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.

  • Looking Sensational Smooth Knit Maxi Dress

    Rise to the occasion looking sensational in this basic smooth knit maxi dress perfect for dressing up or down! It features a sleeveless scoop neck, sleek spaghetti straps, a bodycon silhouette, and a flirty back-slit accent composed of double-lined smooth knit fabric. Complete the look in lucite mules for a bridal shower or casual party!

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Bodycon silhouette
    • Back slit accent
    • Maxi-length hem
    • Double-lined smooth knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5158

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Sun Tropical Tie Front Crop Top

    The perfect tropical crop top to enjoy the island sun on vacation! Featuring a V-neckline, adjustable spaghetti straps, and a trendy tie-front design, this top is perfect for warm weather while the cropped hem and tropical print add a touch of flirty fun! Complete the look with the matching bottoms.

    Shop Matching Bottoms: Island Sun Tropical High Rise Palazzo Pants

    Fit & Features

    • Tropical print, knit fabric
    • Adjustable spaghetti straps
    • V-neckline
    • Tie front design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5160

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Refresh Flocked Mesh Mini Dress

    This chic mini dress will refresh your wardrobe for the season! It features a sleeveless V-neckline, adjustable spaghetti straps for a customized fit, all-over ruching for a flattering look, a mini-length hem, a bodycon silhouette that will hug your curves, and a flocked velvet design in a pretty scroll pattern on mesh fabric. Style this mini-length dress with rhinestone fringe earrings and platform heels.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • All-over ruching
    • Mini-length hem, bodycon fit
    • Flocked velvet design, scroll pattern
    • Sheer mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2384

    Category Name: Vacation Looks

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Era Oversized Square Sunglasses

    Enter your trendy era with these fabulous oversized shades! The sunglasses feature an angled square-shaped design with a plastic frame, built-in nose pads, a sleek gold metal nose bridge, small studded accents on each side, and ombre-tinted lenses. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Oversized angled square-shaped design
    • Plastic frame
    • Built-in nose pads
    • Gold metal nose bridge
    • Small studded accents
    • Ombre-tinted lenses

    Style Number/Barcode: 07008-1092

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Forward Chiffon Puff Sleeve Skater Dress

    Spring forward and add this adorable skater dress to your wardrobe! The short dress features a square neckline with ruching at the bust, short puff sleeves, an empire waist seam, an open back with a tie-back accent, and a short skater skirt with a flirty fit and flare silhouette. The airy chiffon fabric provides a lightweight feel. Style with strappy mules.

    Fit & Features

    • Square neckline, ruched bust
    • Short puff sleeves, elastic cinched hems
    • Empire waist seam
    • Open back, tie-back accent
    • Short skater skirt, fit and flare silhouette
    • Sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2024

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stun And Only Mock Neck Floral Mesh Mini Dress

    Leaving people speechless is easy with this floral mesh mini dress! Crafted from a mesh fabric showcasing a cute floral print perfect for mixing it up this season. This dress features sheer fitted long sleeves with slit flare cuffs, a stylish mock neck, and a flattering bodycon fit. The mini-length hem adds a touch of sass to this stunning dress. Complete the look in stiletto heels.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Mock neck
    • Sheer long sleeves with slit flare cuffs
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5698

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Vine Lace Trim Rose Print Bustier

    Stop and smell this romantic rose print bustier to dress up your favorite bottoms. The delicate lace trim neckline and straps create a stunning silhouette, while the fitted crop hem gives you a flattering look.

    Fit & Features

    • Rose print, eyelet woven fabric, sewn-in woven lining
    • Lace trim sweetheart neckline
    • Lace trim adjustable shoulder straps
    • Hidden front hook and eye closures
    • Stretchy smocked back panel
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000014

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Ditsy Floral Eyelet Strapless Mini Dress

    Keep your summer brunch vibe sweet and stylish in this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a flirty ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with espadrille wedges and a mini handbag.

    Fit & Features

    • Ditsy floral print
    • Stretchy eyelet knit fabric with knit lining
    • Strapless straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5800

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Party Scene Sweetheart Mini Dress

    Steal the scene at every party in this sweetheart mini dress! It features a sleeveless sweetheart neckline, a padded underwire bust tie-shoulder straps, a bodycon silhouette, and side and back ruched seams to accentuate your curves. The smooth knit fabric offers plenty of stretch. Style this mini-length dress with chic earrings.

    Fit & Features

    • Sleeveless sweetheart neckline, padded underwire bust
    • Tie-shoulder straps
    • Back zipper and hook-eye closure
    • Short, bodycon silhouette
    • Side and back ruched seam
    • Knit fabric, lined bodice, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-5259

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stroll The Beach V-Neck Floral Paisley Maxi Dress

    Wherever your summer travels take you, always be in style with this casual floral paisley maxi dress! Featuring adjustable spaghetti straps and a stretchy smocked V-neckline, you'll have the perfect fit for a day in the sun. The crisscross back adds a playful touch, while the ruffled hem gives a flirty flair to the flowy silhouette. Complete the look with a cute hair accessory and sandals!

    Fit & Features

    • Floral paisley print, woven fabric, stretchy knit lining
    • Adjustable spaghetti straps, crisscross back
    • Stretchy smocked V-neckline
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5566

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girly Twirl Bow Short Sleeve Tee

    Twirl your hair and bring the aesthetic with this adorable short sleeve tee perfect for coquette girlies! This tee features short sleeves and a crew neckline, embroidered bow adds a touch of sass, while the fitted crop hem and stretchy rib knit fabric create a flattering silhouette. Complete the look in a lace trim mini skirt.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Embroidered bow
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1836

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkly Flirt Satin Heatstone Corset

    Sparkly and flirty, add this femme satin corset for a stunningly sultry vibe! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, underbust support, and flexible boning inserts along the bodice with all-over heatstone embellishments. Complete the look in wide-leg pants and heels.

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Underbust support
    • Flexible boning inserts
    • All-over heatstone embellishments
    • Cropped hem
    • Back hook-eye closures
    • Sleek satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-2059

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shadow Blooms Floral Skater Dress

    Delicate and dainty, unveil this skater dress for every soiree this season! The short dress features breezy peasant long sleeves, a sweetheart neckline, a padded bust, a smocked back, and a fit and flare silhouette with a ruffled short hem. The dress is designed with a floral jacquard pattern on an airy fabric with a smooth woven lining and no stretch. Complete the look with espadrille wedges for a baby or wedding shower!

    Fit & Features

    • Peasant long sleeves, elastic cinched hems
    • Sweetheart neckline, padded bust, smocked back
    • High waist seam, fit and flare, skater silhouette
    • Short-length hem
    • Floral jacquard pattern
    • Airy fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2604

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Blis Sleeveless Bodycon Knit Midi Dress

    Sit back and watch the compliments roll in when you're seen in this knit midi dress over the weekend! Crafted from a unique knit fabric offering a stretchy knit lining for comfort. It features adjustable spaghetti straps, a square neckline with a flirty bust tie, and a flattering bodycon midi-length silhouette. Complete the look in strappy sandals and a purse.

    Fit & Features

    • Unique knit fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • Square neckline, bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5712

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Vacay Tropical Print Woven Romper

    Look like you're ready to jet-set off to a dreamy vacay in this bold tropical print romper! The lightweight woven fabric is accented with an abstract tropical palm leaf print with bright hues perf for sunny days by the water. The romper features a sleeveless sweetheart neckline with a dainty eyelet lace trim, a ruched bust with a tie-front detail, thin tank straps that lead to a smocked back for added stretch, a fitted high waist, and flowy shorts for a relaxed look. Style with strappy sandals!

    Fit & Features

    • Abstract tropical print
    • Woven fabric with top knit lining, eyelet lace trim
    • Sweetheart neckline, ruched bust, tie-front detail
    • Thin tank straps, stretchy smocked back, zipper with hook and eye closure
    • Fitted high waist, flowy shorts
    • Runs true to size

    Style Number/Barcode: 06403-0462

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Babe Gingham Print Side Tie Bikini Bottoms

    Channel that flirty babe style in these adorable gingham printed side tie bikini bottoms with a dainty eyelet trim. Pair with one of the matching bikini tops for a sweet and sassy look.

    Shop Matching Tops: Flirty Babe Gingham Print Triangle Bikini Top, Flirty Babe Gingham Print Bandeau Bikini Top

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Gingham print
    • Eyelet trim
    • High-cut design, side tie closures
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-0865

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Silhouette Bodycon Midi Dress

    Show off a stunning silhouette in this sleek knit midi dress featuring a sleeveless square neck, ruching to flaunt your figure, and a hanky hem with a chic flared fit. Style with stilettos for cocktail hour!

    Fit & Features

    • Smooth knit fabric, high stretch, stretch knit lining
    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching
    • Bodycon silhouette
    • Midi-length hanky hem
    • Runs true to size

    Style Number/Barcode: 05101-4112

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just A Girl Mid-Rise Striped Boxer Skort

    You're just a girl who loves to look cute and casual, and this striped boxer skort is just the ticket! With a flattering mid-rise waist with button accents and a form-hugging fit, you'll love having this skort in the lineup.

    Fit & Features

    • Striped print, woven fabric
    • Elasticized mid-rise waist, button accents
    • Form-hugging fit
    • Shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06303-000024

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall Favorite Turtleneck Braided Sleeve Sweater

    Look no further for your new favorite turtleneck sweater this season! It features long sleeves with an eye-catching braided design, a cropped hem, and is crafted from a soft rib knit fabric perfect for keeping cozy and cute. Complete the look in a trendy pleated mini skirt for a coffee date and movie!

    Fit & Features

    • Long sleeves, braided design
    • Turtleneck
    • Cropped hem
    • Soft rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1751

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Style Short Sleeve Ruched Mini Dress

    Level up your everyday style with this simple yet chic mini dress! The lightweight smooth nylon fabric includes a knit lining and offers plenty of stretch for ultra-comfortable wear. Shaped with a classic scoop neckline and short sleeves, the mini-length dress features ruching down the side seams to flaunt your figure on the bodycon silhouette. Pair with a denim jacket and sneakers.

    Fit & Features

    • Smooth nylon fabric with knit lining, plenty of stretch
    • Scoop neckline
    • Short sleeves
    • Ruched side seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5669

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Appeal Puff Sleeve Eyelet Knit Skater Dress

    The sweet eyelet design and adorable details give this puff sleeve skater dress a charming appeal! Made with an airy sheer eyelet knit fabric with a partial knit lining, this short dress is perfect for your spring and summer weekend outings. It features a square neckline with chic ruching at the bust, sheer short puff sleeves with a dainty ruffled trim, a sheer corset-style bodice to create a cinched look, and a fit-and-flare skater silhouette for a flirty vibe. Complete your outfit with hoop earrings!

    Fit & Features

    • Sheer eyelet knit fabric, partial knit lining, plenty of stretch
    • Square neckline with ruched bust
    • Sheer short puff sleeves, ruffled trim, elastic cinched hems
    • Sheer corset-style bodice, stretchy high waist seam
    • Fit and flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5427

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Stand Out Faux Leather Suede Sneakers

    Are you looking to make your casual 'fits stand out? These sneakers feature a round toe and lace-up placket for the perfect fit. The faux suede pattern adds a touch of contrast while the rubber sole provides traction. Crafted from sleek faux leather, these sneakers are a must-have! Style with a trendy denim jumpsuit for weekend plans!

    Fit & Features

    • Round toe
    • Lace-up placket
    • Faux suede contrast pattern
    • Rubber traction sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07407-0224

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Greetings From Mallorca Graphic Tee

    A cute knit tee to pack with you on vacay! It boasts a front graphic with a script that reads "Greetings From Mallorca" and a fitted crop hem perfect for styling with high-rise bottoms.

    Fit & Features

    • Stretchy cotton-blend knit fabric
    • Crew neckline
    • Short sleeves
    • Front graphic, script reads "Greetings From Mallorca"
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-000038

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Squad Faux Leather Rhinestone Sneakers

    Make any outfit shine in these fashion sneakers! With a round toe, rhinestone embellished lace-up placket and tongue, a platform rubber sole, and a sleek faux leather upper, these sneakers are perfect for stepping out with your glam squad. Complete the look in a smooth knit dress to elevate your style for day or night plans!

    Fit & Features

    • Round toe
    • Rhinestone-embellished lace-up placket
    • Rhinestone embellished tongue
    • Platform rubber sole
    • Faux leather upper
    • Cushioned footbed
    • Runs true to size

    Style Number/Barcode: 07407-0218

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale