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.

  • Total Trendsetter O-Ring Chain Belt

    This sleek O-ring chain belt was made to complete your trendy 'fits! It features an all-around linked O-ring design and includes an adjustable fit with a lobster clasp closure. Style over a bodycon dress with strappy stilettos for a fab going-out look.

    Fit & Features

    • Linked O-ring design
    • Adjustable fit
    • Lobster clasp closure

    Style Number/Barcode: 07301-0702

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Destination Tropical Ruffle Maxi Dress

    Arrive at your destination in this tropical maxi dress looking stunning and ready for fun! The maxi dress features a strapless neckline, non-slip grip lining, flexible boning, a form-hugging fit, and an effortless high front slit and ruffled flowy hem. Complete your vacation look with a handbag and sandals!

    Fit & Features

    • Strapless neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Flexible boning
    • Form-hugging fit
    • High front slit, ruffled flowy maxi hem
    • Tropical print, airy mesh fabric, partial knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5383

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Cut One Shoulder Cutout Mini Dress

    Let your style speak volumes with this mini dress perfect for dates or birthday brunch! The mini-length dress features a one-shoulder neckline with a puff short sleeve, a side drawstring cutout, and a flattering form-hugging silhouette on texture woven fabric. Complete the look with an envelope clutch and heels.

    Fit & Features

    • One-shoulder neckline, puff short sleeves
    • Side drawstring cutout
    • Form-hugging silhouette
    • Mini-length hem
    • Texture woven fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5401

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl Power Leopard Print Strapless Midi Dress

    Show off major girl power in this sexy leopard print midi dress that was made for all eyes on you. It features a strapless straight-across neckline, ruching down the side seams, a midi-length hem, and a bodycon silhouette to put your gorgeous figure on display. The lined sheer mesh fabric features an all-over leopard print pattern to amp up the look. Style this midi dress with strappy stilettos for a nightclub!

    Fit & Features

    • Strapless straight-across neckline, no-slip strip
    • Ruched side seams, hidden side zipper, hook and eye closure
    • Midi-length hem
    • Bodycon silhouette
    • Leopard print
    • Sheer mesh fabric, mini-length knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-3211

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Maldives Please Tropical Mesh Mini Skirt

    Pack your bags with this stunning tropical mesh mini skirt on your way to the Maldives! Enjoy fun in the sun in this sultry mini skirt featuring a high-rise waist, flattering ruching, and a bodycon silhouette. Style with the matching top and duster to complete the look!

    Shop Matching Top And Duster: Maldives Please Tropical Mesh Bustier, Maldives Please Tropical Mesh Duster

    Fit & Features

    • High-rise elastic banded waist
    • Dual front vertical seams, ruched detailing
    • Back zipper, hook and eye closure
    • Bodycon silhouette
    • Tropical print
    • Sheer lightweight mesh fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0933

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Maldives Please Tropical Mesh Duster

    Pack your bags with this stunning tropical mesh duster on your way to the Maldives! Enjoy fun in the sun in this sultry duster featuring sheer fitted long sleeves, an open front design with tie-front closure, and a flowy silhouette. Style with the matching top and skirt to complete the look!

    Shop Matching Top And Skirt: Maldives Please Tropical Mesh Bustier, Maldives Please Tropical Mesh Mini Skirt

    Fit & Features

    • Fitted long sleeves
    • Open-front design, tie-front closure
    • Flowy silhouette
    • Tropical print
    • Sheer lightweight mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0429

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Maldives Please Tropical Mesh Bustier

    Pack your bags with this stunning tropical mesh bustier on your way to the Maldives! Enjoy fun in the sun in this sultry top featuring a sleeveless wired V-notch neckline, sleek bungee spaghetti straps, a padded bust, and flattering ruched seams and crop hem. Style with the matching skirt and duster to complete the look!

    Shop Matching Duster and Skirt: Maldives Please Tropical Mesh Duster, Maldives Please Tropical Mesh Mini Skirt

    Fit & Features

    • Sleeveless wired V-notch neckline
    • Bungee spaghetti straps
    • Ruched seams
    • Cropped hem
    • Tropical print mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 06001-5025

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • New Trend On The Block Shoulder Bag

    This shoulder bag is currently trending! It features a large silhouette, a shoulder strap, an adjustable drawstring on the bottom to create a scrunching effect, and a zipper closure revealing a lined spacious interior with a zipper pocket and slot pockets for holding all your essentials. Complete the look in a trench coat for traveling or running errands!

    Fit & Features

    • Large silhouette
    • Shoulder strap
    • Adjustable drawstring on the bottom, scrunch effect
    • Zipper closure
    • Lined spacious interior, zipper pocket and slot pockets
    • Smooth nylon woven material

    Style Number/Barcode: 07203-1955

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Cutie Faux Leather Mini Handbag

    This cute faux leather handbag is ready to be your mini BFF. With a detachable chain shoulder strap, top handle, and a top zipper closure revealing a spacious lined interior for keeping your essentials, this versatile bag is ready for an evening out or a day in the office. Complete the look in knee-high boots.

    Fit & Features

    • Detachable chain shoulder strap
    • Top handle
    • Mini silhouette design
    • Top zipper closure
    • Spacious lined interior
    • Faux leather material

    Style Number/Barcode: 07203-1973

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Plans Mid-Rise Linen Shorts

    Cute for casual plans, these mid-rise linen blend shorts offer a breezy style to your look! Shop the matching top.

    Fit & Features

    • Woven linen-blend fabric
    • Elasticized mid-rise waist
    • Flowy dolphin trim hem
    • Runs true to size

     

    Shop The Matching Top: Casual Plans Button-Down Linen Top

    Style Number/Barcode: 06303-000001

    Category Name: Vacation Looks

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • New Lover Heart Charm Mini Satchel Handbag

    Fall head over heels for this adorable mini satchel handbag! With its top handle, detachable chain shoulder strap, and front flap with snap-button closure plus a pretty strap with dazzling rhinestones and a metal heart lock charm, this mini bag is a must-have. Plus, its lined interior and faux leather texture make it as practical as it is chic. Style with stiletto heels for day or night plans.

    Fit & Features

    • Top handle, detachable chain shoulder strap
    • Front flap, snap-button closure
    • Strap accent, rhinestones, metal heart lock charm
    • Spacious lined interior
    • Faux leather texture material

    Style Number/Barcode: 07203-1972

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Happy Face Faux Sherpa Slippers

    These cozy slippers will put a smile on your face! The slippers feature a round closed toe, smiling happy face on faux sherpa material, an ultra-soft lining, an open back for easy slip-on and off styling, and a comfort sole with a rubber traction bottom. Complete the look with a cute pajama set for a night in or a slumber party!

    Fit & Features

    • Round closed toe
    • Smiling happy face
    • Faux sherpa exterior
    • Ultra-soft lining
    • Open back, slip-on-and-off styling
    • Comfort sole, rubber traction bottom
    • Runs true to size

    Style Number/Barcode: 07408-0113

    Category Name: Vacation Looks

    Price: $12.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Mini Travel Jewelry Case

    This sleek mini travel jewelry case is just what you need to have all of your accessories organized for your next trip. It features a structured small square shape with a fold-over design, an all-around zipper closure, and a felt-like interior with square-shaped compartments, cushioned ring holders, and flexible necklace hooks with a pouch to avoid getting your pretty pieces tangled. Pack your favorite statement earrings, layered necklaces, and dainty rings in this jewelry case for your next vacay or weekend getaway!

    Fit & Features

    • Square shape
    • Fold-over design
    • All-around zipper
    • Four square-shaped compartments, cushioned ring holders
    • Three flexible necklace hooks and pouch
    • Faux leather exterior material
    • Felt-like interior material

    Style Number/Barcode: 07308-0614

    Category Name: Vacation Looks

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hello Fabulous Fuzzy Platform Slippers

    Say hello to fabulous! These cartwheel-worthy fuzzy platform slippers are sure to give you that Y2K feel. They feature a square toe, a wide foot strap, and a chunky platform sole and heel on soft fuzzy material. Complete the look in a cute smooth dress for a casual hang!

    Fit & Features

    • Square toe
    • Wide foot strap
    • Chunky platform sole and heel
    • Soft fuzzy material
    • Runs true to size

    Style Number/Barcode: 07408-0111

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Slick Faux Leather Puffer Jacket

    Elevate your cold weather look with this faux leather puffer jacket! Its comfy long sleeves with elasticized cuffs, crop hem, and standing collar neckline help keep you extra warm while the front zipper closure and pockets create functionality. The puffer jacket is designed with a sleek faux leather fabric with an insulated nylon-woven lining that helps keep you warm and protected from the elements. Complete the look in trendy denim jeans.

    Fit & Features

    • Long sleeves, elasticized cuffs
    • Standing collar neckline
    • Front zipper closure
    • Lined pockets
    • Elasticized crop hem
    • Faux leather fabric, insulated nylon-woven lining
    • Runs true to size

    Style Number/Barcode: 06201-0442

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Buttoned Up High-Rise Flare Denim Jeans

    A pair of denim jeans that effortlessly hug your curves for the perfect silhouette! Your new favorite jeans feature a flattering high-rise waist, front seam detailing down the front, a hip-hugging fit, and a raw flared hem. Crafted on dark wash denim fabric, they offer a slight stretch and a vintage-inspired color fading. Complete the look in a bodysuit for day or night plans!

    Fit & Features

    • High-rise waist
    • Front seam detailing down the front
    • Hip-hugging fit
    • Raw flared hem
    • Front five-button fly closures, belt loop accents
    • Dark wash denim, color fading, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0467

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Hottie Cutout Ruched Midi Dress

    This curve-hugging cutout midi dress will show off your major hottie status! The mid-length dress features an off-the-shoulder straight-across neckline, long fitted sleeves, alluring front and back waist cutouts, ruching down the side seams, and a bodycon silhouette to flaunt your figure. The lined knit fabric offers plenty of stretch. Style this midi dress with layered chain necklaces and clear strap heels for a rooftop bar.

    Fit & Features

    • Off-the-shoulder straight-across neckline, elasticized hem
    • Long fitted sleeves
    • Front and back waist cutouts
    • Ruched side seams
    • Midi-length hem, bodycon silhouette
    • Knit fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5366

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Check Ya Later Plaid Flannel Shacket

    This plaid flannel shacket will make you look effortlessly stylish! With long sleeves, button cuffs, and a classic collar neckline, you'll be the talk of the town. Featuring a button-down front, front pocket, and oversized silhouette, and is crafted on soft flannel woven fabric with a classic plaid print you'll adore this season. Style with sleek leggings and boots for the perf cold-weather fit'!

    Fit & Features

    • Long sleeves with button cuffs
    • Collar neckline
    • Button-down front, pocket
    • Oversized silhouette
    • Soft flannel woven fabric
    • Plaid print
    • Runs true to size

    Style Number/Barcode: 06204-1609

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • City Slicker Faux Leather Sherpa Lined Jacket

    Layer up in this faux leather crop jacket for a day or night out in the city! The faux sherpa lined jacket features slouchy long sleeves with faux sherpa cuffs and collar neckline, a front zipper closure, faux sherpa trim side pockets with woven lining, and a faux sherpa trim cropped hem. Style the cozy jacket with sleek booties and high-rise denim!

    Fit & Features

    • Slouchy long sleeves, faux sherpa cuffs
    • Faux sherpa collar neckline
    • Front zipper closure
    • Faux sherpa trim side pockets, woven lining
    • Faux sherpa trim cropped hem
    • Faux leather fabric, faux sherpa lining
    • Runs true to size

    Style Number/Barcode: 06201-0394

    Category Name: Vacation Looks

    Price: $30.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ever-So-Trendy Plaid Fringe Scarf

    This ever-so-trendy plaid fringe scarf is perfect for the cold season ahead! Wrap yourself up in this comfy and ultra-soft scarf for day or night plans. Complete the look in a trendy moto jacket.

    Fit & Features

    • Plaid pattern
    • Fringe 
    • Ultra-soft knit material

    Style Number/Barcode: 07305-0458

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Arrive In Style Faux Leather Large Tote Bag

    Arrive in style toting this faux leather bag for weekday activities to weekend travel! The large tote bag features shoulder straps with an attached mini zipper pouch for carrying small items, a front quilted design on the faux leather material, a zippered pocket at the back, and a top zipper closure that reveals a spacious woven interior with pockets. Complete the look with a sweater and boots!

    Fit & Features

    • Large tote bag
    • Shoulder straps, attached mini zipper pouch
    • Front quilted design
    • Faux leather material, four studs at the bottom
    • Back zippered pocket
    • Top zipper closure
    • Spacious woven interior, two pockets, one zippered pocket

    Style Number/Barcode: 07203-1424

    Category Name: Vacation Looks

    Price: $18.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Girl Mode Turtleneck Sweater Topper

    Enter cozy girl mode in this sweater topper to give your outfit the perfect touch! The sweater features slouchy long sleeves with ribbed cuffs, a fold-over turtleneck, a surplice front and back design, and an ultra-cropped hem on ribbed sweater knit fabric. Complete the look in a basic tank top and trendy cargo jeans.

    Fit & Features

    • Slouchy long sleeves, ribbed cuffs
    • Fold-over turtleneck
    • Surplice front and back design
    • Ultra-cropped hem
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1753

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunday Funday Baseball Cap

    The perfect baseball cap to show your gameday energy! It features a classic curved wide brim and a front embroidery that reads, "Sunday Funday" with a football. Complete the look in a trendy denim jacket to root for your team in style!

    Fit & Features

    • Classic baseball cap design
    • Curved wide brim
    • Front embroidery reads, "Sunday Funday" with a football
    • Adjustable back strap, metal clip closure

    Style Number/Barcode: 07302-1537

    Category Name: Vacation Looks

    Price: $3.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Talkin' Flirty Halter Floral Bodycon Mini Dress

    Get ready to turn heads in this mesh mini dress! The ruffled floral trim halter neckline adds a touch of elegance, while the bodycon silhouette and mini-length hem accentuate your curves.

    Fit & Features

    • Mesh-lined fabric
    • Ruffled floral trim halter neckline, spaghetti strap tie
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000111

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free