Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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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.
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Trendy Glitz Rhinestone O-Ring Chain Belt
This rhinestone O-ring chain belt will give your looks that trendy glitz! It features a bold O-ring linked design embellished with sparkling rhinestones for pretty glamour. Includes a back adjustable chain with a lobster clasp closure. Layer this belt over a mini dress, a blazer, a mini skirt, or dress pants!
Fit & Features
- Large O-ring linked design
- Front rhinestone embellishments
- Back adjustable chain, lobster clasp closure
Style Number/Barcode: 07301-0697
Category Name: Vacation Looks
Price: $4.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tied In Cozy Chenille Tie-Waist Robe
Tie yourself up in this cozy chenille robe perfect for lounging around! The robe features long sleeves, an open-front design, a tie-waist belt, front pockets for keeping your hands warm, and a mid-length hem on ultra-soft chenille knit fabric. Complete the look in the matching pajama top and bottoms for a chill night!
Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top
Shop Matching Pajama Bottoms: Fuzzy Feels Chenille High-Rise Jogger Pajamas
Fit & Features
- Long sleeves
- Open-front design
- Tie-waist belt, front pockets
- Mid-length hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0942
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hello Cutie Chenille Crop Pajama Top
Look and feel like a cutie in this chenille pajama top! The tank top features a sleeveless square neckline, tank-style straps, and a cropped hem on ultra-soft and cozy knit chenille fabric. Complete the look in the matching pajama bottoms and robe for the perfect lounge sesh!
Shop Matching Pajama Bottoms: Fuzzy Feels Chenille High-Rise Jogger Pajamas
Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe
Fit & Features
- Sleeveless square neckline
- Tank-style straps
- Cropped hem
- Ultra-soft and cozy
- Chenille knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 07103-0938
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling The Vibe High-Rise Chenille Joggers
Feel the cozy vibes in these chenille joggers perfect for lounging on the weekend! The jogger pants feature a high-rise elastic drawstring waist, a skinny jogger-style leg, and are crafted from ultra-soft and stretchy chenille rib knit fabric. Complete the look in the matching pajama top and cardigan for the perfect lounge sesh!
Shop Matching Pajama Top: Chill Night Chenille Crop Tank Top
Shop Matching Cardigan: Cuddle Time Chenille Crop Cardigan
Fit & Features
- High-rise elastic drawstring waist
- Skinny jogger-style leg
- Ultra-soft chenille rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 07103-0947
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free