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.

  • Under The Sun Chevron Knit Sweater Top

    Let the sun kiss your shoulders in this sweater knit top for festivals, concerts, or any weekend plans! It features a sleeveless halter neckline with a tassel tie-neck closure, a fitted crop hem with tassel trim, and a sultry open-back with a tassel tie-back closure. The top is designed with a multi-colored chevron knit fabric with minimal stretch. Complete the look in flare denim jeans.

    Fit & Features

    • Sleeveless halter neckline
    • Tassel tie-neck closure
    • Fitted crop hem, tassel trim
    • Open-back, tassel tie-back closure
    • Multi-colored chevron knit
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1660

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • For The Frill Ruffled Tie-Back Skater Dress

    You'll totally be eyeing this skater dress for its frills! Have your twirl-worthy moment in this short dress featuring a square neck, short puff sleeves, a tie-back detail, and a flowy fit and flare silhouette with a tiered ruffle trim skirt. Complete the look with a trendy purse and mules for a baby shower or celebration!

    Fit & Features

    • Square neck, short puff sleeves
    • Tie-back detail
    • Flowy, fit and flare silhouette
    • Tiered ruffle trim skirt
    • Short-length hem
    • Lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4851

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Flare To Remember Skater Dress

    You'll be unforgettable in this short skater dress perfect for twirling into baby showers, brunches, and family parties! Featuring a sleeveless plunge v-neckline, spaghetti straps that cross and tie along the open back, and a fit-and-flare silhouette. The dress is composed of airy printed chiffon fabric with a smooth woven lining. Style with strappy mules and a clutch! 

    Fit & Features

    • Sleeveless plunge v-neckline
    • Spaghetti straps
    • Open back, cross strap design, tie closure
    • Fit and flare skater silhouette
    • Short-length hem
    • Airy printed chiffon fabric, smooth woven lining
    • Runs true to size

    Style Number/Barcode: 05102-4988

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winged Beauty Butterfly Sunglasses

    Adorn your outfit with whimsical beauty! These statement sunglasses feature retro-style butterfly frames with tinted lenses, side rhinestone accents, nose supports, and metal arms. Complete the look with dainty fringe earrings.

    Fit & Features

    • Retro-style butterfly frames
    • Tinted lenses
    • Side rhinestone accents
    • Nose supports, metal arms

    Style Number/Barcode: 07008-0988

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Dream Floral Strappy Maxi Dress

    POV: You just entered the group chat looking like a vacay dream. This mesh maxi dress hugs in all the right places with a strappy back that turns heads on vacation and summer parties!

    Fit & Features

    • Tropical floral print, mesh-lined fabric, moderate stretch
    • V-neckline
    • Bungee spaghetti straps
    • Strappy open back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000389

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Step Espadrille Lace-Up Wedges

    These espadrille wedges will put a spring in your step! They feature a faux leather square toe, wide toe strap, and lace-up ankle straps with a supportive ankle band. Complete the look with a trendy handbag.

    Fit & Features

    • Square toe
    • Wide toe strap
    • Lace-up ankle strap with supportive band
    • Espadrille sole
    • Faux leather trim
    • Wedge heel

    Style Number/Barcode: 07406-0325

    Category Name: Vacation Looks

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Savannah High-Rise Straight-Leg Jeans by Windsor Denim

    The Savannah straight-leg jeans by Windsor Denim are a major must-have in your everyday wardrobe! They feature a high-rise waist, destructed detailing down the front, a straight-leg fit, and a subtle frayed hem. The medium-wash denim fabric features a color-faded design for a cool vintage look. Style with a crop top and mules.

    Fit & Features

    • High-rise waist
    • Destructed detailing
    • Straight-leg fit, frayed hem
    • Five-pocket and belt loop styling
    • Front button, hidden zipper closure
    • Denim fabric, color-faded design, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0414

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Polished Paperbag Shorts

    Chic and polished, these woven paperbag shorts will elevate your casual looks! They feature a high-rise paperbag waist with small slit accents at the front, a tie-front belt, front pockets, a cuffed hem, and a fitted silhouette. The smooth twill fabric offers a lightweight feel. Style with a crop top and denim jacket.

    Fit & Features

    • High-rise paperbag waist, front slit accents
    • Tie-front belt
    • Hidden front zipper, hook and bar closure
    • Dual front pockets
    • Cuffed hem, fitted silhouette
    • Woven twill fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0284

    Category Name: Vacation Looks

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • True Staple Short Skater Dress

    A true staple for daytime soirees and celebrations! This short skater dress features a classic sleeveless square neck, adjustable spaghetti straps, a tie-front bust, flexible boning inserts along the bodice, and is composed of smooth woven fabric with a stretchy knit lining. Complete the look with a bracelet and heels.

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Tie-front bust, flexible boning inserts
    • Skater silhouette
    • Short-length hem
    • Woven fabric stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2016

    Category Name: Vacation Looks

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Budding Romance Floral Chiffon Skater Dress

    Create a dreamy spring date outfit in this adorable floral chiffon skater dress! It features a square neckline, ruching at the bust, a tie-front accent and keyhole cutout, short puff sleeves, a high waist seam, and a short skater skirt with a fit and flare silhouette. The airy chiffon fabric features an all-over dainty floral print pattern for the prettiest look. Style with espadrille sandals.

    Fit & Features

    • Square neckline, ruched bust, tie-front detail, keyhole cutout
    • Short puff sleeves, elastic cinched hems
    • Back zipper, hook and eye closure
    • High waist seam, short skater skirt, fit and flare silhouette
    • Dainty floral print
    • Chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1838

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Remy High-Rise Frayed Shorts By Windsor Denim

    Pick up the phone, the Remy jean shorts by Windsor denim are calling to be your number one this season! They feature a flattering high-rise waist, front and back heavy distressed accents, and a trendy frayed cut-off hem. The shorts are composed of vintage-inspired medium-wash denim fabric with color fading. Complete the look in a crop top and cowboy boots for the perfect festival or concert outfit!

    Fit & Features

    • High-rise waist
    • Front and back heavy distressed accents
    • Frayed, cut-off hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, color fading, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0244

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachside Stroll Printed Maxi Skirt

    You'll look effortlessly pretty as you take a beachside stroll in this fab maxi skirt! It features a high-rise waist, a faux wrap-front design creating a high slit, a form-hugging fit at the hips, and a maxi-length hem with a flowy silhouette. The knit fabric features an abstract tropical print for major vacay vibes. Style with a crop top and sandals.

    Fit & Features

    • High-rise elasticized waist
    • Faux wrap-front design
    • High front slit
    • Hip-hugging fit, maxi-length hem, flowy silhouette
    • Abstract tropical print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0819

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Resort Bound Tropical Print Flare Pants

    You'll look resort-ready in these trendy tropical print flare pants! They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, and a flared hem. The stretchy knit fabric features a bold tropical palm leaf print that is perfect for pairing with a basic crop top. Complete your vacay look with strappy sandals.

    Fit & Features

    • High-rise elasticized waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Tropical palm leaf print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2269

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flawless Floral Mesh Tie Crop Top

    Keep it fresh looking flawless in this floral mesh crop top to pair with your favorite bottoms! It features an off-the-shoulder neckline, sheer peasant sleeves, a tie-front closure with a keyhole accent, and a ruched bust and fitted hem. Style with new skinny jeans to complete the look!

    Fit & Features

    • Off-the-shoulder neckline
    • Sheer peasant sleeves
    • Tie-front closure, keyhole accent
    • Ruched bust
    • Fitted crop hem
    • Floral print, mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4413

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Whatever Rib Takes Cutout Mini Dress

    Take on the day in style wearing this mini dress featuring a trendy, sleeveless, high neck, bodycon silhouette, and a cutout accent for a flash of skin. Complete the look in sunnies and sandals for the perf day date look.

    Fit & Features

    • Sleeveless, high neck
    • Bodycon silhouette
    • Cutout accent
    • Mini-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1270

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Total Vibe Halter Bodysuit

    You in this sultry-chic bodysuit would be a total vibe! Featuring a sleeveless twist-front halter neckline with a center keyhole cutout at the bust, this bodysuit will elevate your basic look. Style with a faux leather skirt and mules.

    Fit & Features

    • Sleeveless twist-front halter neckline
    • Center keyhole cutout
    • Open back
    • Thong bottom, dual snap-button closure
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4808

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • One More Moment Sweater Dress

    Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless square neck, spaghetti straps that lead to an open back with lace-up closure, a form-fitting silhouette, and a high side slit atop the midi-length hem. Complete the look with sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Open back, lace-up closure
    • Form-fitting silhouette
    • Side slit, midi-length hem
    • Sweater knit fabric, slightly sheer, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1688

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Easy Breezy In Floral Chiffon Dress

    Easy, breezy, and beautiful! You'll adore this floral chiffon dress perfect for bridal showers or dressy spring parties. It features an off-the-shoulder, sweetheart neck, ruffled short-sleeve cuffs, a padded bust, a smocked back, and a flowy skater silhouette with a ruffled short hem. The dress is composed of an airy chiffon with a rose floral bouquet print and a stretchy knit lining. Complete the look in strappy sandals.

    Fit & Features

    • Off-the-shoulder, sweetheart neck, padded bust
    • Ruffled short sleeve cuffs
    • Smocked back, zipper nad hook-eye closure
    • Flowy skater silhouette, ruffled short hem
    • Rose floral bouquet print
    • Airy chiffon, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2052

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Charm Ditsy Floral Skater Dress

    Show off your cute charm in this adorable ditsy floral skater dress! It features a square neckline with a ruffled trim, a ruched bust with a tie-front detail, short puff sleeves, a fitted high waist seam, and a short flared-out skater skirt with a flowy silhouette. The lightweight woven fabric features a dainty ditsy floral print pattern. Style with espadrille sandals for a picnic date.

    Fit & Features

    • Square neckline, ruffled trim
    • Ruched bust, tie-front detail
    • Short puff sleeves, elastic cinched hems
    • Back zipper, hook and eye closure
    • High waist seam, short skater skirt, fit and flare silhouette
    • Ditsy floral print, woven fabric, bust knit lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4854

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flourish In Floral Print Mini Dress

    Flourish for spring in this dainty floral mini dress you'll love styling for casual plans! It features a sleeveless scoop neck with a tie-front bust, spaghetti straps, and a bodycon fit on stretchy rib knit fabric. Complete the look with new trendy sandals.

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Tie-front bust
    • Bodycon fit
    • Mini-length hem
    • Dainty floral print, stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4930

    Category Name: Vacation Looks

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bae Breeze Cotton A-Line Short Dress

    Enter looking like bae just breezed in! Capture cuteness in this cotton short dress featuring short puff sleeves, a square neck, an open lace-up back, and an A-line silhouette. Style with a trendy crossbody bag and heels.

    Fit & Features

    • Short puff sleeves
    • Square neck
    • Open lace-up back, zipper and hook-eye closure
    • A-line silhouette
    • Short-length hem
    • Cotton fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4876

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dream Look Floral Ruched Mini Dress

    Create your dream look for a spring date in this adorable floral mini dress! It features a sleeveless sweetheart neckline with ruching at the bust, spaghetti straps, an open back with a lace-up strappy design, ruching down the side seams, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric features a dainty rose print pattern for the prettiest look. Style with clear heels.

    Fit & Features

    • Sleeveless sweetheart neckline, ruching at the bust, spaghetti straps
    • Open back, lace-up strappy design, tie closure
    • Ruching down the side seams
    • Mini-length hem, form-hugging fit
    • Dainty rose print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4888

    Category Name: Vacation Looks

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picnic Time Gingham Mini Dress

    You'll be the cutest girl in this gingham casual dress at the picnic! It features ruffle trim puff short sleeves, a sweetheart neck with a lace-up bust, a bodycon silhouette, and a mini-length hem on stretchy rib knit fabric. Complete the look in sandals.

    Fit & Features

    • Ruffle trim puff short sleeves
    • Sweetheart neck, lace-up bust
    • Bodycon silhouette
    • Mini-length hem
    • Gingham print
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4995

    Category Name: Vacation Looks

    Price: $27.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Flare High Rise Denim Jeans

    Show off your cute style in these denim jeans you've been eyeing all over social media! They feature a flattering high-rise waist, hip-hugging fit, front seam detailing, and a flared hem. Complete the look in a trendy corset top and sandals for a casual dinner!

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Front seam detailing
    • Flared hem
    • Front button and hidden zipper closure
    • Light wash denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0434

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance