neckline, spaghetti straps, an alluring backless design, a flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with slip-on sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Backless design, single lattice strap
    • Flowy floor-length hem, high front slit
    • Tropical palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4997

    Category Name: Vacation Looks

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smooth Silhouette Crop Tube Top

    This smooth tube top is designed to flatter and elevate every look! It features a strapless neckline, a form-hugging fit, and a sleek cropped hem. The double-lined stretchy knit fabric offers a seamless design and has an ultra-buttery feel. Style with the matching bottoms for a chic look! 

    Shop Matching Blue And Black Bottoms: Smooth Silhouette Bodycon Mini Skirt

    Shop Matching Rust Bottoms: Smooth Silhouette Slit Midi Skirt

    Fit & Features

    • Strapless neckline
    • Form-hugging fit
    • Cropped hem
    • Double-lined, buttery knit fabric
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 06002-1615

    Category Name: Vacation Looks

    Price: $11.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Me Cute Linen V-Neck Skater Dress

    Color you cute in this linen skater dress perfect for layering over your swimsuit on a beach day or pool party! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty ruffled underbust trim, and a tiered color block ruffled short-length silhouette. Style with trendy espadrille wedges.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruffled underbust trim
    • Tiered ruffle layered skater silhouette
    • Short-length hem
    • Color block pattern
    • Airy woven linen fabric, partial lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4994

    Category Name: Vacation Looks

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Perfection Straw Clutch

    Accessorize all your summer looks with this straw clutch for a perfect casual-chic vibe. It features a rectangular shape, a curved fold-over design, and is composed of a braided straw material. Style with an adorable matching set.

    Fit & Features

    • Rectangular shape
    • Curved fold-over design
    • Braided straw material

    Style Number/Barcode: 07203-1166

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Stunner Dangly Earrings

    Set out to stun with these dangly earrings featuring sun-shaped post and bottom charms with a post-back closure. Complete the look with a dainty anklet for a boho-chic style!

    Fit & Features

    • Sun-shaped post and bottom charms
    • Dangly design

     

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

    Style Number/Barcode: 07001-1626

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Charm Swiss Dot Chiffon Midi Dress

    Unlock your sweet charm in this chiffon midi dress perfect for bridal showers, graduation parties, and more! It features a sleeveless V-neck with a twisted bust, adjustable spaghetti straps, a flirty tie-back design, and a flowy silhouette and ruffled hem. The dress is composed of an airy chiffon fabric with a swiss dot pattern and a smooth woven lining. Complete the look in faux pearl heels.

    Fit & Features

    • Sleeveless V-neck, twisted bust
    • Adjustable spaghetti straps
    • Tie-back design
    • Flowy silhouette, ruffled midi-length hem
    • Airy chiffon fabric, swiss dot pattern, smooth woven lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05102-5047

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Charming Floral Eyelet Lace Dress

    Always charming and cute, this floral eyelet lace dress boasts adorable allure! It features puff short sleeves, a square neck, a tie-back design, and a flattering skater silhouette and short-length hem. Complete the look in strappy sandals for a baby shower or family party.

    Fit & Features

    • Puff short sleeves
    • Square neck
    • Tie-back design
    • Skater silhouette
    • Short-length hem
    • Ditsy floral print, eyelet lace, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5030

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready To Ruffle V-Neck Mini Dress

    You'll bring the flirty flare with this mini dress for bridal showers or day dates! The dress features a sleeveless ruffle V-neckline, straps with ruffle trim, and a bodycon silhouette on stretchy and smooth knit fabric with lining. Complete the look in trendy flat sandals and a purse!

    Fit & Features

    • Sleeveless ruffle V-neckline
    • Straps with ruffle trim
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy, smooth knit fabric with lining
    • Runs true to size

    Style Number/Barcode: 05102-5049

    Category Name: Vacation Looks

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Allure Sheer Lace Bodycon Mini Dress

    Show off a romantic allure in this chic sheer lace bodycon mini dress. It features a sleeveless high crew neckline with a scalloped lace hem that continues throughout the dress, a sheer mesh bust insert with a sultry V-shaped plunging design, a sheer mesh back with a zipper closure, a mini-length hem with a sheer mesh ruffled trim, and a curve-hugging silhouette. The floral lace fabric includes a partial lining. Style with clear heels.

    Fit & Features

    • Sleeveless high crew neckline, scalloped lace hem
    • Sheer mesh bust insert, V-shaped plunging design
    • Sheer mesh back, zipper and hook-eye closure
    • High waist seam, mini-length hem, sheer mesh ruffled trim
    • Bodycon fit
    • Sheer floral lace fabric, partial sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2128

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flower Garden Tie Strap Bustier

    Fresh and flirty, flaunt your florals on this bustier featuring a sleeveless, square neck, trendy tie-straps, a fitted crop hem, and a back zipper closure. Complete the look in high-rise jeans and sandals for a day date.

    Fit & Features

    • Sleeveless, square neck, tie-straps
    • Fitted crop hem
    • Back zipper closure
    • Floral print
    • Woven fabric, lined, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1876

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Love Me Floral Crepe Skort Romper

    Love is in full bloom this spring! Embrace the romance in this flirty floral skort romper featuring a sleeveless, criss-cross wrap halter neck with tie closure, front cutout bodice, and a ruffled skort-style bottom. Complete the look in lace-up heels for a dressy occasion.

    Fit & Features

    • Sleeveless, criss-cross wrap halter neck, tie closure
    • Front cutout bodice
    • Ruffled skort-style bottom
    • Partial open-back, smocked panel, zipper closure
    • Floral print crepe-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06303-0197

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Crochet Cutie Long Sleeve Crop Top

    You'll be the cutest gal at festivals or country bars in this crochet crop top featuring sheer fitted long sleeves, a square neck, front cutout accents, and a dual tie-back closure. Style with printed flare pants and a hat to complete the look!

    Fit & Features

    • Sheer fitted long sleeves
    • Square neck
    • Front cutout accents
    • Ultra-cropped hem
    • Dual tie-back closures
    • Crochet knit, sheer design, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1631

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ticket To Flirty Ditsy Floral Mini Dress

    Your ticket to looking fun and flirty is this ditsy floral mini dress perfect for a staycation or weekend getaway! It features a sleeveless sweetheart neckline, spaghetti straps, a front bust tie with a keyhole accent, and a bodycon silhouette. The soft brushed knit fabric offers plenty of stretch. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Front bust tie, keyhole accent
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5115

    Category Name: Vacation Looks

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casually Cute Floral Off-The-Shoulder Dress

    Step out looking casually cute in this floral mesh mini dress for lunch with the girls or a bridal shower! It features an off-the-shoulder neckline, sheer short-sleeve cuffs, a ruched bust, and side, and back ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a dainty ring set and heels.

    Fit & Features

    • Off-the-shoulder neckline
    • Sheer short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Ruched bust, side and back seams
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print, mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4914

    Category Name: Vacation Looks

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Braided Beauty Straw Strappy Flat Sandals

    Create an effortless summer look in these flat sandals perfect for a beach day, vacations, and casual plans! They feature a square toe, a strappy straw braided design, a flat sole, and a faux leather material. Complete the look in cute sunglasses.

    Fit & Features

    • Square toe
    • Strappy straw braided design
    • Flat sole
    • Slightly cushioned footbed
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1086

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mojito Please Tropical Halter Jumpsuit

    This tropical halter jumpsuit is ready for sippin' mojitos and dancing the night away on your next vacay! It features a sleeveless halter neckline with tie-back straps, a cutout bodice, a partially open back, and a hip-hugging slim-leg silhouette. Complete the look in espadrille wedges.

    Fit & Features

    • Sleeveless halter neckline, tie-back straps
    • Cutout bodice, partially open back
    • Hip-hugging, slim-leg silhouette
    • Tropical palm print
    • Smooth knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06502-2311

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Level Up Cargo Bermuda Denim Shorts

    Level up your street style in these bermuda denim shorts! They feature a flattering high-rise waist, a baggy leg silhouette, cargo pocket detail, and an above-the-knee length. The shorts are composed of premium medium-wash denim with a color fade effect. Complete the look with a basic top and sleek hoop earrings for a cute throwback vibe!

    Fit & Features

    • High-rise waist, baggy leg silhouette
    • Cargo pocket detail
    • Above-the-knee length
    • Front button closure, belt loop accents, five-pocket styling
    • Medium wash denim fabric, color fade effect
    • Slight stretch
    • Runs true to size

    Style Number/Barcode: 06603-0349

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shine Away Rhinestone Flat Sandals

    Shine all day or into the night in these sparkly faux leather sandals featuring an on-trend square toe, a wide strap with colored rhinestone embellishments, and a flat sole. Style with a chic mini tote bag for a backyard dinner party.

    Fit & Features

    • Square toe
    • Wide strap, colored rhinestone embellishments
    • Falt sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1089

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • See Me Sparkling Rhinestone Strappy Sandals

    Everyone will catch sight of your sparkle in these trendy flat sandals featuring a sleek almond toe, rhinestone embellished dainty and strappy design and a faux leather footbed. Style with a glitter crossbody purse to complete the look!

    Fit & Features

    • Almond toe
    • Rhinestone embellished dainty and strappy design
    • Faux leather footbed
    • Flat sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1082

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free